History Characters / Cuphead

* [[Characters/CupheadTheDeliciousLastCourse The Delicious Last Course]]

For ease of reading, this page has been split into sub-pages. '''Beware unmarked {{spoiler}}s!'''

'''Beware unmarked {{spoiler}}s!'''

* [[Characters/CupheadNPCsAndEnemies Allies and Enemies]]

* [[Characters/CupheadNPCsAndEnemies NPCs and Enemies]]

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[[foldercontrol]]

!Main Characters
!!!Heroes
[[folder:Cuphead & Mugman]]
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/cuphead_winning_screen.png]]
->''"Well, Cuphead and his pal Mugman, they like to roll the dice…"''
The PlayerCharacters and protagonists of the story, two brothers that are anthropomorphic cups with bodies.
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* AbnormalAmmo: Judging by the fact that the different types of weapons you can buy come in bottles, it seems that Cuphead and Mugman shoot moonshine and other beverages at their enemies. Further, the first super attack has them firing the contents of their cups as [[WaveMotionGun giant lasers]] -- and WordOfGod has stated that the cups contain their ''souls''. {{Invoked}} while using their airplanes' machine guns, their Ex Move, ''Chomper Missile'', launches a large missile with a chomping jaw on it that deals damage with each bite.
* ActionBomb: In flying stages, their supers turn them into literal bombs that they can ram into their opponents. It's fittingly named ''Super Bomb Morph''.
* AintTooProudToBeg: At the beginning, when the boys lose in a game of Craps against the Devil, who's about to claim their souls, [[https://i.ytimg.com/vi/GThW_rqcYO8/maxresdefault.jpg they kneel down and beg for their lives to be spared]]. Needless to say, it works.
* {{Autocannibalism}}: Mugman drinks the liquid from his own head (stated to be his soul by WordOfGod) through his own straw at the start of every boss battle and mausoleum stage in co-op. Presumably it just ends up being put back into his head.
* BadassAdorable: They're cute little homages to cartoon protagonists from the 30s that, eventually, can become strong enough to beat up {{Satan}}. [[https://twitter.com/EvanSkolnick/status/953431259161673728 It helps that Cuphead and Mugman are adolescents, too.]]
* BadassBaritone: While it was more than likely a nod to something like [[https://www.youtube.com/watch?v=OLKDV-_SCBs this]], it's still worth noting that their "Thank You" upon getting resurrected in multiplayer is surprisingly deep for beings that look like they'd sound like Mickey Mouse (though it isn't really their actual voices; it's just an amusing case of BreakingTheFourthWall).
* BadassInDistress: [[spoiler:If you are using Ms. Chalice for the final boss of the DLC, whichever brother she was swapped for is being held captive by Chef Saltbaker as the final ingredient of his Wondertart.]]
* BashBrothers: A literal example, as Cuphead and Mugman are actual brothers.
* BigLittleBrother: Though the brothers may seem to be around the same height, Mugman is noticeably slightly taller than Cuphead.
* BreakingTheFourthWall: When playing two players. If one dies and the remaining player can parry their ghost before they float away, they will give out a direct "Thank you!" at the player before reforming back to normal and rejoining the battle.
* BugCatching: The first page of a storybook at the very beginning shows the boys catching some bugs with the Elder Kettle in the forest (as Cuphead indicates by holding a bug-catching net).
* CharlesAtlasSuperpower: At the beginning of the game, they're no stronger than average civilians. At the end, after all their trials and tribulations acting as the Devil's hitmen, they become strong enough to [[DidYouJustPunchOutCthulhu beat the crap out of him]].
* ColorCodedForYourConvenience: Cuphead's red and Mugman's blue. [[RedOniBlueOni Even their personalities reflect this.]]
* DealWithTheDevil: What kicks off the whole adventure when the two tried to play a game of Craps against the Devil and lost. They pleaded for their lives and he claimed he might spare their lives if they do his bidding.
* DidYouJustPunchOutCthulhu: [[spoiler:In the good ending, they beat the crap outta The Devil himself.]]
* DistressedDude: In ''The Delicious Last Course'', [[spoiler:if you face the final boss as Ms. Chalice, the brother she swaps out for is captured by Chef Saltbaker as the final ingredient of his Wondertart]].
* TheDragAlong: Mugman understood the dangers of taking the Devil's gamble but Cuphead was blinded by the prize. Mugman now has to be a debt collector alongside Cuphead on the Devil's behalf, though Mugman was willing to gamble in the Devil's casino at first, only stopping upon realizing the dangers of taking the Devil's gamble, though it was too late by that time.
* EmptyEyes: Or "Empty Eye Sockets", rather: [[spoiler:if you lose to the Devil's second phase and onwards, he [[DecapitationPresentation holds up the lifeless, decrepit heads of Cuphead and Mugman]]. [[https://vignette.wikia.nocookie.net/cuphead/images/9/9b/DevilIcon2.png You can see that their heads have no eyes at all (and there are some cracks in their black, hollowed-out eye sockets), as if they're both deprived of their souls.]]]]
* EvilDebtCollector: A rare non-villainous variation of this trope, since they are basically forced to collect the Devil's soul contracts from other Inkwell Islanders to save themselves. [[spoiler:The good ending can subvert this, since they opt to turn against the Devil and free all other debtors instead.]]
* {{Expy}}: Both of them evoke many old-school animation protagonists in both design and personality, particularly WesternAnimation/FelixTheCat, WesternAnimation/OswaldTheLuckyRabbit, and WesternAnimation/MickeyMouse. Indeed, they were both modeled after a cartoon character with a teacup for a head who pours a liquid into his head, then transforms into a tank in a 1936 Japanese propaganda cartoon.
* FaceHeelTurn: In the bad ending, [[spoiler:they become the Devil's servants]].
* FingerGun: They attack by making finger guns and firing shots from them, with the shots apparently being drawn from the liquid in their heads. Comes in nine flavors:
** ''Peashooter'': Basic attack in blue, single-line shot with high rate of fire. Ex Move is Mega Blast, a KamehameHadouken EnergyBall attack.
** ''Spread'': SpreadShot in red, powerful three-way shotgun attack but has a [[ShortRangeShotgun limited range]]. Ex Move is Eight Way, a MultiDirectionalBarrage in all 8 directions.
** ''Chaser'': HomingProjectile in green, homes in on enemies (and some projectiles) but has low damage output. Ex Move is Chaos Orbit, an OrbitingParticleShield[=/=]ReverseShrapnel move of four orbiting projectiles.
** ''Lobber'': [[GrenadeLauncher Arcing projectile]] in purple, slower rate of fire but bounces off the ground until it makes contact. Ex Move is Kablooey, a much [[BigBulkyBomb bigger arcing bomb]].
** ''Charge'': ChargedAttack in orange, single-line shot that can be charged and released to deal more damage. Ex Move is Radial Barrage, a [[HavingABlast close-range explosion from the player's hands]] to inflict massive damage.
** ''Roundabout'': BattleBoomerang attack in cyan, single-line shot that will travel for a short range then reverse direction to hit enemies behind the shooter. Ex Move is Jumbo Roundabout, a giant [[DeadlyDisc sawblade]] that will fly around until it returns to Cuphead (dodging it on the return allows it to make another round and deal more damage in the process).
** ''Crackshot'': Straight shot in pink, after traveling a set distance without hitting anything [[RecursiveAmmo it splits off a weaker shot]] aimed directly at the closest enemy. Ex Move is P. Turret, a pink planet-shaped turret that automatically shoots at enemies and can be parried to lob it at opponents. Introduced in ''The Delicious Last Course''.
** ''Converge'': SpreadShot of [[ShockAndAwe lightning bolts]] in yellow, travels farther than Spread, has an adjustable spread angle, and pierces through enemies, but has a slower rate of fire and lower damage. Ex Move is Electro-Bolt, an [[LightningGun electric beam]] that pierces through everything it hits. Introduced in ''The Delicious Last Course''.
** ''Twist-Up'': SpreadShot of [[BlowYouAway mini-tornadoes]] in turquoise, high rate of fire combined with average damage, but travels in strange arcs. Ex Move is Cyclone Spiral, a bigger tornado that moves in a spiral motion. Introduced in ''The Delicious Last Course''.
* FireballEyeballs: [[spoiler:The boys have these when they are turned into the Devil's servants in the bad ending.]]
* ForcedIntoEvil: They have no choice but to be the Devil's enforcers; if they don't collect the souls then they too are doomed to live in hell for all eternity.
* FoolishSiblingResponsibleSibling: Cuphead and Mugman, respectively. Case in point, Mugman tried to discourage Cuphead from gambling their souls for the Devil's loot, but the latter was so blinded by his own greed that he took the bet and lost.
* TheGamblingAddict: Cuphead and Mugman get a winning streak at the Devil's Casino and end up betting their souls for the Devil's entire treasure. Mugman tries to convince Cuphead to stop, but Cuphead is so blinded by greed and overconfidence that he plays the dice game and loses.
* GrinOfAudacity: Both brothers grin fearlessly when shooting at their enemies or when flying a plane.
* KidHero: Although these two are adolescents, they seem to fit the bill quite nicely when they are fighting for their souls. [[spoiler:Indeed, the only way for them to be true Kid Heroes is when they can save the Inkwell Isles from the Devil himself... if they play the cards right.]]
* LimitBreak: The boys can collect three super moves during their adventures, granted by the Legendary Chalice at Mausoleums around the island. They can be used once all 5 Ex Cards are filled.
** I -- ''Energy Beam'': The first Super Art they receive allows them to jump into the air and fire a giant stream of liquid, WaveMotionGun-style, at their opponent.
** II -- ''Invincibility'': The second Super Art they get is, as stated, an InvincibilityPowerUp that lasts for a limited time (after they somehow turn their heads huge and give off a creepy laugh... for some reason).
** III -- ''Giant Ghost'': The third super they can gain allows them to manifest [[FightingSpirit a ghostly, stronger form of themselves]] which will [[SpinAttack float and spin around and hit their enemies repeatedly]], after which it will vanish and leave behind a pink heart they can parry for extra mana.
* LiteralAssKicking: The boys are on the receiving end of this one after the Devil offers them a chance to collect the Soul Contracts of other debtors who have lost to him. [[http://assets1.ignimgs.com/2017/10/02/11-1506958306104_1280w.jpeg You can even see the Devil's foot kicking their butts out the door!]]
* LosingYourHead: Played for laughs for a bit. When Cuphead and Mugman drink the potion for the Peashooter from the Elder Kettle or get a Super Powerup from the Legendary Chalice, they get a tingling sensation in their bodies, and then they hold up their smiling heads by their handles in a tip-off before placing them back on their own necks.
* MacrossMissileMassacre: While using their airplane bombs, their Ex Move becomes ''Magnet Mine/Missile'', which launches a missile barrage that homes in on nearby enemies and works great for screen-clearing.
* MockyMouse: Their designs of having mostly black bodies while wearing white gloves, shoes and shorts is clearly evocative of WesternAnimation/MickeyMouse.
* MrViceGuy: Cuphead may be greedy and short-sighted, but he, along with Mugman, frees the souls they collected for the Devil after beating him up.
* NaughtyIsGood: The boys who gambled at Satan's casino despite the Elder Kettle's warnings to stay away happen to be the same ones who saved many of Inkwell Isle's residents from eternal servitude to Satan.
* NiceJobBreakingItHero: Cuphead was basically the one who got the duo into their nasty situation in the first place by taking a high-stakes game against the Devil and losing, though Mugman was willing to gamble in the Devil's casino at first, only stopping upon realizing the dangers of taking the Devil's gamble, though it was too late by that time. [[spoiler:Though if it weren't for that, the brothers wouldn't have been able to collect the soul contracts, which would let them get close to the Devil, beat the ever-loving tar out of him, then burn all the soul contracts, freeing the Inkwell Isle residents from eternal servitude to the Devil.]]
* NonHumanHead: They have a cup and a mug for heads, respectively.
* OhCrap: When the boys face the Devil in combat, they both get this reaction when the Devil gives them a DeathGlare which plays out [[OffWithHisHead what he will do to them]], and they both let out a terrifying scream in fright. This is the only battle intro where they get scared out of their wits instead of being prepped up for battle, though they quickly recover their HeroicResolve and fight like it's now or never.
** In the DLC, they and Ms. Chalice also react this way to [[spoiler:Chef Saltbaker, once he reveals [[EvilAllAlong his true intentions]] and AxCrazy personality.]]
* PaletteSwap: Aside of multiple different possible combinations of arsenal you can use, they plays exactly the same to each other, which is more apparent with the introduction of Ms. Chalice as playable character.
* ParryingBullets: A non-sword variant. When being shot at by pink-colored bullets, the two can jump off of them or slap them aside to avoid damage and possibly collect one special charge. The patched version makes this very essential in the final part of Dr. Kahl's stage, where they will be parry-slapping his pink bullets ''a lot'' while attacking him and avoiding electric barriers.
* PintSizedPowerhouse: Both of them are outright dwarfed by their opponents (and if the TokenHuman characters like Sally Stageplay are to go by, about half the size of an average person), but the two of them can send anyone packing.
* PolarOppositeTwins: Cuphead is known for being the hot-blooded, courageous, and sometimes devious older twin brother. [[http://kingfeatures.com/licensing/licensed-brands/cuphead/ "A shoot-first-and-ask-questions-later type of guy."]] Mugman is known for being the good-humored, industrious, and rascally younger twin brother. [[http://kingfeatures.com/licensing/licensed-brands/cuphead/ "Calculated in battle and a tricky adversary."]] While both of them have a rebellious streak, Mugman does try to stop Cuphead when he gets too overconfident when betting against the Devil.
* RedAndBlackAndEvilAllOver: Cuphead has loads of red and black in his design and is doing the Devil's work, [[SubvertedTrope though not by choice]]. [[spoiler:Oddly enough, if you side with the Devil, all of Cuphead's red bits change to purple.]]
* RedOniBlueOni: According to the [[http://kingfeatures.com/licensing/licensed-brands/cuphead/ King Features licensing page]], Cuphead is the hot-blooded red oni and Mugman is the calculated blue oni. While both of them have a rebellious streak, Mugman does try to stop Cuphead when he gets too overconfident betting against the Devil.
* SchmuckBait: Cuphead leaps onto the Devil's offer to raise the stakes in the craps game. Mugman realizes the danger, but is too late to stop his brother.
* SiblingTeam: See BashBrothers stated above.
* SpinToDeflectStuff. Their Parry move that allows them to deflect pink-coloured attacks has them do a somersault, deflecting the attack with a hand that grows out of the straw on their head.
* StoneWall: The Heart charm turns them into this, reducing damage output in exchange for an extra heart. The Double Heart charm nerfs your damage even more in exchange for one more additional heart (two total).
* TookALevelInBadass: They begin with no fighting prowess whatsoever, but they eventually become strong enough to defeat [[spoiler:''[[{{Satan}} the Devil]]'' in the good ending]].
* UnwittingPawn: [[spoiler:Cuphead and Mugman eventually discover that they are becoming unwitting pawns of the Devil, to their own misfortune, and they have to decide whether they can back out of a deal or not. It happens again in "Delicious Last Course" as well, with Chef Saltbaker duping the Brothers and Ms. Chalice by leaving out the important ingredient in the Wondertart, a soul.]]
* VagueAge: The two look rather young and live with their mentor, the Elder Kettle. And while the plot is kicked off by gambling, it's hard to tell if they're actually legal gambling age or not, because it's unlikely that a casino run by the Devil would even care about that. According to Twitter, [[https://twitter.com/studiomdhr/status/949297839594704896 Studio MDHR jokingly describes both of them as "kidults".]] But according to writer Evan Skolnick, [[https://twitter.com/EvanSkolnick/status/953431259161673728 Cuphead and Mugman are adolescents,]] though their exact age is still unknown.
* WeakButSkilled: On their own, they are extremely weak and fragile, with three direct hits being enough to shatter them to pieces. However, they are very agile and persistent, capable of constantly dodging their enemies' attacks and firing at them non-stop with their {{Finger Gun}}s until they are [[DeathOfAThousandCuts too injured to fight further]].
* WingdingEyes: At the beginning, Cuphead's eyes show dollar signs when he plays the dice game against Mugman's warning, unaware that the dice turn out to be snake eyes.
* WouldHitAGirl: Not that they have a choice in the matter, really, but they are more than willing to fight the female bosses.
[[/folder]]

[[folder:Legendary Chalice/Ms. Chalice]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/chalice.png]]
[[quoteright:320:https://static.tvtropes.org/pmwiki/pub/images/ms_chalice_infobox_image.png]]
[[caption-width-right:320: As Ms. Chalice]]
->''"Speaking of magic... please accept this gift, it should help!"''
A spiritual beverage-holder investigating magic. Grants a super move each time the players protect the urn imprisoning her at a mausoleum in the Inkwell Isles (three in all).\\\

She becomes playable in the downloadable side story, ''The Delicious Last Course'', where she goes by the name Ms. Chalice. She can played as by equipping the Astral Cookie charm, obtained at the start of the DLC, which swaps her out for your current character (even in the main game).
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* ActionGirl: She's a playable character in the DLC campaign and arguably more skilled at fighting than the two main brothers.
* AdaptationDeviation: Spinoff materials and merchandise largely ignore Ms. Chalice's past as the Legendary Chalice, instead depicting her as a peer of Cuphead. In ''The Delicious Last Course'', she's only able to temporarily swap forms, while ''The Cuphead Show!'' depicts her as being able to change at will.
* AndStarring: Her appearance in the trailer for ''The Delicious Last Course'' implies that she plays the role of Ms. Chalice as herself.
* AxCrazy: [[spoiler:Chalice appears to be even more deranged than the boys when she become the Devil's servant in the main game's bad ending.]]
* BackFromTheDead: The central plot of the DLC is that Chef Saltbaker can make her cookies that can bring her back to life temporarily, but at the cost of swapping her spirit with one of the cup brothers. The goal is to find ingredients for Saltbaker to bake a tart that can bring her back permanently.
* BadassAdorable: As Ms. Chalice, she's just as adorable as Cuphead and Mugman, and just as badass.
* BodySurf: In a sense. By allowing the boys to eat the astral cookie, Chalice can swap mortality with either Cuphead or Mugman into the living world and fight in their (altered) body. This is also the way you can play as her.
* BreakoutCharacter: She starts off as an NPC who only serves to give both Cuphead and Mugman their Super Arts once they manage to save her from the ghosts in each of the three Mausoleums. With ''The Delicious Last Course'', she's become a much more prominent figure as Ms. Chalice, both in how she's PromotedToPlayable and how tie-in material has made her the third member of the PowerTrio.
* DamselInDistress:
** In all three mausoleums, she's always found stuck inside an urn and needing rescue from the ghosts within. However, she always rewards the boys with a new powerup that she found.
** This is {{Averted|Trope}} as Ms. Chalice, as she's capable of fighting alongside the boys.
** [[spoiler:If you face Chef Saltbaker as Cuphead and/or Mugman, Ms. Chalice will be the one held captive by him as the final ingredient of his Wondertart.]]
* DeathSeeker: {{Inverted|Trope}}. The Legendary Chalice has been searching the Inkwell Isles for a way to go back to life and escape the astral plane, a search that leads her to the Mausoleums and finally to Chef Saltbaker.
* {{Determinator}}: Chalice will stop at nothing to find a way to return to life, even if it gets herself into trouble like being trapped by the ghosts in the Mausoleums. [[spoiler:When her quest to get the Wondertart rendered pointless upon learning that it requires a living soul to bake and Chef Saltbaker intends to use one of the trio's soul for it, she deems the treat unworthy but vows to the boys that she will find another way regardless.]]
* DoubleJump: Has one as Ms. Chalice.
* ExperiencedProtagonist: ImpliedTrope. She's heavily implied to have a storied past as a heroine of the land as the Legendary Chalice before becoming an optional PlayerCharacter in the DLC. It'd probably explain all the unique and helpful skills she has along with having 4 HP with no damage reduction unlike the brothers who only have 3 HP by default unless they use the Heart charms that also reduce their damage output.
* EveryoneHasStandards: Chalice may willing to trick Mugman as a test subject for the astral cookie and swap mortality with him without consent early on in the DLC campaign, [[spoiler:but upon learning that the Wonderart she's after requires a living soul to bake, she deems the pastry unworthy, as she doesn't want to sacrifice anyone in order for her to live]].
* FaceHeelTurn: [[spoiler:She join the brothers as the Devil's servant in the bad ending of the main game.]]
* FallenHero: [[spoiler:If her history as the land's hero back when she was alive is any indication, then her FaceHeelTurn as the Devil's servant in the main game's bad ending makes her fall into this.]]
* FountainOfYouth: She seems around Cuphead and Mugman's age in the DLC, compared to in the base game where she looked considerably older than them as a ghost. Might have something to do with the [[BodySurf method she uses]] to regain a living form.
* GreaterScopeParagon: An angelic ghost, patterned after the Holy Grail, who gives the boys valuable tools to help in their quest in exchange for their aid. [[spoiler:As revealed in the castle ruins of Rugged Ridge, before she died, she was one of the land's heroes.]]
* InformedAttribute: The [[AllThereInTheManual art book]] describes Legendary Chalice as "inquisitive and zany" and having a penchant for curiosity that constantly leads her to trouble, but the only sign of this in-game is her getting trapped in the mausoleums by the Spectre Syndicate for spelunking for magical arts (and even then, she later does this to help Cuphead and Mugman after they rescue her from the first one). Her appearances as Ms. Chalice have rectified this, with ''The Delicious Last Course'' showing her spunkiness directly and spin-off material taking that to heart.
* LadyOfWar: Appeared to be this back when she was alive, judging by her statue in Rugged Ridge. Her Super Art 3 variant allows her to assume this form temporarily.
* {{Leitmotif}}: She's associated heavily with xylophone. In the base game, [[https://studiomdhr.bandcamp.com/track/legendary-ghost her theme]] is played on xylophone, while ''The Delicious Last Course'' adds several xylophone tunes associated with her, the main one being [[https://studiomdhr.bandcamp.com/track/recipe-for-ms-chalice "Recipe for Ms. Chalice"]].
* LimitBreak: Ms. Chalice has three different super moves than Cuphead and Mugman.
** I -- ''Spiral Pillar'': Her first Super Art has her jump into the air and launch a giant stream of golden liquid straight up and down.
** II -- ''Shield Pal'': Her second Super Art has her [[SummonMagic summon]] a floating shield that will completely negate the next hit she takes.
** III -- ''Ghostly Barrage'': Her third Super Art has her turn back into the hero she once was and call in a CavalryOfTheDead of the Calix Animi, damaging almost every enemy on screen with the charge. Afterward, her spear turns pink and floats in the air for a moment, and parrying it extends the spirit stampede.
* MechanicallyUnusualFighter:
** In addition to having unique movesets compared to Cuphead and Mugman, you don't choose her character directly. But instead, your current character has to equip the "Astral Cookie" charm so she can swap mortality with them and enter the fight.
** Additionally, Ms. Chalice is unable to parry normally; her dash parry is her only method of parrying pink objects and projectiles.
** This extends to flying stages as well: Her plane's main fire is a three-shot spread with more coverage but less damage per bullet, and the secondary fire sends out a cluster of smaller bombs.
* MockyMouse: Her living appearance invokes this just like the boys, though her skirt is more evocative of WesternAnimation/MinnieMouse.
* PromotedToPlayable: Made playable in "The Delicious Last Course", both for the new DLC and on the original Isles.
* SkillGateCharacter: One of the goals with her being playable is to make finishing the game more accessible, and thus she has a double jump, a dodge roll, and her dash also works as a parry, akin to the "little brother/sister" characters of Peach and Toadette in the ''Mario'' games and Tails in the ''Sonic'' games. On top of all these unique and useful benefits, she starts battles with 4 HP unlike the brothers who only have 3 by default and have to decrease their damage output if they want any more HP.
* SpeakingSimlish: She's one of the few characters with voiced dialogue, and it's done in this way.
* TertiarySexualCharacteristics: She's got prominent eyelashes.
* TooDumbToLive: Subverted. Despite being captured in every Mausoleum she visits, she keeps hunting for Super Arts to give to Cuphead and Mugman.
* TheTrickster: At the start of ''The Delicious Last Course'', she tricks Mugman into taking a bite of the astral cookie without telling him that it'll cause him to switch places with her as a ghost while she comes back to life. Naturally, Chalice is overjoyed despite Mugman's visible distress. Once she takes the time to explain the situation and how Saltbaker can bring her back to life permanently, however, the boys have no ill will and agree to help her.
* UnexplainedRecovery: In the final page of the credits, she's shown [[spoiler:celebrating with the boys, Saltbaker, and the rest of the island residents in her corporeal body with nobody in sight being benched in the astral plane on her behalf. Whether Saltbaker managed to bake the Wondertart (hopefully not at the expense of a soul, somehow) or some liberty was taken for an optimal GroupPhotoEnding is left up in the air. The same occurs in the vanilla game's bad ending, in which she's shown under the Devil's rule alongside Cuphead and Mugman, completely alive and fine (besides having her soul become the Devil's property).]]
* UnwittingPawn: [[spoiler:She had no idea that Chef Saltbaker needed a soul to make the Wondertart she was after to gain a physical body, Saltbaker just left that out when She and the Brothers went to gather the rest of the ingredients]]
* WouldHurtAChild: There's nothing stopping the player from using her to attack Wally Warbles' kid or the Howling Aces' puppies.
[[/folder]]

[[folder:Elder Kettle]]
[[quoteright:171:https://static.tvtropes.org/pmwiki/pub/images/kettle.png]]
->''"What a fine pickle you boys have gotten yourselves into!"''
Cuphead and Mugman's mentor and legal guardian. An anthropomorphic tea kettle who gives them a special potion to defend themselves against the Devil's debtors.
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* AmbiguouslyRelated: Is stated to be the caretaker of Cuphead and Mugman, but it's unclear if he's actually their father, grandfather, foster parent, or otherwise. Considering that he's an anthropomorphic kettle, and they're cup-headed people, they do look somewhat different.
* BigGood: Cuphead and Mugman’s mentor who is responsible for giving them the tools to solve their current problem.
* DisappointedInYou: His conversation at the beginning implies that he feels this way towards Cuphead and Mugman for gambling in the Devil's Casino.
* DoWrongRight: He gives Cuphead and Mugman a potion that will help them fight the runaway debtors. He also says that ideally Cuphead and Mugman wouldn't have to do it, but the boys have no choice.
* MentorArchetype: He acts as a father figure to Cuphead and Mugman, though it's not made clear if they're actually family. [[https://twitter.com/EvanSkolnick/status/953431259161673728 On Twitter, writer Evan Skolnick confirmed that the Elder Kettle is Cuphead and Mugman's legal guardian.]]
* ReasonableAuthorityFigure: Despite the fact that he's disappointed that Cuphead and Mugman gambled in the Devil's Casino, he also helps them by offering a magic potion which will allow them to fight the debtors for their contracts. He also hopes that if they get powerful enough, that they can take on the Devil and free their souls.
* RetiredBadass: Implied, as he "passes the torch" down to Cuphead and Mugman by giving them a magic potion for their Peashooter ability. There's also a sword hanging on the wall of his cottage, and just ''where'' he got that potion is never clarified, suggesting it came from an adventure in his youth. [[spoiler:In the ruins in the Rugged Ridge level, there is a statue of him kneeling with sword in hand.]]
* ShoutOut: His design may be based on Mr. Coffeepot from the 1935 Van Beuren cartoon ''Picnic Panic''.
* SoProudOfYou: [[spoiler:The good ending when the boys free the Inkwell Isles residents of their debts.]]
[[/folder]]


