Characters / Cuphead

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Main Characters

     Cuphead & Mugman 
http://static.tvtropes.org/pmwiki/pub/images/cupfingerguns.png
"Well, Cuphead and his pal Mugman, they like to roll the dice..."

The player characters and protagonists of the story, two brothers that are anthropomorphic cups with bodies.
  • Abnormal Ammo: Judging by the fact that the different types of weapons you can buy come in bottles, it seems that Cuphead and Mugman shoot moonshine at their enemies.
    • Further, the first super attack has them firing the contents of their cups as giant lasers - and Word of God has stated that the cups contain their souls.
  • Action Bomb: In flying stages, their supers turn them into literal bombs that they can ram into their opponents.
  • Ain't Too Proud to Beg: At the beginning, when the boys lose in a game of Craps against the Devil, who is about to claim their souls, the boys kneel down and beg for their lives to be spared, as shown in the picture. Needless to say, it works.
  • Autocannibalism: Mugman drinks the liquid from his own head 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.
  • Badass Adorable: They're cute little homages to cartoon protagonists from the 30s that, eventually, can become strong enough to beat up Satan. It helps that Cuphead and Mugman are adolescents as well.
  • Badass Baritone: While it was more than likely a nod to something like 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 might not be their actual voices, it's just an amusing case of Breaking the Fourth Wall.)
  • Bash Brothers: A literal example, as Cuphead and Mugman are actual brothers.
  • Breaking the Fourth Wall: 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.
  • Bug Catching: 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).
  • Charles Atlas Superpower: 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 beat the crap out of him.
  • Colour-Coded for Your Convenience: Cuphead's red and Mugman's blue. Even their shots reflect this.
  • Deal with the Devil: 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.
  • Did You Just Punch Out Cthulhu?: In the good ending, they beat the crap outta The Devil himself.
  • The Drag-Along: 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.
  • Empty Eyes: Or "Empty Eye Sockets", rather: If you lose to the Devil's second phase and onwards, he holds up the lifeless, decrepit heads of Cuphead and Mugman. 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.
  • Evil Debt Collector: A rare non-villainous variation of this trope, since they are pretty much forced to collect the Devil's soul contracts from other Inkwell Islanders to save themselves. 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 Felix the Cat, Oswald the Lucky Rabbit, and Mickey Mouse. In fact, they were both modeled after a cartoon character with a teacup for a head who fights off the "Mickey Mice" in the 1936 Japanese propaganda cartoon.
  • Face–Heel Turn: In the bad ending, they become the Devil's servants.
  • Fighting Spirit: The third super they can gain allows them to manifest a ghostly, stronger form of themselves which will spin around and hit their enemies repeatedly, after which it will vanish, leaving behind a pink heart they can parry for extra mana.
  • Finger Gun: They attack by basically making a gun motion in their hands and firing shots from them. The shots apparently being drawn from the liquid in their heads.
  • Fireball Eyeballs: The boys have these when they are turned into the Devil's servants in the bad ending.
  • Foolish Sibling, Responsible Sibling: Cuphead is the Foolish Sibling to Mugman's Responsible Sibling. In point of fact, Mugman was the one who tried to discourage Cuphead from gambling their souls for the Devil's loot, but Cuphead was so blinded by his own greed that he took the bet and lost.
  • The Gambling Addict: 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.
  • Invincibility Power-Up: Their second special they receive allows them to invincible for a limited time (after they somehow turn their heads huge and give off a creepy laugh for some... reason).
  • Kid Heroes: Although these two are adolescents, they seem to fit the bill quite nicely when they are fighting for their souls. In fact, 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.
  • Literal Ass-Kicking: 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. You can even see the Devil's foot kicking their butts out the door!
  • Losing Your Head: 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.
  • Mr. Vice Guy: Cuphead may be greedy and shortsighted, but he, along with Mugman, frees the souls they collected for the Devil after beating him up.
  • Naughty Is Good: 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.
  • Nice Job Breaking It, Hero!: Cuphead was pretty much the one that got the duo into the 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. 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 and free the Inkwell Isle residents from eternal servitude to the Devil.
  • Non-Human Head: They have a cup and a mug for heads, respectively.
  • Oh, Crap!: When the boys face the Devil in the fight against him that starts up, they both get this reaction when the Devil gives out his Death Glare that plays out what he will do to them, and they both let out a terrifying scream in fright. This is the only battle intro when they get scared out of their wits instead of being prepped up for battle, though they quickly recover their Heroic Resolve and fight like it's now or never.
  • Orbiting Particle Shield: Chaos Orbit, the Ex Move for the Chaser, shoots out 4 bullets that will briefly circle around the player.
  • Parrying Bullets: A non-sword variant. When being shot at by pink colored bullets, the two can jump off them or slap them aside to avoid damage. 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.
  • Polar Opposite Twins: Cuphead is known for being the hot-blooded, courageous, and sometimes devious older twin brother. "A shoot-first-and-ask-questions-later type of guy." Mugman is known for being the good-humored, industrious, and rascally younger twin brother. "Calculated in battle and a tricky adversary." While both of them have a rebellious streak, Mugman does try to stop Cuphead when the latter gets too overconfident when betting against the Devil.
  • Pint-Sized Powerhouse: Both of them are outright dwarfed by their opponents (and if the Token Human 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.
  • Red and Black and Evil All Over: Cuphead has a lot of red and black in his design and is doing the devil's work, though not by choice. Oddly enough, if you side with the devil, all of Cuphead's red bits change to purple.
  • Red Oni, Blue Oni: According to the 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.
  • Schmuck Bait: 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.
  • Spread Shot: The Spread weapon, which shoots shots in a spread but they disappear after a certain range.
  • Unwitting Pawn: 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.
  • Vague Age: 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 by writer Evan Skolnick, Cuphead and Mugman are adolescents, though the exact age is still unknown. However, in a Twitter response to a fan, the Studio MDHR describe both of them as "kidults".
  • Wave Motion Gun: The first super they receive allows them to jump into the air and fire a stream of liquid at their opponent.
  • Wingding Eyes: 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.
  • Would Hit a Girl: Not that they have a choice in the matter, really, but they are more than willing to fight the female bosses.

     The Elder Kettle 
http://static.tvtropes.org/pmwiki/pub/images/kettle.png
"What a fine pickle you boys have gotten yourselves into!"

Cuphead and Mugman's mentor. An anthropomorphic tea kettle who gives them a special potion to defend themselves against the Devil's debtors.
  • Big Good: Cuphead and Mugman’s mentor who is responsible for giving them the tools to solve their current problem.
  • Disappointed in You: His conversation at the beginning implies that he feels this way towards Cuphead for gambling in the Devil's Casino.
  • Do Wrong, Right: He gives Cuphead and Mugman a potion that will help them fight the Devil's debtors. He also says that ideally Cuphead wouldn't have to do it, but the boys have no choice.
  • Mentor Archetype: He acts as a father figure to Cuphead and Mugman, though it's not made clear if they're actually family.
  • Reasonable Authority Figure: 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.
  • Retired Badass: Seems to be implied, as he "passes the torch" down to Cuphead and Mugman. 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. In the ruins in the Rugged Ridge level, there is a statue of him kneeling with sword in hand.
  • So Proud of You: The good ending when the boys free the Inkwell Isles bosses of their debts.
  • Strong Family Resemblance: If he is related to Cuphead and Mugman, then it's fitting that he's a kettle.

    The Devil 
http://static.tvtropes.org/pmwiki/pub/images/cupheadfinalboss2.png
"Anyone who opposes me will be destroyed!"