!!!Villains
[[folder:The Devil]]
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/cupheadfinalboss2.png]]
->''"Anyone who opposes me will be destroyed!"''
[[{{Satan}} The ruler of Hell]], the owner of The Devil's Casino, and a collector of souls. He wins a Craps game against Cuphead and Mugman, but supposedly agrees to spare them if they do his bidding. Fights you in "One Hell of a Time".
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* ZeroPercentApprovalRating: All of the residents of Inkwell Isle hate The Devil due to many of them being in debt to him to the point where many of the residents refuse to hand their soul contracts over to him. Once Cuphead and Mugman defeat him, the residents celebrate being free of their debt to The Devil.
* AerithAndBob: Most other bosses have creative (and often [[AlliterativeName alliterative]]) names, but he is plainly referred to as "The Devil".
* AmbiguousSituation: He only appears to have been merely knocked out by the cups after his battle, but [[spoiler:the ''Delicious Last Course'' introduces the Dream Devil, a boss who is encountered at a gravestone on Inkwell Isle 4, and is represented by a good and evil Devil spirit in front of a large Devil skeleton. This may imply that the cups actually killed him and he's now dead & buried and trying to seek revenge, although it may just be a dream.]]
* AntagonistTitle: Sorta. His name appears in the game's subtitle, "''Don't Deal with the Devil''".
* AttackOfTheFiftyFootWhatever: He's already quite large during the final battle with him, but then you get to the second phase of the fight, where you battle him in Hell itself. He proceeds to unleash his inner {{Kaiju}} on the player, to the point that the protagonists are about as big as his pupil.
* BackgroundBoss: He spends the first phase of the fight on his throne in the background, reaching into the foreground to do various attacks. Taken further during his second phase and onward, where his giant head takes up most of the background.
* BadassBoast: Lose to him in the second phase of the fight and onwards, and his death taunt is this, complete with a picture of him [[DecapitationPresentation holding the lifeless, decapitated heads of Cuphead and Mugman]].
-->'''The Devil:''' Anyone who opposes me will be '''''destroyed!'''''
* BadBoss: Immediately after the brothers defeat King Dice, his most loyal employee and the only one who tried to warn him that they might pose a threat, the Devil dismisses him as a "good-for-nothing lackey". And he was a prick to him before then, too.
* TheBadGuyWins: [[spoiler:In the main game's bad ending, he succeeds with gathering all soul contracts from the runaway debitors and turning the cups into his servants]].
* BerserkButton: '''Don't''' break a deal with the Devil. ''[[VillainousBreakdown Ever.]]''
-->'''The Devil:''' Welching on me just like all the others, eh... I'll teach you for backing out of a deal — '''[[LetsGetDangerous have at you!!]]'''
* BigBad: He's the one who starts the whole adventure by sending the two boys out on errands.
* BigRedDevil: Although he has black fur rather than red skin, he otherwise fits this trope, with features like horns and a pointy tail and ears. [[spoiler:Played more straight during his kaiju-sized Phase 2 and onward, where his body takes on a more noticeable dark red tone.]] [[spoiler:The evil Dream Devil from the ''Delicious Last Course'' outright resembles a red version of him]].
* BreakTheHaughty: During the final battle, the Devil goes from smug, to angry, to crying tears of frustration as the brothers wear him down.
* CigarChomper: The Devil casually smokes a cigar at his desk while counting his casino's earnings.
* ClippedWingAngel: The Devil's final phase is just him crying (parryable) tears in pain and frustration while the arena is reduced to a single platform under his face on which a single chip falls down. Said chip can be dodged without parrying, and these two attacks are the only ones he has at that point.
* TheCorrupter: If the brothers agree to join him and hand over the soul contracts, it leads to a bad ending where the Devil turns them into his demonic servants.
* DarkIsEvil: He has a dark, threatening appearance, fitting for the Devil himself.
* DeathGlare: His fight begins with a one-eyed glare, so thorough his pupil briefly transforms and ''plays out'' [[OffWithHisHead what he plans to do to Cuphead and Mugman]]. It seems to work; this intro is the only one in the game where Cuphead and Mugman [[OhCrap scream out in terror]] instead of getting hyped up for battle.
* DecapitationPresentation: The opening theme song isn't kidding if you lose to his second phase and onwards!
* TheDevilIsALoser: The final phase of his boss battle has him ''crying'', and when Cuphead and Mugman finally beat him, he surrenders without hesitation. For being hyped as the ultimate evil of the game, his loss is honestly kinda pathetic.
* EvilIsBurningHot: As with most depictions of the Devil, he's associated with fire.
* FangsAreEvil: Most of the other characters have normal, rectangle-shaped teeth. Not him. He has very pointy teeth.
* FatalFlaw: Fittingly for the Devil, [[SmugSnake pride]]. While he's undeniably powerful and cunning, the Devil overestimates his abilities and never once considers the possibility that he can actually ''lose''. King Dice tries to warn him not to underestimate Cuphead and Mugman, but he dismisses Dice's concerns and [[UnderestimatingBadassery clearly sees the heroes as no threat to him]]. This ultimately becomes his undoing, as the brothers eventually become powerful enough to actually defeat him. It's even reflected in the boss fight — once you've pushed him into his final phase and [[BreakTheHaughty shattered his pride]], he just starts [[VillainousBreakdown crying]].
* FauxAffablyEvil: He seems like a pleasant fellow when he first introduces himself to Cuphead and Mugman, but once the brothers lose his game of dice, he wastes no time showing his true demonic colors.
* FinalBoss: Should go without saying, but indeed, he's the last boss faced in the game.
* FlunkyBoss: His battles - both of them - have him flanked by purple-coloured demons. Smaller ones which dies in one shot in the first phase, and larger, purple GiantMook-types in the second.
* GracefulLoser: Well, his [[VillainousBreakdown display]] at the end is far from graceful, but... He really does stick by his words when he talks about how "a bet is a bet". After his defeat, he pulls no strings or backstabbings and instead, truly frees Cuphead and Mugman and lets them even burn the bosses' Soul Contracts.
* GruesomeGoat: During the first phase of his boss fight. One of his attacks is having his face morph into a goat head (complete with rectangular-shaped pupils) and his hands turn into hooves. Even his EvilLaugh sounds like goat bleats during that attack.
* HoistByHisOwnPetard: He deliberately rigged the dice game so he could get Cuphead and Mugman to get the soul contracts from his indebtors and complete his takeover of Inkwell Isle. However, he didn't expect the two boys to get so strong and ultimately is defeated by them, losing the contracts in the process.
* HornsOfVillainy: He has long, bone-white horns.
* HumanoidAbomination: The Devil may be humanoid in appearance, but is so powerful that he is capable of shapeshifting into various terrifying forms.
* {{Jerkass}}: Anyone who loses to him in his casino has to repay him with their soul in eternal servitude. And if that weren't enough... ''he's the Devil.''
* LosingYourHead: One of his attacks has him remove his head before transforming it into a spider, not that it kills him.
* NiceJobFixingItVillain: Sending the brothers on their quest to collect his wayward debtors bites him big-time: after their TrainingFromHell, Cuphead and Mugman end up becoming strong enough to defeat him.
* NotSoDifferentRemark: If Cuphead and Mugman decide not to hand over the Soul Contracts after all, the Devil accuses them of "welching on [him] just like all the others" before doing battle with them.
* ObviouslyEvil: Again, ''he's the Devil''. It should ''really'' go without saying.
* OffWithHisHead: The previous trailers had him threaten to cut off Cuphead and Mugman's heads when he's set to claim their souls in the trailer. [[ShadowDiscretionShot The shadow on the wall illustrates this point when he makes the cutthroat motion.]]
* OffscreenMomentOfAwesome: Based on how many contracts that Cuphead and Mugman have to collect, the Devil has tricked ''many'' toons into losing their souls.
* OneWingedAngel: Once the Devil brings the fight to his turf, his head takes over most of the screen due to his now humongous size.
* OrcusOnHisThrone: He mostly stays at his casino while the heroes do his dirty work. King Dice even warns him that Cuphead and Mugman are getting pretty strong, but [[UnderestimatingBadassery the Devil refuses to listen]]. The first phase of his boss fight even has him mainly seated on his throne.
* RedAndBlackAndEvilAllOver: His eyes are sometimes {{red|eyestakewarning}}, he's mainly colored black, and he's the Devil.
* RedEyesTakeWarning: He's a dangerous foe and, when particularly malicious, his normally black eyes become red.
* ReptilesAreAbhorrent: Able to transform his head into a draconic serpent.
* {{Satan}}: [[ExactlyWhatItSaysOnTheTin He's the Devil himself, of course]].
* ScaledUp: One of his transformation attacks has his head become a draconic serpent.
* ShoutOut:
** The part where he gives a WeCanRuleTogether offer to the heroes, complete with yes/no option, a bad ending scene if accepted, and a boss fight against him if rejected, hearkens back to [[spoiler:Colonel Bahamut's similar offer]] in one story path of ''[[VideoGame/{{Contra}} Contra: Hard Corps]]''.
** Being defeated in phase two causes him to quote M. Bison/Vega from ''VideoGame/StreetFighterII''.
* SmugSnake: He's dangerous and cunning, that's for sure. But he's far from invincible and is far too overconfident for his own good.
* TurnsRed: Halfway through his fight, his skeleton leaps out of his body into a hole in the ground, where the player finds he has grown so large his head encompasses the entire background and his fur takes on a hue of dark red.
* VileVillainSaccharineShow: Can't get any viler than having [[{{Satan}} Old Scratch]] serve as the main villain of the game. The game itself is a lighthearted throwback to 1930s cartoons with an anthropomorphic cup and mug serving as the protagonists that provides AnAesop on the dangers of gambling. Then there's the Devil himself, who has no qualms with forcing two innocent people to do his dirty work for him and also [[spoiler:killing said people if they back out of his deal, or turning them into his demonic servants if they agree to join him]].
* VillainousBreakdown: He initially has this reaction when the player decides not to hand over the soul contracts after all, triggering the fight with him. As the second phase of his fight progresses on, he gradually grows angrier and more frustrated. By the final phase, he's lost all composure, is reduced to pitifully crying parryable tears, and no longer has the strength or will to summon anything other than a lone poker chip on the only remaining platform. Upon defeat, his pride is completely shattered and he can only clutch his head in pain.
* VoluntaryShapeshifting: Pulls a number of these in his fight, turning into a draconic serpent, spider, and goat-like creatures.
* WeCanRuleTogether: He offers for Cuphead and Mugman to join his team when they collect all of the soul contracts. The player can choose whether or not to accept his offer.
* WhiteFlag: He's shown holding one in the good ending after getting heavily beaten up by Cuphead and Mugman.
* WingdingEyes: Aside from the DeathGlare above, he ''weaponizes'' this in his second phase.
* YellowEyesOfSneakiness: Usually depicted with yellow sclerae, befitting his trickster nature.
* YourSizeMayVary: In the opening cutscene, the Devil is large, but is only seemingly slightly bigger than King Dice. In his fight, he's absolutely gigantic. And there's his form in Hell itself, which is the largest boss in the entire game, to the point that his ''pupils'' are taller than the Cup brothers!
[[/folder]]

[[folder:King Dice]]
[[quoteright:222:https://static.tvtropes.org/pmwiki/pub/images/kingdice_2.png]]
!!!Voiced by: Alana Bridgewater ("Die House", "Closing Credits")
->''"So clever, so dapper, ya betta' believe this dice is loaded. Hi-de-ho!"''
A man with a die for a head, who serves as the manager of The Devil's Casino and as TheDragon to the Devil. Fights you in "All Bets Are Off".
----
* BerserkButton: Don't make him lose a bet.
* BossBonanza: His boss battle in 'All Bets Are Off' can potentially make you play through one via a dice game. Depending on how you play his game, you can end up fighting three to ''nine'' bosses before you get to him (though neither they nor he have multiple forms, thankfully).
* CardCarryingVillain: His theme song, "Die House," proudly proclaims "I never play nice, I'm the Devil's right-hand man!" Indeed, when you actually fight him, he becomes a ''literal'' card-carrying villain.
* DastardlyWhiplash: His appearance resembles this style of villain. He even has the pencil-mustache.
* DeathDealer: His main attack when he finally deigns to confront you by himself consists of rows of giant playing cards that come marching toward you.
* TheDragon: He's the self-described "Devil's right-hand man", his boss' main face and enforcer on the island, and the last boss that needs to be fought to get to the Devil.
* EatTheCamera: When he sends you to fight one of his mini-bosses, he leans toward the camera and swallows it.
* EvilCounterpart: To Cuphead and Mugman. In addition to the details covered below, his attacks are fired from his hands just like Cuphead and Mugman, his colors mirror theirs (purple to the brothers' red and blue respectively), and he represents what Cuphead and Mugman would turn into under the Devil's rule.
* EvilEyebrows: Both his eyes and eyebrows are constantly arched upward in maniacal glee.
* EvilIsPetty: Once you reach the casino, King Dice forces you to fight his minions because he's lost a bet with the Devil over whether you'd make it that far.
* EvilLaugh: During the boss fight with him, he laughs when sending his cards to attack you.
* EvilSoundsDeep: He sings with a deep, Music/LouisArmstrong-esque voice.
* EvilSoundsRaspy: Goes hand-in-hand with having a Music/LouisArmstrong-esque voice.
* ExcessiveEvilEyeshadow: Unless his eyelids are just naturally purple.
* FauxAffablyEvil: Despite being the Devil's right-hand man, he acts surprisingly friendly and personable. Even when he confronts the brothers for his boss fight, he still keeps up the polite persona, although he's clearly pissed at them for making him lose a bet with his boss. Of course, as a casino manager, he's got to keep a friendly and welcoming attitude up to convince people to come there in the first place. Also goes hand-in-hand with his status as a sort of AnthropomorphicPersonification of gambling and games of chance — tempting with the promise of riches, yet deceitful and dangerous.
* FlunkyBoss: King Dice never actually attacks you directly. For most of his boss fight, he instead sends you to a BossBonanza of various minibosses, and even when he does fight you himself, he sends lines of cards marching towards you; if you can't parry off the pink heart cards, you'll get hurt.
* {{Foil}}: Seems to be one for Cuphead and Mugman. Both are cartoony people with {{Non Human Head}}s who partake in gambling, but while Cuphead and Mugman seem more innocent and hardworking, King Dice is more gaudy and arrogant. Notice how he wears a fancy tuxedo, while Cuphead and Mugman wear much simpler clothes. He also has friends in high places, while Cuphead and Mugman are stuck doing said friend's dirty work.
* TheFourthWallWillNotProtectYou: Frequently does this throughout his boss fight. When you parry the dice to select which member of his court you fight, he'll wink at the camera and then EatTheCamera to teleport you there, as if he's fully aware there are people watching him.
* TheGambler: He has a dice motif, down to the "game" he makes you play when reached (a roll of dice determines your progress in his BossBonanza). Also the bosses he sends at you are, as a majority, based on all sorts of games of chance, from poker chips, a living roulette, dominoes, a racing horse, and even a claw machine and its evil toy.
* GenreSavvy: It's implied King Dice grew privy to the idea that the Devil might just replace him with Cuphead and Mugman should they successfully bring him the contracts, so he decides to fight the boys for them and deliver the contracts himself. Given who his [[TheDevil boss is]], he has all the reason to be wary of his job security.
* GreenAndMean: He's got green eyes and he's one of the game's main villains.
* TheHeavy: A downplayed example, but throughout the game, King Dice is the one who checks on Cuphead and Mugman's progress and allows or refuses them passage further on as necessary, while his boss, The Devil, is not seen outside of cutscenes until the final battle.
* LeanAndMean: He's tall and skinny, and ''certainly'' wicked.
* LightIsNotGood: He wears some white and is TheDragon to the Devil.
* ManOfWealthAndTaste: While he isn't the Devil ''himself'', King Dice is [[TheDragon his right-hand man]], and is dressed in a sharp tuxedo.
* NoCelebritiesWereHarmed: According to artist Jake Clark, the character was heavily inspired by Music/CabCalloway.
** This is further emphasized in ''The Cuphead Show'', where he appears [[https://www.youtube.com/watch?v=FToJAi_RQH0 singing and dancing on stage]] in a very similar fashion to [[https://www.youtube.com/watch?v=8mq4UT4VnbE Calloway's famous "Minnie the Moocher" routine]].
* NonHumanHead: He has a humanlike body and a giant six-sided die for a head.
* NPCRoadblock: His Die Houses block the bridges between the isles, and he'll only let you through once you've defeated all the bosses on that island. Even his ''boss fight'' is this, as the route to the Devil will only open up once he's played his game with the boys. Referenced in his VillainSong.
-->I can't let you pass 'cause you ain't done everything!\\
Bring me those contracts! Come on, bring 'em to the king!
* ObviouslyEvil: He's a guy with a dice for a head who constantly has an evil smile on his face and manages a casino owned by the Devil himself. His VillainSong has him openly and proudly boast that he's not a nice person and that he's the Devil's right-hand man. Hell, even the ''opening narration'' calls him a "sleazy manager".
* PerpetualSmiler: Dice is almost never seen without that trademark grin of his.
* PlayingCardMotifs: Goes hand-in-hand (heh) with the hand of cards that he deals out of his hand. Unlike the other suits, the heart suit cards are pink and are thus parry-able.
* ProperlyParanoid: A mid-game cutscene has him chatting with the Devil about the boys' progress and worrying if they may be getting ''too'' strong in their quest to claim the Soul Contracts. The Devil just brushes it off, stating he'll deal with them if they turn against him. [[spoiler:King Dice ends up turning out to be right.]]
* PurpleIsPowerful: As the strong-arm of the Devil himself, his purple outfit definitely means power. However, it appears gold in the teaser image that introduces him, due to the image's intentionally limited palette.
* SecondaryColorNemesis: Wears a [[SharpDressedMan purple tux]] and has green eyes.
* SharpDressedMan: Wears a purple tux.
* ShoutOut:
** The dice game BossBonanza he puts you through is one toward ''VideoGame/GunstarHeroes'', which likewise had a similar gimmick in Black's stage (though this can be manipulated by skillful parries rather than being based on pure luck).
** His horrible wide grin and flashing green eyes also [[https://vignette.wikia.nocookie.net/cuphead/images/c/c3/King_Dice_and_The_Coachman.JPG bear a close resemblance]] to the Coachman from Disney's ''{{WesternAnimation/Pinocchio}}''.
** Aside from being partially modeled after him (see NoCelebritiesWereHarmed), King Dice makes many references to Cab Calloway. His game over quote ends with "Hi-de-ho!", which was a phrase Calloway often used while singing. While using his card attack, his hand moves in a manner similar to Calloway's dancing.
* SlasherSmile: He sports a rather potent grin.
* StealingTheCredit: Implied in his VillainSong. Despite the fact that Cuphead and Mugman have to collect soul contracts ''for'' the Devil, King Dice won't let you see him, even if you have all of them. Instead, you have to beat him before facing the Devil.
-->''Bring me those contracts, pronto!\\
[[BerserkButton Don't you mess with me!]]\\
Bring me those contracts! Come on, bring 'em to the king!''
* SuddenEyeColour: When he's being particularly menacing, his irises turn green.
* TranquilFury: When you finally confront him for his boss fight, despite the fact that he's clearly pissed at the brothers for making him lose a bet with the Devil, [[StepfordSmiler that smile of his never leaves his face]].
* VillainousBreakdown: He begins losing it when Cuphead and Mugman defeat him.
* VillainSong: [[https://studiomdhr.bandcamp.com/track/die-house Die House]], in which he bosses Cuphead and Mugman around and introduces himself as a major threat and unrepentant villain.
-->''"I'm Mr. King Dice, I'm the gamest in the land.\\
"I never play nice, I'm the Devil's right-hand man!"''
* WinkDing: Pulls this before sending you to fight one of his Court.
* YourSizeMayVary: During the storybook cutscenes and Die House segments, he appears to be no taller than an average person compared to Cuphead and Mugman. Come "All Bets Are Off", he's [[AttackOfThe50FootWhatever gigantic]].
[[/folder]]

!Run 'n' Gun Enemies
[[folder:General]]
The various, basic enemies and mini-bosses found in the various stretches in between the bosses. They run a wide spectrum of shapes and sizes, but they are relentless enough to be large threats in their own right.
----
* BadassNormal: The majority have no real powers or transformations to speak of, but they can still wallop you something fierce if you let them.
* GameOverMan: Like the bosses, losing in their respective stages will have the respective Mooks mocking you with a pun related to your defeat. The Cyclops in Rugged Ridge gets one separate from the other enemies in that level.
* GiantSpaceFleaFromNowhere: None of these guys have any real bearing on the plot at large, they aren't under the servitude of the Devil or Debtors as far as we know, and are mostly used as fodder material whenever a player wants to take a break from fighting bosses or get more coins for better weapons and items.
* HairTriggerTemper: For the most part, it seems that all of these enemies want to kill Cuphead and Mugman [[DisproportionateRetribution simply because they had the nerve to set foot in their territory]].
* HardLevelsEasyBosses: In particular because there's no way to change the difficulty for these stages besides switching from two players to one. Run 'n' Gun levels are ''merciless'' challenges, but the mini-bosses have fairly simple attack patterns to avoid.
* KillerRabbit: No matter how cartoony or cute these guys appear, they will take you down if they can.
* PacifistRun: It's possible to get through all of these levels without killing any enemies. It is ''not'', however, easy.
* RespawningEnemies: Some stages have enemies (sometimes literally) jump out at you without end until you move on to the next section of the level.
* SkippableBoss: ''All'' of the minibosses are skippable in some matter, to facilitate the [[PacifistRun Pacifist Rank]]. Some can be smoke bombed past, some can be skipped with clever parries, and sometimes you can just take damage and let your MercyInvincibility do the rest.
[[/folder]]

[[folder:Forest Follies' Foes]]
[[quoteright:218:https://static.tvtropes.org/pmwiki/pub/images/forestfollies.png]]
->''"Nowhere to run, nowhere to go — this forest is yer foe!"''
The inhabitants of the woods leading to Goopy le Grande.
----
* BlobMonster: The tiny slimes with limbs that run back and forth, and [[RevivingEnemy respawn after being defeated]].
* FoulFlower: The most basic enemies on this level are humanoid flowers that run after Cuphead and Mugman to harm them the moment they appear. There are also purple tulips that fire exploding beans.
* TheGoomba: The flower people that parachute from the sky are the most basic enemies on this level and can be defeated in several shots.
* IncendiaryExponent: The purple tulips fire purple beans that explode into flames when they hit the ground.
* InvincibleMinorMinion: There are [[VideoGame/SuperMarioBros Piranha Plant-esque]] plants that jump from bottomless pits as a stage hazard, which can't be destroyed.
* ManEatingPlant: Giant black flytrap-esque plants appear as stage hazards.
* MookMaker: The Acorn Maker, a furnace-like machine endlessly cranked by a single flower enemy.
* PlantPerson: With the exception of the slimes and the mechanical Acorn Maker, all of the enemies are animated plants (or animated fungi, or living seeds).
* RevivingEnemy: The tiny slimes that run about fall into a puddle when shot once, but reform themselves a second later to continue running around.
[[/folder]]

[[folder:Treetop Trouble's Terrors]]
[[quoteright:231:https://static.tvtropes.org/pmwiki/pub/images/treetoptroubles.png]]
->''"Who invited you into our tree? Only members are welcome, ya see?"''
A bunch of insects and other creatures that live in a hollowed-out tree and the canopy above.
----
* AirborneMook: The beetle enemies constantly fly mid-air.
* BigCreepyCrawlies: The level is populated with tumbling ladybugs, fanged beetles, [[HelpfulMook helpful mosquitoes]], and a giant dragonfly as a miniboss.
* DreadfulDragonfly: A giant fire-breathing dragonfly serves as the MiniBoss in this level.
* {{Fireballs}}: The giant dragonfly mini-boss breathes fireballs at Cuphead and destroys the mosquito platforms floating around.
* HelpfulMook: The mosquitoes that hold up leaves for Cuphead and Mugman to walk on. Likely because they're so helpful to the boys, they get shot out of the air by the mini-boss as soon as they are leapt on.
* InvincibleMinorMinion: The woodpeckers that peck into the ramp of the first section.
* MindScrew: Did Cuphead enter a MacroZone by shrinking, or is he the same size and it's just a big tree? There are sawed logs that spit projectiles at him, but there are also giant woodpeckers and bugs.
* MosquitoMiscreants: {{Averted|Trope}}; mosquitoes are actually [[HelpfulMook very helpful]], providing Cuphead and Mugman the platforms to stand on. Indeed, this helpfulness is most likely the reason why they get shot out of the sky by the level's MiniBoss.
* StealthPun: The ladybugs seen in the level are rolling or bouncing down the ramps during the first area of the level. [[spoiler:In other words, they're literal "tumble bugs".]]
* TreeTrunkTour: Their level sees the player climbing up and through a gigantic, hollow tree, facing a variety of insects, living logs and gigantic woodpeckers on the way.
* VisualPun: The large dragonfly miniboss spits {{fireballs}} like a dragon. It's a dragon-fly.
* WhenTreesAttack: Living wood logs appear as enemies in this level.
[[/folder]]

[[folder:Funfair Fever's Fighters]]
[[quoteright:218:https://static.tvtropes.org/pmwiki/pub/images/funfairfever.png]]
->''"You did look foolish today, but clown tryouts are next week."''
The entertainers and living treats and trinkets that reside within the circus of Isle Two.
----
* AirborneMook: Both the magicians and the balloons count as this. The former is stationary — except when they teleport away from your attacks — while the latter can move, but only in one direction, and aren't especially interested in attacking you.
* AnimateInanimateObject: The walking trampoline actually seems to think it's a dog, given how it barks at you. Additionally, the other enemies are a bunch of balloons with faces, a row of frowning cannons and a shotgun-totting shooting gallery as a miniboss.
* AnthropomorphicFood: A giant dancing hotdog appears as a MiniBoss at the end of the level. There are also giant pretzels that hop up and down, serving as obstacles.
* EdibleAmmunition: The dancing hotdog mini-boss at the end of the level fires blobs of mustard, ketchup, and relish at you.
* HelpfulMook: The walking trampoline is absolutely necessary for getting past the barriers in the first tent.
* MagiciansAreWizards: Lots of disappearing magicians float around firing circles of magic at the boys.
* SpreadShot: The balloons that float past you explode if damaged, shooting out bullets in all directions.
* VillainousHarlequin: The vertical rows of clowns under one of the big top tents. One of the enemies is also a tiny clown on a ball that rolls around a tiny area. Destroying the clown only makes the ball itself roll around faster.
[[/folder]]

[[folder:Funhouse Frazzle's Frights]]
[[quoteright:260:https://static.tvtropes.org/pmwiki/pub/images/funhousefrazzle.png]]
->''"We ain't toyin' around with you, now scram!"''
A bunch of bizarre oddities living within the even weirder carnival funhouse.
----
* ActionBomb: Small rocket enemies who appear in the second gauntlet will try to ram themselves into you and blow up, or if you happen to be under/above them from the gravity-reversing cards, then they'll rocket themselves towards you instead.
* EldritchLocation: The tent where the toys live in starts out normal enough, but then the boys run through what looks like an obviously fake cardboard set of the moon before they find a [[LivingStructureMonster one-eyed wall]] blocking their path. Getting past that opens the way to a house filled with doors, swirling hallways, and stairs going in nonsensical directions. After that, they go through a place where giant musical instruments and cardboard eyeballs are suspended in a background of clouds, rainbows, and spinning wheels before it abruptly ends and turns back into a normal hallway when they get past the exit. Could be a case of MaybeMagicMaybeMundane, as mostly everything is a cardboard cutout being hung by strings in the background, with a pile of unused props stuffed in a corner being seen at the end of the level.
* EvilLaugh: The jack-in-the-box toys let out a childlike laugh when appearing before sending their spiked hat out to home in on the player.
* {{Expy}}: The tuba enemies are quite clearly modelled after [[http://disney.wikia.com/wiki/File:Music-land-king-model.jpg the king baritone sax]] from the ''WesternAnimation/SillySymphonies'' short "WesternAnimation/MusicLand".
* InvincibleMinorMinion: The clown-cars from the first half. The [[GravityScrew gravity-reversing cards]] are absolutely ''essential'' to escaping them.
* LivingStructureMonster: The living walls that need to be defeated to head deeper into the level.
* LivingToy: Giant wind-up ducks, rows of toy cars, jacks with eyes at the ends of them, and a jack-in-the-box make up most of the enemies in the level
* LovecraftLite: The LivingStructureMonster mini-bosses are this in spades, being living walls that serve as the entrance and exit to the weirder parts of the funhouse that not only fire lips at you from bike horns, but also spit lines of clown-cars and use their OverlyLongTongue to attack. Shooting their eyes actually takes longer to defeat them; instead, running into their gaping mouths kills them just too.
* MusicalAssassin: The last leg pits our heroes against sentient tubas that attack with [[WordsCanBreakMyBones sound effects]].
* StealthPun: The giant ducks can be avoided by crouching. In other words, you can '''duck''' under the ducks!
* VillainousHarlequin: The four-way jack-in-the-boxes with eyeballs in the center of their bodies.
[[/folder]]

[[folder:Rugged Ridge's Rabble]]
[[quoteright:227:https://static.tvtropes.org/pmwiki/pub/images/ruggedridge.png]]
->''"You'll never best a bluff, persevere a peak, or curb a cliff — just give up now!"''\\
''"Fee fi fo fum, I'm the guardian of this ruined land."''
Enemies that made their home in a particularly precarious set of mountains with an interesting secret.
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* AdvancingBossOfDoom: The giant gorilla-like cyclops at the end. Apparently he's the chief guardian of the ruins.
* ClassicalCyclops: A grey-skinned cyclops with a single centrally-positioned horn appears as an AdvancingBossOfDoom, starting to chase the player halfway through and destroying any platform in its way.
* DeathMountain: Rugged Ridge is a treacherous mountain area featuring plentiful pits and slopes, and home to a variety of enemies based on both actual mountain wildlife and mythical creatures associated with mountainous areas.
* EvilLivingFlames: The animated flames that circle around in the air in the first half of the level, chuckling nastily.
* FaunsAndSatyrs: Satyrs appear in the third quarter of the level.
* TheGoomba: The satyrs are basically this, dying in one hit and having no special abilities other than being able to run (slightly) faster than our heroes. Interestingly enough, they only appear in the second half, mostly to provide backup for tougher {{Mooks}}.
* GratuitousLatin: [[spoiler:When the boys come upon the ruined castle, they see a plaque of a shield bearing a teacup and some kitchen utensils, below which is an inscription that says "Calix Animī" (which, when translated from Latin, means "The Courageous Cups" or "The Animated Cups").]]
* HailfirePeaks: One part steep mountain range, one part ruined fairy tale castle ''in'' that mountain range.
* ImprobableUseOfAWeapon: The mountain goat miners use their pickaxes as BattleBoomerang projectiles.
* OurDragonsAreDifferent: During the ancient elevator sequence, tiny dragons constantly appear to spew {{fireball}}s at Cuphead and Mugman.
* RockMonster: The lion heads made of rocks appear as more dangerous enemies, [[BlowYouAway blowing Cuphead and Mugman back]] with their roars.
* TheUnfought: [[spoiler:The Cyclops. Outrun him all the way through and he falls into the {{Bottomless Pit|s}} all by himself.]]
* UniqueEnemy: The Cyclops is the only non-boss enemy in the game to get his own individual game-over card.
* WhamEpisode: Somewhat; at first, the stage is simple — just a fairly treacherous mountain range — but halfway through, the boys go down an ancient elevator and more mythical creatures begin to serve as enemies. Then they go into the ruined castle grounds and find out it was the home of the [[spoiler:Legendary Chalice back when she was alive, via a statue of her in the background, and that most of the enemies are guarding what's left of her home. There's also a statue of what appears to be Elder Kettle]].
[[/folder]]

[[folder:Perilous Piers' Pests]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/perilouspiers.png]]
->''"The Fish Federation and the Crustacean Nation are victorious once again!"''
An army of angry sea life that swim along the pier of Isle Three.
----
* AirborneMook: The flying fish are constantly airborne.
* {{Determinator}}: The lobster mini-boss of the third area will always come back ten seconds later, no matter how many times you beat him, until you get to the boat.
* FiendishFish: The flying fish are some of the most common enemies in this level.
* FlyingSeafoodSpecial: The flying fish and starfish trapped within bubbles that serve as airborne obstacles, among others.
* GiantEnemyCrab: The large crabs with boxes on their heads in the second area and a vicious lobster in the third area.
* HelpfulMook: The buoys that you parry to gain extra distance, and the octopus that takes you to the end of the level. It even spits cannonballs for you!
[[/folder]]

!The Mausoleums
[[folder:The Spectre Syndicate]]
[[quoteright:218:https://static.tvtropes.org/pmwiki/pub/images/mausoleum.png]]
->''"Is success achievable? Not when we are this un-boo-lievable!"''
A gang of ghosts that hang around the Mausoleums of Inkwell Isle, trapping any unfortunate soul to wander inside.
----
* AsteroidsMonster: The third Mausoleum has large ghosts that move slowly, but split into two smaller and faster ghosts when parried.
* BedsheetGhost: They all have this appearance.
* ColourCodedForYourConvenience: Their pink colouring hints that they're all parryable, and this is vital since parrying is the only way to beat them.
* GhostlyGape: Nearly all of them have empty eye sockets.
* KungFuProofMook: As an NPC outside the first mausoleum will warn you, ''none'' of your usual attacks will work on them; the only way to kill them is by parrying. By the same token, there's nothing they can do to hurt ''you'' — except by [[ProtectionMission getting to the urn]] [[spoiler:where the Legendary Chalice is imprisoned]] in the center of the stage.
* NightOfTheLivingMooks: Ghost enemies who have no goal but to capture souls in the Mausoleum.
* TouchTheIntangible: You can only interact with them by parrying. Anything else will just go straight through them.
[[/folder]]

!The Runaway Debtors
[[folder:Bosses in general]]
A veritable RoguesGallery of toons who owe the Devil their souls for one reason or another. As part of the deals they made, they own soul contracts — which, as the name suggests, signify that the Devil owns their souls...

Or at least he would, if these individuals hadn't run off with their own contracts to parts all around the Isles, depriving the Devil of his due.

It falls upon both Cuphead and Mugman to get these strange people in strange lands to cough up the contracts in order to save themselves, even as they take on increasingly vile forms and use a variety of weapons against them.
----
* AntiVillain: The only reason they're fighting Cuphead and Mugman is because they're acting as the Devil's agents, and throw a big celebration in honor of the duo after they defeat the Devil and destroy the contracts.
* AttackOfThe50FootWhatever: While they vary in size, many of the bosses seen tower over Cuphead and Mugman.
* DealWithTheDevil: All of them likewise have made deals with the Devil, but skipped out on paying them. Cuphead and Mugman's role is to get their soul contracts from them.
* EveryoneHasStandards: They all ''refused'' to work for the Devil [[ScrewThisImOuttaHere and ran off with their own contracts]]. Needless to say, it doesn't look good on the player [[spoiler:if they decide to [[YouBastard pick the bad ending]]]].
* EvilIsBigger: Downplayed. The Runaway Debtors are {{Anti Villain}}s to various degrees and vary in size; however, many of the bosses seen tower over Cuphead and Mugman.
* FlunkyBoss: Almost all of them have at least one phase where they send out {{Mooks}} to do their dirty work. Some of them do nothing ''but''.
* GameOverMan: If they beat you, you get a card with their face on it [[HaveANiceDeath mocking you with a pun related to your defeat]]. To really rub it in, there's a little chart at the bottom showing how close (or far) you were to beating them.
* {{Leitmotif}}: Every boss has their own unique theme named after the level where they are fought, and they get most of the SugarWiki/AwesomeMusic in the game. [[invoked]]
* NoodleIncidents: All of them made deals with The Devil, and managed to get away with it somehow.
* OneWingedAngel:
** Considering the theme of the game, you can bet that most if not all the bosses are gonna transform or change shape at least once in their respective fights. The real fun is seeing how or what they'll transform into.
** Elder Kettle actually {{Lampshade|Hanging}}s all the shape-shifting when you first talk to him, stating that they will turn into beasts to confront the two. It's subtly implied that the Soul Contracts give them this ability.
* PungeonMaster: The vast majority of their game over taunts.
* RiddleForTheAges: We never do find out what they made their deals with the Devil for.
* SequentialBoss: So many of them, enough [[SequentialBoss/{{Cuphead}} for its own page]].
* SmugSmiler: A solid majority of them also flash a big, sinister smile of some sort at least once in their boss fights. Indeed, most of them don't seem to be all that worried that Cuphead and Mugman are trying to collect their soul contracts. [[NintendoHard Granted…]]
* TheUnreveal: The deals they made with the Devil are never fully addressed beyond being PlotCoupons. If they simply had lost to the Devil at the casino, they probably wouldn't be on the run from his influence, so the Contracts must be for other desires the Devil promised them in the past. Possibly {{Subverted|Trope}} in that it's implied during battle what they got from the Devil (like Rumor rifling through a spell book to transform and move on to her third phase).
* WouldHurtAChild: The bosses are more than willing to fight Cuphead and Mugman, although both of them are adolescents. Granted, it's in self-defense, since the only other option is to give up without a fight and let the Devil claim their souls.
* YourSizeMayVary: When you battle them, many of the Runaway Debtors are gigantic and absolutely tower over Cuphead and Mugman. In the ending cutscene where most of them were there, many of them were only the size of an average person -- even the largest debtor, Grim Matchstick is only twice as tall as one.
[[/folder]]

!!!Inkwell Isle One
[[folder:The Root Pack]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/rootpack.png]]
->''"Buttered, smashed and mashed, it's over for you."''\\
''"Hey, little guy, it's okay if you have to cry!"''\\
''"I'm lean, mean and full of beta-carotene!"''
A group of vegetables whom you fight in a garden in "Botanic Panic". They consist of three main characters; Sal Spudder (a potato), Ollie Bulb (an onion), and Chauncey Chantenay (a carrot). A fourth character, Horace Radiche (a radish), also appears under certain conditions.
----
* AlliterativeName: '''S'''al '''S'''pudder and '''C'''hauncey '''C'''hantenay.
* AnthropomorphicFood: They're all vegetables.
* CardCarryingVillain: Judging from his win quote, Chauncey Chantenay knows he's a villain and he's proud of it.
* DishingOutDirt: Sal Spudder starts the battle off by spitting out dirt clods and earthworms at you.
* DualBoss: In the secret phase of the fight, Horace and Chauncey attack at the same time, and you can only safely stand on the ground once Horace dies.
* EdibleAmmunition: Chauncey can launch {{homing|Projectile}} carrots at you.
* EverythingsBetterWithSpinning: Horace, who spins around like a top and dashes across the arena at high speed.
* EyeBeams: One of Chauncey's attacks has him firing some beams from his ThirdEye.
* HypnoticEyes: Chauncey wields these when you fight him, which he uses to send carrots at you or launch psychic beams.
* InnocentlyInsensitive: A variant in how Ollie is definitely the most benevolent of the trio, but his defeat card can be taken as accidental TrashTalk.
-->''"Hey, little guy, it's okay if you have to cry!"''
* MacrossMissileMassacre: Chauncey Chantenay uses one with homing carrots of all things.
* OcularGushers: Ollie attacks this way by crying, with his tears raining down projectiles at you.
* OnionTears: Ollie's attack is a reference to the idea that onions make you cry.
* PsychicPowers: Chauncey Chantenay wields psychic abilities.
* PunnyName:
** Sal Spudder is based on 'spud', a colloquialism for potato.
** Chauncey Chantenay's last name is taken from a variety of carrot.
** Ollie Bulb's last name is a synonym for onion
** Horace Radiche has his name originating from 'horse radish'.
* SheatheYourSword: A post-launch update added an EasterEgg to skip Ollie Bulb's phase. If he isn't hit by any projectiles, he exits without attacking, but Horace Radiche pops out during Chauncey Chantenay's phase, making it slightly more difficult.
* ShoutOut:
** Their name references the Creator/RatPack.
** A subtle one, but if you look in the background of the fight, you'll see the root pack was grown using a bag of [[WesternAnimation/LooneyTunes ACME Grow]].
* SkippableBoss: Ollie Bulb and Horace Radiche, interchangeably. If you attack Ollie, you'll battle him normally and Horace will be skipped, but if you instead decide to SheatheYourSword, he'll leave without a fight while Horace Radiche pops up to attack you in tandem with Chauncey Chantenay.
* StationaryBoss: Compounding on the rest of their easiness factors, the main trio can't move from where they're rooted. Averted with Horace, who continuously sweeps across the arena.
* TerribleTrio: All three of them seem to be the debtors.
* ThirdEye: Chauncey opens his up when he starts firing his EyeBeams.
* ThrowTheDogABone: As of the 1.2 update, Ollie will pause after he appears, looking around with a scared expression. If you don't start fighting him, he'll breathe a sigh of relief and disappear back into the ground while smiling, then Horace and Chauncey will both appear instead.
* TokenGoodTeammate: Ollie is the only of the three who doesn't mock the heroes in his win quotes, showing him to be nicer than his friends. Indeed, he doesn't directly attack at all, and (as of an update) can actually be skipped if he isn't attacked.
* WarmUpBoss: One of the first few bosses in the game (if not ''the'' first), and definitely one of the easiest; all three have incredibly obvious tells to their attacks and their projectiles don't have anywhere near high enough density to be a big threat to you. The only member of the trio that might give someone a rough time would be Chauncey, but even then, he's pretty [[{{Pun}} small potatoes]] compared to some of the bosses you'll be facing later.
* WhatHappenedToTheMouse: None of the trio are seen in the ending. Of course, being {{Stationary Boss}}es, it's unlikely that they could leave the garden they were planted in, though by that logic, Cagney Carnation would be the same way, and yet he's one of the bosses that appear in the ending (although one of Cagney's attack animations turns his stem into legs, so who knows).
[[/folder]]

[[folder:Goopy Le Grande]]
[[quoteright:258:https://static.tvtropes.org/pmwiki/pub/images/goopylegrande.png]]
->''"I'm a handsome slime bringing pain — one bounce at a time!"''
A blue slime-like boss you fight in a forest in "Ruse of an Ooze".
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* AffablyEvil: He might anatognize Cuphead and Mugman, but at least he's well-mannered.
* AlliterativeName: '''G'''oopy le '''G'''rande.
* AttackItsWeakPoint: Shooting his portrait on the tombstone is the only way to hurt him in his final phase.
* BaldOfEvil: He's one of the debtors that sold his soul to {{Satan}}, and the little tip on his head is tipped like a hat before the fight.
* BlobMonster: He's a blue slime monster, if the name of the boss and level didn't tip you off.
* BoxingBattler: His attacks in the first two phases consist largely of devastating punches complete with boxing gloves.
* ClippedWingAngel: His Tombstone has only one attack (as opposed to the two his other forms have), and it's pretty easy to dodge if you stand still until he uses it. The only real upside is the element of surprise against players who thought the fight was over.
* CloseRangeCombatant: Out of all the bosses in the entire game, he's the only one that lacks any ranged attacks or even helpers, instead preferring to crush the player characters or punch them.
* ConMan: The title and the stunt he pulls with the gravestone implies it.
* DeaderThanDead: He's implied to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cup brothers end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies he's dead.
* {{Determinator}}: The third phase of his fight involves his ''gravestone'' attacking you.
* DoesThisRemindYouOfAnything: He's a boxer who takes a special pill that turns him bigger and stronger, which gives off implications of steroid use (and the fact that [[DrugsAreBad he's implied to have died by the end of the second phase]] pushes it further.)
* TheFightingNarcissist: Each one of his win quotes talks about how handsome he is. [[RhymesOnADime Some of them are even in rhyme!]]
* GuideDangIt: Getting the parry bonus for this fight is not immediately obvious, since he does not have any projectile attacks. In order to get it, you need to parry the three pink question marks that appear when he shifts into his second phase.
* HalfTheManHeUsedToBe: Upon being knocked out in his third phase, his gravestone form cracks vertically into half.
* InstantGravestone: His third phase has one drop onto him. Then ''the gravestone'' attacks you, complete with taunting you as though it's still him if it kills you.
* KingMook: Basically, a larger version of the slime enemies from Forest Follies. Indeed, a piece of DummiedOut code reveals that, upon being smashed by his tombstone, Goopy was once supposed to [[AsteroidsMonster split off]] into [[FlunkyBoss two of the slime enemies]].
* LetsFightLikeGentlemen: Tips his "slime hat" to you before the brawl commences.
* TheLostWoods: Fought in a forest clearing.
* MakeMyMonsterGrow: His second phase has him eating a pill and getting much bigger.
* MeaningfulName: His surname means "the great" in French and refers not only to his ego but also his size (although the grammar is incorrect; "le" is masculine, but "grande" is feminine, so technically speaking, it should be "Le Grand" or "La Grande").
* MegatonPunch: His first phase has him forming his body into a boxing glove to hit you. His second form has him literally donning a boxing glove to punch at you.
* NinjaProp: The pink question marks that surround him when he transitions to his second phase are actually parryable. You'll want to remember this if you want that A+ rank.
* ObviousRulePatch: The pink question marks that appear when he takes the pill exist for the sole purpose of being parried for the A+ rank, since Goopy doesn't use projectiles.
* OneWingedAngel: After swallowing an unknown pill-like object, he becomes bigger and tougher-looking. His tombstone form may also count, although it's doubtful he intended to take the form of the tombstone in the first place.
* RedBoxingGloves: On his right hand, which he uses to rough up Cuphead and Mugman.
* ShoutOut: His blue appearance and pointed top allude to the famous Slimes from ''VideoGame/DragonQuest''. When he transitions from his first phase to his second phase, he changes shape similar to how [[VideoGame/ABoyAndHisBlob the blob shapeshifts]]. Likewise, his final form is, [[StealthPun literally]], a [[Music/TheLivingTombstone Living Tombstone]].
* UnskilledButStrong: His attacks are insanely telegraphed (even by the standards of games of this nature), but they cover a wide area.
* VictoryFakeout: The transition from his second to third phase. Goopy gets a dazed look on his face, an InstantGravestone drops on him and splatters him into a million droplets… and then the ''gravestone'' starts moving around trying to squash you!
* WarmUpBoss: One of the first bosses in the game that you'll face, his attacks have incredibly obvious tells and are fairly easy to avoid, plus they have fairly simple patterns. Also, he's the only boss with no projectile attack to speak of.
* WhatHappenedToTheMouse: He's nowhere to be found during the finale of the good ending, implying that he really is dead.
[[/folder]]

[[folder:Hilda Berg]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/hildaberg.png]]
->"''You won't get too far... it's been foretold in the stars."''
A woman that can turn her body into a blimp whom you fight in the skies in "Threatenin' Zeppelin".
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* AmbiguouslyHuman: Is seemingly human, but has [[AmazingTechnicolorPopulation bright pink skin]] and odd powers like being able to transform into a blimp, cloud constellations and a mechanical crescent moon with her face.
* TheArcher: Hilda's Sagittarius form, where she turns into [[GenderBender a man on a cloud]] and shoots arrows at you.
* BalloonBelly: Her transformation into a blimp starts with her inhaling so deeply, her belly inflates.
* BlowYouAway: She can summon tornados from the weather vane on her head to throw at you.
* BrutishBulls: Hilda's Taurus form, which has her turning into a bull made of clouds to ram at you.
* EvilLaugh: [[WordsCanBreakMyBones Weaponised in her standard form]], no less! In her first phase and between her Zodiac forms, Hilda can attack you by sending "HA HA HA"s your way. When she transforms into her final form, this attack's gone, but she still opens the phase with a more menacing "HEH HEH HEH..."
* {{Faceship}}: Played with, she turns into a ship and her face happens to be at the front.
* FlunkyBoss: Little planes aid her in the fight in the first two phases. In the third phase, she can summon {{Flying Saucer}}s.
* FlyingSaucer: She summons these in her final phase. Red ones will prepare to fire as soon as they're above you, so you'll have to move forward to avoid their beams, while brown ones will prepare to fire as they approach you, so it's best to move back away from them as soon as they prepare to fire.
* GenderBender: Of the three constellation forms fought in her second phase, only Gemini is female, with Taurus and Sagittarius both being male, true to their depictions in reality.
* TheHyena: Cackles incessantly in her blimp form, with [[WordsCanBreakMyBones lethal results]]. She later unleashes a much more impressive, yet non-harmful example upon transforming into her Moon form.
* TheManInTheMoon: Her final phase has her shifting into a huge crescent moon form where she can not only attack you with her face, but summon [=UFOs=] to hit you with their beams.
* MoreDakka: The energy balls summoned from her Gemini form shoots a stream of bullets in rotating motion.
* OneWheeledWonder: While the top half of her body (before going OneWingedAngel, anyway) is merged with a blimp, the bottom half is a pair of perfectly human legs riding a unicycle — in all likelihood, [[HamsterWheelPower the thing's power-source]].
* OneWingedAngel: Her "[[NinjaPirateZombieRobot Alien Clockwork Crescent Moon]]" phase.
* PainfulTransformation: Before she changes into her final phase, she holds her head, clenches her eyes, and makes a pained moan, then her body starts spasming uncontrollably.
* PunnyName: Her name is Hilda Berg and it's a pun on the [[https://en.wikipedia.org/wiki/LZ_129_Hindenburg Hindenburg]].
* RammingAlwaysWorks: Tries this during phase 2, both as herself when transforming into one of her UsefulNotes/{{Constellations}}, and when in her Taurus form, in which this is her sole attack.
* ShoutOut: Her hairstyle was clearly inspired by ''WesternAnimation/BettyBoop''.
** Her airship form appears to be a reference to recurring boss Kabula from the ''{{Franchise/Kirby}}'' series.
** Her DubNameChange in the Portuguese language is Geni Buarque, a reference to the Brazilian song "Geni e o zepelim ("Jenny and the zeppelin", loosely based on Music/PirateJenny) and its author, Chico Buarque.
** The whole boss fight is one big homage to ''VideoGame/ThreeWonders'' 's Chariot: all the constellation-based minibosses (save for Taurus) apppear in the Capcom title, and the final phase is the spitting image of [[ThatsNoMoon Hypnos]], the second level boss.
* SinisterSchnoz: Has a very long nose, and when she shifts into her moon form, it gets even longer.
* SpreadShot: The green flunky blimps during her battle fire a spread[[note]]the number of shots is dependent on difficulty[[/note]], while her Sagittarius phase fires a spread of blue homing stars.
* StarPower: Many of Hilda's attacks are themed after celestial objects, with her initial transformations being based on the western zodiac and her final form resembling a moon and firing star projectiles and flying saucers. Each of the Zodiac forms are introduced with an illustration of their respective constellation upon Hilda transforming into them.
* StationaryBoss: She takes up enough of the screen in her moon form to prevent her from moving, other than popping her face out to signal her UFO attack.
* TricksterTwins: Hilda's Gemini form, where she turns into two girls on clouds and forms an energy ball to hurl at you.
* VoluntaryShapeshifting: She begins the fight by turning into a blimp, and then takes two of three different constellation-themed forms. Her final transformation into the moon, however, appears to be involuntary.
* WarmUpBoss: As the first shoot-em-up boss, she mostly serves to introduce you to the new mechanics. Much like a lot of the other early bosses, her attack tells are fairly easy to read, any gimmicks she throws out are not very difficult to manage, and even when she goes OneWingedAngel in her final phase, the bullet density is ''nowhere near'' as bad as later shoot-em-up bosses.
* WickedWitch: The 'wicked' part is [[AntiVillain downplayed]], but Hilda certainly seems to have this theme going for her, what with her evil cackles, transformation magic, and the snout. Even her tornado attack might be a reference to [[Film/TheWizardOfOz the trope codifier]].
* WingdingEyes: All her constellation forms have stars for pupils; this extends to her second-phase Game Over card.
* WordsCanBreakMyBones: Her starting phase has her shooting out "[=HAs=]" at you.
[[/folder]]

[[folder:Cagney Carnation]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/cagneycarnation.png]]
->''"Extreme pollination and total domination!"''
A flower boss whom you fight in a forest clearing in "Floral Fury".
----
* AlliterativeName: '''C'''agney '''C'''arnation.
* BattleBoomerang: One of his early projectiles is a sycamore seed that flies to the left over the platforms, then back across the right over the ground.
* BossArenaIdiocy: Cagney's arena contains tons and tons of obstacles on ground level... and three floating platforms which makes those obstacles avoidable. Granted, every now and then Cagney will use his vines to cover one of the platforms, but how about picking a platformless arena instead (Assuming he isn't rooted into the ground like a normal flower is and has a choice of where he can fight, of course)?
* BulletSeed: He forms a machine gun that shoots out seeds (one of them pink) into the air before they fall to the ground and become monstrous plants.
* EvilLaugh: He lets out a manic laugh as he transforms.
* EyeScream: When he's beaten, his eyes completely disappear. You can see straight through one eye hole and out the other.
* FieryRedhead: Gives the impression of one, with his orange petals and maniacal temperament.
* FlunkyBoss: In his first two stages, he occasionally launches seeds that sprout into enemies.
* FoulFlower: A giant flower boss who acts innocent before quickly revealing his true, AxCrazy colors.
* GRatedDrug: Cagney's fuzzies are the quickie type in the patched version.
* GreenThumb: Many of his attacks are plant-based.
* InterfaceScrew: In the patched version, if you get hit by one of the fuzzies Cagney spits at you, the screen will get blurry and distorted for a second or two.
* KingMook: Looks like a much larger, thorn-covered, and malicious version of the flower people you fight in Forest Follies.
* NightmareFace: Starts his fight off by giving an innocent smile, then suddenly roars at you, stretching his mouth open. He can even stretch his face to attack you. It gets even ''more'' nightmarish-looking in his final phase. And when beaten, his face ''completely loses its eyeballs'' and his mouth hangs agape in a soundless despair wail.
* OneWingedAngel: Becomes slightly bigger and [[SpikesOfVillainy spikier-looking]] in his final phase.
* ShoutOut:
** The way Cagney moves his hands is similar to the animation of a ghost character from Fleischer Studios' short ''WesternAnimation/SwingYouSinners'', who in turn is a reference to Monroe Silver, an actor and comedian of the Depression era known for incorporating similar hand motions into his routine.
** His name is obviously a pun on Creator/JamesCagney. The fact that one of his moves involves turning ''his own head'' into a crank-driven Tommy Gun (because of some of James' most memorable roles being gangsters) says a lot. For triple points, one of the first great [[https://en.wikipedia.org/wiki/Dean_O%27Banion Real Life mobsters]] was an accomplished florist who often did arrangements for gangland funerals; to this day, flower shops are still a semi-stereotypical 'front' for cartoon mobsters.
** His pre-fight adorable-looking design is a homage to the sentient flora from ''WesternAnimation/FlowersAndTrees'', a 1932 ''WesternAnimation/SillySymphonies'' animation, and the background is also inspired by the background artwork of the same short.
* SlasherSmile: Wears a maniacal grin through his boss battle, with him really ratcheting it up in the final phase.
* SoundtrackDissonance: His battle theme, "[[https://studiomdhr.bandcamp.com/track/floral-fury Floral Fury]]", appropriately spices up the battle with adrenaline-pumping fast Latin/samba music, which is a fine tune to go along with getting yourself killed by a psychopathic flower. Then again, it's also a play on the Latin American {{Gangster Land}}s, which fits with his aforementioned gangster theme.
* StationaryBoss: After spreading spiky vines along the ground, Cagney stays in a hunched position for the rest of the battle. His first phase isn't quite stationary because he can occasionally shoot his face out on the upper or lower halves of the screen (his face lunges are much faster in the patched version).
* VineTentacles: He can grow thorny vines through the soil when battling Cuphead or Mugman and stick them up to spike the brothers from below.
* WakeUpCallBoss: Unlike the Root Pack and Goopy, Cagney is the first ground boss to start invoking BulletHell and will force you to pay attention to not only where the attacks come from, but also stay cognizant of his distinct wind-ups and whatever follows after; things that you'll ''need'' to learn if you're going to get far in the game. Fittingly, he's the final boss unlocked for the first world.
[[/folder]]

[[folder:Ribby and Croaks]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/ribbyandcroaks.png]]
->''"We've had fightin' souls since we've been tiny tadpoles."''
Two frog brothers in boxing gloves fought in a showboat club setting (ironically run by flies) in "Clip Joint Calamity". Ribby is the shorter one and wears white trunks, while Croaks is taller and wears red.
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* AmphibianAssault: Two giant frog boxers that are not surrendering their soul contracts without a fight.
* AmphibianAtLarge: They tower over Cuphead and Mugman, and appear to be human-sized, if not larger.
* BashBrothers: A pair of frogs who've been enjoying brawls since they were tadpoles. While not stated in the game to be related, ''The Art of Cuphead'' book confirms them to be brothers.
* BlowYouAway: Croaks can turn himself into an electric fan in the 2nd phase of the battle. This attack doesn't do any damage, but the pushing wind does make Ribby's [[ShockwaveClap projectile claps]] harder to dodge.
* BoxingBattler: They are styled after boxers and Ribby fights by using [[ElementalPunch elemental punches]].
* DualBoss: You have to fight them both at the same time, with Ribby going to the opposite side of the screen in the 2nd phase and Croaks turning into a makeshift fan to blow you into him while Ribby sends sonic blasts at you. However, unlike the Lollipop Ghouls on the Phantom Express and the Tipsy Troop, the two frogs share health, so it doesn't matter which one is attacked.
* FrogMen: The pair are frogs who fight for the amusement of the crowd in a showboat club, they made a bet with the devil and have now refused to pay their debts.
* FusionDance: Their final phases on normal mode has Croaks swallow Ribby whole and suddenly combine into a [[FusionDissonance slot machine]] that's only vulnerable when it starts attacking after you parry-slap the handle.
* KamehameHadouken: Ribby fires these off in his first phase.
* MirrorCharacter: Not explicitly stated in the game itself, but they're a pair of BashBrothers who got in trouble with the Devil, and who are now fighting for their lives to avoid having to pay up on the bargain they made. That's not very far removed from Cuphead and Mugman, is it? The artbook does indeed confirm them to be brothers and even states that this relationship is unique only to them and the cup brothers.
* OcularGushers: Ribby will be left gushing with tears with Croaks pounding the floor when they are defeated in Simple difficulty.
* OneWingedAngel: Their slot machine form, the result of a FusionDance as seen above.
* PlayingWithFire: In the first phase, Croaks will sometimes spit out burning fireflies that fly towards you.
* RapidFireFisticuffs: Ribby starts his attacking by punching rapidly, which produces projectiles that zip toward you.
* ShoutOut:
** The characters and their color scheme are very similar to the ones from the series ''Literature/FrogAndToad'' by Arnold Lobel.
** To Ryu and Ken from ''Franchise/StreetFighter'', made apparent by their boxing gloves and karate gi. They even do their more well-known taunts before battle (Croaks does Ken's BringIt, while Ribby lets out a {{Kiai}} as he gets into a fighting stance). In their final phase, they turn into a slot machine that includes tigers (which result in uppercuts) and bison (which result in psycho power) as part of its roulette.
** Additionally, the background featuring a cheering audience is another ''Street Fighter'' reference.
* StationaryBoss: While Ribby rolls across the screen to start the second phase (and then returns to Croaks for the final phase), neither frog moves around while attacking during each phase, and the slot machine is obviously immobile.
* VisualPun:
** Croaks spits out glowing bugs on fire that fly at you. They're literal fireflies.
** The flies watching the fight in the background are literal barflies.
* WhatHappenedToTheMouse: Croaks doesn't show up for the ending, probably because he has to stay at home. Ribby, however, does appear along with the remaining debtors on behalf of his brother.
* WrongSideOfTheTracks: According to their second phase's game over card, they're from the wrong side of the lily pad, [[RhymesOnADime which is why they're crude and bad]].
[[/folder]]

!!!Inkwell Isle Two
[[folder:Baroness Von Bon Bon]]
[[quoteright:231:https://static.tvtropes.org/pmwiki/pub/images/baronessvonbonbon.png]]
->''"I won't sugarcoat it… you never stood a chance!"''
The ruler of a candy area and boss of the "Sugarland Shimmy" level. Sends a random assortment of confectionery bosses (Muffsky Chernikov, a cupcake; Sgt. Gumbo Gumbull, a gumball machine; Sir Waffington III, a flying waffle; Lord Gob Packer, a multi-layered jawbreaker; and Kernel Von Pop, a giant candy corn[[note]]all unnamed in the game itself, but given pet names by [[WordOfSaintPaul animator Tina Nawrocki]][[/note]]) at you from atop her living castle Whippet Creampup before you are able to attack her directly.
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* AdvancingBossOfDoom: In the final stage of the battle, the castle where she hides in begins to chase Cuphead and Mugman.
* AmbiguouslyHuman: It's unclear if she's meant to be human, or a strange humanoid. Especially since [[TheNoseless she lacks a nose]], has [[AmazingTechnicolorPopulation pink skin]], and lives in a chiefly candy-inhabited setting.
* AngryFistShake: She ''frequently'' angrily shakes her fist at you whenever you defeat one of her minions.
* AnthropomorphicFood: Among her minions are a living cupcake, a sentient waffle, an animate jawbreaker, a monster candy corn, and a mobile gum ball dispenser. Her castle is a living cake monster, which can dispense jelly bean soldiers and rolling peppermints with faces. It's hard to notice except for [[LosingYourHead in the game over quote for her final phase]], but Bon Bon herself is actually a bottle of soda, with her head functioning as the cap.
* AuthorityEqualsAsskicking: Although most of the time she sends her mooks to do the bidding, she can also attack using a sugar cane as a shotgun.
* TheBaroness: That's her title, after all.
* BerserkButton: The Baroness herself doesn't have one, but her cake castle Whippet Creampup certainly does: getting its towers pulled on. Indeed, this is how she initiates the final phase of the battle; by pulling on Whippet's towers, sending it into a rage and causing it to chase the boys down.
* BossArenaIdiocy: The arena she's fought contains a floating green candy platform right in its very middle, which can be jumped on to avoid most of her attacks.
* DetachmentCombat:
** Sir Waffington III breaks his body apart and launches the pieces in a SpreadShot attack.
** The Baroness will throw her head during the final phase.
* FlunkyBoss:
** The first part of her boss battle is fighting three randomly-chosen minions, each with their own game over screen:
*** A candy corn that flies around horizontally or vertically, occasionally spawning smaller candy corns that fly upwards.
*** A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.
*** A cupcake that [[BouncingBattler jumps into the air]] and slams into the ground, unleashing frosting [[ShockwaveStomp shockwaves]].
*** A jawbreaker that slowly chases after Cuphead, trailed by InvincibleMinorMook jawbreakers (none on Simple, one on Regular, and two on Expert).
*** A winged waffle that flies around, [[DetachmentCombat splitting itself apart before putting itself back together]].
** During the minion phase of the battle, jellybean soldiers will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging the castle to chase the boys down, while sending large peppermints rolling out.
* HighClassGloves: Wears a pair of pink opera gloves.
* HomingProjectile: Her own head acts as one, chasing down the player character to try to damage them.
* ImprobableWeaponUser: Her candy cane can somehow be used as a ''shotgun''.
* KickingAssInAllHerFinery: Averted. While she does have a stunning appearance, she never engages the boys directly at any point in her battle.
* LevelAte: Fought in a kingdom of candy.
* LosingYourHead: At the beginning of the fight, her head briefly detaches while giving Cuphead and Mugman a ThroatSlittingGesture. Also, she can detach her own head and regrow it, even using the spare heads as projectiles in the last phase!
* MatryoshkaObject: Lord Gob Packer is surrounded by several layers of candy shell. Once he's defeated, each shell cracks open to reveal a smaller jawbreaker until the tiny original is exposed, [[WingedSoulFliesOffAtDeath which then floats away]].
* OffWithHisHead: More like, "Off with Their Heads!"; she threatens the duo with this at the start of the battle via giving them a ThroatSlittingGesture, complete with her briefly [[LosingYourHead losing her head]].
* OneWingedAngel: Not her so much as her cake castle, which transforms into an angered beast in the final phase.
* OverlyLongName: According to a series of tweets, all of her minions have extremely long names.
* PimpedOutDress: Wears one with a peppermint-striped bodice, puff sleeves, and flounces that resemble piped icing, topped off with an ice cream cone hennin hat.
* ShockwaveStomp: Muffsky Chernikov produces waves made of icing whenever he slams onto the floor.
* ShotgunsAreJustBetter: Her cane functions as this in the third phase of her fight, adding additional projectiles for the duo to worry about.
* ShoutOut: The appearance of the Baroness and her barony are inspired by various cartoons' candy kingdoms, but most noticeably Cookietown from "WesternAnimation/TheCookieCarnival". One of her minions, Lord Gob Packer, is also a jawbreaker version of VideoGame/PacMan.
** Marie Antoinette may be also a strong contender, due to the infamous quote often (but [[BeamMeUpScotty incorrectly]]) attributed to her, ''"let them eat cake"'', and the fact that she indeed [[LosingYourHead loses her head]]. [[invoked]]
** Her name is a reference towards Baron Von Blubba from the ''[[VideoGame/BubbleBobble Bubble Bobble]]'' franchise.
** Design-wise, she was influenced by various actresses from the era of the game's design (like Betty Grable, Bebe Daniels, and Loretta Young).
* SlasherSmile: [[https://68.media.tumblr.com/a04f9e10845bfda98e4ef84b650b66db/tumblr_oxeln7w6hH1wnrdtzo1_1280.png Makes a wide, unstable-looking smile]] just before she initiates the final stage of the battle.
* SoreLoser: She bursts into angry tears upon defeat (complete with a VolumetricMouth). In Regular mode, Whippet also beats the ground in frustration while crying.
* StationaryBoss: She stays on top of her castle for most of the fight, but can't be damaged until the end. On Simple difficulty, she stays still and keeps firing cotton candy blasts when her third minion is defeated. On Regular and higher, she instead progresses the fight by turning into an AdvancingBossOfDoom.
* VaudevilleHook: Blink and you'll miss it, but her candy cane functions as this at the very start of her level, implying her candy castle may have some control over it.
* VisualPun: When Muffsky is defeated, the cherry on his head swells up as its stem turns into a fuse and blows itself up along with the cupcake. It turned into a cherry bomb, see.
* VolumetricMouth: She breaks down into sobbing in this way upon her defeat.
* WheelOfFeet: Sgt. Gumbo Gumbull's feet are animated this way.
* WingedSoulFliesOffAtDeath: Lord Packer gains a halo when defeated, floating off the screen while Bon Bon prepares for the next phase.
* YourHeadASplode: Happens to Sgt. Gumbull in his death animation; his glass head shatters and it scurries off.
[[/folder]]