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".
  • 0% Approval Rating: 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.
  • Attack of the 50-Foot Whatever: 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. There he proceeds to unleash his inner Kaiju on the player. When he does that, the protagonists are about as big as his pupil.
  • Background Boss: 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.
  • Badass Boast: Lose to him in the second phase of the fight and onwards, and his death taunt is this, complete with a picture of him holding the lifeless, decapitated heads of Cuphead and Mugman.
    The Devil: Anyone who opposes me will be destroyed!
  • Bad Boss: 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.
  • Berserk Button: Don't break a deal with the Devil.
    The Devil: Welching on me just like all the others, eh... I'll teach you for backing out of a deal — have at you!!
  • Big Bad: He's the one who starts the whole adventure by sending the two boys out on errands.
  • Big Red Devil: Although he has black fur rather than red skin, he otherwise fits this trope, with features such as horns and a pointy tail and ears. Played more straight during his kaiju-sized Phase 2 and onward where his body takes on a more noticeable dark red tone.
  • Break the Haughty: During the final battle, the Devil goes from confident, to angry, to crying tears of frustration as the brothers wear him down.
  • Cigar Chomper: The Devil casually smokes a cigar at his desk while counting his casino's earnings.
  • Clipped-Wing Angel: 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.
  • The Corrupter: If the brothers agree to join him and hand over the soul contracts, it leads to a bad ending where the Devil will turn them into his demonic servants.
  • Dark Is Evil: He has a dark, threatening appearance, fitting for the Devil himself.
  • Death Glare: His fight begins with a one-eyed glare, so thorough his pupil briefly transforms and plays out what he plans to do to them. It seems to work; this intro is the only one in the game where Cuphead and Mugman scream out in terror instead of getting hyped up for battle.
  • Decapitation Presentation: Heck, the opening theme song isn't kidding if you lose to his second phase and onwards! They don't call this pure Nightmare Fuel in a kids' game for nothing!
  • The Devil Is a Loser: The final phase of his boss battle has him crying (see Villainous Breakdown below), and when Cuphead and Mugman finally beat him, he surrenders without hesitation.
  • Evil Is Burning Hot: As with most depictions of the Devil, he's associated with fire.
  • Fangs Are Evil: Most of the other characters have normal, rectangle-shaped teeth. Not him. He has very pointy teeth.
  • Fatal Flaw: Fittingly for the Devil, 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 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 shattered his pride, he just starts crying (see Clipped-Wing Angel, The Devil Is a Loser, Villainous Breakdown).
  • Faux Affably Evil: 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.
  • Final Boss: Should go without saying, but indeed, he's the last boss faced in the game.
  • Hoist by His Own Petard: 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.
  • Horns of Villainy: He has long, bone-white horns.
  • 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.
  • Losing Your Head: One of his attacks has him remove his head before transforming it into a spider.
  • Obviously Evil: Again, he's the Devil. It should really go without saying.
  • Off with His Head!: 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. The shadow on the wall illustrates this point when he makes the cutthroat motion.
  • Offscreen Moment of Awesome: Based on how many contracts that Cuphead and Mugman have to collect, the Devil has tricked many toons into losing their souls.
  • One-Winged Angel: Once the Devil brings the fight to his turf, his head takes over most of the screen due to his now humongous size.
  • Orcus on His Throne: 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 the Devil refuses to listen. The first phase of the boss fight with him has him mainly seated on his throne.
  • Red Eyes, Take Warning: When particularly malicious, the Devil's normally black eyes become red.
  • Satan: He's the Devil himself, of course.
  • Shout-Out: The part where he gives a We Can Rule Together 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 Colonel Bahamut's similar offer in one story path of Contra: Hard Corps.
    • Being defeated in phase two causes him to quote M. Bison/Vega from Street Fighter II.
  • Smug Snake: He's dangerous, that's for sure. But he's far from invincible and is far too overconfident for his own good.
  • Turns Red: 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.
  • Vile Villain, Saccharine Show: Can't get any viler than having 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 An Aesop 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 killing said people if they back out of his deal, or turning them into his demonic servants if they agree to join him.
  • Villainous Breakdown: 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.
  • Voluntary Shapeshifting: Pulls a number of these in his fight, turning into a snake, spider, and goat-like creatures.
  • We Can Rule Together: 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.
  • White Flag: He's shown holding one in the good ending after getting heavily beaten up by Cuphead and Mugman.
  • Wingding Eyes: Aside from the Death Glare above, he weaponizes this in his second phase.
  • Yellow Eyes of Sneakiness: Usually depicted with yellow sclerae, befitting his trickster nature.

    King Dice 
http://static.tvtropes.org/pmwiki/pub/images/600_king_dice.png
"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 The Dragon to the Devil. Fights you in "All Bets Are Off".
  • Berserk Button: Don't make him lose a bet.
  • Boss Bonanza: 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).
  • Card-Carrying Villain: 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.
  • Dastardly Whiplash: His appearance resembles this style of villain.
  • Death Dealer: His main attack when he finally deigns to confront you by himself are entire decks up his sleeve that come charging at you.
  • The Dragon: In his song, he describes himself as "The Devil's right-hand man." Not surprisingly, he's the penultimate boss before the Devil.
  • Eat the Camera: When he sends you into one of the mini-bosses in his stage, he goes to eat the camera when he does so.
  • Evil Counterpart: 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.
  • Evil Eyebrows: Both his eyes and eyebrows are constantly arched upward in maniacal glee.
  • Evil Is Petty: He forces the duo into a fight against him due to losing a bet with the Devil on if the two could carry out their task when you reach him.
  • Evil Laugh: During the boss fight with him, he laughs when sending his cards to attack you.
  • Evil Sounds Deep: He sings with a deep, Louis Armstrong-esque voice.
  • Evil Sounds Raspy: Goes hand-in-hand with having a Louis Armstrong-esque voice.
  • Excessive Evil Eyeshadow: Unless his eyelids are just naturally purple.
  • Faux Affably Evil: 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 even though he's clearly pissed at them for making him lose a bet with his boss. Of course, as a casino manager, he has to put clients at ease and get them comfortable, the better to strip them of their hard-earned money. Also goes hand-in-hand with his status as a sort of Antropomorphic Personification of gambling and games of chance — tempting with the promise of riches, yet deceitful and dangerous.
  • Foil: Seems to be one for Cuphead and Mugman. Both are cartoony people with Non Human Heads 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.
  • The Fourth Wall Will Not Protect You: 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 Eat the Camera to teleport you there, as if he's fully aware there are people watching him.
  • The Gambler: He has a dice motif, down to the "game" he makes you play when reached (a roll of dice determines your progress in his Boss Bonanza). Not to mention 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.
  • Green Eyes: He gets these when he turns serious, fitting his shady personality. They're most noticeable during his boss fight.
  • The Heavy: 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.
  • Lean and Mean: He's tall and skinny, and certainly wicked.
  • Man of Wealth and Taste: While he isn't the Devil himself, King Dice is his right-hand man, and is dressed in a sharp tuxedo.
  • No Celebrities Were Harmed: According to artist Jake Clark, the character was heavily inspired by Cab Calloway.
  • Non-Human Head: He has a humanlike body and a dice for a head.
  • NPC Roadblock: Guards the path to the next area, only allowing you past when you turn in enough contracts. Referenced in his Villain Song.
    I can't let you pass 'cause you ain't done everything!
    Bring me those contracts! Come on, bring 'em to the king!
  • Obviously Evil: 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 Villain Song 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".
  • Perpetual Smiler: Dice is almost never seen without that trademark grin of his.
  • Properly Paranoid: 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. King Dice ends up turning out to be right.
  • Purple Is Powerful: 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.
  • Shout-Out:
    • The dice game Boss Bonanza he puts you through is one toward Gunstar Heroes, which likewise had a similar gimmick in Black's stage (though this can be manipulated by skillful parries rather than just luck).
    • His horrible wide grin and flashing green eyes also bear a close resemblance to the Coachman from Disney's Pinocchio.
    • Aside from being partially modeled after him (see No Celebrities Were Harmed), King Dice makes a lot of 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.
  • Sharp-Dressed Man: Wears a purple tux.
  • Slasher Smile: He sports a rather potent grin.
  • Tranquil Fury: 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, that smile of his never leaves his face.
  • Villain Song: Die House, in which he bosses Cuphead and Mugman around and introduces himself as a major threat.
  • Wink "Ding!": Pulls this before sending you to fight one of his Court.
  • Your Size May Vary: 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 gigantic.

Run 'n' Gun Enemies

     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.
  • Badass Normal: The majority have no real powers or transformations to speak of, but they can still wallop you something fierce if you let them.
  • Game-Over Man: 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 seperate from the other enemies in that level.
  • Giant Space Flea from Nowhere: 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.
  • Hair-Trigger Temper: For the most part, it seems that all of these enemies want to kill Cuphead and Mugman simply because they had the nerve to set foot in their territory.
  • Hard Levels, Easy Bosses: 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.
  • Killer Rabbit: No matter how cartoony or cute these guys appear, they will take you down if they can.
  • Pacifist Run: ALL of them can be avoided outright if you are skilled enough, even mini-bosses with the help of the smoke bomb charm. This goes a long way to full completion and unlocking the Black and White Mode from the turtle sitting at the docks in Isle Three.
  • Respawning Enemies: Some stages have enemies (sometimes literally) jump out at you without end until you move on to the next section of the level.
  • Skippable Boss: It is possible to bypass some minibosses by dashing through them with the Smoke Bomb or simply by taking damage and using your Mercy Invincibility to walk through them. They die immediately when you complete the level.