[[folder:Beppi the Clown]]
[[quoteright:222:https://static.tvtropes.org/pmwiki/pub/images/beppitheclown.png]]
->''"What do you call a cup that falls off a swing? A tumbler!"''
An evil clown you fight on the roller coaster in "Carnival Kerfuffle".
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* AmbidextrousSprite: Since he's the only character with an asymmetrical design. It's moot in his second and fourth phases, where he directly faces the player, but in his first and third phases, the red half of his face is dominant no matter which way he turns. The artbook states [[StylisticSuck this was an intentional design choice]] to harken back to past examples of ambidextrous sprites in retro games.
* AmusementParkOfDoom: Seemingly fights you in one; the rides he [[VoluntaryShapeshifting becomes]] are certainly killer, and the rollercoaster he fights you on is a constant, deadly stage hazard.
* BaldOfEvil: Completely bald, even underneath that little top hat of his, as shown in the ending.
* BalloonOfDoom: Has a stretchy, balloon-like body, most noticeable with his bulbous head. In phase 2 of his battle, his body is attached to a giant helium pump, and his head inflates into a giant balloon tied to his body with a string. The pump also shoots out balloon dog heads that [[FlunkyBoss swarm the arena to attack you]].
* BerserkerTears: Has an ''absolute tantrum'' if you shoot down his merry-go-round horse.
* CarFu: Leaps into a bumper car for the first phase of the fight and tries to ram you.
* CheshireCatGrin: Has a creepy wide, toothy grin.
* CircusOfFear: Fought on a roller coaster in a rather bleak-looking amusement park.
* EverythingsBetterWithPenguins: Nope. In his final phase, he spawns penguin enemies that throw baseballs at you.
* FlunkyBoss: His final phase has him summoning penguins who [[IKnowMaddenKombat throw baseballs at you]].
* FunPersonified: Really seems to be having a blast throughout the fight, particularly when he's riding a horse and is actually ''bouncing'' and cheering with excitement.
* GravityIsAHarshMistress: Falls off the roller-coaster ''twice'' during the fight, yet refuses to give up.
* KnockKnockJoke: One of his death quotes falls under this if you get killed by his horse; see "PungeonMaster".
* MagicalClown: A clown who can transform into and summon amusement park rides and other objects.
* MonsterClown: A clown boss who will not hesitate to fight you.
* NiceHat: Wears a tiny top hat on his head.
* NonIronicClown: During the ending, he has a genuinely pleasant smile on his face.
* OneWingedAngel: While he transforms into a balloon pump for his second phase, his transformation into a chair swing ride in the final one fits the trope better.
* PungeonMaster: All of his death lines are jokes at Cuphead's expense:
-->'''Beppi:''' [''Bumper Car Phase''] Why did the clown drive over the cup? He wanted to crack him up!\\
'''Beppi:''' [''Balloon Phase''] What did the balloon animals think of the cup? Quite the gob-let-down!\\
'''Beppi:''' [''Horses Phase''] Knock-knock! Who's there? Charlie. Charlie who? ''Charlie horse!''\\
'''Beppi:''' [''Swing Ride Phase''] What do you call a cup that falls off of a swing? A tumbler!
* ShoutOut: According to [[http://studiomdhr.com/surprise-cuphead-is-coming-to-playstation-4-and-its-out-today/ a post on the Studio MDHR blog]], Beppi's design is based on a character from ''[[VideoGame/BubbleBobble Super Bust-A-Move 2]]'' (most likely Katze, who is also split into a red side and a blue side).
* StationaryBoss: He can't move while he's a balloon pump/swing ride, which isn't a problem since he relies on minions and arena hazards for those phases.
* VillainousHarlequin: A clown with terrifying transformations and DerangedAnimation, though he isn't outright evil and is mainly just trying to avoid paying up to his end of a DealWithTheDevil. The ending shows he is nice otherwise.
* VoluntaryShapeshifting: Sure, the DerangedAnimation allows everyone to get transformations going on, but Beppi stands out due to how much use he gets out of them; the man can apparently play the whole damn carnival if he wants to, and has no problem becoming a balloon pump or even a giant, spinning, and laughing chair swing ride if pushed.
* YellowEyesOfSneakiness: Has yellow sclerae, and is definitely sinister.
[[/folder]]
[[folder:Djimmi the Great]]
[[quoteright:238:https://static.tvtropes.org/pmwiki/pub/images/djimmithegreat.png]]
->''"You look the fool, falling for the first trick I learnt at genie school."''
A genie fought above the desert in "Pyramid Peril".
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* AmazingTechnicolorPopulation: Probably because he's been in the desert too long, but his skin is red as a tomato.
* AsideGlance: Performs one complete with an EvilLaugh and IdeaBulb replacing his turban when he decides to create the marionette.
* BadWithTheBone: During the first stage, one of his methods to attack is shooting out his own skull ''[[BodyHorror right from his face]]''.
* BagOfHolding: The first phase of his fight — he rummages around in a treasure chest, tossing out three possible types of projectiles:
** [[CatsAreMagic Cat mummies]]: Lowest density, but the only one of the bunch [[HomingProjectile that can home in on you]], and considered the worst of the bunch because of this.
** [[GemstoneAssault Jewelry]]: [[MoreDakka Highest density]], but not too hard to navigate as long as you keep one finger on the Shrink button at all times.
** {{S|tormOfBlades}}words: Probably the scariest-looking, but universally considered the easiest to dodge.
* BaldOfEvil: A FreezeFrameBonus shows that Djimmi is bald under that turban of his.
* BeatThemAtTheirOwnGame: His fourth phase (third if not counting his DeathCourse) has him making a Cuphead puppet named Cuppet and sending it at the boys. If you shrink while he's doing this, he instead makes a mini-Cuppet that can't really fight the boys on its own, so Djimmi transitions right to his final phase while the mini-Cuppet backs him up by shooting pellets from the center of the screen.
* BlowingSmokeRings: Or "a Smoke Teacup", actually: At the beginning of the fight, he blows out some smoke that forms a teacup with [[WingdingEyes X's for eyes]] and a frowning mouth, indicating that the boys have no chance against him.
* CheatCode: [[spoiler:Spinning around three times on the overworld summons him (as '[[UsefulNotes/GameGenie Game Djimmi]]'), granting you 3 extra health (4 if you have the Twin Heart charm equipped) on Simple and Regular mode until you win a fight, [[NoFairCheating though you can't get an A+ grade while the effect is active]]. Dying to his final phase in his boss fight with the cheat on even gives you a new unique death quote!]]
* DeathCourse: The second phase of the fight has him turn into a death trap obstacle course consisting of advancing pillars with vulnerable faces for the players to destroy for bypassing, and sawblade traps in between.
* DualBoss: The miniature Cuppet attacks during Djimmi's final phase if its secret phase is accessed, serving as another obstacle in a very crowded screen until it gets destroyed.
* EthnicMagician: Has some elements of the "Arabian stage magician" sort, considering he's found in a carnival area, his title, and the fact that he speaks about needing a new volunteer ([[RhymesOnADime because this one has collapsed in fear]]) if you die to him on his final phase.
* EvilLaugh: A [[EvilSoundsDeep pretty deep one]] he belts out whenever he's unleashing something new on you. When he decides to create Cuppet, he even unleashes a slightly-robotic laugh to match his [[IdeaBulb lightbulb turban]]. The most impressive one of all in his repertoire comes as he enters the final phase of his fight.
* GoodSmokingEvilSmoking: Constantly smokes a pipe throughout the fight, even making smoke shapes to taunt you at the beginning and having a bad coughing fit when defeated. Indeed, the battle opens with Djimmi appearing in a plume of smoke released from the pipe.
* {{Homage}}: The background as you fight him in the sky is drawn in the style of [[WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor the old Popeye two-reelers]].
* IdeaBulb: Has one while he [[AsideGlance laughs maliciously to the screen]] before starting the fourth phase of the battle.
* JackassGenie: He fits this down to a T, although he is kind of an AntiVillain himself.
* NiceShoes: Wears ''magic lamps'' as shoes.
* OneWingedAngel: Becomes so huge in his final phase that only his head fits onscreen.
* OurGeniesAreDifferent: He's not here to give any wishes, and he attacks with several summoning and shapeshifting methods. And apparently there's a school for them, if the game over quote from his first phase is of any indication.
* PunnyName: His name is a pun on "djinni" (the formal romanization of "genie") and "Jimmy", referencing the Moldenhauer brothers' father Jim.
* PyramidPower: In the final stage of the fight, he summons three floating pyramids with eyes encircling a half of the stage while firing cross-shaped [[EyeBeam beams from them]].
* ShoutOut: The way he moves and acts seems to be a villainous version of the Genie from ''WesternAnimation/{{Aladdin}}''. In particular, his fourth phase has him turn into a giant disembodied hand, which was a quirk of the Genie's.
** During his first phase, he also does the [[Series/IDreamOfJeannie Jeannie dance]] while his treasure chest takes care of all the actual attacking.
* SinisterScimitar: Used in the StormOfBlades up there, natch. Also, if you try to sneak behind him during the fight, [[NoFairCheating one of these immediately descends from the top of the screen and shish-kebobs you]].
* SkippableBoss: Cuppet in its regular size can be avoided by transforming into a mini-plane while Djimmi is analyzing you, skipping straight to the fifth phase. To compensate, however, a miniature version of Cuppet will appear and attack you alongside the giant Djimmi.
* SmokingBarrelBlowout: One of the Game Over cards shows Cuppet blowing smoke from the tip of his finger gun after he has beaten you.
* SpreadShot: The treasure chest he summons in his first phase fires out a stream of shots in a spread pattern, while his hat in his third phase will also fire out spreads of shots. The last phase, the pyramids, fire cross-shaped beams that span throughout the stage.
* StationaryBoss: Only in his first phase (where he's standing still as his treasure chest attacks) and his last phase (where he takes up the entire right side of the screen).
* WeaksauceWeakness: Well, "weaksauce" is over-stating it, but the bomb upgrade you get before fighting him makes his death course significantly easier, as a direct hit with one shot breaks the vulnerable parts. It also lets you find a quite comfortable position to bomb him from during the Sarcophagus phase, where any ghost that'd hit you will get nuked and the eyeball projectiles fall short.
* WeaponizedHeadgear: During his fourth phase where he attacks you with Cuppet, his turban also acts as an obstacle that attempts to collide with the player and fire out a spread of shots every now and then. In his final phase, he also shoots out beams of energy out of his turban's gem.
[[/folder]]

[[folder:Grim Matchstick]]
[[quoteright:254:https://static.tvtropes.org/pmwiki/pub/images/grimmatchstick.png]]
->''"Don't m-m-misunderstand my flames — I just meant fun and games."''
A dragon fought in the clouds circling a tower in "Fiery Frolic".
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* AdvancingBossOfDoom: In the second half of the fight, he begins to chase you while he spouts out the walking flames on his tongue in the second phase, and when he becomes three-headed in the final phase.
* ApologeticAttacker: Losing to him in his first has him saying he's misunderstood, and losing to him in the second phase has him apologizing for being forced to put the players in a hot seat. Even his third phase has him suggesting the player run away.
* BattleInTheRain: The moment he enters his third phase and grows two extra heads, the weather goes from pleasant and sunny to stormy and violent.
* BigFun: He's clearly enjoying fighting you more than he should, considering the contract for his soul is on the line — trying to do the spooky fingers routine at the beginning, and going LaughingMad at [[BreakingTheFourthWall the player]] when he grows two extra heads.
* BloodKnight: He is a somewhat ambiguous example of this trope. While he apologies for fighting you and in general, seems like the nicer bunch of the villains, several of his expressions clearly indicate that he enjoys fighting you.
* BreakingTheFourthWall: He makes a "Boo!" motion toward the player at the start of his battle, and his two extra heads are seen glancing at the screen moments after the second to third phase transition.
* BreathWeapon: In three different flavors, no less. He shoots {{fireballs}} in his first phase, spits out living flames in his second, and spews both flaming bubbles and jets of flame, complete with his middle head ''[[VoluntaryShapeshifting turning into an actual flamethrower]]'', during Phase 3.
* DelightfulDragon: He's endearingly goofy, and even his win quotes make him seem sympathetic. This does not stop him from being one of the hardest bosses the player will have faced up to that point.
* EnergyRingAttack: In his first phase, Grim Matchstick attacks with Eye Beams that manifest themselves as a short row of rings flying in the player character's direction. The last ring in a row is pink, allowing Cuphead and Mugman to parry-slap it.
* EvilLivingFlames: During one phase of his battle, he opens his mouth and stretches out his tongue, and a marching band of flames walks out.
* EyeBeams: His first phase has him firing rings from his eyes at you.
* FatFlex: In his first phase, he breathes {{fireballs}} by lifting his gut while inhaling and releasing it when he spits the flame.
* FeatherFingers: A slightly more justified bat-winged example. The gesture he makes during the opening is done with his wings and his actual hands.
* LaughingMad: He unleashes a bellowing laugh once he transforms into his final phase, and all three heads perform various comical smiles.
* MultipleHeadCase: He grows two extra heads for the final phase of the fight.
* OneWingedAngel: After taking enough punishment from the boys, he suddenly grows two extra heads.
* PlatformBattle: His fight consists of you shooting him while jumping from one moving cloud to the next.
* PlayingWithFire: Aside from [[BreathWeapon the obvious]], which he uses in his first and third phase, his second phase has him opening his mouth and sending out fire soldiers along his tongue, creating a makeshift pit of death below you as you keep hopping from cloud to cloud. What's more, a few of the soldiers will jump toward you, which you must likewise dodge.
* PorkyPigPronunciation: All of his win quotes have him stuttering.
* ShoutOut: His first form's design and moveset resembles the Mecha Dragon from ''VideoGame/MegaMan2'', with his final three-headed form adding in aspects of [[Franchise/{{Godzilla}} King Ghidorah]] for good measure, while his name itself is an homage to legendary Fleischer animator Creator/GrimNatwick; he even has a pronounced stutter in his game-over quotes, [[https://twitter.com/AtroxChobatsu/status/914206756665884672 much like the real Grim did]].
* SpeechImpediment: As you can tell with all his quotes, he has a stutter.
* SpreadShot: In the third phase, his flame projectiles explode into a cross-shaped 4-way spread if they're damaged. Moreover, they also draw in your Chaser shots.
* StationaryBoss: He doesn't move during any of his phases, though he shifts to the left side of the screen after the first.
* TailSlap: He will sometimes try to stab you with his tail in the first phase.
* VictoryFakeout: An especially nasty one. Made it through the flame-soldier phase with 1 HP? Watch him cough and wheeze and cringe and... [[OhCrap grow two extra heads that make faces at you while the sky itself darkens in utter terror]].
* WeaksauceWeakness: Very downplayed, but the Lobber weapon is probably the best to use against him. Grim is massive enough that the curve of the projectiles is no issue in the first phase, and becomes a blessing during the second phase (where you want to stay on the highest clouds to avoid his flaming minions, but if you're too high up, you cannot damage him with the Peashooter). The curve also helps in his last phase, making it less likely to accidentally detonate his fire bubbles, and letting the player keep a healthy distance on the highest clouds to avoid his flamethrower attack.
[[/folder]]

[[folder:Wally Warbles]]
[[quoteright:224:https://static.tvtropes.org/pmwiki/pub/images/wallywarbles.png]]
->''"I own the air — I fly where eagles dare!"''\\
''"My dad's the brawn and I'm all brains! Together, we bring the pain."''
A bird who lives within a cuckoo house, and the boss of "Aviary Action". After he takes a beating, his son, Willy Warbles, comes out of the birdhouse to attack you. You fight them in the skies.
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* AlliterativeName: '''W'''ally '''W'''arbles and '''W'''illy '''W'''arbles.
* AndShowItToYou: A case where Wally literally coughs up his own heart to attack you.
* BrainsAndBrawn: A dynamic that Wally shares with Willy, even lampshaded if the latter beats you.
* BulletHell: The second phase of the fight has Wally flap wildly and send his feathers all over in a spread, everywhere.
* ClippedWingAngel: Played with. Most of the debtors turn into fearsome abominations for their last stand... but Wally instead arrives flightless and featherless in a stretcher. Gameplay-wise, however, he is no less deadly, being able to unleash an utter onslaught of bullets with the help of his doctors.
* DeadlyDoctor: The paramedics carrying Wally in a stretcher during his final phase will assist him in battle by spitting pills at you.
* {{Determinator}}: Even when you destroy the house around Wally, he ''still'' comes back, featherless, being carried by two medic birds, and attacks by not only turning his head into a trash can to spew trash at you, but also ''kicking his stomach, which shoots his heart out of his mouth'' to fire projectiles at you. Considering that you just recently defeated his son, [[PapaWolf no wonder he's pissed]].
* EatenAlive: Presumed to be Wally's fate when beaten, as the medic birds are seen pouring salt and pepper on him with hungry looks in their eyes, and that he is among the few characters not present in the game's closing scene. But WordOfGod states that he's still alive.
* EggLayingMale: Despite being a male bird, spits out eggs as a main weapon.
* EnfantTerrible: Willy is as deadly as his father is, and arguably more malevolent.
%%zce* {{Expy}}: Of Sindbad's giant Rokh from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''
* FeatherFlechettes: Wally does this in the second phase of his attack by flapping wildly and sending feathers at you. By the end of the phase, he's run out of feathers.
* FlunkyBoss: Wally's first and second phases has him accompanied by birds with nails on their heads who fly at you. The fourth has the medic birds spit out pills that turn into homing shots and fly at you.
* GadgeteerGenius: Willy during the third phase, who presumably built the hovering, spiked invulnerable eggs surrounding him, his raygun, and possibly even the birdhouse that protects his father.
* HighPressureEmotion: At the start of the second phase, Wally's anger [[RageBreakingPoint reaches its tipping point]], and he sounds off like a steam whistle, with his head even briefly turning into one for good measure!
* HumiliationConga: Hoo boy, Wally took it much worse than other bosses in the game. Over the course of battle, he ends up losing his house, gets defeathered, has his son get beaten up, and then he himself gets beaten unconscious as his own medics decide to eat him alive, while the ones who gave him said beating take his soul contract to deliver it to the Devil who would gladly reclaim his soul.
* InstantlyDefeatheredBird: After beating him in the second phase, Wally ends up losing all his feathers and falls out of his house. Doesn't stop him from coming back in the final phase.
* MisterSeahorse: Wally can apparently produce eggs.
* OrbitingParticleShield: Willy is surrounded by spiked eggs that constantly circle him, moving closer in then farther away.
* OverlordJr: Willy takes over for the third phase and attacks you with a ray gun and orbiting spiked eggs.
* PapaWolf: Despite being left injured and naked from the first two stages of the fight, hearing Willy cry for help gets Wally to confront Cuphead while two medic birds carry him on a stretcher.
* PerpetualFrowner: In contrast to most of the other bosses, Wally spends basically the entire battle angrily scowling. The closest thing to a smile he's seen with is if you lose to his final phase.
* {{Projeggtile}}: Spitting eggs is Wally's main form of attack in the first phase. Later, in the third phase, Willy employs a telekinetic OrbitingParticleShield variant of the same eggs.
* RageBreakingPoint: While he almost never looks happy, Wally's second phase is initiated by him turning his head into a steam whistle, and his only attack is to send a storm of his own feathers out while screaming in anger.
* Music/RideOfTheValkyries: Played briefly during their theme music, 'Aviary Action'.
* ShoutOut:
** Wally's temper tantrums during the second phase are reminiscent of Donald Duck's own fits of rage.
** Wally's color scheme and elongated beak are also similar to Woody Woodpecker. They, and Willy, all even have alliterative names beginning with W.
* SpreadShot: Wally has ''several'' — during the first phase, the eggs he spits out explode into a spread of three (five on expert) when they hit the left side of the screen, and his FingerGun head transformation can fire out a spread of two to three bullets. His second phase uses a massive spread of FeatherFlechettes on the player characters.
* ToothyBird: Both Wally and his son have beaks full of teeth. Willy's are most visible when he grins right before firing his gun.
* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. It was never confirmed or denied whether he was eaten or did he manage to survive. If the fact he is absent from the good ending is any indication, his fate might not be a pleasant one.
* VisualPun: Wally's attack in the fourth phase where his head morphs into a trash can and spits out trash to shoot you out of the sky. He's literally talking trash at you.
** Another attack in his final phase while he's being carried by paramedics has him kick up his own heart to attack you. In other words, it's his heart attack.
* VoluntaryShapeshifting: Wally can turn his head into [[FingerGun a hand to fire out bullets at you]]. In the final phase, he turns his head into a trash can to spew trash projectiles at you.
* WakeUpCallBoss: Wally is the first shoot-em-up boss that is likely to give players trouble; his attacks are a fair bit harder to avoid, he throws quite a few curveballs with the variety in his projectiles and forms, and has a far higher density of bullets to avoid than Hilda or even Djimmi, making him a test of spacial awareness and quick reaction time. His final phase also highlights the importance of your secondary weapon in plane battles, as the bombs can help you hit targets you can't easily reach or destroy with the default shot.
* WhatHappenedToTheMouse: Neither Wally nor Willy are seen in the ending.
[[/folder]]

!!!Inkwell Isle Three
[[folder:Rumor Honeybottoms]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/rumorhoneybottoms.png]]
->''"Hey sugar, this honey is off limits. Now scram."''
A queen bee fought in an office building for bees (naturally) in "Honeycomb Herald".
----
* AnimalStereotypes: She's the Queen Bee and fought in the hive, a company building with exhausted drones who will defend their queen with their lives.
* TheBadGuysAreCops: Before the Queen fights you, you have to fight one of her hive's police officers first. If he defeats you, he accuses you of attempting a honey heist.
* BeeAfraid: She's very dangerous and is not handing over her Soul Contract without a fight... especially when her [[RiseToTheChallenge flooding honey attempts to drown you]].
* BeeBeeGun: One of her attacks consists of spitting bees that look like bullets... or are they bullets that look like bees?
* BigCreepyCrawlies: A honeybee and one of the larger bosses not fought in a plane in the game. The security bee is also roughly human-sized too. [[AllThereInTheManual Concept art shows]] that her bottom half is even more human-like, with legs in high-heels, and her "abdomen" is, indeed, a very flouncy dress.
* ChainsawGood: Her circular saw attack late in the game.
* EvilLaugh: One in her plane phase, when she uses her buzzsaw attack.
* FingerWag: Does this from off-screen during the second phase (in other words, the first phase where she takes an active role). Pay attention to where her finger pops out from — the rest of her will follow a moment later.
* FlunkyBoss: Her first phase has her summoning a police officer to take you on and some regular bee employees that fly across the screen.
* HornetHole: Fought in a beehive-themed office building.
* ImAHumanitarian: The start of the battle has her looking hungrily at the boys while rubbing a fork and knife together.
* InsectQueen: She's a queen bee. [[GodSaveUsFromTheQueen A dangerous one, too.]]
* LosingYourHead: Sorta. In the second phase, she lowers her head from her body via a chain and dangles it in the middle of the screen to spit projectiles at you.
* MagicStaff: Her giant honey dipper that she wields. She also has a [[SpellBook spell book]] she uses to transform.
* NoblewomansLaugh: In her second phase, fitting for a queen bee. In her final phase, it turns into a deeper EvilLaugh.
* OneWingedAngel: Transforms into a bomber plane in her final phase.
* APigNamedPorkchop: She is a bee named Rumor Honeybottoms, which references honey, the food product that bees make.
* PlatformBattle: A vertical one where you have to keep jumping up on honeycombs to stay ahead of the [[RiseToTheChallenge rising honey]] in the first few phases. The last one has her fly to the bottom of the screen in a plane form and attack you from there.
* RocketPunch: One of her later attacks have her launching fist-shaped missiles.
* ShoutOut:
** She starts the battle rubbing a knife and fork together in hunger, just like [[VideoGame/{{Darkstalkers}} Q-Bee]].
** The bee/bullet projectiles she spits look and move an awful lot like [[Franchise/SuperMarioBros Bullet Bills]].
* SpreadShot: The police officer bee plants bombs that explode into spreads of spiked shots. During the second phase, she may also summon a triangular energy thing that fires shots in 3 directions.
* VisualPun: Her turning into a plane to fight you in the final phase. She's a "Buzz Bomber" "Bee-plane". Or, alternatively, a "[[{{Pun}} Bee]]-17 Flying Fortress"[[note]](which would be era-appropriate, and which she vaguely resembles)[[/note]]. In this phase, she also attacks you by turning one of her wings into a "Buzz Saw."
** The bees work in an office building that's drenched in dripping honey. A sticky business, in other words.
*** The worker bees have a SalaryMan look, in other words: They're office drones.
** The bee police officer that attacks you, if you use period-appropriate British slang, is a [[https://www.britannica.com/topic/bobby Bob]]-[[{{Pun}} bee]].
* VoluntaryShapeshifting: In her final phase, she uses her powers to turn herself into a plane and attacks from the bottom of the screen. Not only does this shoot out projectiles, but she can turn her arm[=/=]wing into a saw to hit you. It should be noted that, unlike almost every other boss in the game, she apparently uses a spell from a book in order to make it happen.
[[/folder]]

[[folder:Captain Brineybeard]]
[[quoteright:232:https://static.tvtropes.org/pmwiki/pub/images/captainbrineybeard_removebg_preview.png]]
->''"Yer skills be like me buried treasure... just a myth!"''
A pirate fought on the docks that can summon sea creatures to help him. The boss of "Shootin' n' Lootin'".
----
* AnimateInanimateObject: The barrel that looms over the player, and the ship itself.
* AttackTheMouth: To defeat the Brineybeard's ship, the player is required to attack the uvula, located in the ship's mouth.
* BaitAndSwitchBoss: Basically the only straight example in the game. The final phase isn't against him, but instead his ship.
* TheBeastmaster: Similar to Cala Maria, he can call in a variety of sea creatures to assist him.
* CaptainColorbeard: Though, according to a trailer from 2013, he was originally named Captain Silver, averting this trope.
* DeathFromAbove: An environmental hazard in his level is a large living barrel suspended over the dock, which will drop down on Cuphead if he stays under it for too long.
* DressedToPlunder: Hits quite a few of the checks, between his eyepatch, bandana, single hoop earring, and two peglegs.
* EyepatchOfPower: Although it's apparently just for show - though it's hard to see in the middle of the battle, he occasionally peeks out of it, revealing a good eye underneath.
* EquippableAlly: He fires bullets from an octopus that he grabs and uses as a shotgun.
* EvilLaugh: The Captain himself has a pretty hearty one, and the narwhal-boat's final phase laughs at you in its game over card.
* {{Expy}}: Inspired by Sindbad from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''.
* FourFingeredHands: Averted. He's the only character in the game, human or otherwise, to have five fingers on each hand.
* FlunkyBoss: For the most part, it's his ship, barrel, and sea creatures that really attack you, with Brineybeard taking potshots at you on occasion.
* InterfaceScrew: Brineybeard will sometimes summon a squid minion who throws ink on the camera, causing the screen to darken with each glob that successfully hits the boys and makes seeing any incoming attacks much more difficult for a few seconds.
* MakeMeWannaShout: Once Brineybeard's ship takes over in the final phase, it will occasionally [[WaveMotionGun scream out a massive laser]] that engulfs most of the screen.
* NonActionGuy: Despite his big physique, the captain doesn't really do any of the fighting himself, instead relying on his ship and the creatures he summons. Even the one attack in the fight that comes directly from him (shooting pellets from the octopus) still has a minion (the octopus, of course) doing most of the work. He doesn't even fight in the final phase, with his ship taking over as the opponent instead.
* OneWingedAngel: Not the captain himself, but his ship inexplicably turns into a narwhal-whale creature in the final phase of the battle.
* {{Pirate}}: Goes without saying.
* PirateBooty: His Game Over taunt states he ''doesn't'' actually have any buried treasure. It's just a myth, [[TrashTalk just like Cuphead's skills]].
* SeadogBeard: Though contrary to his name, it doesn't look very briney.
* SeadogPegLeg: Concept art shows ''both'' his legs are these, though in the game itself it's hard to see even one, [[https://78.media.tumblr.com/e61bf9a033a3e260d416c516bae2079e/tumblr_oym1m4dIAm1wnrdtzo1_400.png though they're still there]].
* SentientVehicle: The ship itself is sentient and spits out cannonballs in the first phase. In the final phase, it even takes over as the boss.
* SpearCounterpart: As stated above, his attacks and affiliation to the sea are very similar to Cala Maria's.
* StationaryBoss: The captain is stuck on the deck of his ship for most of the fight. Once he gets knocked off, the weak point moves to the ship's uvula but otherwise stays motionless.
* ThreateningShark: He can summon small dogfishes that act as tiny sharks in front of him to attack, and a bigger, more traditional one that will try to bite you if you try to cheese the fight by sitting on the left side of the arena.
* VisualPun: The small brown sharks with chains he summons are ''dogfishes''. Or, put another way, they're ''seadogs''.
* TheUnintelligible: The ship does not have any spoken taunts in its Game Over screen; instead, it simply makes gnarling noises.
-->'''Ship:''' ''"HAW-HAW-HAW-HAW-HAW!"''
* WaveMotionGun: In the final phase, the ship itself can fire one of these from the mouth on its uvula.
* WhatHappenedToTheMouse: In the third phase, the ship turns into a narwhal and throws Brineybeard off of it into the ocean. That's the last you see of him for the rest of the battle. He still shows up in the epilogue, though.
[[/folder]]

[[folder:Sally Stageplay]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/sallystageplay.png]]
->''"Stay away from center stage or succumb to the power of a starlet's rage!"''
An actress you fight on a stage in front of an live audience in "Dramatic Fanatic".
----
* AlliterativeName: '''S'''ally '''S'''tageplay.
* ActionDressRip: Bursts out of her wedding dress before the battle, though she's wearing a different dress underneath.
* ActionMom: Assuming the babies in her second phase are her actual children (which is likely, as they resemble her and her husband).
* AllPartOfTheShow: The whole battle is treated as just part of the play she's in. Her third phase even has her sending out cardboard props at you.
* AnachronismStew: The "play" in her battle starts out rather normally for the time period, but in her third phase, she "transforms" into what is essentially a [[EasternRPG JRPG]] final boss. So despite the game taking place in a 1930s cartoon, her play manages to reference games that would come out about six decades later.
* AnimateInanimateObject: Her parasol seems to have teleportation abilities and can drop pieces of itself and grow them back.
** Sally herself apparently turns into one in the third phase. Despite being a cardboard cutout, she's able to change expressions, clutch her chest in pain when defeated, and taunt you if she beats you.
* ArtShift: In the third phase of her battle, she appears as a cardboard prop, which is drawn with watercolors and LimitedAnimation rather than the usual fluid ink animation.
* AscendedExtra: Not Sally herself so much as her husband; if you take the secret route where you drop the chandelier on him, he goes from being a background element into being an active hazard in the third phase of the fight, blocking off a significant part of the stage floor and sending cherubim to push flame-colored pinwheels across the stage.
* AttentionWhore: Sally certainly seems like this, doesn't she? She calls herself a starlet, tells you not to get in the way of her performance, and in the final phase of her fight, she doesn't even focus on Cuphead; she's too busy drinking up the applause from the audience.
* BadassNormal: Basically the only boss who fights without being assisted by or transforming into some sort of giant monster (or being one to begin with). Additionally, her final form is perhaps the most mundane in the game.
* BattleCouple: She and her husband were originally intended to be this for their battle with the boys. After a post-game update, they can potentially be this in the third phase if you end the first phase by [[VideoGameCrueltyPotential dropping a light fixture on her husband in the first phase]].
* CameBackStrong: Parodied. As part of the play, she "dies" after the second phase, complete with a costume change into an angel outfit and either the actor portraying her husband crying tears of sorrow or a priest bowing down in agonizing prayer if you squished the husband earlier. Then she goes OneWingedAngel, as detailed below.
* CurtainCall: In the patched version, Sally's co-stars will appear in the background to take a bow for the audience during her final phase.
* DramaticWind: At the beginning of the boss battle, you notice that the wind is blowing on her wedding dress and veil as she looks at you with disdain before she makes the ActionDressRip mentioned above (although the battle takes place in a ''stage!'').
* DualBoss: If the secret path of the fight is taken, Sally's third phase will have a cardboard cutout of her husband participating alongside her cutout. Unlike the other secret double-bosses, both of them share the same health and the only thing added is an reoccurring new attack during that phase.
* EnfantTerrible: The babies in the second round can drop their bottles on you. And one of them will push out a "fireball" at you in the alternate third round.
* EverythingsBetterWithSpinning: She'll do a spin dive kick for most of her attacks and send out a spinning parasol in the final phase.
* FallingChandelierOfDoom: In the post-game update, during the first phase of Sally Stageplay's battle, you can stand on the two floating cherubs to lower them down and bring down the chandelier on her husband and squish him, shocking Sally so much that she'll cut the first round short to mourn over him and change the course of the second and third rounds.
* FieryRedhead: While her hair is usually blonde, the valkyrie cardboard cutout of her that serves as the third phase has red hair (and so does she in the death cards when you lose, where she's costumed as one).
* FunnyBackgroundEvent: Get hit in the first phase and her fiancé will do a little heel click. Hit Sally, and he'll tug on his hat. Jump on both of the platforms, and a light fixture will crush him, causing Sally to cut the first phase short to mourn for him and the second phase to take place at a nunnery.
* GigglingVillain: She's constantly cackling and clearly having fun with her battle. [[{{Mooks}} Her babies]] also giggle as they drop bottles on you.
* HenpeckedHusband: The guy that portrays Sally's husband in the "play" just stands in the background acting cowardly, doing little to contribute to the battle except drive his wife in his car (that is, until you bring down the FallingChandelierOfDoom on him in the post-game update, changing the course of the second and third rounds). That being said, [[AwLookTheyReallyDoLoveEachOther she does reward him with a smooch in the epilogue]].
* ImagineSpot: The third phase of the fight can be taken as this.
* LargeHam: Her mannerisms really come off as over the top. She is a stage actress, after all.
* NeutralFemale: Gender inverted by Sally Stageplay's husband during her boss fight; despite [[TopHeavyGuy looking fairly capable]], he runs around uselessly in the background and looks concerned in the manner associated with this trope, while his wife delivers all the beatings to Cuphead. Unused sprites do suggest that he was originally intended to be fought at some point during the battle... and he can be, if you go out of your way to squash him flat as of a post-launch update.
* OneWingedAngel: Also parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the boys, which plays a large part in her BadassNormal status.
* ParasolOfPain: One that's tremendously versatile at that, playing roles like "MookMaker", "teleporter", and "spinning top of death".
* PietaPlagiarism: During her third phase, the cardboard cutout of her husband (if you squished him via FallingChandelierOfDoom) parodies the ''Pieta'' by striking a pose similar to that of the "Rest" part of the Statue of the Gods in ''VideoGame/FinalFantasyVI'' (see ShoutOut below).
* ShoutOut:
** Like the final boss battle in ''VideoGame/FinalFantasyVI'', Sally's third stage begins in the clouds, where she descends from the rafters as a painted angel backdrop sporting multiple purple wings. In the post-game update, the cardboard cutout of her husband you've squished earlier (complete with HolyHalo) also bears [[https://vignette.wikia.nocookie.net/finalfantasy/images/2/23/FFVI_iOS_Rest.png/revision/latest/scale-to-width-down/350?cb=20140815010558 a striking pose similar to that of]] the "[[https://finalfantasy.fandom.com/wiki/Rest Rest]]" part of the [[https://finalfantasy.fandom.com/wiki/Statue_of_the_Gods Statue of the Gods]] in that game. There's even cards in the upper-left corner that display her next attacks.
** Her battle may be a stylistic reference to ''VideoGame/DynamiteHeaddy''. Whereas that game's setting is a puppet show, Sally fights Cuphead during her vaudeville act.
* SlouchOfVillainy: Not done by Sally herself, but her husband is seen leaning on a bed and eating grapes (invoking the Greek god Dionysus) in the alternate path for the third phase, while otherwise contributing little in terms of new attacks.
* SmoochOfVictory: In the ending, Sally can be seen triumphantly planting a kiss on her husband as Cuphead and Mugman announce that they are free from the Devil's debt.
* SmugSnake: Spends the entirety of her final phase smiling smugly as she takes in the audience's applause. Even before that, most of her death-quotes are self-aggrandizement or telling Cuphead to [[GreenEyedMonster get out of her spotlight]].
* StationaryBoss: The cardboard cutout/s in the third phase don't move ''or'' directly attack; all of their attacks come from other places on the stage.
* SternNun: In the alternate second round, there's a nun who appears from window to window at St. Timothy's Nunnery, intending to drop cardboard crosses at you, some of which are pink and parryable.
* TogetherInDeath: A strange sort of in-universe take. She mourns her husband's death on the secret route, and once she is also "killed" at the end of her second phase both of them return as cardboard cut out angels you have to fight.
* TokenHuman: One of only three human bosses, and notably the only battle in the game where you ''only'' fight a human.
* TrashTheSet: Quite literally; in the final phase, the stage is basically a mess as she sends her umbrella after you.
* {{Valkyries}}: She "transforms" into one in the third phase of her battle. We say "transforms" in quotes because it's not actually her; it's a cardboard prop that "casts" spells and is meant to stand in for her as Sally herself recovers for an encore performance. Though, given the sorts of transformations other bosses undergo, it may well be the case that she literally transformed into a cardboard cutout.
* WidowedAtTheWedding: In the Switch and Patch 1.2 versions, if you take the secret route, you end up 'killing' her fiancé/husband by crushing him with the chandelier.
* WingedSoulFliesOffAtDeath: When Sally's second phase is defeated (thus dying in her play), she [[InstantCostumeChange instantly switches into an angel outfit]] and "flies" off the stage on wires.
* YouExclamation: Although a bit hard to hear, she does this during the start of the second phase when she sees that Cuphead and Mugman are still on the stage. It makes more sense if the first phase ended with her fiancé's death.
[[/folder]]

[[folder:Werner Werman]]
[[quoteright:220:https://static.tvtropes.org/pmwiki/pub/images/wernerwerman.png]]
->''"Zis tank is ze ultimate veapon! You vill not vin!"''
A giant rat that controls a tank built from a soup can to fight you. Meanwhile, a massive cat by the name of Katzenwagen watches the battle, and eventually intervenes in the final stretch. You encounter them in "Murine Corps".
----
* AlliterativeName: '''W'''erner '''W'''erman.
* BackgroundBoss: The third phase turns the battle into this once Katzenwagen suddenly decides to have Werner for a snack and goes on to attack you.
* BadassNormal: Werner is an expert machine pilot, and that's all he really needs to fight the Cup Brothers. As a result, he's notably one of only two examples of this in the entire game, the other being Sally Stageplay.
* BambooTechnology: [[spoiler:Katzenwagen aside]], Werner uses a tank made out of a soup can and simple machines which shoots bottlecaps and chewed gum. His second phase also has bottlecaps that act like circular saws.
* CarFu: One of his first phase's attacks is simply running you down with his tank. You can avoid him by using the springboards he tosses out, or with the Smoke Bomb if you have it equipped.
* CatsAreMean: Katzenwagen, who seemingly eats Werner and then sets its sights on you. [[spoiler:In this case, it's a mecha-kitty that's piloted by Werner himself.]]
* CavalryOfTheDead: The third phase has ghost mice backing the Katzenwagen.
* CigarChomper: Werner starts his battle off by lighting a cigar and keeps it in his mouth through the entire fight.
* CoolHelmet: Werner sports a [[https://en.wikipedia.org/wiki/Pickelhaube Pickelhaube]].
* DefectorFromDecadence: The medals in the background of the fight indicate that Werner was born in Austria and he defected to the British during the first world war. The third medal is harder to determine but the dark blue edges of his ribbon indicate that he spent the remainder of his service in the Royal and Merchant Navies (also evident by the ghosts in the 3rd phase of the battle, they either fought alongside him in the war or were ''prisoners of war''). The light blue center of his ribbon indicates that he served in the air force, likely referencing the Battle of Jutland 1916 since it involved Naval Aviation.
* EatenAlive: After beating Werner's second phase, Katzenwagen suddenly knocks down the wall and eats him. [[spoiler:Or so it appears; it's actually a clever method of him entering the mechanical cat and manually controlling it in a last-ditch effort to put the boys down.]]
* EpicFail: The transition from Werner's first phase to his second involves his can tank bringing out a firework, only for the mechanical arm carrying to fail and drop it inside the can, causing it to blow up.
* {{Expy}}: Katzenwagen resembles a pre-ArtEvolution WesternAnimation/{{Tom|AndJerry}} quite a bit. Werner himself resembles [[Characters/ClassicDisneyShorts Mortimer Mouse]].
* FakingTheDead: [[spoiler:After the second phase, he's seemingly eaten by Katzenwagen, which forces Cuphead and Mugman to defend themselves from it. However, Katzenwagen is revealed to be a mecha designed to scare off any intruders or give Werner the advantage]].
* {{Foreshadowing}}: When your bullets hit Katzenwagen in the third phase, [[spoiler:it makes a metal clinking sound]]. Additionally, after Katzenwagen bursts in and eats Werner, the brothers don't get the latter's contract, hinting that [[spoiler:he's still alive]]. Speaking of Katzenwagen, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.
* FunetikAksent: Werner's game over quotes have him speak in an exaggerated German accent.
* GadgeteerGenius: That tank looks like just a soup can on treads, but it's equipped with a cigar lighter, bomb cannon, catapult, firework launcher, and flamethrower. The house is rigged with bottlecap buzzsaws. [[spoiler:And did we mention the giant mechanical cat Werner's got on standby just outside?]]
* HumongousMecha: [[spoiler:It's not very obvious at first, but Katzenwagen serves as Werner's trump card in the final phase of the fight, and is revealed to be one upon his defeat.]]
* HurricaneOfPuns: Nearly everything about Werner is a pun in some way: his name, who he's based off of, the name of his level...
* {{Kaiserreich}}: Werner is based primarily on World War I-era German soldiers, with his Pickelhaube and soup-can tank. He also has war medals and bullet shells hanging around his mouse hole, although a Union Jack flag can be seen near the ceiling, oddly enough, and 2 British medals.
* MacroZone: They are fought in a mouse hole in a giant house.
* TheManBehindTheCurtain: [[spoiler:Werner is revealed to be the one controlling the mecha-cat Katzenwagen, once you beat the third phase.]]
* MeaningfulName:
** [[spoiler:Katzenwagen means "Cat Cart" and it is Werner's last resort in the fight]].
** Werner means "soldier" and he's a veteran of World War 1. Wermin is a German pronunciation of "vermin".
* MegaNeko: Katzenwagen.
* OneWingedAngel: Double Subverted. [[spoiler:What initially appears to be a BaitAndSwitchBoss in the final phase turns out to actually be this.]]
* OurGhostsAreDifferent: Ghost mice that fly out of Katzenwagen's mouth and shoot out parryable projectiles. These are actually spirits who were left trapped inside Katzenwagen's stomach.
* PerpetualFrowner: Werner lapses into this unlike most of the other bosses, though this may just be an animation quirk from the cigar in his mouth. He does, however, smile in the good ending.
* PlayingWithFire: Werner's second phase has him using chair-mounted {{f|ireBreathingWeapon}}lamethrowers.
* PunBasedTitle: The title of their stage is "Murine Corps". "Murine" is an adjective that pertains to the subfamily of old world rats and mice.
* PunnyName: Along with having a case of AccentDepundent, Werner's last name also sounds like the German word "Wehrmann" which is an old way to address soldiers, fitting well with his Pickelhaube helmet. [[invoked]]
* ResourcefulRodent: Werner fights by using a tank that's been made from various household junk (a tin can, rubber bands, and wood) and he was able to turn a bottlecap into a buzz saw.
* RoboticReveal: [[spoiler:When beaten, Katzenwagen's face falls off and is revealed to be actually a mecha piloted by Werner.]]
* RodentsOfUnusualSize: Werner is shown to be roughly the same size as other humans in the ending.
* ScreamsLikeALittleGirl: When Werner can't seem to control his tank anymore and when he gets eaten by Katzenwagen.
* ShoutOut: The whole fight is based off war cartoons and ''WesternAnimation/TomAndJerry''; not only does Katzenwagen bear a striking resemblance to Tom in his early years (when he was known as Jasper), but Werner's screams sound vaguely like [[https://www.youtube.com/watch?v=4eHCxCLYuE0 Tom's]] too. [[GeniusBonus This also makes sense on another level]]: "Jerry" was a common nickname for German soldiers during UsefulNotes/WorldWarI.
** His physical appearance is partially based on [[WesternAnimation/ClassicDisneyShorts Mortimer Mouse]].
** Katzenwagen's attack patterns and Main/RoboticReveal are taken straight from the [[https://www.youtube.com/watch?v=FcmSxIUbVLE Cheshire Cat]] in ''VideoGame/TheAdventuresOfBatmanAndRobin''.
** Katzenwagon's preferred attack method, being a stationary body in the background while using his arms to attack in the foreground, is borrowed from the giant gorilla boss from ''VideoGame/TecmoKnight''.
* SpreadShot: In Werner's first phase, the tank can catapult a spread of random garbage at the heroes.
* TacticalSuicideBoss: You'd expect a military-themed boss to be more, ahem, "tactful".
** Werner's first phase have him launching various debris, before sending his tank in a charging tackle. Problem is, those debris include a pair of spring-loaded platofrms allowing Cuphead and Mugman to leap over his tackling move.
** Then there's the Katzenwagen, which can attack forward (evidenced when it [[spoiler:collects Werner as its pilot]]) and yet chooses to lunge at Cuphead and Mugman from the ''side''.
* TankGoodness: Werner pilots a makeshift tank made from a giant soup can in his first two phases.
* VisualPun: The cannon on Werner's tank shoots literal cherry bombs.
* TheUnintelligible: Katzenwagen does not have any spoken taunts in its Game Over screen; instead, it simply hisses and meows.
* WartimeCartoon: Being a rat with a German accent and pickelhaube helmet, which were often shown in [[UsefulNotes/WorldWarI WW1 depictions]], it can be assumed Werner came from one of these.
* YouDirtyRat: He fights with a homemade tank, [[spoiler:he also created Katzenwagen as a mobile tank]]. Since he's in debt to the devil, it's suggested by the background of his home that the Devil may have assisted him in defecting to the British army during [=WW1=].
[[/folder]]

[[folder:Dr. Kahl and his Robot]]
[[quoteright:223:https://static.tvtropes.org/pmwiki/pub/images/drkahl.png]]
->''"OBJECTIVE COMPLETED. TARGET SCRAPPED."''\\
''"I've got the perfect equation to hinder yer evasion!"''
A mad scientist piloting a giant robot (which is named as the debtor) that fights you in the junkyard in "Junkyard Jive".
----
* AfterTheEnd: His level looks like a utter warzone. Justified, in that the fight takes place in a junkyard.
* AndroidsArePeopleToo: The contract specifies Dr. Kahl's robot specifically, so it is not only autonomous but capable of signing into contracts and ''has a soul''.
* AttackItsWeakpoint: The robot has several of them, its main weakpoint being its own heart.
* BattleshipRaid: His robot's first phase is the only boss in the game with destructible "parts" on its body.
* BulletHell: The final phase has Dr. Kahl take out the gems, which fire massive spreads of bullets ''everywhere''. Thankfully, some of these bullets are pink and parryable among the death-inducing ones in the patched version, so that's a bit of a relief.
* ClothingDamage: After defeating Dr. Kahl in his final phase, the resulting explosion blows all of his clothes off.
* DownInTheDumps: Fought in the junkyard.
* DroneDeployer: One of the first attacks.
* EarlyBirdCameo: While the robot's an Isle 3 boss, a miniature version can be seen in mobile form during Djimmi's fight in Isle 2 if you trigger the alternate route.
* EatingMachine: The robot is seen chewing bubblegum in his intro, blowing a bubble before the match starts.
* EnergyWeapon: Uses two in the first phase against you, one that fires at the last spot you were flying in, and another that takes the whole screen but can be deactivated with a parry to the device emitting it. The gems Dr. Kahl himself has at the last phase also shoot these out on a [[BulletHell smaller but more frequent scale]].
* EvilLaugh: Dr. Kahl delivers a huge one in his final phase when using the gems. The robot itself also lets out some short ones in the first phase.
* FourEyesZeroSoul: Downplayed for Dr. Kahl. Although he wears glasses and uses the power of the gems to attack you, he's more of an AntiVillain, as he and his robot still have souls, [[spoiler:but though the robot's Soul Contract is destroyed in the good ending, the two of them are absent, but at least they are still grateful that they won't have to work for the Devil anymore]].
* GiantScrapRobot: Dr. Kahl's robot is presumably this, if their stage is any indication.
* HumongousMecha: Dr. Kahl's robot itself is a huge robot that he pilots to attack you.
* MadScientist: Looks the part with glasses, a lab coat, wild hair, mustache and beard, and crazy expressions.
* MorallyAmbiguousDoctorate: Unknown what he's a doctor of, but clearly the evil kind.
* NoCelebritiesWereHarmed: His design may reference a caricature of [[Creator/MarxBrothers Groucho Marx]] that was frequently used in late '30s and early '40s cartoons.
* OhCrap: The Knockout animation has the doctor making this expression, upon realizing his robot is about to blow.
* OneWingedAngel: The robot becomes just a head in the final phase, with Kahl now being visible and using magical gems to fight.
* PetTheDog: His ''robot'' is the debtor, not him; he still helps it fight.
* PapaWolf: Implied to be the reason why Dr. Kahl is helping his robot fight against you, he doesn't want his creation face you alone.
* PurpleIsPowerful: A genius scientist with purple hair.
* RidiculouslyHumanRobots: Let's see... it has a heart, a soul, emotions, chews bubblegum, and can feel/express pain. Who knows what else of its personality this war machine is hiding?
* RoboSpeak: Both of the robot's death screen quotes are robotic messages.
-->''"OBJECTIVE COMPLETE. TARGET SCRAPPED."''\\
''"MALFUNCTION. MALFUNCTION."''
* SelectiveMagnetism: One attack in the first phase after the middle part of the robot is damaged is a magnet that pulls Cuphead and Mugman to the bottom-left of the screen, leaving other objects unaffected.
* ShoutOut: His name is a shout-out to legendary animator [[Creator/DisneysNineOldMen Milt Kahl]]. Design-wise, he's a clear one to both [[Franchise/MegaMan Dr. Wily]] and [[VideoGame/SonicTheHedgehog Dr. Robotnik]] — a spiky-haired mad scientist who uses robots and has his own flying capsule (what remains of his robot's head in the final phase even resembles a Wily Capsule), but later uses the power of magical, multi-colored gems and skull-motif bombs to attack you. His robot's design clearly takes after ''WesternAnimation/TheIronGiant'' (as in, the original book's take - Ted Hughes' ''The Iron Man'' -on the Giant's design, not the 1999 movie based on it), and being very close to the boxing robot from ''[[WesternAnimation/ClassicDisneyShorts Mickey's Mechanical Man]]''. His intro also has him [[EyebrowWaggle waggling his eyebrows]] in a similar manner to Dr. Wily.
* SmartPeopleBuildRobots: Dr. Kahl himself, of course.
* SmartPeopleWearGlasses: Wears a pair of lime green glasses.
* SpreadShot: Once the laser on his head in the first phase is beaten, the robot gets the ability to spit out a spread of nuts and bolts. In the third phase, the boss attacks with a BulletHell version of this (whose load is at least lightened a bit in the patched version).
* StationaryBoss: The robot doesn't move in its first phase, but unlike other shoot-em-up bosses, you can't just open fire on it, since it has three weak spots on its body to destroy.
* StealthPun: The robot's weak point in the first phase is a large, metal heart. Looks like the tin man has a heart, after all.
* TinCanRobot: The robot has the classic old-fashioned clunky robot look.
* WhatHappenedToTheMouse: Neither he nor his robot are seen in the ending.
[[/folder]]

[[folder:Cala Maria]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/calamaria.png]]
->''"You are a cutie... I am not sure if I should catch and release!"''
A gigantic mermaid fought over the ocean in "High-Seas Hijinx".
----
* AttackOfTheFiftyFootWhatever: A giant mermaid who basically towers over the two boys and their planes.
* TheBeastmaster: In the first two phases, she fights primarily by summoning sea creatures to attack the two brothers.
* BodyHorror: When using her petrifying gaze, two of the snakes on her loop around to the back of her skull and [[EyeScream emerge from her eye sockets with both her eyes in their mouths.]]
* BreathWeapon: In her first phase, she exhales ghosts that target Cuphead and/or Mugman's position(s).
* CuteMonsterGirl: She's a giant mermaid/gorgon hybrid, and a complete MsFanservice.
* CuteGiant: A gigantic mermaid with large eyes and an adorable smile. Somehow, she still manages to retain some cuteness after turning into a gorgon.
* EquippableAlly: Can obtain two different coloured fish that spit different elemental projectiles at you. The red fish spit {{fireballs}}, while the yellow fish spits a {{homing|Projectile}} [[ShockAndAwe electrified]] dolphin.
* EyeScream: From a distance, Cala Maria's petrifying gaze can look like she's using binoculars to focus the beams it produces. Look closer, and you'll see that two of her snakes are halfway out of her eye sockets, holding her eyes in their mouths.
* EyelashFluttering: Starts her battle by adjusting the octopus on her head and batting her eyes with a xylophone "doink doink!" sound.
* FlunkyBoss: She summons all manner of aquatic life to attack you with.
* {{Gasshole}}: She belches out pirates ghosts as an attack.
* GiantWoman: Well, giant mermaid, but she's one of the most human-like characters of the game.
* GigglingVillain: Lets out a high-pitched giggle everytime she dives underwater to weaponize a giant fish. She outright cackles after transforming into a gorgon.
* GoodScarsEvilScars: Averted. She has what looks like some type of scar on her left arm if you look. It doesn't really make her any less attractive or look like any sinister markings. And as for the evil part, well, as noted above, she and the other bosses aren't necessarily evil, just trying to save their souls.
* GorgeousGorgon: Turns into a gorgon after taking enough damage, yet still doesn't look that bad despite the scary upgrade.
* HartmanHips: She's got some nice wide hips, and they're in constant motion too!
* LosingYourHead: The final phase of her fight has her detaching her head from her body and floating though a spiked cave.
* MsFanservice: She's quite the dish and she knows it. Her Gorgon form doesn't look too bad either. [[GorgeousGorgon As noted above]].
* NonStandardCharacterDesign: Compared to the other female characters, like Sally Stageplay and Baroness von Bon Bon, Cala Maria has a figure and flaunts it.
* OhCrap: When she uses a giant fish to send projectiles at you (some of which are pink and parryable in the patched version), she reacts in this way when it slips out of her hands. A more pronounced such reaction follows just before her eels shock her and trigger her second phase.
* OneWingedAngel: As mentioned several times, her gorgon form. Her floating head phase is more of a ClippedWingAngel due to not being as powerful and relying more on the surrounding environment to hurt you.
* OurMermaidsAreDifferent: About fifty feet tall, wears an octopus, can turn into a gorgon...
* PainfulPointyPufferfish: She can summon them to damage the players.
* PsychoElectricEel: Two of them appear during the 2nd phase, turning Cala Maria into a gorgon. More show up to assist her in battle too. And they shoot many bullets, some of which are pink and parryable in the patched version.
* PunnyName: Besides the obvious "calamari" pun, Calamaria is a species of snake, and Cala Maria is a beach in Spain, so it's a pileup of puns!
* PurpleIsPowerful: She's got purple "hair", lavender-tinted skin, and she's a powerful foe.
* SeashellBra: Befitting a mermaid.
* ShoutOut:
** One to ''VideoGame/{{Parodius}}'', which likewise featured a giant mermaid with a green tail as a boss in ''Gokujyo Parodius''. And a giant gorgon boss in a later game, ''Sexy Parodius'', which itself was a shout out to ''Franchise/{{Castlevania}}'', since it was virtually a giant Medusa Head[[note]]both ''Parodius'' and ''Castlevania'' were made by Creator/{{Konami}}[[/note]].
** Additionally, when her body turns to stone in her last phase, her head breaks off first, and then her arms. This causes the resulting torso to resemble the famous incomplete statue of Venus de Milo.
** The sea turtle she summons in her first phase looks like a very angry Toby Tortoise from Disney's ''WesternAnimation/SillySymphonies'' (specifically "WesternAnimation/TheTortoiseAndTheHare"), and his fisticuffs pose alludes to the boxing match held in "Toby Tortoise Returns".
* SnakePeople: She takes on some serpentine features once she turns into a gorgon, gaining fangs, snake-like eyes, and a forked tongue. Even in her first phase, her undulating movements evoke the spirit of the trope.
* SpreadShot: Her first phase can use a spread shot via a red fish "weapon" (some of whose bullets are pink in the patched version), and can also call in a turtle that fires mines into the air that explode into 8-way spikes. Her second phase has the respawning electric eels that fire spreads of 5 (some of which, again, are also pink via patch).
* StationaryBoss: Only during the second phase, where she loses the ability to retreat underwater.
* SwallowedWhole: Implied. She uses ghosts of dead sailors as a BreathWeapon.
* TakenForGranite: In her gorgon form, she can fire out a huge beam that'll turn our heroes into stone, which will put them in danger of getting hit by a real bullet if they're not quick to break out of their stoned forms. This eventually gets turned on her in her second-to-third phase transition, where her whole body (sans her head) turns to stone and crumbles into the ocean, forcing her to detach her own head and continue battling the boys. In simple difficulty, her entire body becomes completely petrified after her defeat.
* TheTease: Not only does she pose before the boys in her intro, but her game over card in her first phase definitely has her flirting with them too.
-->"You are a cutie... I am not sure if I should catch and release!"
* TentacleHair: She has an entire octopus adorning her head, its tentacles forming her hair. When she transforms into her [[{{Medusa}} gorgon]] OneWingedAngel form, though, these tentacles become live snakes.
* ThroatSlittingGesture: Shown doing this in her first phase game over card, as seen in her page image.
* UnexplainedRecovery: By the time you get to her third phase, her body has been completely shattered aside from her head, which is now floating. And this is not even taking in an account her gorgon transformation. The ending shows that she's fine, back to her initial appearance, and also much smaller, [[YourSizeMayVary apparently no taller than Cuphead and Mugman]].
* WorldsSmallestViolin: When she's beaten in Regular Mode, one of her snake hairs plays a tiny violin.
* XRaySparks: When being electrocuted by the eels during the transition into the second phase.
* YourSizeMayVary: She's absolutely enormous during her battle, but relatively normal-sized in the ending.
[[/folder]]