     Forest Follies' Foes 
http://static.tvtropes.org/pmwiki/pub/images/pc_computer_cuphead_mugshots_copy.png
"Nowhere to run, nowhere to go — this forest is yer foe!"

The inhabitants of the woods leading to Goopy le Grande.
  • The Goomba: The flower people that parachute from the sky.
  • Incendiary Exponent: The purple tulips fire purple beans that explose into flames when they hit the ground.
  • Invincible Minor Minion: The tiny slimes that run about fall into a puddle when shot once, but reform themselves a second later to continue running around. There are also Piranha Plant-esque plants that jump from bottomless pits as a stage hazard, which can't be destroyed either.
  • Mook Maker: The Acorn Maker, a furnace-like machine endlessly cranked by a single flower enemy.
  • Plant Person: With the possible exception of the slimes, Acorns, and the Acorn Maker, all of the enemies are living plants.

     Treetop Trouble's Terrors 
http://static.tvtropes.org/pmwiki/pub/images/2_treetop_troubles_contenders.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.
  • Big Creepy-Crawlies: The level is populated with tumbling ladybugs, fanged flies, helpful mosquitoes, and a giant dragonfly as a miniboss.
  • Helpful Mook: 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.
  • Invincible Minor Minion: The woodpeckers that peck into the ramp of the first section.
  • Mind Screw: Did Cuphead enter a Macro Zone 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.
  • Playing with Fire: The giant dragonfly mini-boss breathes fireballs at Cuphead and destroys the mosquito platforms floating around.
  • Stealth Pun: The ladybugs seen in the level are rolling or bouncing down the ramps during the first area of the level. In other words, they're literal "tumble bugs".
  • Visual Pun: The large dragonfly miniboss spits fireballs like a dragon. It's a dragon-fly.

     Funfair Fever's Fighters 
http://static.tvtropes.org/pmwiki/pub/images/3_funfair_fevers_fighters.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.
  • Airborne Mook: 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.
  • Animate Inanimate Object: 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.
  • Edible Ammunition: The dancing hotdog mini-boss at the end of the level fires blobs of mustard, ketchup, and relish at you.
  • Helpful Mook: The walking trampoline isn't quite as harmless as the mosquitoes from Treetop Trouble — it's fanged, so you will get hurt if you touch it from the side — but it's absolutely necessary for getting past the barriers in the first tent.
  • Magicians Are Wizards: Lots of disappearing magicians float around firing circles of magic at the boys.
  • Villainous Harlequin: 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.
  • Spread Shot: The balloons that float past you explode if damaged, shooting out bullets in all directions.

     Funhouse Frazzle's Frights 
http://static.tvtropes.org/pmwiki/pub/images/4_funhouse_frazzles_frights.png
"We ain't toyin' around with you, now scram!"

A bunch of bizarre oddities living within the even weirder carnival funhouse.
  • Action Bomb: 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.
  • Eldritch Location: The tent where the toys live in starts out normal enough, where the boys run through what looks like an obviously fake cardboard set of the moon before they find a 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 Maybe Magic, Maybe Mundane 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.
  • Evil Laugh: 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 the king baritone sax from the Silly Symphonies short "Music Land".
  • Invincible Minor Minion: The clown-cars from the first half. The gravity-reversing cards are absolutely essential to escaping them.
  • Living Toy: 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
  • Lovecraft Lite: The Living Structure Monster 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 Overly Long Tongue to attack. Shooting their eyes actually takes longer to defeat them; instead, running into their gaping mouths kills them just as well.
  • Musical Assassin: The last leg pits our heroes against sentient tubas that attack with sound effects.
  • Villainous Harlequin: The four-way jack-in-the-boxes with eyeballs in the center of their bodies.

     Rugged Ridge's Rabble 
http://static.tvtropes.org/pmwiki/pub/images/05full_5.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.
  • Advancing Boss of Doom: The giant Gorilla-like cyclops at the end. Apparently he's the chief guardian of the ruins.
  • Altum Videtur: 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").
  • Fauns and Satyrs: Satyrs appear in the third quarter of the level.
  • The Goomba: The satyrs are pretty much 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.
  • Hailfire Peaks: One part steep mountain range, one part ruined fairy tale castle in that mountain range.
  • Improbable Use of a Weapon: The mountain goat miners use their pickaxes as Battle Boomerang projectiles.
  • The Unfought: The Cyclops. Outrun him all the way through and he falls into the Bottomless Pit all by himself.
  • Unique Enemy: The Cyclops is the only non-boss enemy in the game to get his own individual game-over card.
  • Wham Episode: 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 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.

     Perilous Piers' Pests 
http://static.tvtropes.org/pmwiki/pub/images/6_perilous_piers_pests.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.
  • 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.
  • Flying Seafood Special: The flying fish and starfish trapped within bubbles that serve as airborne obstacles, among others.
  • Giant Enemy Crab: The large crabs with boxes on their heads in the second area and a vicious lobster in the third area.
  • Helpful Mook: The dinghies that you parry to gain extra distance, and the octopus that takes you to the end of the level.

The Mausoleum

     The Spectre Syndicate 
http://static.tvtropes.org/pmwiki/pub/images/000_main_copy_19.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.
  • Asteroids Monster: The third Mausoleum has the large ghosts, which are slow but when parried, will split into two smaller and faster ghosts.
  • Bedsheet Ghost: They all have this appearance.
  • Colour-Coded for Your Convenience: Their pink colouring hints that they're all parryable, and this is vital since parrying is the only way to beat them.
  • Ghostly Gape: Nearly all of them have empty eye sockets.
  • Kung Fu-Proof Mook: 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 getting to the urn where the Legendary Chalice is imprisoned in the center of the stage.
  • Night of the Living Mooks: Ghost enemies who have no goal but to capture souls in the Mausoleum.

The Runaway Debtors

     Bosses in general 
A veritable Rogues Gallery 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.

That is, they would've, if these individuals hadn't run off with their own contracts to parts all around the Isles, depriving the Devil 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.
  • Ambiguously Evil: It's never made clear if the debtors are really evil, or just happened to get indebted through a reasonable situation similar to our heroes and now have to fight to protect their souls from being taken by the Devil, although most do seem to enjoy beating the crap out of Cuphead and Mugman, though it might be out of enjoying fighting in general. At the end, they even throw Cuphead and Mugman a celebratory party for freeing them from their debts.
  • Anti-Villain: The ones with Soul Contracts, at least to some degree. 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.
  • Attack of the 50-Foot Whatever: While they vary in size, many of the bosses seen tower over Cuphead and Mugman.
  • Deal with the Devil: 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.
  • Everyone Has Standards: They all refused to work for the Devil and ran off with their own contracts. Needless to say, it doesn't look good on the player if they decide to pick the bad ending.
  • Flunky Boss: 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.
  • Game-Over Man: If they beat you, you get a card with their face on it 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.
  • Noodle Incident: All of them made deals with The Devil at his casino, and managed to get away with it somehow.
  • One-Winged Angel:
    • 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 Lampshades 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.
  • Pungeon Master/Rhymes on a Dime: The vast majority of their game over taunts.
  • Smug Smiler: A solid majority of them also flash a big, sinister smile of some sort at least once in their boss fights. In fact, most of them don't seem to be all that worried that Cuphead and Mugman are trying to collect their soul contracts. Then again...
  • The Unreveal: The deals they made with the Devil are never fully addressed beyond being Plot Coupons. 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 in that it's implied during battle what they got from the Devil (such as Rumor rifling through a spell book to transform and move onto her third phase).
  • Would Hurt a Child: The bosses are more than willing to fight Cuphead and Mugman, even though both of them are adolescents.

Inkwell Isle One

     The Root Pack 
http://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-carotine!"