[[folder:Phantom Express]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/phantomexpress.png]]
->''"I can... see... into the future. You... will be... counting worms."''\\
''"All aboard!! Next stop — your funeral."''\\
''"Sorry! This train is only for the dead... but we can help you with that."''\\
''"What a glorious night for me to bring the fright!"''
A haunted train comprised of the Blind Specter, an eyeless ghost; the Conductor, a skeletal conductor; the Lollipop Ghouls, two giant animate pistons; and finally, the train's living engine, the Head of the Train. You fight them on a rail cart in "Railroad Wrath".
----
* AfterlifeExpress: Inhabited by many spectral beings who attack you.
* AnimateInanimateObject: In the third phase, the heroes fight against a pair of train pistons with faces protruding from the wagons, and during the final phase, they fight the train's engine.
* AttackItsWeakPoint: In the final phase, you must parry off the engine's tail to expose his boiler core and shoot at that.
* BiggerOnTheInside: It must be, considering the Conductor and the Lollipop Ghouls only partially emerge from the train cars.
* BlindSeer: The Blind Spectre's game-over quote invokes this, though it's not clear if this is just his way of trash-talking our heroes.
* BreathWeapon: The Lollipop Ghouls in the third phase attack you by breathing columns of [[ShockAndAwe lightning]].
* DeathFromAbove: The Head of the Train has many of these attacks, since he's galloping after you on stilt legs. Not only can he drop [[BadWithTheBone rings made of bone]] on you, but if you open his boiler core, the hot coals inside will also start dropping on your head.
* DemBones: The second phase sends out the Conductor, a giant skeleton conductor to try and crush you.
* DiscOneFinalBoss: The final runaway debtor that you need to get a contract from, but the game isn't over just yet.
* EveryoneCallsHimBarkeep: The Conductor has no official name aside from...well, the Conductor.
* EyesDoNotBelongThere: The Blind Specter in the first phase has eyes it can shoot out from its palms... and yet ironically, it never has an eye in its actual socket.
* EyelessFace: The Blind Specter's one eye socket is completely empty at all times.
* GhostTrain: The Phantom Express is a creepy living train who carries a ghost, a skeleton conductor, and two lightning-shooting creatures through a dark forest.
* HighSpeedBattle: You spend the whole fight racing alongside them in a rail cart with parryable controls, while continually-appearing minions try to mess with your positioning.
* ImpliedDeathThreat: Every phase except the final does this in their respective game over quotes.
* SentientVehicle: Aside from the fact that the train ''owes the Devil its soul'', the train engine itself attacks the heroes in the final phase.
* ShoutOut: The final phase could be one to Sleeper Brakeman's fight from ''VideoGame/NoituLove 2'', involving a train engine on legs with an object at its back which has to be hit in order to make the boss vulnerable. Doom Train from ''VideoGame/FinalFantasyVI'' may also have been an inspiration, since you start fighting the "guests", then the conductor and finally the train itself. Even the Game Over text claiming it is meant only for the dead is something said once in Final Fantasy 6 when the group arrives at the train station.
* SpiderTank: At the final phase, the engine stops the train to reappear galloping like a horse with [[RubberHoseLimbs spindly legs]].
* StationaryBoss: Unlike the other parts of the boss, the Blind Specter stays on the right side of the screen and doesn't require moving the handcart to hit it. It compensates by tossing eyeballs that can block shots and spawning pumpkin enemies that can ''parry'' the pink handles at the end of your cart, either yanking it out from under you while you're in mid-air, or sending it straight towards the Specter itself.
* WhatHappenedToTheMouse: The Head of the Train, the Conductor, and the Lollipop Ghouls aren't seen in the epilogue (indeed, the latter are seen melting upon defeat). The Blind Specter from the first phase does, though, perhaps on behalf of the entire train.
* WrongSideOfTheTracks: Their tracks, that is - Inkwell Hell is just on the other side on the map.
* {{Youkai}}: All of the ghosts inhabiting the Phantom Express are subtly based on different types of youkai. The Blind Specter is based on ''tenome'', an eyeless old man with eyeballs on his hands; the Conductor is based on ''{{gashadokuro}}'', a giant skeleton; the Lollipop Ghouls appear to be based on ''rokurokubi'', women that have long serpentine necks; and the Head of the Train is based on ''oboroguruma'', oxcarts with faces found on roads late at night.
[[/folder]]

!!The King's Court
[[folder:General]]
A set of nine minibosses that are under the command of King Dice. You have to fight a few of them in order to finally fight King Dice himself.
----
* AnimateInanimateObject: Among the Court is a trio of alcohol filled cups, a stacked pile of chips, a cigar, a two faced domino, a ballerina roulette wheel, an 8 ball and a toy monkey waiting for you to fight them.
* AnthropomorphicVice: The Tipsy Troop and Mr. Wheezy represent drinking and smoking, respectively, whereas the others, inluding Chips Bettigan, Phear Lap and King Dice himself, represent various forms of gambling.
* ObviouslyEvil: Unlike the debtors, who can be classified as [[AntiVillain Anti-Villains]], as King Dice's lackeys they clearly don't have much in the way of a moral compass and are fighting the boys to hinder their progress.
* OptionalBoss: A skilled player can manipulate the dice enough to only fight just three of them, but those seeking a ''real'' challenge can battle all nine.
* PunchClockVillain: Seeing as how many of them seem to be animate forms of various aspects of gambling, it's probable that for these nine minibosses, they're simply doing their job.
* QuirkyMinibossSquad: They don't even have multiple forms; they're all just stepping stones to get to King Dice.
[[/folder]]

[[folder:Tipsy Troop]]
[[quoteright:240:https://static.tvtropes.org/pmwiki/pub/images/tipsytroop.png]]
->''"Go sleep *hic* it off...you look a little *hic* rough!"''
Ginette (a martini), Ol' Ethan (a shot glass filled with whiskey) and Rumulus (a bottle of rum), all fought on a regular table.
----
* AlcoholHic: These guys hiccup while they talk in their Game Over quotes, due to the alcohol in their bodies.
* AlliterativeName: The '''T'''ipsy '''T'''roop.
* BigThinShortTrio: Rumulus is big, Ginette is thin, and Ol' Ethan is short.
* DeathFromAbove: Rumulus shoots out streams of booze into the air which then falls on your position.
* DrunkenMaster: All of them appear quite tipsy on themselves, and this reflects in their losing animations -- Ginette becomes dizzy and disoriented, Ol' Ethan gets sentimental and weepy, and Rumulus turns raucous and loud. In spite of this, they can be one of the trickier fights to deal with thanks to the density of the amount of things waiting to hurt the player (Rumulus's DeathFromAbove, Ol' Ethan's ground-sweep, and Ginette's [[MookMaker endless flying olives]] taking up airspace).
* DualBoss: Taken an extra step since you fight against three here.
* EdibleThemeNaming: All based on alcoholic drinks (gin, rum, and ethanol - the actual alcohol in them).
* FlunkyBoss: Ginette summons flying olives who shoot their eyes at you.
* GrimyWater: Ol' Ethan attacks by spilling booze out of himself across the tabletop at you.
* LadyDrunk: Ginette resembles one.
* MookMaker: Ginette serves as one of these with the aforementioned flying olives.
* StationaryBoss: They stay to the right of the screen at all times, never really trying to move toward you. Then again they're all rather drunk on themselves so...
* TurnsRed: Inverted -- as you progress through the battle, the trio will fall one by one, making the fight get progressively easier.
[[/folder]]

[[folder:Chips Bettigan]]
[[quoteright:218:https://static.tvtropes.org/pmwiki/pub/images/chipsbettigan.png]]
->''"Hey short stack! This isn't a place you wanna be hanging 'round."''
A stack of poker chips fought on a card table.
----
* AttackItsWeakPoint: Only the blue stack of chips where his face is can be damaged by the player's attacks.
* {{Cowboy}}: Seems to evoke this image, what with his Stetson, yee-hawing and constant galloping motions.[[note]]A reference, no doubt, to Texas Hold 'Em being ''the'' poker-chip game in America.[[/note]]
* DetachmentCombat: Separates his body into different segments that you then have to dodge.
* NiceHat: Wears a nice Stetson on his head.
* PunnyName: His first name is pretty obvious, given what he is. As for his surname... well, just say it out loud.
* ShoutOut: His main attack resembles that of the signature move of the Devil series bosses from ''Franchise/MegaMan''.
[[/folder]]

[[folder:Mr. Wheezy]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/mrwheezy.png]]
->''"Looks like you could use some fresh air."''
A giant cigar you fight on two ashtrays over a pit of flames.
----
* BattleAmongstTheFlames: His fights take place right above a pit of flames.
* EvilIsBurningHot: He's fought above some flames and he can attack you with {{Fireballs}}.
* EvilSoundsRaspy: Due to being a living cigar, his voice is as coarse and raspy as a frequent smoker's voice would sound.
* {{Fireballs}}: Spits out fireballs during his battle.
* FlunkyBoss: Smaller winged cigarettes fly in the middle of the stage, making it difficult to jump between platforms.
* GoodSmokingEvilSmoking: Definitely evil, considering he's literally a living cigar under the employ of the Devil's [[TheDragon Dragon]].
* MeaningfulName: Wheezing is one of the natural results of smoking for lengthy periods of time, after all.
* OneToMillionToOne: Every so often, he'll burn ''himself'' up and reform from the ashes on the other ashtray.
* ShoutOut: To Music/CabCalloway, especially notable in his picture on the right; it's an expression Cab made and had photographed many times, [[http://e-cdn-images.deezer.com/images/artist/1f32653ae25880d6839313dbc9ddbce1/500x500.jpg like so]].
* VaderBreath: He constantly coughs and wheezes during his fight, more so after being defeated.
* VillainTeleportation: Going hand-in-hand with his ash-regeneration technique.
* YouHaveFailedMe: When beaten, King Dice [[GiantFootOfStomping stomps on him]] for his failure. Also doubles as a StealthPun; what's the most common method people use to put out a cigarette?
[[/folder]]

[[folder:Pip and Dot]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/pipanddot.png]]
->''"You set them up, I'll knock them down."''
A domino with a male half on top and a female half on the bottom. You fight them in a room with a conveyor belt pulling you toward a wall of spikes.
----
* AmazingTechnicolorBattlefield: Notably one of two bosses in the Dice Palace that fight you in one of these, and the only one where ''what'' it's supposed to be is very vague, being some sort of strange void with domino tiles floating, appearing, and disappearing everywhere (although it could be interpreted as a dominoes board).[[labelnote:*]]According to the artbook, the initial plan was for the fight to take place in the casino's power room, or some other behind-the-stage room.[[/labelnote]]
* ArcNumber: 4. They have four eyes in total (which are reminiscent of dots on dominos), and they're fought if you land on space number 4 on King Dice's board.
* BattleCouple: They fight together as one boss, and their designer Tina Nawrocki considers them a married couple.
* TheCameo: In the "King Dice" clip for ''The Cuphead Show!'', they make an appearance in the audience.
* EyelashFluttering: Dot starts the battle by looking up at Pip and batting her eyes with a xylophone tinkling sound, while Pip looks down at her and tips his hat.
* FlunkyBoss: Occasionally, Pip will release small domino-bird creatures from his top hat, which will circle around the battlefield before leaving.
* HenpeckedHusband: Pip gets kicked in the face by Dot when they lose the battle.
* MoreTeethThanTheOsmondFamily: Their middle section holds a third mouth that has many fangs in the middle of it.
* MultipleHeadCase: Both the male and female faces have separate personalities.
* NiceHat: Pip wears a blue top hat, which he tips to you before the battle begins.
* PunnyName: A "pip" and a "dot" are both terms that refer to the dots on a domino.
* ScaryTeeth: Their middle section opens up to reveal a mouthful of razor-sharp teeth, from which they spit d20-die-shaped projectiles at you.
* ShoutOut: The ConveyorBeltODoom in their boss battle that pulls you toward a spiked wall is a reference to the 1931 cartoon ''WesternAnimation/BimbosInitiation,'' in which Bimbo was faced with a similar trap.
* TertiarySexualCharacteristics: Cleverly, the bow in the center pulls double duty: it serves as a masculine bow tie for Pip and a feminine bow for Dot. The latter also has prominent eyelashes.
* YouHaveFailedMe: Humorously, not from King Dice, but from Dot, who kicks Pip in the face for losing.
[[/folder]]

[[folder:Hopus Pocus]]
[[quoteright:223:https://static.tvtropes.org/pmwiki/pub/images/25_hopus_pocus_removebg_preview.png]]
->''"...and PRESTO!! The cup has completely disappeared."''
A crazed rabbit magician fought in a room with playing cards.
----
* {{Expy}}: Based on the WesternAnimation/BugsBunny prototype from the cartoon ''Prest-o Change-o''.
* HairRaisingHare: He's an evil rabbit magician. Interestingly, he ''averts'' KillerRabbit in all but the most literal sense; he's at least twice the size of our heroes, and makes absolutely ''no'' effort to look cute.
* LaughingMad: Begins laughing as soon as the battle begins, and won't stop until either himself or you are defeated.
* MagiciansAreWizards: A magician rabbit that can use magic to attack.
* MoreTeethThanTheOsmondFamily: And far, ''far'' more teeth than any rabbit should have, let alone sharp ones.
* PlayingCardMotifs: Similar to King Dice, one of his attacks is a wall of of bubble-like projectiles that advance through the battlefield, shaped like the four card suits. The heart bubbles are colored pink and thus are parry-able. Additionally, an Ace of Spades card is provided on the battlefield as a platform for you to stand on.
* PullARabbitOutOfMyHat: How King Dice "summons" him at the start of the battle.
* PunnyName: Based on the words "Hocus Pocus" and "hop."
* RabbitMagician: He's a magician rabbit that can use magic tricks to attack.
* SlasherSmile: He sports a ''very'' demented grin throughout the entirety of his battle. His smile seen on his game over card (see the image) is even ''more'' crazed looking.
* StageMagician: His motif; he uses his magic to send projectiles at you.
* StationaryBoss: Sits in his top hat for the entire fight.
[[/folder]]

[[folder:Phear Lap]]
[[quoteright:227:https://static.tvtropes.org/pmwiki/pub/images/26_phear_lap_removebg_preview_5.png]]
->''"This derby is over and the results are in. Last place...YOU!"''
A skeletal racing horse who is fought via planes above a haunted horse racing track.
----
* DemBones: Again, he's a skeleton horse.
* {{Expy}}: Despite being skeletal, he bears quite a resemblance to [[WesternAnimation/ClassicDisneyShorts Horace Horsecollar]].
* FlunkyBoss: Pay attention to the skeletal jockeys at the bottom of the screen - the cloaked ones will fly up at you once they get underneath.
* HellishHorse: A skeletal racehorse.
* InterfaceScrew: Phear Lap's racetrack has the most obstructive foreground setting of any arena in the game, and the artbook confirms that this is an intentional design choice in order to disrupt the player's view of the fight.
* ShoutOut: His name is one to the famous racehorse, [[https://en.wikipedia.org/wiki/Phar_Lap Phar Lap]].
* SpreadShot: The giftboxes he fires out explode into an 8-way spread of horseshoe projectiles.
* StationaryBoss: While his bucking affects the position of his hitbox, he is otherwise the least mobile plane boss in the game.
* VisualPun: Attacks by launching giftwrapped boxes that explode into horseshoes from his mouth, in a play on the phrase "[[ComplainingAboutThingsYouHaventPaidFor Looking a Gift Horse in the Mouth]]". Additionally, this fight has you literally beating a dead horse.
[[/folder]]

[[folder:Pirouletta]]
[[quoteright:223:https://static.tvtropes.org/pmwiki/pub/images/pirouletta.png]]
->''"Ah-ha! You've noticed that my style is very Russian!"''
A fairly tall roulette wheel who's likewise a ballerina. Fought on a roulette betting table.
----
* DanceBattler: Dances across the area where you either must use the poker chips to jump over her or dash through her. When she spins, she throws out roulette balls which can hit you.
* DeathFromAbove: As mentioned above, said roulette balls fall from the top of the screen.
* GagNose: She's got quite the honker on her face.
* PunnyName: A portmanteau of the words "pirouette" and "roulette".
* StatuesqueStunner: Very tall and lanky, yet oddly pretty too.
* StealthPun: She's a roulette wheel who claims to have a "very Russian" style. [[RussianRoulette Think about it]].
[[/folder]]

[[folder:Mangosteen]]
[[quoteright:224:https://static.tvtropes.org/pmwiki/pub/images/mangosteen_18.png]]
->''"Fault, scratch and choke -- are you trying to hustle me?"''
A giant eight ball fought on a pool table.
----
* AmazingTechnicolorBattlefield: Where he's fought is less of a pool table and more of a bizarre pool dimension.
* ArcNumber: 8, of course. He is a living eight-ball, and you fight him if you land on space number 8 on King Dice's board.
* BadGuysPlayPool: In this case, bad guys '''are''' pool.
* BodyHorror: He's just eyes and a mouth over an eight-ball, which looks very disturbing. Even more so in his defeated animation, which reveals his "body" is actually a mass of floating ink. Creepy.
* EdibleThemeNaming: Named after the mangosteen, a round, purplish-black fruit.
* FlunkyBoss: He is aided by blocks of cue chalk which drop down from the side of the screen and bounce across the area.
* ShoutOut: His design is a reference to Melon Bread from ''VideoGame/GunstarHeroes'' and other ''Creator/{{Treasure}}'' games, which inspired Cuphead. Indeed, analogous to his inspiration (who's named after a fruit-based food), he's named after a fruit. He even fires a single ball of energy as his sole direct method of attack, just like his inspiration. Additionally, while pool does have some luck elements, he's also based off of the Magic 8-Ball, which is a game of luck as you hope it reveals a good fortune for you when you shake it.
* StationaryBoss: The cue chalks handle the ground for him; he just floats still above the table, occasionally firing energy blasts.
* WaterfallPuke: He barfs out black goo upon his defeat... which, judging from how his body seems to be melting as he does so, means he's quite literally vomiting himself.
[[/folder]]

[[folder:Mr. Chimes]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/mrchimes.png]]
->''"Monkey see, monkey doom."''
A toy monkey fought via planes in a crane game machine.
----
* AnachronismStew: Despite the game's 1930s setting, Mr. Chimes is based on the cymbal-banging monkey toy, which wasn't invented until the 1950s in real life.
* ArsonMurderAndJaywalking: The various members of The King's Court all represent common casino paraphernalia, such as cigars and poker. Mr. Chimes represents a crane game, which is more common in arcades. That said, crane games are often seen as rigged against the player, which fits with the Devil's other rigged games.
* CymbalBangingMonkey: A toy monkey who's being hoisted around by the claw of a crane machine. When active, he uses his cymbals to send out music notes to try and hit you.
* EyelessFace: His eye sockets are completely hollow.
* HoistByHisOwnPetard: When defeated, the crane holding him starts to move its front two claws to start slamming his cymbals together into his face.
* PuzzleBoss: While deactivated, Mr. Chimes is immune to being shot. In order to attack, the player has to flip two cards in a memory-match mini-game using the parry movement. Matching the wrong pair speeds up the boss' movements, but matching the correct pair will wake him up and expose him to attacks. How long he stays active depends on his current health; the fight is designed so that you'll ultimately have to match all the cards in order to defeat him.
* ShoutOut: Mr. Chimes himself is a toy monkey, and also seen in the crane game are a Godzilla-like lizard and a wolf. WordOfGod is that the three are a reference to George, Lizzie, and Ralph, the three main characters from ''VideoGame/{{Rampage}}''
* SpreadShot: Every time he bangs his cymbals, a spread of 6 projectiles are fired out radially.
[[/folder]]

!Other Characters
[[folder:Porkrind]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/porkrind.png]]
->''"You gots to equip those new purchases if you want to use them. Look at your equip card, ya bums!"''
A pig who runs the shop where you can buy power ups.
----
* {{Expy}}:
** Seems to be inspired by the purple smoking pirate pig from ''VideoGame/WonderBoyIIITheDragonsTrap''; he also sells various liquors, like the dragon bartender from ''VideoGame/WonderBoyInMonsterLand''.
** He also seems similar to WesternAnimation/{{Pete}} in terms of design and voice, especially Billy Bletcher's performance as Pete in early cartoons.
* EyepatchOfPower: He has an eyepatch, and although we never see him get in on the action, he does look pretty tough and burly.
* FaceOfAThug: Being a [[FullBoarAction pig]] with a large physique, eyepatch, dastardly-looking mustache, gruff voice, [[SlasherSmile menacing smile]] (especially on his icon), and [[DarkIsNotEvil some black on his outfit]], he looks like an ObviouslyEvil cartoon villain. But, he in fact helps Cuphead and Mugman by selling them power ups.
* GutturalGrowler: Has a very deep, growly voice.
* JerkWithAHeartOfGold: He rather rudely tells Mugman and Cuphead off for not immediately equipping what they bought from him when you exit his shop for the first time, but he only does it once and he's an indispensable ally for the rest of the game, seeing as he sells the boys their weapons and gear.
* PigMan: An anthropomorphic pig.
* APigNamedPorkchop: A pig named Porkrind.
* ShoutOut: His gravelly "Welcome!" is one to the shopkeep from ''VideoGame/ResidentEvil4''.
* WhatTheHellIsThatAccent: In his voice lines, he seems to have a German or [[HuskyRusskie Russian]] accent. However, his written dialogue after you leave his shop for the first time gives him more of a [[UsefulNotes/AmericanAccents Bronx]] accent.
[[/folder]]

[[folder:Canteen Hughes]]
A canteen who's responsible for maintaining and upgrading Cuphead and Mugman's airplanes, as well as teaching them how to fly a plane.
----
* AcePilot: He's good enough to keep up with the Howling Aces, while keeping the plane steady enough that the Cups can walk on its wings!
* AscendedExtra: Takes an active role in the fight against the Howling Aces, flying the plane Cuphead and co. use as a platform.
* GadgeteerGenius: Implied to have made the planes Cuphead and Mugman ride, and in Isle 2 he fits the planes with a bomb upgrade.
[[/folder]]

[[folder:Quadratus]]
A mysterious being who keeps track of how many times the brothers have failed.
----
* {{Expy}}: He might remind one of the Magic Mirror in ''WesternAnimation/SnowWhiteAndTheSevenDwarfs'', being a disembodied head in a reflective surface dispensing wisdom and knowledge in verse.
[[/folder]]

[[folder:The Four-Mel Arrangement]]
!!!Voiced by: Shoptimus Prime
A barbershop quartet (of barber poles) whose fourth member has gone missing.
----
* AntiPoopSocking: Your reward for finding the fourth member is the quartet singing a song telling you to take a break.
[[/folder]]

[[folder:The Calix Animi]]
An ancient order of heroes alluded to in the ruins of Rugged Ridge.
----
* AmbiguousSituation: Given they are only referenced in one level, it's difficult to say if they are even around in the present day or even what happened to them in the first place.
* CavalryOfTheDead: Ms. Chalice's Super Art 3 has her summon the spirits of the Calix Animi to lay waste to her opponents.
* GratuitousLatin: "Brave / courageous cups" or "living / animated cups", depending on your interpretation, both of which fit them well.
* GreaterScopeParagon: They seem to be the old heroes of Inkwell Isle.
[[/folder]]

[[folder:The Ferryman]]
A compass-headed boatman who appears to deliver Cuphead and Mugman a message from the Legendary Chalice.
----
* WarpWhistle: In addition to being the gateway to the DLC content, he also functions as the game's fast travel system.
[[/folder]]

[[folder:Inkwell Isle 1 Residents]]
The [=NPCs=] that reside within the first Inkwell Isle, consisting of the apple-headed Mac, Quint the coin man, axe-headed Chip, and Angel the fishing goldfish.
----
[[/folder]]

[[folder:Inkwell Isle 2 Fairgoers]]
The [=NPCs=] that appear in the second Inkwell Isle, consisting of Ginger the cookie girl, Lucien the scholarly lightbulb, and Buster the juggler.
----
[[/folder]]

[[folder:Inkwell Isle 3 Cityfolk]]
The [=NPCs=] that you meet in the third Inkwell Isle, consisting of Cora the pirate girl, music rivals Wolfgang the radio and Ludwig the phonograph, Silverworth the socialite fork, and Tully the pacifistic turtle.
----
[[/folder]]

!The Delicious Last Course
[[folder:Chef Saltbaker '''(UNMARKED DLC SPOILERS)''']]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/saltbaker.png]][[caption-width-right:350:[[labelnote:Click here to see his true nature.]]https://static.tvtropes.org/pmwiki/pub/images/screenshot_20220702_163501.jpg ''"When [his/her] soul is baked into the Wondertart, the cosmic powers of the Astral Plane will be mine!"'' ]][[/labelnote]]

!!!Voiced by: Peter [=McGillivray=] ("A Chef's Coda")
->''"Stay on your guard, intrepid cups! Fetching those ingredients will be a test of wit and wills. But remember — like any good bake, heart and soul is the secret ingredient!"''

A chef who resides in Inkwell Isle Four, known as "the best baker in all the lands". Introduced in ''The Delicious Last Course'', he's seeking to bake the legendary Wondertart to bring Ms. Chalice to life, and has Cuphead and Mugman aid him in collecting the necessary ingredients from the inhabitants of the island.\\\

After collecting the ingredients, however, he goes mad with power, and captures one of the three cups to use their soul as the final ingredient of the Wondertart. The remaining two are forced to battle him in "A Dish to Die For" to save their friend.
----
* AllYourPowersCombined: Uses the ingredients the player gathered as weapons against them.
* AnIcePerson: Uses the Icy Sugar Cubes as projectiles in his first phase.
* ArcWords: "[[OminousLatinChanting Caute Cave Mortem]]", as heard in the two themes leading up to his boss fight (one of them even being ''named'' "Caute Cave Mortem" on the soundtrack), as well in the beginning of the boss fight itself. It translates to "Beware of death" or "Be cautious of death", presumably as a warning not to mess with mortality - something that one could do with the Wondertart.
* AttackOfTheFiftyFootWhatever: Chef Saltbaker towers over the cups in his boss fight, and then he uses a mushroom to grow ''even bigger'' - so big, in fact, that it renders his bakery an unstable wreck.
* AxCrazy: He's downright ''unhinged and psychotic'' when his true colors are revealed, in addition to abusing his sentient ingredients with glee and using them as his attacks during the first phase of his boss fight. Essentially, he's just as terrifying as, if possibly moreso than ''The Devil himself!''
* BadassFingersnap: Does this to summon the pepper shakers and signal the start of his second phase.
* BadBoss: The dough and limes in the kitchen that he uses for his attacks are sentinent and afraid of him. He attacks the basket of strawberries to use the fruit as a weapon and makes the basket cry. The sugar cube chef doesn't like him either, but he's too confused to react.
* BattleBoomerang: Uses the Desert Limes this way in his first phase.
* BigBad: He's revealed to be the main antagonist of ''The Delicious Last Course'' after collecting all the ingredients, having captured one of the trio to use for his Wondertart.
* BackgroundBoss: His first two phases in his boss fight are in the background. The first phase can be hit normally, but the gigantic Saltbaker in the second is far too large to hurt; he can only take damage from getting hit by his pepper-shaker minions.
* BigFun: He's rather portly, and he has a clearly jolly demeanor, which takes [[AxCrazy a dark turn]] upon his EvilAllAlong reveal.
* BitchInSheepsClothing: He's all smiles in front of the cups, and seems like he genuinely wants to help Ms. Chalice with his Astral Cookies, but shows his true colors when he attempts to use one of their souls to bake the Wondertart.
* BodyHorror: The only way to describe his final form, where his glass body shatters and he turns into a mass of living salt that then forms into a storm that consolidates into two huge salt pillars, covered in spiraling, howling faces...
* BreakingOldTrends: The theme for his boss fight is the only theme in the whole game to ''not'' be named after the level it plays on (it's named "Baking the Wondertart" in the soundtrack as opposed to "A Dish to Die For"), though presumably this is only so that the identity of the final boss wouldn't be immediately spoiled on the track listings for the OST.[[note]]There's also the technical example of "Admission to Perdition", the Devil's first phase theme; his second phase theme, "One Hell of a Time", is the one named after the level.[[/note]]
* BreakTheHaughty: He has a big ego, and he experiences a big HumiliationConga upon defeat.
* CallBack: Much like the Devil in Cuphead's main game, Saltbaker has four phases, and the last one's relatively easier in terms of the carnage you have to deal with — though ''unlike'' the Devil, Saltbaker's final phase is not him sobbing or crying, but [[DefiantToTheEnd still trying to kick Chalice and friends' asses]], even though he's been reduced to a heart and two streams of salt.
* ChefOfIron: As the final boss of the DLC, Saltbaker has ''tremendous'' fighting chops. His ending song implies that he gained his power from his studies of the Wondertart recipe, since he mentions the power went to his head.
* ChekhovsGun: All the ingredients that the cups had to collect for the Wondertart come back into play as Chef Saltbaker's attacks (he's baking the Wondertart while fighting them, after all), with most of them being in the first phase.
** Icy Sugar Cubes: One of two ingredients that have a chance of being already stacked as the fight begins. Chef Saltbaker picks up a sugar cube person and chisels them into a pile of sugar cubes before blowing them off the screen, as the sugar cubes then float back into the player field in a wavy motion.
** Desert Limes: The other ingredient that can be already stacked at the start of the fight. Saltbaker chops living limes into slices and shoves them off-screen with his knife. The lime slices then spin into the player's field, going straight forward until they reach the other end of the screen, as they then u-turn back to where they came from.
** Distillery Dough: A wad of living dough will occasionally plop onto the counter, which Saltbaker immediately flattens with a pin roller, and uses cookie cutters to make animal crackers out of it. He then motions the animal crackers away, and they hop into the player field.
** Gnome Berries: A living basket full of these will occasionally pass by, and Saltbaker wastes no moment to squeeze the Gnome Berries out it, sending them upwards. They then [[DeathFromAbove drop down into the player field]] in a diagonal motion.
** Pineapple Mint: The only ingredient to appear in the second phase rather than the first, Saltbaker grabs a handful of mint leaves and throws them upwards, after which they slowly descend into the player field.
* ChubbyChef: He's a pudgy-looking chef.
* ContrastingSequelAntagonist: He's this to the Devil. Both are the BigBad of their respective sections of the game, with multiple phases, but otherwise they contrast in almost every way:
** The Devil is a CardCarryingVillain and TheDreaded due to being {{Satan}}, while Saltbaker is a VillainWithGoodPublicity due to being a SupremeChef.
** The Devil’s [[TheDragon Dragon]] is King Dice, who is also a CardCarryingVillain, while Chef Saltbaker mostly works alone and uses the Cups as {{Unwitting Pawn}}s.
** Chef Saltbaker is a FatBastard, while the Devil is LeanAndMean.
** During the first phase of their battles, the Devil mainly uses magical spells and transformations that he naturally has, while Chef Saltbaker uses the ingredients of the Wondertart to attack.
** The Devil's imp minions are happy to assist him in battle, while Chef Saltbaker’s sentient, terrified ingredients are forcibly butchered into projectiles.
** The Devil's final phase is him [[TheDevilIsALoser crying and weeping]] despite not showing damage while Saltbaker's last phase is him [[DefiantToTheEnd desperately fighting to the end]] even after his body shatters, displaying VillainousValor and backbone the Devil just doesn't possess.
** Saltbaker is able to go through a HeelFaceTurn and redeem himself, while the Devil remains evil after his defeat.
** During a game over screen of their last phases, The Devil quotes [[VideoGame/StreetFighterII M. Bison]], while Saltbaker paraphrases [[VideoGame/StreetFighterIII Gill]].
* CreepyShadowedUndereyes: In the battle against him, and the cutscene preceding it, Saltbaker has suddenly gained dark circles around his eyes. Combined with his SlasherSmile, these help him look especially psychotic.
* DeathFromAbove: Uses the Gnome Berries like this in his first phase, and follows up with the Pineapple Mint doing this in a different way in his second phase.
* DefeatMeansMenialLabor: The battle ends with him arrested for his crimes and sentenced to menial labor, serving all the other bosses in the game. However, in doing so, [[DefeatMeansFriendship he reforms and sincerely befriends Cuphead's group.]]
* EarnYourHappyEnding: While he has to perform hard labor to make up for his crimes, he's eventually freed and allowed to rebuild his bakery.
* EasilyForgiven: His sentence for trying to kill Cuphead, Mugman, and Ms. Chalice, and willfully injuring a whole lot of innocent living food during his boss battle? Community service. Though he finds many of the tasks rather grueling, everyone else seems genuinely appreciative of his help, judging by the illustrations seen in the credits. He's even allowed to rebuild and re-open his destroyed bakery. That being said, he does make an honest effort to reform, and admits that he's learned his lesson; furthermore, most of what he ends up doing is restoring the harm he's done, so his victims get restitution, which presumably made it easier to forgive him.
* EvilAllAlong: He's been manipulating Cuphead, Mugman, and Ms. Chalice to gather up the ingredients for the Wondertart for his own dastardly deeds, and the final ingredient happens to be one of the characters' souls[[note]]depending on if anyone is presently swapped with Ms. Chalice or not[[/note]].
* EvilChef: He's an AxCrazy chef who plans to use one of the Cups' souls as the final ingredient for his Wondertart recipe.
* EvilLaugh: Throws these like they're going out of style in his boss fight. He ends his final song with a much kinder laugh, indicating how he's changed for the better.
* EvilLivingFlames: During the first phase of his fight, there will be a sentient, invulnerable flame (two on Expert) that jumps down from the ceiling and back up as an obstacle. The second phase has those flame(s) now jump around on his hand.
* EvilSorcerer: His food has magical properties, which he uses to great effect in his boss fight.
* ExactWords:
** As the game begins, Saltbaker tells the cups "But remember — like any good bake, heart and soul is the secret ingredient!" As it turns out, the most important, secret ingredient just so happens to be [[LiteralMetaphor quite literally]] a living soul.
** He also tells them "I just know you'll put yourself fully into bringing the Wondertart to life." He already knows that the final ingredient is a living soul, and he intends to take one of the Cups to do it with — so yes indeed, one of them ''will'' be putting themselves fully into bringing the pastry to life, in the darkest way possible.
* FatalFlaw: His {{pride}}. He's clearly proud of being the best baker in the land, and his obsessive desire to create the Wondertart and prove his superiority causes him to become the villain of the campaign.
* FatBastard: He's pudgy and the campaign's true villain.
* FinalBoss: It turns out that Saltbaker's greed and pride in constructing the legendary treat ("the Wondertart will be my finest work yet!") has caused him to go off the deep end, and two of the trio have to battle him last to save the currently-swapped-out character's soul from being sacrificed.
* GagNose: His nose is noticeably long and pointy. Also counts as a SinisterSchnoz given his true nature.
* GracefulLoser: While he doesn't take it well at first, Saltbaker eventually becomes content with his punishment of community service, which leads to his redemption.
* HeavyVoice: Judging by the ''Delicious Last Course'' launch trailer and the epilogue, Chef Saltbaker's got quite the baritone to go along with his hefty physique.
* HeelFaceTurn: As the epilogue suggests, he eventually makes an effort to reform during his grueling community service and takes joy in it. He's even allowed to rebuild and reopen his bakery afterward.
* HumiliationConga: After he's beaten by one or two of the trio, his bakery [[LoadBearingBoss collapses]], to which Cuphead gives him NoSympathy. The epilogue sequence shows him getting arrested and tried in court. Despite getting on his knees, the judge forces him to do community service for the residents of Inkwell Isle Four -- replanting Glumstone's and the Gnomes' Gnome Berries, hauling around barrels of the Moonshine Mob's baking powder, cleaning the teeth of Mortimer's whale, repainting the boatman's boat, serving Esther's saloon customers, and repairing the Howling Aces' airplane. He's pretty upset about it at first, [[GracefulLoser but eventually seems to find happiness in helping the others out]], leading him to reform for good.
* LaserGuidedKarma: For taking the locals' food and attempting to cook the cups for the sake of his own pride, Saltbaker loses his bakery, gets arrested, and ends up sentenced to community service.
* {{Leitmotif}}: While Saltbaker has his own singing as a more general leitmotif in the advertising, he has [[https://www.youtube.com/watch?v=wEbqv2va4Vw a self-titled theme]] in the soundtrack. [[BossRemix It features prominently in his boss battle.]] Notably, it has extremely prominent ''organ'' notes, sounding almost like a ''Castlevania'' or ''Final Fantasy'' theme; the game's more common jazz stylings only really become prominent towards the end of his battle, representing the player overcoming Saltbaker.
* LetsMeetTheMeat: Not Chef Saltbaker himself, but the ingredients that Cuphead, Mugman, and Ms. Chalice had brought for him. Turns out, many of the ingredients are sentient and are either mortally terrified or confused when they're about to be served up by the Chef.
* LoadBearingBoss: After his defeat, his entire bakery collapses thanks to the damage it took during the fight.
* ManipulativeBastard: He tricks the trio to get the ingredients for the Wondertart so he can get the pastry for himself to harness the cosmic powers of the Astral Plane without a care for his promise to help Chalice back to life, if her possible captivity as the final ingredient is any indication.
* MaskOfSanity: He does a very good job of hiding the fact that he's nutbar from the Cups until he nabs one of their souls.
* MiracleFood: His specialty seems to be magic recipes, such as the special cookies that allow one to switch places with a ghost. Then there’s the Wondertart. The whole plot of the DLC revolves around finding ingredients for this mystical pastry, as according to Chef Saltbaker, whoever eats it gains control over the Astral Plane itself. The price is that it requires a living soul to be sacrificed in order to bake it.
* NonHumanHead: His head is a big salt shaker with a humanlike face, similar to Cuphead, Mugman, Ms. Chalice, and King Dice.
* OminousLatinChanting: Present in the first movement of his boss theme, as well as the two themes that lead into his true nature's reveal. The chants are "Caute Cave Mortem", [[ThisIsGonnaSuck and it translates to "Beware of death"]].
* OminousPipeOrgan: A particularly epic one predominates most of the first movement of his boss theme.
* OneWingedAngel: Breaking his body will reveal his living part is actually the salt and the heart controlling it, and he manipulates it to attack you in his later two phases.
* PlayingWithFire: He has a small flame helping him out in his first two phases, presumably a cooking fire.
* PunnyName: His name is a portmanteau of "salt shaker", "salt bake", and "baker".
* ShoutOut:
** As he shifts to his second phase, he uses a [[VideoGame/SuperMarioBros glowing red and white mushroom to grow in size]].
** His Pineapple Mint attack during said phase is a wholesale reference to Wood Man's leaf attack from ''VideoGame/MegaMan2''.
** Should you die during his final phase, his quote for that phase's death card has him channel his inner [[VideoGame/StreetFighterIII Gill]].
--->'''Saltbaker:''' "The mark of my salinity shall scar thy fired glaze!"
* ShowsDamage: In his second phase, there's a lot of focus on how cracked his glass body is becoming, most prominently a massive chip in his nose. The start of his third phase is his glass body falling apart entirely, Saltbaker reverting to the salt inside; while the salt forms a battlefield for the third phase, it falls away entirely in the final phase, and the player has to stand on the raining chunks of glass from his original body to stay alive.
* {{Sizeshifter}}: Uses a glowing mushroom to reach gigantic size during his fight.
* SlasherSmile: He sports a pretty deranged and psychotic grin throughout his boss fight.
* SupremeChef: The best chef and baker in all the Inkwell Isles.
* TreacherousAdvisor: At first, he seems to be a character who serves as a mentor for the DLC campaign like Elder Kettle with the main campaign. After collecting all the ingredients for the Wondertart, however, he shows his wicked true nature and intends to use one of trio's soul as the final ingredient, revealing his role as the main antagonist of the campaign.
* TreacherousQuestGiver: Gives the cups a quest to find the ingredients for the Wondertart guarded by powerful bosses, on the promise that it can restore Ms. Chalice's physical body. Turns out, he's the villain of the campaign, and plans to bake the ingredients you've collected alongside one of the cups' souls into the Wondertart, which he wants to use to achieve control over the astral realm.
* UnexplainedRecovery: At the end of his boss battle, Saltbaker's glass body has been reduced to a broken shell, and all that remains are sentient pillars of salt and his heart. But in the cutscene right after the battle, Saltbaker is seen having been brought back to his normal size with no injuries in sight.
* VillainWithGoodPublicity: Chef Saltbaker is loved by all for his delicious treats, with a news reporter at the beginning calling him "the best baker in all the lands". While this might have been genuine at one point, by the time the DLC ends, it only serves to disguise his nefarious true intentions, in contrast to the Devil's open and upfront villainy.
* VisualPun: He's in desperate need of a check-up from the neck up and his second phase prominently shows his cracks. The more cracks he gets, the more [[IncrediblyLamePun cracked]] he becomes.
* WalkingSpoiler: It's hard to talk about him without mentioning his role as the FinalBoss.
* WhamShot: The hallway leading to his boss fight can count as this for players who thought of him as just a jolly old chef. After the trio gather all 5 Wondertart ingredients, they return to Saltbaker's Bakery only to find a trapdoor that leads to an ominous-looking dungeon. If that and the foreboding music didn't tip you off, you can later find Saltbaker's shadow visibly relishing in an EvilLaugh with a knife in hand, giving away his true nature.
* WithGreatPowerComesGreatInsanity: He mentions in his ending song that he shouldn't have let the power go to his head. This apparently is why he turned on Chalice and her friends for the final battle.
* WouldHurtAChild: At the end of the DLC, not only does he try to kill Cuphead, Mugman, and Ms. Chalice, but in the first phase of his fight, he hurts a sentient sugar kid, a basket of little strawberries, and many sentient scared lime children to cook them.
* YellowEyesOfSneakiness: His black eyes turn bright yellow as you face him, to help illustrate that he's taken a swan dive off the deep end.
* YourSizeMayVary: Saltbaker is about the size of a regular adult consistently. But in his boss fight specifically, he towers over the cups as they fight on his kitchen table.
[[/folder]]

[[folder:Inkwell Isle 4 Villagers]]
The [=NPCs=] that you meet in the fourth Inkwell Isle introduced in the DLC.
----
[[/folder]]

!!!Wondertart Ingredient Guardians
[[folder:In General]]
* AnimationBump: The animation quality of Inkwell Isle Four's bosses are ''vastly improved'' over the original game, [[BeyondTheImpossible and considering the original game, that's saying something.]]
* BadassNormal: Because they never dealt with the Devil, none of them have any transformations outside the logical scope of their abilities, unlike the main game bosses. Glumstone the Giant, the Moonshine Mob, and the Howling Aces don't transform at all; Mortimer Freeze can magically control snow, but doesn't transform into anything himself; Esther Winchester only [[LetsMeetTheMeat gets cooked]] due to freak accidents. Even [[spoiler:Chef Saltbaker]] only attacks you with his established skill, [[spoiler:creating magic food]]. Despite this, they're still among the more formidable foes in the game.
* EdibleAmmunition: Every one of the ingredient guardians will try and attack you with food:
** In Glumstone's third phase, he'll occasionally shoot chicken drumsticks at you. [[DownplayedTrope Downplayed]] in that the real purpose of the drumsticks is to make the skeleton monsters stop acting like platforms.
** Some of the {{Mooks}} in the Moonshine Mob's second phase are [[AnimateInanimateObject dancing barrels of moonshine.]]
** [[spoiler: In the Howling Aces' secret phase, the puppies will throw literal [[GrenadeSpam pineapple grenades]] at you. These same pineapples are served with the Pineapple Mint you need for the Wondertart.]]
** Mortimer's snow golem can throw popsicles at you, and when Mortimer himself turns into a snowflake, he'll occasionally attack you with ice cream missiles.
** Esther Winchester, aside from [[LetsMeetTheMeat becoming quite edible herself]], attacks you with T-bone steaks and baked beans in her third phase, and attacks you with sausage strings and chili peppers in her fourth.
* PunchClockVillain: The Ingredient Guardians, even more than the main game's bosses; they haven't signed any contracts with the Devil, they're just between the Cups and the Wondertart that will bring Ms. Chalice back to life. [[spoiler: Given what Saltbaker plans, one could even make an argument that the Guardians are actually Punch-Clock ''Heroes''.]]
* PhysicalMysticalTechnological: Three of the five ingredient guardians fit this trope:
** Glumstone the Giant is the Physical, using either his or his gnomes' physical prowess to fight, including his own digestive system.
** Mortimer Freeze is the Mystical, being a wizard who uses ice-themed spells, hammerspace tricks, and summons to fight.
** The Howling Aces are the Technological, being a family of dogs who utilize flying vehicles and gadgets to fight.
[[/folder]]

[[folder:Glumstone the Giant]]
[[quoteright:217:https://static.tvtropes.org/pmwiki/pub/images/death_card_mugshot_oldman_ph1.png]]
-->''"You thought you were bold, but I am boulder."''
A mountain giant who is faced on a mountaintop in "Gnome Way Out". Defeating him gets you the Gnome Berries.
----
* AcidPool: The third phase of his fight takes place in his acid-filled stomach, touching that will obviously hurt the player. You need to stand on the skeletal reptiles' heads that float on the pool.
* BeardOfEvil: Has a massive flowing beard that covers the mountain platform the players are standing on. It also has an army of gnomes living in it.
* BearsAreBadNews: One of his attacks in the first phase is to pull a bear from...somewhere, and dangle it closer to the player from the left side of the screen.
* BizarreAlienBiology: Glumstone has irregular ridges of fleshy spikes, like a mountain range, poking through his hair and running down his back, and getting swallowed by him reveals a living ulcer inside his stomach. He also seems to have a semi-symbionic relationship with the colony of gnomes that live on his body.
* BurpOfFinality: Emits one after swallowing the player, though given this is the transition to the last phase, the battle's far from over.
* TheCameo: Glumstone uses handpuppets of King Dice and the Devil as part of his second phase.
* CaveMouth: Glumstone initially appears as a stone mountain, and the gnomes are seen working in a mine that's actually his mouth.
* DemBones: In his third phase, skeletal reptiles floating in the stomach acid serve as your only platforms.
* {{Expy}}: Clearly modelled after the titular character of ''WesternAnimation/TheOldManOfTheMountain''.
* FlunkyBoss: He's assisted by several gnome minions in all three phases, with the gnomes hammering the platforms or shooting from their hats in the first phase, jumping out of his beard in the second, and jumping out of the stomach acid to fire darts in the third.
* FoulWaterfowl: During his battle, he can summon a flock of geese to attack the players.
* FourFingeredHands: Averted. Like Captain Brineybeard, Glumstone has 5 fingers per hand.
* GagNose: A huge red one. It actually turns into a whistle used to summon his flock of geese.
* HandPuppet: Brings out two resembling King Dice and the Devil as part of his second phase.
* MonsterShapedMountain: Apparently a common trait of giants in this universe; much like Glumstone, one can see various other mountain giants in the background of his battle, albeit more benign and docile, or are just dormant.
* NonStandardCharacterDesign: Not Glumstone himself, but the gnomes have simple lines for arms, unlike every other character who has RubberhoseLimbs at the skinniest.
* OurGnomesAreWeirder: Glumstone appears to have been made the home of an entire community of gnomes living on and around him, like on the rocks, in his beard, on the geese, in his mouth, ''inside his stomach'', etc.
* ThePollyanna: The gnomes appear to be a whole race of these -- none of them are ever seen not smiling, even when they're being blasted away in the battle intro.
* SwallowedWhole: The final phase of the fight starts with him throwing the player characters into the air and swallowing them. You end up fighting his digestive system as the last phase.
* ThatsNoMoon: The initial scene of his fight has a bunch of gnomes working in a mine cut into the side of an oddly-shaped mountain. Then one of the gnomes hits a gold deposit, the mountain starts shaking, the stone shatters off to reveal skin, the "snow" is revealed to actually be beard hair, the gold is actually a gold tooth...
[[/folder]]

[[folder:Moonshine Mob]]
[[quoteright:217:https://static.tvtropes.org/pmwiki/pub/images/death_card_mugshot_rumrunners_ph1.png]]
[[quoteright:217:https://static.tvtropes.org/pmwiki/pub/images/death_card_mugshot_rumrunners_ph2.png]]
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-->''"One-two punch, you and the cops are eatin' dirt. Bingo bingo!"''\\
''"This dance is over, there's no excuse... you couldn't handle the giggle juice."''\\
''"One thing this nose knows is, youse cups gonna be pushin' up roses!"''\\
[[labelnote:Click here to see spoilers]]''"Surprise! Forgetting about da boss ain't wise."''[[/labelnote]]
A gang of liquor-bootlegging bugs (and one anteater) that you fight in an underground distillery in "Bootlegger Boogie". Defeating them gives you the Distillery Dough.
----

* AardvarkTrunks: The anteater's mouth is placed at the base of the snout rather than at the tip, making the snout a trunk of sorts. Despite this, the tip of the snout still has a tongue come out of it, making him essentially have ''[[TooManyMouths two mouths]]''!
* AttackOfTheFiftyFootWhatever: The anteater is huge.
* BackgroundBoss: The anteater fights you from the background.
* BigBallOfViolence: The anteater will use its tongue to pull a bunch of mob flies and ant police, which causes them to get into one of these as a destructible projectile that bounces all over the area.
* BigCreepyCrawlies: Played with. While all of the bugs and such in the battle are about the same size as Cuphead and co., in comparison to all of the other bosses they are tiny, especially in comparison to the anteater who appears in the battle.
* CartoonBugSprayer: Amusingly, the ant police arm themselves with these, with the smoke from them acting as a ranged attack.
* ChasingYourTail: The second phase has the gramophone in the middle of the area perform the "fire in a loop" sort, where three of its rotating streams turn hazardous and force you to run around them (or Smoke Bomb dash through them).
* ClippedWingAngel: [[spoiler:The snail's only real combat advantage is the element of surprise -- once he loses that, his projectiles are simple to dodge or parry (unless you let your guard down), and he goes down in seconds.]]
* EnemyCivilWar: There are police officers trying to attack them during the fight, but they're harmful to you as well. You've essentially walked in on a huge police raid. Notably, the cops will shoot insect killer at where the Spider is.
* {{Expy}}:
** The caterpillar that the spider tosses against you is inspired by Hoppity from ''WesternAnimation/MrBugGoesToTown''.
** The female bug that dances is reminiscent of the moth in the WesternAnimation/SillySymphonies short "The Moth and the Flame"
** The anteater is possibly based off of the Anteater from the 1940 Fleischer cartoon "Ants in the Plants". He also may be based off the Aardvark from ''WesternAnimation/TheAntAndTheAardvark''.
* FastballSpecial: The spider can enter with a caterpillar goon, which he kicks into the area and causes it to bounce around as a destructible projectile.
* FlunkyBoss: The spider can call in fly minions, kick in a caterpillar goon, and the local ant police will also pop in from the sides to shoot at him but their bug spray projectiles can also hurt you. The female bug has dancing barrels and ant police move along the top and bottom rows.
* FourLeggedInsect: The spider has only 6 limbs instead of 8, and the other bugs have only 4 limbs instead of 6. In a curious non-insect inversion, the snail has a pair of arms.
* GiantSpider: The first bug you face is one of these.
* HostileShowTakeover: The normal announcer intro sounds different and if you look closely, you'll see the snail is yelling on a megaphone, implying he's taken over the announcer's role for the fight. [[spoiler: There's even a fake "Knockout", and when you beat the snail the real announcer can be heard clearing his throat before announcing the real knockout, either implying they somehow held him hostage, or showing just how annoyed he is that some upstart gastropod muscled in on his turf.]]
* MakeMeWannaShout: [[spoiler:The snail's only attack is firing sound waves at you from his megaphone.]]
* MeleeATrois: The battle has you fighting not only the Moonshine Mob, but also the local ant police. Notably, the police only target the mob and generally ignore you.
* MusicalAssassin: The female bug "fights" you by placing down a gramophone that fires out six streams of harmless music, three of which periodically turn into deadly sound waves.
* LawmanBaton: Some of the ant police that appear in their bossfight complete their OldFashionedCopper look by arming themselves with old-fashioned police batons.
* PaintingTheMedium: In the second phase, the background music will distort whenever the phonograph uses its sound wave attack.
* ReformedCriminal: The epilogue scene [[spoiler:shows the snail mob boss shaking hands with a member of the ant police and one of the sentient barrels properly labeling itself as baking soda, implying that the gang have gone straight]].
* TheReveal: The ingredient obtained from this level is dough, and in the epilogue, the barrels are relabeled as "baking XXX". It's not alcohol they're bootlegging -- it's baking soda.
* {{Scatting}}: Vocals by Alana Bridgewater form part of their theme. In-game, it's implied to be coming from the gramophone that the female bug dances to.
* SecretWeapon: The anteater is implied to be the mob's ultimate weapon against the ant cops -- it's not shown in the fight intro, is only revealed as the [[spoiler:fake]] final phase after the spider and lady bug go down, and its very nature as an anteater gives the mob a decisive WeaponOfXSlaying against the ant police.
* ShoutOut: The spider gangster's phase resembles that of the fight against Lololo and Lalala in ''VideoGame/KirbysDreamLand'', and subsequent derived boss fights in the ''Dream Land'' sequels; namely [[VideoGame/KirbysDreamLand2 Nelly and Nruff]] and [[VideoGame/KirbysDreamLand3 Pon and Con]].
* VictoryFakeout: [[spoiler:After defeating the anteater, you're presented with a fake knockout screen made of flypaper -- but a few moments later, the snail pops out from under the anteater's hat and starts yelling sound waves at you.]]
* VisualPun: The anteater is ''massive'', which makes it a [[https://en.wikipedia.org/wiki/Giant_anteater giant anteater]].
* WeakBossStrongUnderlings: The leader of the mob is the snail, and [[spoiler:when he comes out to fight you during the VictoryFakeout, he goes down ''much'' faster than his underlings and only has a single, easily-avoidable attack]].
[[/folder]]

[[folder:The Howling Aces]]
[[quoteright:217:https://static.tvtropes.org/pmwiki/pub/images/death_card_mugshot_dogfight_ph1.png]]
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-->''"You thought you were top dog, but you never had a sniff."''\\
''"Affirm Roger Fox! Affirm Roger Fox!"''\\
''"Looks like your skills have gone AWOL, fleabags."''
A plane-flying bulldog, his saluki mate piloting an airship, and their pups (referred to as the "Yankee Yippers" in the code) that have an assortment of various gadgets that you fight in the sky riding Canteen Hughes' plane in "Doggone Dogfight". Defeating them gets you the Pineapple Mint.
-----
* AbnormalAmmo: With the exception of the yarn balls (which are shot out from a cat), [[spoiler: and the (literal) pineapple grenades in the secret phase]], most of the weapons that the Aces use are dog-themed, such as tennis balls, bones, fire hydrants, dog bowls, and even [[WeaponsGradeVocabulary the letters BOW]].
* BadassFamily: The bulldog, saluki, and all their children are capable of combat, be it themselves or via the very vehicles they pilot. Should [[spoiler:the player manage to activate the secret phase, the saluki and her pups will even fight alongside each other]].
* BoomerangComeback: The bulldog's crossbone tattoos will fly to one side of the screen, stick there for a while, before flying backwards.
* BreakingOldTrends: The Howling Aces are the first and only boss [[spoiler:with a secret phase where said secret phase isn't a variation on a preexisting phase, but rather a completely different boss phase and attack pattern.]]
* BullyBulldog: The pilot in the first phase is a brutish bulldog who pulls out all the stops to attack you.
* CanisMajor: The dachshund airship, which appears to be based on a Chinook.
* CaptainSmoothAndSergeantRough: The two adults give off this impression. The female saluki is more refined and graceful, flies the much bigger and more powerful vehicle, and is also the one to formally salute the Cups ([[MyFriendsAndZoidberg and Hughes]]) when the battle begins, while the male bulldog is much more rough and tough, flies the smaller plane, and doesn't bother with the niceties, just immediately attacking.
* CoolPlane: All their vehicles, as might be expected. The plane the bulldog flies for the flight has hatches for his kids to attack from. Once he and the pups are down, the [[CoolAirship massive airship shaped like a dachshund]] flies back in, piloted by the saluki; it appears to be a Chinook. Both come fully equipped with a multitude of weaponry to go after the Cups. [[spoiler:In the epilogue, Chef Saltbaker has to help them repair the former as part of his community service]].
* DoWellButNotPerfect: [[spoiler:In order to fight the secret alternate final phase, you need to get all four puppies to low health ([[ShowsDamage indicated by their jetpack smoke turning grey]]) without actually defeating any of them.]]
* InterfaceScrew: In the final phase, the warship grabs the camera and the screen rotates ninety degrees every time the warship opens or closes its mouth. This can result in the screen being upside-down for huge chunks of the battle. [[spoiler:The secret phase won't do this, but it comes at the cost of having to deal with the mother and all four children at the same time]]. The game includes a control option just for this phase of the fight, which changes how the game controls relative to the shifting camera. Control type A has Cuphead always aim and move relative to his perspective, such that pressing up has Cuphead aim above his head, even if the plane is upside-down. Control type B has Cuphead aim and move relative to the screen's orientation, such that pressing up will aim towards the top of the screen, regardless of how Cuphead is turned.
* JetPack: The family is fond of these; the bulldog has one in the first phase, and the kids have them in their second phase.
* LadyOfWar: The saluki is elegant and graceful, even when turned to the side due to the mechanics of her phase of the fight. Even her defeat animation is more shocked and surprised than goofy. [[spoiler: Though defeating her during the secret phase or the "outside" phase of her fight leaves her wringing her hat in shame, she's still more composed than a lot of the other bosses are.]]
* MaleMightFemaleFinesse: The male bulldog fights in direct combat, even jumping into the fray to do so. The female saluki never attacks directly, with all her attacks launched by the airship she pilots and commands with great skill.
* MercyRewarded: {{Downplayed|Trope}} in that [[spoiler:you just beat them up again a while later, but choosing not to shoot down any of the Yankee Yippers completely changes the third phase to an easier one with no InterfaceScrew.]]
* MilitaryAlphabet: The pups' quote if you lose to them is "Affirm Roger Fox! Affirm Roger Fox!", or "ARF! ARF!" in UK pre-NATO terms.
* MoreDeadlyThanTheMale: The saluki is implied to be in charge; she's the one that salutes the player at the fight's start, she's driving the bigger Daschund Chinook compared to her husband's smaller plane, and she's the final opponent [[spoiler: in both the normal and secret phases, though in the latter, her kids assist her like they do their dad in the first phase.]] She overall gives off an impression of being a commanding officer.
* {{Pun}}: They're dogs, and you fight them on a plane. It's a literal dogfight.
* RecursiveAmmo: The [[spoiler:pineapple grenades thrown by the pups in the secret phase will explode into a SpreadShot of three shrapnel fragments if shot]].
* ShowsDamage: When one of the pups in the second phase is at low health, the smoke trail from their jetpack turns from white to grey. [[spoiler:This is useful to know if you're going for the secret phase, when you need to get all four to this state without defeating any of them]].
* SpreadShot:
** In the first phase, the pups will throw a spread of three tennis balls downwards.
** In the [[spoiler:secret phase, shooting any of the pineapple grenades that the pups throw causes them to explode into a 3-way downward spread of shrapnel]].
* TestosteronePoisoning: The bulldog is oozing with testosterone, being an absolute beefcake wearing [[SleevesAreForWimps a sleeveless top]], fingerless gloves and is so damn manly that he can attack you with his crossbones tattoos just by flexing!
* VisualPun: [[spoiler: In the secret phase, the pups will throw pineapple grenades at you... ''literal'' pineapples with grenade pins. These same pineapples are served with the Pineapple Mint you get for defeating the Howling Aces.]]
* WeaponsGradeVocabulary: The second phase has the pups attack you by shouting the letters B, O, and W at you.
* WhackAMonster: In the [[spoiler:secret phase, the saluki and her puppies will pop in and out from five of the 6 holes of the aircraft's paws. While the puppies can be shot at to be deterred, they pop back into the fight after a short while, and your main target in this phase is the saluki]].
* WolfpackBoss: In a near-literal example, the four pups will attack you together in the second phase by circling around you and [[WeaponsGradeVocabulary shouting the letters B, O, and W]] at you.
[[/folder]]