A trio of vegetables whom you fight in a garden in "Botanic Panic". They are Moe Tato (a potato), Weepy (an onion), and Psycarrot (a carrot).
  • Dishing Out Dirt: Moe Tato starts the battle off by spitting out dirt clods and earthworms at you.
  • Edible Ammunition: Psycarrot can launch homing carrots at you.
  • Eye Beams: One of Psycarrot's attacks has him firing some beams from his Third Eye.
  • Hypnotic Eyes: Psycarrot wields these when you fight him, which he uses to send carrots at you or launch psychic beams.
  • Innocently Insensitive: A variant in how Weepy is definitely the most benevolent of the trio, but his defeat card can be taken as accidental Trash Talk.
    "Hey, little guy, it's okay if you have to cry!"
  • Macross Missile Massacre: Psycarrot uses one with homing carrots of all things.
  • Ocular Gushers: Weepy attacks this way by crying, with his tears raining down projectiles at you.
  • Onion Tears: Weepy's name and attack is a reference to the idea that onions make you cry.
  • Psychic Powers: As indicated in his name, Psycarrot wields psychic abilities.
  • Punny Name: Moe Tato is a pun on potato, while Psycarrot is a Portmanteau of "psychic" and "carrot".
  • Shout-Out:
    • Their name references the Rat Pack.
    • 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 ACME Grow.
  • Stationary Boss: Compounding on the rest of their easiness factors, none of the Root Pack members can move from where they're rooted.
  • Terrible Trio: All three of them seem to be the debtors.
  • Third Eye: Psycarrot opens his up when he starts firing his Eye Beams
  • Token Good Teammate: Weepy is the only of the three who doesn't mock the heroes in his win quotes, showing him to be nicer than his friends.
  • Warm-Up Boss: 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 Psycarrot, but even then, he's pretty small potatoes compared to some of the bosses you'll be facing later.
  • What Happened to the Mouse?: None of the trio are seen in the ending. Of course, being Stationary Bosses, 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.

     Goopy Le Grande 
http://static.tvtropes.org/pmwiki/pub/images/12_goopy_le_grande.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".
  • Attack Its Weak Point: Shooting his portrait on the tombstone is the only way to hurt him in his final phase.
  • Bald of Evil: 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.
  • Blob Monster: He's a blue slime monster, if the name of the boss and level didn't tip you off.
  • Clipped-Wing Angel: 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.
  • Close-Range Combatant: 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.
  • Con Man: The title and the stunt he pulls with the gravestone implies it.
  • Determinator: The third phase of his fight involves his gravestone attacking you.
  • The Fighting Narcissist: Each one of his win quotes talks about how handsome he is. Some of them are even in rhyme!
  • Guide Dang It!: 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.
  • Instant Gravestone: 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.
  • King Mook: Pretty much a larger version of the slime enemies from Forest Follies. In fact, a piece of Dummied Out code reveals that, upon being smashed by his tombstone, Goopy was at one point supposed to split off into two of the slime enemies.
  • Let's Fight Like Gentlemen: Tips his "slime hat" to you before the brawl commences.
  • The Lost Woods: Fought in a forest clearing.
  • Make My Monster Grow: His second phase has him eating a pill and getting much bigger.
  • Meaningful Name: 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").
  • Megaton Punch: 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.
  • One-Winged Angel: 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.
  • Shout-Out: His blue appearance and pointed top allude to the famous Slimes from Dragon Quest. When he transitions from his first phase to his second phase, he changes shape similar to how the blob shapeshifts. Likewise, his final form is, literally, a Living Tombstone.
  • Unskilled, but Strong: His attacks are insanely telegraphed (even by the standards of games of this nature), but they cover a wide area.
  • Warm-Up Boss: One of the first bosses in the game that you'll face, his attacks have incredibly obvious tells and are fairly easy to avoid, in addition to having fairly simple patterns. Also, he's the only boss with no projectile attack to speak of.
  • What Happened to the Mouse?: He's not seen in the ending. Sure, he outright died during his own boss fight, but his tombstone speaks as though it's still him when taunting you, yet the tombstone doesn't show up either.

     Hilda Berg 
http://static.tvtropes.org/pmwiki/pub/images/13_hilda_berg.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".
  • The Archer: Hilda's Sagittarius form, where she turns into a man on a cloud and shoots arrows at you.
  • Blow You Away: She can summon tornados from the weather vane on her head to throw at you.
  • Constellations: Most of her second phase has her turning into these when she attempts to dart at you, then shifting into them when she comes back onto the screen.
  • Faceship: Played with, she turns into a ship and her face happens to be at the front.
  • Flunky Boss: Little planes aid her in the fight in the first two phases. In the third phase, she can summon Flying Saucers.
  • Flying Saucer: 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.
  • The Hyena: Cackles incessantly in her blimp form, with lethal results.
  • A Load of Bull: Hilda's taurus form, which has her turning into a bull made of clouds to ram at you.
  • More Dakka: The energy balls summoned from her Gemini form shoots a stream of bullets in rotating motion.
  • One-Wheeled Wonder: While the top half of her body (before going One-Winged Angel, anyway) is merged with a blimp, the bottom half is a pair of perfectly human legs riding a unicycle — in all likelihood, the thing's power-source.
  • One-Winged Angel: Her "Alien Clockwork Crescent Moon" phase.
  • Painful Transformation: Before she changes into her final phase, she holds her head, clenched her eyes and makes a pained moan then her body starts freaking out.
  • Punny Name: Her name is a pun on the Hindenburg.
  • Shout-Out: Her hairstyle was clearly inspired by Betty Boop.
  • Sinister Schnoz: Has a very long nose, and when she shifts into her moon form, it gets even longer.
  • Spread Shot: The green flunky blimps during her battle fire a spreadnote , while her Sagittarius phase fires a spread of blue homing stars.
  • Stationary Boss: 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.
  • That's No Moon!: 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.
  • Trickster Twins: Hilda's Gemini form, where she turns into two girls on clouds and forms an energy ball to hurl at you.
  • Warm-Up Boss: 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 One-Winged Angel in her final phase, the bullet density is nowhere near as bad as later shoot-em-up bosses.
  • Wicked Witch: 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 the trope codifier.
  • Wingding Eyes: All her constellation forms have stars for pupils; this extends to her second-phase Game Over card.
  • Words Can Break My Bones: Her starting phase has her shooting out "HAs" at you.

     Cagney Carnation 
http://static.tvtropes.org/pmwiki/pub/images/14_cagney_carnation.png
"Extreme pollination and total domination!"

A flower boss whom you fight in a forest clearing in "Floral Fury".
  • Battle Boomerang: One of early projectiles is a sycamore seed that flies to the left over the platforms, then back across the right over the ground.
  • Bullet Seed: He forms a machine gun that shoots out the seeds (one of them pink) into the air before they fall to the ground and become monstrous plants.
  • Evil Laugh: He lets out a manic laugh has he transforms.
  • Eye Scream: When he's beaten, his eyes completely disappear. You can see straight through one eye hole and out the other.
  • Flunky Boss: In his first two stages, he occasionally launches seeds that sprout into enemies.
  • Foul Flower: A giant flower boss who acts innocent before quickly revealing his true, Ax-Crazy colors.
  • G-Rated Drug: Cagney's fuzzies are the quickie type in the patched version.
  • Green Thumb: A lot of his attacks are plant-based.
  • Interface Screw: 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.
  • King Mook: Looks like a much larger, thorn covered and malicious version of the flower people you fight in Forest Follies.
  • Nightmare Face: Starts his fight off by looking innocent enough, 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.
  • One-Winged Angel: Becomes slightly bigger and spikier-looking in his final phase.
  • Shout-Out:
    • The way Cagney moves his hands is similar to the animation of a ghost character from Fleischer Studios's short Swing, You Sinners!.
    • His name is obviously a pun on James Cagney. 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.
    • Intentionally or not, the fact that he's a flower that acts all innocent before quickly revealing its true monstrous colors, as well as the structure of his name, invoke comparisons with Flowey the Flower.
  • Slasher Smile: Wears a maniacal grin through his boss battle, with him really ratcheting it up in the final phase.
  • Soundtrack Dissonance: His battle theme, "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.
  • Stationary Boss: 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).
  • Wake-Up Call Boss: Unlike the Root Pack and Goopy, Cagney is the first ground boss to start invoking Bullet Hell 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.

     Ribby and Croaks 
http://static.tvtropes.org/pmwiki/pub/images/15_ribby_and_croaks.png
"We've had fightin' souls since we've been tiny tadpoles."

Two frogs in boxing gloves fought in a showboat club setting (ironically run by flies) in "Clip Joint Calamity". Ribby is in white, Croaks is in red.
  • Bash Brothers: Yep. They definitely hop into this trope.
  • Blow You Away: Croaks can turn himself into an electric fan in the 2nd phase of the battle. This attack doesn't do any damage though, but the pushing wind does make Ribby's projectile claps harder to dodge.
  • Dual Boss: 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 pistons on the Phantom Express and the Tipsy Troop, the two frogs share health, so it doesn't matter which one is attacked.
  • Frog Men: These two guys fit the bill right down to a "T".
  • Fusion Dance: Their final phases on normal mode has Croaks swallow Ribby whole and suddenly combine into a slot machine that's only vulnerable when it starts attacking after you parry-slap the handle.
  • Kamehame Hadouken: Ribby fires these off in his first phase.
  • Not So Different: Not explicitly stated, but they're a pair of Bash Brothers 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?
  • Ocular Gushers: Ribby will be left gushing with tears with Croaks pounding the floor when they are defeated in Simple difficulty.
  • One-Winged Angel: Their slot machine form, the result of a Fusion Dance as seen above.
  • Playing with Fire: In the first phase, Croaks will sometimes spit out burning fireflies that fly towards you.
  • Rapid-Fire Fisticuffs: Ribby starts his attacking by punching rapidly, which produces projectiles that zip toward you.
  • Shout-Out:
    • The characters and their color scheme are very similar to the ones from the series Frog and Toad by Arnold Lobel.
    • To Ryu and Ken from Street Fighter, made apparent by their boxing gloves and karate gi. They even do their more well-known taunts before battle (Croaks does Ken's Bring It, 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.
  • Stationary Boss: 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.
  • Visual Pun: Croaks spits out glowing bugs on fire that fly at you. They're literal fireflies.
  • What Happened to the Mouse?: 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.
  • Wrong Side of the Tracks: According to their second phase's game over card, they're from the wrong side of the lily pad, which is why they're crude and bad.

Inkwell Isle Two

     Baroness Von Bon Bon 
http://static.tvtropes.org/pmwiki/pub/images/161_baroness_von_bon_bon.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 (a cupcake, a gumball machine, a flying waffle, a multi-layered jawbreaker, and a giant candy cornnote ) at you before you are able to attack her directly.
  • Advancing Boss of Doom: In the final stage of the battle, the castle where she hides in begins to chase Cuphead and Mugman.
  • Angry Fist-Shake: Does this A LOT whenever you defeat one of her minions.
  • Anthropomorphic Food: 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 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.
  • Authority Equals Asskicking: Although most of the time she sends her mooks to do the bidding, she can also attack using a sugar cane as a shotgun.
  • The Baroness: That's her title, after all.
  • Berserk Button: The Baroness herself doesn't have one, but her cake castle certainly does: getting its towers pulled on. In fact, this is how she initiates the final phase of the battle; by pulling on the castle's towers, sending it into a rage and causing it to chase the boys down.
  • Detachment Combat:
    • The waffle minion breaks its body apart and launches the pieces in a Spread Shot attack.
    • The Baroness will throw her head during the final phase.
  • Flunky Boss:
    • The first part of her boss battle is fighting three randomly chosen minions, each with their own game over screen:
    • 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.
  • High Class Gloves: Wears a pair of pink opera gloves.
  • Homing Projectile: Her own head acts as one, chasing down the player character to try to damage them.
  • Improbable Weapon User: Her candy cane can somehow be used as a shotgun.
  • Level Ate: Fought in a kingdom of candy.
  • Losing Your Head: She can detach her own head and regrow it, even using the spare heads as projectiles in the last phase!
  • Matryoshka Object: Her jawbreaker minion is surrounded by several layers of candy shell. Once it's defeated, each shell cracks open to reveal a smaller jawbreaker until the tiny original is exposed, which then floats away.
  • Off with His Head!: The Baroness threatens the duo with this at the start of the battle.
  • One-Winged Angel: Not her so much as her cake castle, which transforms into an angered beast in the final phase.
  • Shockwave Stomp: Her cupcake minion produces waves made of icing whenever it slams onto the floor.
  • Shotguns Are Just Better: Her cane functions as this in the third phase of her fight, adding additional projectiles for the duo to worry about.
  • Shout-Out: The appearance of the Baroness and her barony are inspired by various cartoons' candy kingdoms, but most noticeably Cookietown from "The Cookie Carnival". One of her minions is also a jawbreaker version of Pac-Man.
    • Marie Antoinette may be also a strong contender, due to the infamous quote often (but incorrectly) attributed to her, "let them eat cake", and the fact that she indeed loses her head.
  • Slasher Smile: Makes a deranged one just before she initiates the final stage of the battle. As this picture so helpfully demonstrates.
  • Sore Loser: She bursts into angry tears upon defeat (complete with a Volumetric Mouth). In Regular mode, her living castle also beats the ground in frustration.
  • Stationary Boss: 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 Advancing Boss of Doom.
  • Vaudeville Hook: 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.
  • Visual Pun: When the cupcake 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.
  • Volumetric Mouth: She breaks down into sobbing in this way upon her defeat.
  • Wheel of Feet: Her gumball machine's feet are animated this way.
  • Winged Soul Flies Off at Death: The jawbreaker midboss gains a halo when defeated, floating off the screen while Bon Bon prepares for the next phase.
  • Your Head A-Splode: Happens to the gumball machine in its death animation; its glass head shatters and it scurries off.

     Beppi The Clown 
http://static.tvtropes.org/pmwiki/pub/images/191_beppi_the_clown.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".
  • Ambidextrous Sprite: 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's facing.
  • Amusement Park of Doom: Seemingly fights you in one; the rides he becomes are certainly killer, and the rollercoaster he fights you on is a constant, deadly stage hazard.
  • Bald of Evil: Completely bald, even underneath that little top hat of his as shown in the ending.
  • Berserker Tears: Has an absolute tantrum if you shoot down his merry-go-round horse.
  • Car Fu: Leaps into a bumper car for the first phase of the fight and tries to ram you.
  • Cheshire Cat Grin: Has a creepy wide, toothy grin.
  • Circus of Fear: Fought on a roller coaster in a rather bleak-looking amusement park.
  • Everything's Better with Penguins: Nope. In his final phase, he spawns penguin enemies that throw baseballs at you.
  • Flunky Boss: His final phase has him summoning penguins who throw baseballs at you.
  • Fun Personified: 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.
  • Gravity Is a Harsh Mistress: Falls off the roller-coaster twice during the fight, yet refuses to give up.
  • "Knock Knock" Joke: One of his death quotes falls under this if you get killed by his horse; see "Pungeon Master".
  • Magical Clown: A clown who can transform into and summon amusement park rides and other objects.
  • Monster Clown: A clown boss who will not hesitate to fight you.
  • Nice Hat: Wears a tiny top hat on his head.
  • Non-Ironic Clown: And during the ending, he has a genuinely pleasant smile on his face.
  • One-Winged Angel: 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.
  • Pungeon Master: 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!
  • Stationary Boss: 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.
  • Villainous Harlequin: A clown with terrifying transformations and Deranged Animation, though he isn't outright evil and is mainly just trying to avoid paying up to his end of a Deal with the Devil. The ending shows he is nice otherwise.
  • Voluntary Shapeshifting: Sure, the Deranged Animation 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.
  • Yellow Eyes of Sneakiness: Has yellow sclerae, and is definitely sinister.

     Djimmi The Great 
http://static.tvtropes.org/pmwiki/pub/images/17_djimmi_the_great.png
"You look the fool, falling for the first trick I learnt at genie school."

A genie fought above the desert in "Pyramid Peril".
  • Amazing Technicolor Population: Probably because he's been in the desert too long, but his skin is red as a tomato.
  • Aside Glance: Performs one complete with an Evil Laugh and Idea Bulb replacing his turban when he decides to create the marionette.
  • Bad with the Bone: During the first stage, one of his methods to attack is shooting out his own skull right from his face.
  • Bag of Holding: The first phase of his fight — he rummages around in a treasure chest, tossing out three possible types of projectiles:
    • Cat mummies: Lowest density, but the only one of the bunch that can home in on you, and considered the worst of the bunch because of this.
    • Jewelry: highest density, but not too hard to navigate as long as you keep one finger on the Shrink button at all times.
    • Swords: Probably the scariest looking, but universally considered the easiest to dodge.
  • Beat Them at Their Own Game: His fourth phase (third if not counting his Death Course) has him making a Cuphead puppet and sending it at the boys.
  • Blowing Smoke Rings: Or "a Smoke Teacup", actually: At the beginning of the fight, he blows out some smoke that forms a teacup with X's for eyes and a frowning mouth, indicating that the boys have no chance against him.
  • Death Course: 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, as well as sawblade traps in between.
  • Ethnic Magician: Has some elements of the "Arabian stage magician" sort, considering he's found in a carnival area, his title and the fact and speaks about needing a new volunteer (because this one has collapsed in fear) if you die to him on his final phase.
  • Evil Laugh: A pretty deep one he belts out whenever he's unleashing something new on you. When he decides to create the marionette, he even unleashes a slightly-robotic laugh to match his lightbulb turban.
  • Good Smoking, Evil Smoking: 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.
  • Homage: The background as you fight him in the sky is drawn in the style of the old Popeye two-reelers.
  • Idea Bulb: Has one while he laughs maliciously to the screen before starting the fourth phase of the battle (the Cuphead puppet).
  • Jackass Genie: He fits this down to a T, although he is kind of an Anti-Villain himself.
  • Nice Shoes: Wears magic lamps as shoes.
  • One-Winged Angel: Becomes so huge in his final phase that only his head fits onscreen.
  • Our Genies Are Different: 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.
  • Punny Name: His name is a pun on "djinni" (the formal romanization of "genie") and "Jimmy".
  • Pyramid Power: The final stage of the fight, he summons three floating pyramids with eyes encircling a half of the stage while firing cross-shaped beams from them.
  • Shout-Out: The way he moves and acts seems to be a villainous version of the Genie from 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 Jeannie dance while his treasure chest takes care of all the actual attacking.
  • Sinister Scimitar: Used in the Storm of Blades up there, natch. Also, if you try to sneak behind him during the fight, one of these immediately descends from the top of the screen and shish-kebobs you.
  • Smoking Barrel Blowout: One of the Game Over cards shows Djimmi's puppet blowing smoke from the tip of his finger gun after he has beaten you.
  • Spread Shot: 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.
  • Stationary Boss: Only in his first phase (where he's waiting still as his treasure chest attacks) and his last phase (where he takes up the entire right side of the screen).
  • Weaksauce Weakness: 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 with during the Sarcophagus phase, where any ghost that'd hit you will get nuked and the eyeball projectiles fall short.
  • Weaponized Headgear: During his fourth phase where he attacks you with a Cuphead puppet, 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.