[[folder:Mortimer Freeze]]
[[quoteright:233:https://static.tvtropes.org/pmwiki/pub/images/mortimer_freeze_phase1.png]]
-->''"It'll be a hot December before I let you be a member."''
A snow wizard whom you face in an ice palace in "Snow Cult Scuffle". Defeating him gets you the Icy Sugar Cubes.
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* AlliterativeName: The Walloping Winter Whale, one of his attacks.
* {{Cult}}: Leads one consisting of snowmen, if his level title's any indication.
* EvilIsDeathlyCold: He's an EvilSorcerer who uses snow-based magic.
* EvilSorcerer: A wicked cryomancer who uses Tarot cards and {{snowlem}}s to attack.
* {{Expy}}: Ice wizard? Check. Lives in an ice palace? Check. Blue skin? Check. Long white beard and a long pointed nose? Check. Just switch out his legion of snowmen for penguins and his hat for a magic crown and you have the Ice King from ''WesternAnimation/AdventureTime''.
* EyeScream: One of his attacks in his third phase has him launch out his own eyeball by wringing his own face until it pops out.
* FlunkyBoss: He's capable of summoning little icicle minions in his first phase that drop down, get stuck in the ground, and walk away. Amusingly, they're also vulnerable to being crushed by the [[ShamuFu Winter Walloping Whale]]. In his second phase, his snowman bodysuit can release a swarm of flying ice lollies that will swoop down and harass you during the boss' attacks, with one of these being pink.
* HulkSpeak: The snowman phase's death quote has poor grammar and [[CapsLock is in all caps]], the latter of which is something he only shares with Dr. Kahl's Robot.
-->'''Snowman''': ICED ALREADY? WHERE PUNY CUPS GO?
* IcePalace: He's fought in one of these.
* AnIcePerson: He's a wizard with snow-based magic, and he attacks the cups with just about anything related to ice -- snow, ice cubes, [[EdibleAmmunition ice cream...]]
* LivingBodysuit:
** Mortimer uses a snowman as a bodysuit in his second phase, but the epilogue reveals that it's actually sentient even without him inside. This is also implied by its death quote, which uses a different speaking style than the other two phases.
** The snowflake phase also melts away when defeated, revealing that Mortimer was piloting it. He occasionally sticks his hands out to cast a spell.
* ShamuFu: One of his attacks involves slamming the heroes with his giant whale. [[spoiler:In the epilogue, Chef Saltbaker is forced to brush its teeth as part of community service]].
* ShoutOut: Both Mortimer and his snowman [[DecompositeCharacter contain elements of the titular villain]] from the 1932 Ted Eshbaugh cartoon ''[[https://cartoonresearch.com/wp-content/uploads/2013/11/SNOWMAN1.jpg The Snow Man]]''.
* {{Snowlem}}: He encases himself in a giant, living snowman in his second phase, which becomes a huge snowflake for the third.
* SpreadShot: In his final phase, Mortimer's hands can throw kettle bombs that explode into a spread of three crescent moons upon hitting the far wall.
* TarotMotifs: His first phase has him summon Tarot cards from a crystal ball to attack you, which likely explains the "{{cult}}" part of his level name.
* TertiarySexualCharacteristics: When he summons his living icicle minions, two have noticeable bows on their head.
* VoluntaryShapeshifting: The snowman, being made of snow, can take the shape of a refrigerator and a snowflake at will.
* WizardClassic: Aside from wearing pants instead of a robe and lacking a MagicStaff, he fits the bill quite nicely.
[[/folder]]

[[folder:Esther Winchester]]
[[quoteright:217:https://static.tvtropes.org/pmwiki/pub/images/death_card_mugshot_cowgirl_ph1.png]]
-->''"Y'all took quite the fall... I s'pose it's last call!"''
An outlaw cowgirl cow who is faced in a desert canyon in "High-Noon Hoopla". Defeating her gives you the Desert Limes.
----
* AbnormalAmmo: Uses bottles of [[SnakeOilSalesman snake oil]] as guns to fire ''oil snakes''.
* AnvilOnHead: Her second phase has her launching safes into the air after using her vacuum gun to suck gold bars and [[StockMoneyBag money bags]].
* BalefulPolymorph: In her third phase, she gets sucked into her vacuum gun and processed into ''sausages''. In the final phase, she turns into a tin can, with sausage strings bursting right out of it.
* BlowingARaspberry: Transitioning to the second phase of her fight, Esther does this as she pulls off the roof of her saloon and sucks up the rest if it with her vacuum gun.
* CoolCar: Esther's first phase starts off with her inside her saloon - which has wheels under it like a horse-drawn carriage.
* {{Determinator}}: [[ExaggeratedTrope Esther might be the biggest Determinator of all the bosses.]] While continuing to fight despite taking massive damage is fairly common in Cuphead, it still takes a special kind of stubborn to continue fighting after being turned into sausages by one's own malfunctioning equipment. Esther not only does that, but takes it one step further: once her sausage-body is packed away into a tin for convenient eating, she ''keeps fighting'', bursting out of the tin with her sausage-link body and spitting chili peppers from the advertising on the tin containing her remains- in effect, she dies ''twice'' during the fight, yet returns from the dead to keep up the battle! One might say she's quite [[{{Pun}} bull-headed.]]
* {{Expy}}: Clearly modeled after [[Creator/{{Disney}} Clarabelle Cow]].
* FlunkyBoss: In her first phase, flying horse outlaws and vulture outlaws will assist her by spitting shots at you and dropping a RecursiveAmmo SpreadShot dynamite respectively.
* HoistByHisOwnPetard: Her own vacuum gun sucks her into it when her third phase starts, turning her into a living string of sausages.
* LetsMeetTheMeat:
** [[PlayedForLaughs Played for]] BlackComedy when in her third phase she is [[HoistByHisOwnPetard sucked into her own vacuum gun]], which turns into a cooker that processes her into a living string of sausages. It's still not enough to stop her.
** The fourth phase as well has her sausage form encased in a tin can with her own regular face on it, happily serving two sausages on a platter.
* LivingDrawing: In her fourth phase, the tin can she's stuffed into has a picture of her own face on it, which comes to life and spits out flaming peppers as EdibleAmmunition.
* MirrorReveal: She pulls out a hand mirror and looks shocked at her new [[LetsMeetTheMeat sausage form]] when she enters her third phase.
* MobileKiosk: Esther's saloon doubles as a carriage, complete with wheels.
* MoneyMauling: An interesting and indirect variant comes up in her second phase where she takes out a vacuum, the gold bars, coins and money bags being sucked in can damage the player. A more straightforward example is where she fires winged safes up into the air that will explode into damaging gold bars, coins and wads of cash when they hit the ground.
* OhCrap: As her second phase ends she gets this expression right before getting sucked into her own vacuum gun. She does this again after her third phase.
* {{Outlaw}}: She's a cowgirl who has a wanted poster of her on her own saloon, bottles of [[SnakeOilSalesman snake oil]], as well as a vacuum gun that sucks up gold, money, and sheriff stars.
* PaintingTheMedium: The death screen for Esther's second phase shows her sucking up part of the card with her vacuum.
* APigNamedPorkchop: A cow named after a brand of beef. Taken even further when she ''[[BlackComedy actually gets turned into beef sausages]]'' partway through her fight.
* RecursiveAmmo: The vulture that flies in during the first phase drops dynamite that explodes into a spread of two, then three smaller sticks in a vertical SpreadShot upon hitting the ground. In Expert mode, it explodes into a spread of four, then three.
* RepetitiveName: ''Esther'' Winch''ester''.
* RollerbladeGood: She manages this trope with just the spurs of her boots.
* SaloonOwner: Esther is confirmed to be one the minute her fight begins, as the first phase of her battle has her lurking inside her saloon on wheels. [[spoiler: In the epilogue, Chef Saltbaker has to help Esther in the saloon as a waiter amidst a hootenanny, as part of his community service.]]
* SausageStringSilliness: Esther becomes a string of sausages for her third phase, and in her fourth phase she shoots two endless strings of sausages at you.
* SpreadShot:
** The dynamite that the vulture drops in the first phase explodes twice into a spread of three, then two smaller fragments upwards. On expert, it instead explodes into four, then three.
** The LivingDrawing of Esther's face on the can in the final phase spits out a spread of flaming pepper projectiles, with more projectiles in the spread on Expert mode.
* TertiarySexualCharacteristics: There's nothing really effeminate about her Cowgirl outfit or overall design except for her long, visible eyelashes.
* UnexplainedRecovery: She gets transformed into a living string of sausages and then stuffed into a can which is shown releasing sausage angels after being defeated, yet the ending credits shows her having turned back to normal.
* VileVulture: A vulture wearing a cowboy hat will occasionally fly by in the first phase to drop a bundle of dynamite
* VisualPun: Winchester is named after both a type of beef and a type of gun. And she's a cow who wields a [[WeaponsThatSuck vacuum gun.]] Then there's the fact that she's a cowgirl who is also a cow. She also has guns that shoot snake oil that takes the shape of snakes, and horsefly minions that are horses with fly wings.
* WantedPoster: Being an outlaw, a wanted poster of Esther's face is on the side of her saloon during the first phase of the fight.
* WeaponsThatSuck: Wields a vacuum gun in battle.
* WingedSoulFliesOffAtDeath: Her defeat animation has sausage angels coming out of her tin can form, with the typical harps replaced by ''banjos''.
* YourSizeMayVary: When she's fought as a boss, she's [[AttackOfThe50FootWhatever as big as her own saloon.]] However, [[spoiler:in the epilogue, she's shown to be around the same size as Chef Saltbaker]].
[[/folder]]

!!!Other Bosses

[[folder:The King of Games and his Champions]]
-->''"One by one by one by one, your chance at victory is done!"''\\
''"A 'W' for me and an 'L' for you!"''\\
''"I've got you beat from every angle!"''\\
''"Beating you was pretty straightforward!"''\\
''"Too little, too late, I dare say that's checkmate!"''
A king who rules over a court consisting of five champions, each based upon a piece in chess, faced aboard his airship, the King's Leap. Defeating each of his champions earns you more coins.
----
* AnAxeToGrind: The Rook is sharpening an axe, although he does not use it directly against you, instead using sparks, severed heads, and [[BadWithTheBone skulls]] while grinding the axe.
* BackgroundBoss: The Queen is out of reach of interaction, and can only be hit by parrying cannons to fire cannonballs at her.
* BlackComedy: In spades with the Rook, who is an executioner...who throws heads of UsefulNotes/MarieAntoinette and UsefulNotes/LouisXVI at you as his TennisBoss schtick...and is introduced daydreaming about a ''female guillotine.''
* BringIt: The Knight will occasionally make this gesture towards the player character. It's actually a clue on how to beat him; he'll only attack the player (and thereby expose his weak spot) if they approach close enough.
* BullfightBoss: The Knight has his weak spot (his mane) in an awkward place; however, when he charges across the screen, he collapses to catch his breath, putting it in an easier spot for Cuphead and Mugman to hit. (Ms. Chalice, on the other hand, can dash into it after every attack due to how her parry works.)
* ChessMotifs: The whole lot of them are based upon a piece in chess.
** The Pawns attack as a group, something that most pawns in chess will do at the start of a game.
** The best way to avoid the Knight's charge is to roll under him, and to hit him you have to jump on his mane, referencing how knights can jump over pieces. The Knight is also a horse, which is how the piece is typically shaped. The way he holds his sword horizontally above him as well as the way his arm and sword move during his upward stab attack resembles the "L" shape that knights move in, and his quote when you lose against him also mentions the letter "L".
** If the Bishop gets the better of you, he'll comment on how he has you beat from every angle, alluding to how the bishops move diagonally.
** The Rook, similarly, says that beating you is straightforward, which references the fact that rooks can only move in a straight line.
** The Queen, of course, is the most powerful of all the Champions, since the Queen is the best piece in the game.
** After all five of the Champions go down, the King congratulates you and concedes without a fight. After all, he’s got no one else left - you put him in checkmate, and it's well-known that the King is the weakest piece in chess.
** Even the name of his stage, "The King's Leap," refers to an old chess rule that evolved into what we now know as "castling."
* CoolOldGuy: The King of Games is a friendly and jovial fellow who recognizes Cuphead and co.'s fighting skill, rewards them for doing well in his tournament, and sticks around after their victory to help them (and the player) polish their parry skills afterward. [[spoiler:He even helps in Chef Saltbaker's rehabilitation!]]
* DeathByIrony: Well, defeat by irony, but when TheExecutioner Rook is defeated, his own head falls off into his hands.
* DuelBoss: The Knight stands out amongst all the other fights for having no minions or even any form of BulletHell; it's simply a melee battle between your parry skills and his sword.
* TheExecutioner: The Rook is based off one -- he wears an executioner's hood, his daydream at the start of the fight references a female guillotine, he wields an executioner's axe, and his attacks consist of shooting severed heads and skulls from his axe sharpening wheel.
* FingerExtinguisher: In a sense with the Bishop. To make his head vulnerable to attack, you must put out all the candles in the room.
* {{Foil}}: The King of Games is sort of a thematic one to King Dice. Both are 'kings' who lead a BossBonanza found in a secondary area on their respective Inkwell Isles, which you challenge in palaces with chess theming, but nearly every other element is in total contrast:
** While King Dice and his Dice Palace are located deep underground (as Hell tends to be), The King's Leap is an airship found high in the sky.
** King Dice, despite his aplomb and bombast, is merely a king InNameOnly, and is subservient to the Devil. The King of Games, on the other hand, is a true sovereign (as far as we know).
** While both are associated with a vocal theme, King Dice's theme is based on the jazz stylings of Cab Calloway, while The King of Games' theme has a classical-styled choral sound.
** King Dice is described as a 'sleazy manager' and shares his boss's infamy throughout the Inkwell Isles (his portrayal in adaptations notwithstanding). Meanwhile, judging from [[spoiler:the epilogue]], the King of Games is a well-respected member of the community.
** King Dice and his court are themed on vices, gambling, and games of chance, while the King of Games and his champions are themed around chess, a highly-celebrated and respectable game of strategy.
*** Playing into this, the feel of their entire game segments reflects their game of origin: King Dice's boss rush basically boils down to "Go in guns blazing and hope you don't get hit by bad RNG". With the King and his Champions, you can't shoot and you need to find the specific strategy to beat all the bosses.
** King Dice is a mandatory encounter and the penultimate boss in the base game, while the King of Games challenges are entirely optional and are mainly just a means to earn more coins.
** King Dice challenges Cuphead out of petty revenge when he lost a bet (after Cuphead successfully acquires the Soul Contracts) and forces him to participate, while the King of Games simply challenges Cuphead and co. in friendly sporting terms after he recognizes their skill in combat, and always gives them a choice to back out if they so choose.
** In King Dice's game, losing at any point forces you to start over again from the beginning. You fight each of the King of Games' champions separately, and you can retry each fight as many times as it takes to win...that said, he does offer you the option to fight all of his champions BossRush style, but ''only'' if you so choose it, and ''only'' after you've beaten all of his champions.
** Once you make it to the end of King Dice's game, he takes over center stage and tries to deal with Cuphead himself, and is humiliated and ousted from his position once he's beaten. Defeating all of the King of Games' champions just simply makes him give you money and congratulatory remarks, letting you fight any of his champions if you so wish to when you visit him afterwards.
* FurryReminder: The Knight is a bipedal horse who fights with a sword and shield, but when defeated he immediately gets on all fours and starts kicking around like a bucking bronco.
* GemstoneAssault: The Queen attacks by whipping out two jewellery boxes and scattering faberge eggs onto you.
* GodSaveUsFromTheQueen: [[AmbiguousSituation Maybe]]. On the one hand, she's a merciless fighter and the strongest of the Champions, and the cannon-loading mice cheer when she's defeated. On the other hand, [[spoiler:she's quite jovial in the epilogue while she's watching the King play against Chef Saltbaker.]]
* GoKartingWithBowser: In the epilogue, the King is seen enjoying a friendly game of checkers with [[spoiler:Chef Saltbaker, as part of his community service. The Queen is shown watching the match, too, and seems to be having as much fun as the King]].
* IShallTauntYou: The Knight. As a close ranged combatant, he tends to stop and make a beckoning [[BringIt "come-closer" hand sign]] should you move too far away during his fight.
* JustLikeRobinHood: The mice in the Queen's battle are dressed like Merry Men, and seem to be invading the royal treasury while you battle her.
* KnightlySwordAndShield: The Knight, appropriately enough, uses a sword and shield.
* {{Leitmotif}}: "King of Games' Castle", which is remixed into "Bouree on the Board" for the Champions, and "The Queen's Riguadon" for the Queen herself.
* LaserGuidedKarma: Implied in the Rook's encounter; When you parry the heads he sends out, they sneer gleefully as they're sent flying back at him, implying that the Rook has beheaded a lot of people, and they are ''all'' looking to return the favor.
* LosingYourHead:
** The Pawns are defeated by knocking all eight of their heads off -- but until then, the headless bodies still chase after you.
** The Bishop removes his head and sends it after you.
** The Rook takes the cake, though- he's almost entirely themed around this concept! He's not only an executioner with an axe who is introduced daydreaming about a Betty Boop-style guillotine, but the central mechanic of his fight is based on the fact he sometimes attacks with severed heads. Some of those heads are parryable; knocking them back into the Rook is the only way to hurt him. And, of course, when you defeat him, his head falls right off his neck and into his own hands.
* NiceMice: During the fight with the Queen, a group of mice -- who seem to be dressed like Robin Hood's famous MenOfSherwood -- load the cannons and assist the Cups in taking down the Queen.
* NoNameGiven: None of the Champions have any names, so on this page, they're referred to by the respective pieces they represent.
* NonStandardCharacterDesign: Like the gnomes in Gnome Way Out, the mice in the Queen's battle have simple lines for limbs rather than proper arms and legs.
* OffWithHisHead:
** Parrying the head of one of the Pawns knocks it off, and you have to repeat that for all 8 of them to win.
** The Rook ''attacks you'' with the disembodied heads he's cut off before. Both his and the Queen's heads fall off upon their defeat.
* OptionalBoss: Fighting on the King's Leap isn't necessary to complete the DLC content, though it does reward you with coins.
* ThePawnsGoFirst: Quite literally; the Pawns are the first of the King's champions you get to face, and the Cups work their way up the ranks from there. Though, the King and his court are far from villainous.
* PuzzleBoss: Direct attacks don't hurt the Champions; you have to use your parry to do so (either directly hitting them with the parry or using it in other ways).
* ShoutOut:
** The guillotine lady the Rook daydreams of in his intro is just WesternAnimation/BettyBoop in the form of an execution device; specifically, it's Betty with red hair and green eyes, referencing the royal-themed two-strip-color short ''WesternAnimation/PoorCinderella''.
** In the Latin American Spanish translation, the Pawns reference [[Music/LuisFonsi Despacito]] in their death quote.
* SinisterMinister: Downplayed with the Bishop, who has a rather creepy ability to remove his head and looks rather scheming in his defeat portrait, but otherwise doesn't seem malicious.
* TennisBoss: The Rook throws severed heads out of his axe grinder, which must be parried to send them flying back into him.
* TheUnfought: Once you beat them all, the King willingly concedes -- fitting since you took down all his champions, so it's checkmate.
* WolfpackBoss: The Pawns. There are eight of them - parrying all of them wins the fight.
[[/folder]]

[[folder:Secret Boss]]
!!Dream Devil
-->''"Wish you may, wish you might, your soul is now trapped in the night."''
Acquiring the Broken Relic from Porkrind and solving a puzzle in the graveyard will cause a well of astral energy to appear in the graveyard. Once the cups take a nap in this spot, they have a rather interesting nightmare...
----
* BigRedDevil: The Demon appears as one.
* BreakingOldTrends: The ''only'' boss in the game to not be a SequentialBoss.
* ChallengeRun: Beating the Dream Devil turns the Broken Relic into the Cursed Relic. While the Cursed Relic is equipped, you're turned into a OneHitPointWonder and your equipment randomly switches every time you dash or use an EX move, though to compensate you receive additional health after parrying enough objects. Attaining 16 points in a secret point system by defeating bosses throughout the Inkwell Isles (Main Game bosses included but not counting the King's Leap bosses) with the Cursed Relic equipped turns it into the [[InfinityPlusOneSword Divine Relic]], which allows you to freely switch between all of your guns and activates the positive effect of every charm you have ''at the same time''.
* DualBoss: Subverted. The fight is against an angel and a demon, but only the demon will actually damage you (and can be damaged in return). The angel's attacks do nothing to you, and they switch places every time you turn around.
* GoodAngelBadAngel: The boss' design has an angel and a demon next to the shoulders of what appears to be a huge skeleton statue of the Devil himself.
* GuideDangIt: You reach this boss by talking to three [=NPCs=] on the map, making note of what they say, and then examining the proper gravestones in the graveyard near the Howling Aces fight location. Not only is this never made clear, but the dialogue that indicates the right gravestones is different on every playthrough. Oh, and make sure you bought and equipped the Broken Relic, or you still can't trigger the fight.
** Likewise, the method to unlock the Divine Relic involves a secret point system that is not elaborated to the player in any manner - the only hint to it's existence is a cryptic statement relating to the Relic: "The greater the foe, the more evill will go", which is meant to be taken that harder bosses awards more points. Datamining reveals that Isle 1 bosses reward 2 points, Isle 2 bosses reward 2.5 points, the bosses of Isles 3 and 4 reward 3 points, and the final bosses (The Devil and [[spoiler:Chef Saltbaker]]) reward 4 points, with King Dice and his minions rewarding 1 point each.
* HarmlessEnemy: The angel's attacks won't hurt you at all. This is a key element of the fight - because the angel and demon swap places every time you turn around, and their attacks switch qualities in the process, you can escape seemingly-unavoidable attacks by turning around.
* OptionalBoss: The entirety of the Broken Relic quest, and by extension this fight, is entirely optional.
* VideoGameRandomizer: The effect of the Broken Relic and, to a lesser extent, the Divine Relic. The Broken Relic fully randomizes weapons and charms with every dash, EX Move, Super, and even when you stop firing. The Divine Relic keeps the same effects for the weapons, but gives you every positive charm effect at the same time instead.
[[/folder]]

[[Characters/CupheadMainCharacters Main Characters]]
[[Characters/CupheadNPCsAndEnemies NPCs and Enemies]]
[[Characters/CupheadRunawayDebtors The Runaway Debtors]]
[[Characters/CupheadTheKingsCourt The King's Court]]
[[Characters/CupheadTheDeliciousLastCourse The Delicious Last Course]]

%%[[Characters/CupheadMainCharacters Main Characters]]
%%[[Characters/CupheadNPCsAndEnemies NPCs and Enemies]]
%%[[Characters/CupheadRunawayDebtors The Runaway Debtors]]
%%[[Characters/CupheadTheKingsCourt The King's Court]]
%%[[Characters/CupheadTheDeliciousLastCourse The Delicious Last Course]]

* ChallengeRun: Beating the Dream Devil turns the Broken Relic into the Cursed Relic. While the Cursed Relic is equipped, you're turned into a OneHitPointWonder and your equipment randomly switches every time you dash or use an EX move, though to compensate you receive additional health after parrying enough objects. Attaining 16 points in a secret point system by defeating bosses throughout the Inkwell Isle (Main Game bosses included but not counting the King's Leap bosses) with the Cursed Relic equipped turns it into the [[InfinityPlusOneSword Divine Relic]], which allows you to freely switch between all of your guns and activates the positive effect of every charm you have ''at the same time''.

* ChallengeRun: Beating the Dream Devil turns the Broken Relic into the Cursed Relic. While the Cursed Relic is equipped, you're turned into a OneHitPointWonder and your equipment randomly switches every time you dash or use an EX move, though to compensate you receive additional health after parrying enough objects. Beating any eight bosses on Regular or Expert difficulty (Main Game bosses included but not counting the King's Leap bosses) with the Cursed Relic equipped turns it into the [[InfinityPlusOneSword Divine Relic]], which allows you to freely switch between all of your guns and activates the positive effect of every charm you have ''at the same time''.

* ExperiencedProtagonist: Heavily implied to have a storied past as a hero of the land as the Legendary Chalice before becoming an optional playable character in the DLC. Would probably explain all the unique and helpful skills she has on top of having 4 HP with no damage reduction unlike the brothers who only have 3 HP by default unless they use the Heart charms that also reduce their damage output.

* ActionGirl: She's a playable character in the DLC campaign.

* FountainOfYouth: She seems around Cuphead and Mugman's age in the DLC, compared to in the base game where she looked considerably older than them as a ghost.

* SkillGateCharacter: One of the goals with her being playable is to make finishing the game more accessible, and thus she has a double jump, a dodge roll, and her dash also works as a parry, akin to the "little brother/sister" characters of Peach and Toadette in the ''Mario'' games and Tails in the ''Sonic'' games.

* IShallTauntYou: The Knight. As a close ranged combatant, he tends to stop and make a beckoning "come-closer" hand sign should you move too far away during his fight.

* GemstoneAssault: The Queen attacks by whipping out two jewellery boxes and scattering their contents onto you.
* GodSaveUsFromTheQueen: [[AmbiguousSituation Maybe.]] On the one hand, she's a merciless fighter and the strongest of the Champions, and the cannon-loading mice cheer when she's defeated. On the other hand, [[spoiler:she's quite jovial in the epilogue while she's watching the King play against Chef Saltbaker.]]

* DefeatMeansMenialLabor / DefeatMeansFriendship: The battle ends with him arrested for his crimes and sentenced to menial labor, serving all the other bosses in the game. However, in doing so, he reforms and sincerely befriends Cuphead's group.

* TreacherousAdvisor: At first, he seems to be a character who serves as a mentor for the DLC campaign like Elder Kettle with the main campaign. After collecting all the ingredients for the Wondertart however, he shows his wicked true nature and intends to use one of trio's soul as the final ingredient, revealing his role as the main antagonist of the campaign.

* UnwittingPawn: [[spoiler:Cuphead and Mugman eventually discover that they are becoming unwitting pawns of the Devil, to their own misfortune, and they have to decide whether they can back out of a deal or not.]]

* CartoonBugSprayer: Amusingly, the ant police's only ranged attacks are through firing smoke/gas rings out of these.

* MeleeATrois: The battle has you fighting not only the Moonshine Mob, but also the local ant police who can damage you.

* LawmanBaton: Some of the ant police that appear in their bossfight complete their OldFashionedCopper look by arming themselves with a old-fashioned police baton.

A plane-flying bulldog, his saluki mate piloting an airship, and their pups (referred to as the 'Yankee Yippers' in the code) that have an assortment of various gadgets that you fight in the sky riding Canteen Hughes' plane in "Doggone Dogfight". Defeating them gets you the Pineapple Mint.

* AbnormalAmmo: With the exception of the yarn balls (which are shot out from a cat), [[spoiler: and the (literal) pineapple grenades in the secret phase]], most of the ammo that the Aces use are dog-themed, such as tennis balls, bones, fire hydrants, dog bowls, and even [[WeaponsGradeVocabulary the letters BOW]].
* BadassFamily: The Bulldog, Saluki and all their children are capable of combat, be it themselves or via the very vehicles they pilot. Should [[spoiler:the player manage to activate the secret phase, the Saluki and her pups will even fight alongside each other]].

* BullyBulldog: The adult male dog, who is the pilot in the first phase.

* CaptainSmoothAndSergeantRough: The two adults give off this impression. The female Saluki is more refined and graceful, flies the much bigger and more powerful vehicle, and is also the one to formally salute the Cups ([[MyFriendsAndZoidberg and Hughes]]) when the battle begins, while the male Bulldog is much more rough and tough, flies the smaller plane, and doesn't bother with the niceties, just immediately attacking.
* CoolPlane: All their vehicles, as might be expected. The plane the bulldog flies for the flight has hatches for his kids to attack from. Once he and the pups are down, the [[CoolAirship massive airship shaped like a dachshund]] flies back in, piloted by the female saluki; it appears to be a Chinook. Both come fully equipped with a multitude of weaponry to go after the Cups. [[spoiler:In the epilogue, Chef Saltbaker has to help them repair the former as part of his community service]].

* JetPack: The family is fond of these; the kids have them in their second phase.
* LadyOfWar: The adult Saluki is elegant and graceful, even when turned to the side due to the mechanics of her phase of the fight. Even her defeat animation is more shocked and surprised than goofy. [[spoiler: Though defeating her during the secret phase or the "outside" phase of her fight leaves her wringing her hat in shame, she's still more composed than a lot of the other bosses are.]]
* LaterInstallmentWeirdness: The Howling Aces are the first and only boss [[spoiler:with a secret phase where said secret phase isn't a variation on a preexisting phase, but rather a completely different boss phase and attack pattern.]]

* MoreDeadlyThanTheMale: The adult female Saluki is subtly implied to be in charge; she's the one that salutes the player at the fight's start, she's driving the bigger Daschund Chinook compared to her husband's smaller plane, and she's the final opponent [[spoiler: in both the normal and secret phases, though in the latter, her kids assist her like they do their dad in the first phase.]] She overall gives off an impression of being a commanding officer.

* TestosteronePoisoning: The Bulldog is oozing with testosterone, being an absolute beefcake wearing [[SleevesAreForWimps a sleeveless top]], fingerless gloves and is so damn manly that he can attack you with his crossbones tattoos just by flexing!

** Parrying the head of one of the pawns knocks it off, and you have to repeat that for all 8 of them to win.

* ThePawnsGoFirst: Quite literally; the pawns are the first of the King's champions you get to face, and the Cups work their way up the ranks from there. Though, the King and his court are far from villainous.

** The guillotine lady the Rook daydreams of in his intro is just WesternAnimation/BettyBoop in the form of a guillotine.

* GratuitousLatin: [[spoiler:When the boys come upon the ruined castle, they see a plaque of a shield bearing a teacup and some kitchen utensils, below which is an inscription that says "Calix Animī" (which, when translated from Latin, means "The Cup of Courage").]]

* BigRedDevil: Although he has black fur rather than red skin, he otherwise fits this trope, with features like horns and a pointy tail and ears. [[spoiler:Played more straight during his kaiju-sized Phase 2 and onward, where his body takes on a more noticeable dark red tone.]]