     Grim Matchstick 
http://static.tvtropes.org/pmwiki/pub/images/195_grim_matchstick.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".
  • Advancing Boss of Doom: 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.
  • Apologetic Attacker: 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.
  • Battle in the Rain: The moment he enters his third phase and grows two extra heads, the weather goes from pleasant and sunny to stormy and violent.
  • Big Fun: 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 Laughing Mad at the player when he grows two extra heads.
  • Breaking the Fourth Wall: 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.
  • Breath Weapon: Complete with his middle head turning into an actual flamethrower during Phase 3.
  • Bubbly Clouds: Fought on the clouds surrounding a tower
  • Eye Beams: His first phase has him firing rings from his eyes at you.
  • Feather Fingers: A slightly more justified bat winged example. The gesture he makes during the opening is done with his wings rather than his actual hands.
  • Laughing Mad: He unleashes a bellowing laugh once he transforms into his final phase, and all three heads perform various comical smiles.
  • Multiple Head Case: He grows two extra heads for the final phase of the fight.
  • One-Winged Angel: After taking enough punishment from the boys, he suddenly grows two extra heads.
  • Platform Battle: His fight consists of you shooting him while jumping from one moving cloud to the next.
  • Playing with Fire: Aside from 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.
  • Porky Pig Pronunciation: All of his win quotes have him stuttering.
  • Shout-Out: His first form's design and moveset resembles the Mecha Dragon from Mega Man 2, with his final three-headed form adding in aspects of King Ghidorah for good measure, while his name itself is an homage to legendary Fleischer animator Grim Natwick; he even has a pronounced stutter in his game-over quotes, much like the real Grim did.
  • Speech Impediment: As you can tell with all his quotes, he has a stutter.
  • Spread Shot: In the third phase, his flame projectiles explode into a cross-shaped 4-way spread if they're damaged.
  • Stationary Boss: He doesn't move during any of his phases, though he shifts to the left side of the screen after the first.
  • Tail Slap: He will sometimes try to stab you with his tail in the first phase.
  • Victory Fakeout: An especially nasty one. Made it through the flame-soldier phase with 1 HP? Watch him cough and wheeze and cringe and... grow two extra heads that make faces at you while the sky itself darkens in utter terror.
  • Weaksauce Weakness: 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.

     Wally Warbles 
http://static.tvtropes.org/pmwiki/pub/images/18.bmp
"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". You fight him in the skies.
  • And Show It to You: A case where he literally coughs up his own heart to attack you.
  • Brains and Brawn: A dynamic he shares with his son, even lampshaded if his son beats you.
  • Bullet Hell: The second phase of the fight has him flap wildly and send his feathers all over in a spread, everywhere.
  • Clipped-Wing Angel: 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, he is no less deadly though, being able to unleash an utter onslaught of bullets with the help of his doctors.
  • Deadly Doctor: The paramedics carrying him 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 him, 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, no wonder he's pissed.
  • Eaten Alive: Presumed to be his fate when beaten, as the medic birds are seen pouring salt and pepper on him with hungry looks in their eyes.
  • Enfant Terrible: His chick is as deadly as he is and arguably more malevolent.
  • Feather Flechettes: 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.
  • Flunky Boss: His 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 at you.
  • Gadgeteer Genius: Wally's son 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.
  • Mr. Seahorse: Wally can apparently produce eggs.
  • Overlord Jr.: His son takes over for the third phase and attacks you with a ray gun and orbiting spiked eggs.
  • Papa Wolf: Despite being left injured and naked from the first two stages of the fight, hearing his son cry for help gets Wally to confront Cuphead while two medic birds carry him on a stretcher.
  • Perpetual Frowner: In contrast to most of the other bosses, Wally spends pretty much the entire battle angrily scowling. The closest thing to a smile he's seen with is if you lose to his final phase.
  • Rage Breaking Point: While he almost never looks happy, the 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.
  • Ride of the Valkyries: Played briefly during his theme music, 'Aviary Action'.
  • Shout-Out:
    • His temper tantrums during the second phase are reminiscent of Donald Duck's own fits of rage.
    • His color scheme and elongated beak are also similar to Woody Woodpecker. They both even have alliterative names beginning with W.
  • Spread Shot: He 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 Finger Gun head transformation can fire out a spread of two to three bullets. His second phase uses a massive spread of Feather Flechettes on the player characters.
  • Visual Pun: His 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.
  • Voluntary Shapeshifting: Can turn his head into 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.
  • Wake-Up Call Boss: 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.
  • What Happened to the Mouse?: Neither he nor his son are seen in the ending. His fight ended with him being presumably Eaten Alive, but considering Cala Maria came back just fine...
    • Considering that Cuphead and Mugman caused him to lose all his feathers, then beat up his son, he probably wouldn't be too pleased with them, so it makes sense that he wouldn't come back.

Inkwell Isle Three

     Rumor Honeybottoms 
http://static.tvtropes.org/pmwiki/pub/images/196_rumor_honeybottoms.png
"Hey sugar, this honey is off limits. Now scram."

A queen bee fought in an office building for bees (naturally) in "Honeycomb Herald".
  • The Bad Guys Are Cops: You have to fight a bee police officer before fighting her. If he defeats you, he accuses you of attempting a honey heist.
  • Bee Afraid: She's very dangerous and is not handing over her Soul Contract without a fight... especially when her flooding honey attempts to drown you.
  • Bee Bee Gun: One of her attacks consists of spitting bees that look like bullets... or are they bullets that look like bees?
  • Big Creepy-Crawlies: A honeybee and one of the larger bosses not fought in a plane in the game. The bee police is also roughly human-sized as well. Concept art shows that her bottom half is even more human-like, with legs in high-heels; and her "abdomen" is, in fact, a very flouncy dress.
  • Evil Laugh: One in her bi-plane phase, when she uses her buzzsaw attack.
  • Finger Wag: 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.
  • Flunky Boss: Her first phase has her summoning a police officer to take you on as well as some regular bee employees that fly across the screen.
  • Hornet Hole: Fought in a beehive-themed office building.
  • I'm a Humanitarian: The start of the battle has her looking hungrily at the boys while rubbing a fork and knife together.
  • Insect Queen: She's a queen bee. A dangerous one too.
  • Losing Your Head: 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.
  • Magic Staff: Her giant honey dipper that she wields. She also has a spell book she uses to transform.
  • Noblewoman's Laugh: In her second phase, fitting for a queen bee. In her final phase, it turns into a deeper Evil Laugh.
  • One-Winged Angel: Transforms into a bomber plane in her final phase.
  • Platform Battle: A vertical one where you have to keep jumping up on honeycombs to stay ahead of the rising honey in the first few phases. The last one has her fly to the bottom of the screen in a plane form and attacking you from there.
  • Shout-Out:
    • She starts the battle rubbing a knife and fork together in hunger, just like Q-Bee.
    • The bee/bullet projectiles she spits look and move an awful lot like Bullet Bills.
  • Spread Shot: 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.
  • Visual Pun: Her turning into a plane to fight you in the final phase. She's a "Buzz Bomber". Or alternatively a "Bee-17 Flying Fortress"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 Salary Man look, in other words: They're office drones.
    • The bee police officer that attacks you, if you use period appropriate British slang, is a Bobbee.
  • Voluntary Shapeshifting: In her final phase, she uses her powers to turn herself into a bi-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.

     Captain Brineybeard 
http://static.tvtropes.org/pmwiki/pub/images/new_bitmap_image_3.bmp
"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'".
  • Animate Inanimate Object: The barrel that looms over the player, and the ship itself.
  • Bait-and-Switch Boss: Pretty much the only straight example in the game. The final phase isn't against him, but instead his ship.
  • The Beastmaster: Similar to Cala Maria, he can call in a variety of sea creatures to assist him.
  • Captain Colorbeard: Though he was originally named Captain Silver, averting this trope.
  • Dressed to Plunder: Hits quite a few of the checks...
  • Evil Laugh: 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 Popeye the Sailor Meets Sindbad the Sailor.
  • Four-Fingered Hands: Averted. He's the only character in the game, human or otherwise, to have five fingers on each hand.
  • Flunky Boss: For the most part, it's his ship, barrel, and sea creatures that really attack you, with Brineybeard taking potshots at you on occasion.
  • Interface Screw: 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 a lot more difficult for a few seconds.
  • Make Me Wanna Shout: Once Brineybeard's ship takes over in the final phase, it will occasionally scream out a massive laser that engulfs most of the screen.
  • One-Winged Angel: 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.
  • Pirate Booty: His Game Over taunt states he doesn't actually have any buried treasure. It's just a myth, just like Cuphead's skills.
  • Sentient Vehicle: The ship itself is sentient and spits out cannonballs in the first phase. In the final phase, it even takes over as the boss.
  • Stationary Boss: 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.
  • Threatening Shark: 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.
  • Visual Pun: The small brown sharks with chains he summons are dogfishes.
  • Wave Motion Gun: In the final phase, the ship itself can fire one of these from the mouth on its uvula.
  • What Happened to the Mouse?: 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.

    Sally Stageplay 
http://static.tvtropes.org/pmwiki/pub/images/000_main_copy_14.png
"Break a leg... nah, break two!"

An actress you fight on a stage in front of an live audience in "Dramatic Fanatic".
  • Action Dress Rip: Bursts out of her wedding dress before the battle, though she's wearing a different dress underneath.
  • Action Mom: Assuming the babies in her second phase are her actual children (which is likely, as they resemble her and her husband).
  • All Part of the Show: 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.
  • Anachronism Stew: 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 JRPG final boss. So despite the game taking place in a 1930's cartoon, her play manages to reference games that would come out about six decades later.
  • Animate Inanimate Object: 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.
  • Art Shift: In the third phase of her battle, she appears as a cardboard prop, which is drawn with watercolors and Limited Animation rather than the usual fluid ink animation.
  • Attention Whore: Sally certainly seems like this doesn't 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.
  • Badass Normal: Pretty much 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.
  • Battle Couple: She and her husband were originally intended to be this for their battle with the boys.
  • Came Back Strong: Parodied. As part of the play she "dies" after the second phase complete with a costume change into an angel outfit and the actor portraying her husband crying tears of sorrow. Then she goes One-Winged Angel as detailed below.
  • Dramatic Wind: 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 Action Dress Rip mentioned above (even though the battle takes place in a stage!).
  • Everything's Better with Spinning: She'll do a spin dive kick for most of her attacks as well as send out a spinning parasol in the final phase.
  • Fiery Redhead: 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).
  • Funny Background Event: Get hit in the first phase and her fiancé will do a little heel click. Hit Sally, and he'll tug on his hat.
  • Giggling Villain: She's constantly cackling and clearly having fun with her battle.
  • Henpecked Husband: 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 being said, she does reward him with a smooch in the epilogue.
  • Large Ham: Her mannerisms really come off as over the top.
  • Neutral Female: Gender inverted by Sally Stageplay's husband during her boss fight; despite 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.
  • One-Winged Angel: 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 Eastern RPG Final Boss (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 and plays a large part in her Badass Normal status.
  • Parasol of Pain: One that's tremendously versatile at that, playing roles such as "Mook Maker", "teleporter", and "spinning top of death".
  • Shout-Out:
    • Like the final boss battle in Final Fantasy VI, Sally's third stage begins in the clouds, where she descends from the rafters as a painted angel backdrop sporting multiple purple wings. There's even cards in the upper-left corner that display her next attacks.
    • Her battle may be a stylistic reference to Dynamite Headdy. Whereas that game's setting is a puppet show, Sally fights Cuphead during her vaudeville act.
  • Smug Snake: 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 get out of her spotlight.
  • Stationary Boss: The cardboard cutout in the third phase doesn't move or directly attack; all of its attacks come from other places on the stage.
  • Trash the Set: Quite literally; in the final phase, the stage is pretty much 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.
  • "You!" Exclamation: 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.

    Werner Werman 
http://static.tvtropes.org/pmwiki/pub/images/000_main_copy_15.png
"Zis tank is ze ultimate veapon! You vill not vin!"

A giant mouse that controls a mechanical soup can to fight you in "Murine Corps".
  • invokedAccent Depundent: His last name, when said with a German accent, sounds like "vermin", fitting for an evil rodent.
  • Background Boss: The third phase turns the battle into this once the cat suddenly decides to have Werner for a snack and goes on to attack you.
  • Badass Normal: An expert machine pilot, 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.note 
  • Bamboo Technology: Cat-mecha aside, he 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.
  • Cats Are Mean: In this case, it's a mecha-kitty that's piloted by Werner himself.
  • Cigar Chomper: Starts his battle off by lighting a cigar and keeps it in his mouth through the entire fight.
  • Cool Helmet: Sports a Pickelhaube.
  • Eaten Alive: After beating his second phase, a cat suddenly crashes into the area and eats him. 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.
  • Expy: The cat in his stage resembles a pre-Art Evolution Tom quite a bit. He himself resembles Mortimer Mouse.
  • Foreshadowing: When your bullets hit the cat in the third phase it makes a metal clinking sound. In addition, after the cat bursts in and eats him, the brothers don't get his contract, hinting that he's still alive.
    • Speaking of the cat, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.
  • Funetik Aksent: His game over quotes have him speak in an exaggerated German accent.
  • Humongous Mecha: It's not very obvious at first, but the cat waiting around outside Werner's home serves as his trump card in the final phase of the fight, and is revealed to be one upon his defeat.
  • Hurricane of Puns: Nearly everything about him is a pun in some way, from his name, who he's based off of, the name of his level.
  • Kaiserreich: He's 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.
  • Macro Zone: Fought in a mouse hole in a giant house.
  • The Man Behind the Curtain: He's the one controlling the cat once you beat the third phase.
  • Mega Neko: The cat.
  • One-Winged Angel: Double Subverted. What initially appears to be a Bait-and-Switch Boss in the final phase turns out to actually be this.
  • Our Ghosts Are Different: Ghost mice that fly out of the cat's mouth and shoot out parryable projectiles. Made all the more strange with the revelation that the cat's just a Humongous Mecha. Werman being what he is, they are likely some kind of holograms.
  • Perpetual Frowner: Unlike most of the other bosses, though this may just be an animation quirk from the cigar in his mouth.
  • Playing with Fire: His second phase has him using chair-mounted flamethrowers.
  • Pun-Based Title: The title of his stage is "Murine Corps". Murinae is the scientific classification for the subfamily of old world rats and mice.
  • Punny Name: In addition to the Accent Depundent entry above, his last name also sounds like the German word "Wehrmann" which is an old way to address soldiers, fitting well with his Pickelhaube helmet.
  • Robotic Reveal: When beaten, the giant cat's face falls off and is revealed to be actually a mecha piloted by Werner.
  • Rodents of Unusual Size: Shown to be roughly the same size as other humans in the ending.
  • Shout-Out: He's based off war cartoons and Tom and Jerry. This makes more sense than it might seem at first: "Jerry" was a common nickname for German soldiers during World War I.
  • Spread Shot: In his first phase, the tank can catapult a spread of random garbage at the heroes.
  • Tank Goodness: Pilots a makeshift tank made from a giant soup can in his first two phases.
  • Visual Pun: His tank's cannon shoots literal cherry bombs.

    Dr. Kahl and his Robot 
http://static.tvtropes.org/pmwiki/pub/images/new_bitmap_image_4.bmp
"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".
  • After the End: His level looks like a utter warzone. Justified, in that the fight takes place in a junkyard.
  • Androids Are People, Too: The contract specifies Dr Kahl's robot specifically, so it is not only autonomous but capable of signing into contracts and has a soul.
  • Attack Its Weakpoint: The robot has several of them, its main weakpoint being its own heart.
  • Battleship Raid: His robot's first phase is the only boss in the game with destructible "parts" on its body.
  • Bullet Hell: 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.
  • Clothing Damage: After defeating Dr. Kahl in his final phase, the resulting explosion blows all of his clothes off.
  • Down in the Dumps: Fought in the junkyard.
  • Drone Deployer: One of the first attacks.
  • Eating Machine: The robot is seen chewing bubblegum in his intro, blowing a bubble before the match starts.
  • Evil Laugh: 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.
  • Frickin' Laser Beams: 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 smaller but more frequent scale.
  • Humongous Mecha: Dr. Kahl's robot itself is a huge robot that he pilots to attack you.
  • Mad Scientist: Looks the part with glasses, a lab coat, wild hair, mustache and beard, and crazy expressions.
  • No Celebrities Were Harmed: His design may reference a caricature of Groucho Marx that was frequently used in late '30s and early '40s cartoons.
  • One-Winged Angel: The robot becomes just a head in the final phase, with Kahl now being visible and using magical gems to fight.
  • Pet the Dog: His robot is the debtor, not him; he still helps it fight.
  • Purple Is Powerful: A genius scientist with purple hair.
  • Ridiculously Human Robots: 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?
  • Selective Magnetism: 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.
  • Shout-Out: A clear one to both Dr. Wily and 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 gems and skull-motif bombs to attack you. His robot's design clearly takes after The Iron Giant (as in, the original book's take on the Giant's design, not the 1999 movie based on it). His name is a shout-out to legendary animator Milt Kahl, as well.
  • Smart People Build Robots / Robot Master: Dr. Kahl himself, of course.
  • Smart People Wear Glasses: Wears a pair of lime green glasses.
  • Spread Shot: 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 Bullet Hell version of this (whose load is at least lightened a bit in the patched version).
  • Stationary Boss: 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.
  • Tin-Can Robot
  • What Happened to the Mouse?: Neither he nor his robot are seen in the ending. Considering that you had to trash the robot (which he helps with fighting the Cup Brothers, seeing as the robot itself is the debtor) in order to obtain its soul contract, it's little wonder why Dr. Kahl wouldn't have much to celebrate about.
  • You Gotta Have Blue Hair: Has purple hair.

     Cala Maria 
http://static.tvtropes.org/pmwiki/pub/images/197_cala_maria.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".
  • Adorkable: Often gasps like Betty Boop in dismay when things don't turn out the way she expected them to, from losing her grip on her giant fish friends to getting zapped by electric eels.
  • Alien Hair: Her "hair" is actually a live octopus (the X shapes on its eyes are just lids-it opens them to back up her summoning gestures), with five of the tentacles turning alive and morphing into snake heads when she goes One-Winged Angel.
  • Attack of the 50-Foot Whatever: A giant mermaid who pretty much towers over the two boys and their bi-planes.
  • The Beastmaster: In the first two phases, she fights primarily by summoning sea creatures to attack the two brothers.
  • Body Horror: When using her petrifying gaze, two of the snakes on her loop around to the back of her skull and emerge from her eye sockets with both her eyes in their mouths.
  • Breath Weapon: In her first phase, she exhales ghosts that target Cuphead and/or Mugman's position(s).
  • Cute Giant: A gigantic mermaid with large eyes and an adorable smile. Somehow, she still manages to retain some cuteness after turning into a gorgon.
  • Eye Scream: 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.
  • Flunky Boss: She summons all manner of aquatic life to attack you with.
  • Gasshole: She belches out pirates ghosts as an attack.
  • Giant Woman: Well, giant mermaid, but she's one of the most human-like characters of the game.
  • Giggling Villain: Lets out a high-pitched giggle everytime she dives underwater to weaponize a giant fish. She outright cackles after transforming into a gorgon.
  • Good Scars, Evil Scars: 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.
  • Gorgeous Gorgon: Can turn into one, yet still doesn't look that bad despite the scary upgrade.
  • Hartman Hips: She's got some nice wide hips that she loves to sashay around.
  • Losing Your Head: The final phase of her fight has her detacting her head off her body and floating though a spiked cave.
  • Ms. Fanservice: She's quite the dish and she knows it. Her Gorgon form doesn't look too bad either. As noted above.
  • Non-Standard Character Design: Compared to the other females, like Sally Stageplay and Baroness von Bon Bon, she has a figure and flaunts it.
  • Oh, Crap!: 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.
  • One-Winged Angel: As mentioned several times, her gorgon form. Her floating head phase is more of a Clipped-Wing Angel due to not being as powerful and relying more on the surrounding environment to hurt you.
  • Our Mermaids Are Different: She can get zapped by some electric eels and turn into a gorgon, for one thing.
  • Painful Pointy Pufferfish: She can summon some of them to damage the players.
  • Psycho Electric Eel: 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 a lot of bullets, some of which are pink and parryable in the patched version.
  • Punny Name: 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!
  • Seashell Bra: Befitting a mermaid.
  • Shameless Fanservice Girl: Strikes a model pose in her intro and sways her hips constantly.
  • Shout-Out:
    • One to Parodius, which likewise featured a giant mermaid with a green tail as a boss in Gokujyo Parodius. As well as a giant gorgon boss in a later game, Sexy Parodius, which itself was a shout out to Castlevania since it was virtually a giant Medusa Head 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.
  • Snake People: 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.
  • Spread Shot: 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).
  • Stationary Boss: Only during the second phase, where she loses the ability to retreat underwater.
  • Swallowed Whole: Implied. She uses ghosts of dead sailors as a Breath Weapon.
  • Taken for Granite: 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.
  • The Tease: 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 as well.
    "You are a cutie... I am not sure if I should catch and release!"
  • Unexplained Recovery: 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, apparently no taller than Cuphead and Mugman.
  • World's Smallest Violin: When she's beaten in Regular Mode, one of her snake hairs plays a tiny violin.
  • X-Ray Sparks: When being electrocuted by the eels during the transition into the second phase.
  • Your Size May Vary: She's absolutely enormous during her battle, but relatively normal-sized in the ending.

    Phantom Express 
http://static.tvtropes.org/pmwiki/pub/images/new_bitmap_image_8.bmp
"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; T-bone, a skeletal conductor; the Blaze Brothers, 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".
  • Afterlife Express: Inhabited by many spectral beings who attack you.
  • Animate Inanimate Object: 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.
  • Attack Its Weak Point: In the final phase, you must parry off the engine's tail to expose his boiler core and shoot at that.
  • Bigger on the Inside: It must be, considering T-bone and the Blaze Brothers only partially emerge from the train cars.
  • Blind Seer: 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.
  • Breath Weapon: The Blaze Brothers in the third phase attack you by breathing columns of fire.
  • Dem Bones: The second phase sends out T-bone, a giant skeleton conductor to try and crush you.
  • Disc-One Final Boss: The final runaway debtor that you need to get a contract from, but the game isn't over just yet.
  • Eyes Do Not Belong There: 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.
    • Eyeless Face: This is of course contrasted by the one eye socket that's actually in its face remaining completely empty at all times.
  • Implied Death Threat: Every phase except the final does this in their respective game over quotes.
  • Sentient Vehicle: Aside from the fact that the train owes the Devil its soul, the train engine itself attacks the heroes in the final phase.
  • Shout-Out: The final phase could be one to Sleeper Brakeman's fight from Noitu Love 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 Final Fantasy VI 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.
  • Spider Engine: At the final phase, the engine stops the train to reappear galloping like a horse with spindly legs.
  • Stationary Boss: 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 block shots.
  • What Happened to the Mouse?: The Head of the Train, T-bone, and the Blaze Brothers 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.
  • 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; T-bone is based on gashadokuro, a giant skeleton; the Blaze Brothers appear to be based on wanyuudou, flaming oxcart wheels with screaming faces; and the Head of the Train is based on oboroguruma, oxcarts with faces found on roads late at night.

The King's Court

     General 
Mini bosses that are under the command of King Dice. You have to fight a few of them in order to finally fight King Dice himself.


  • Animate Inanimate Object: 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.
  • John Barleycorn and Friends: The Tipsy Troop and Mr. Wheezy represent drinking and smoking, respectively.
  • Obviously Evil: Unlike the debtors, who can be classified as 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.
  • Optional Boss: A skilled player can manipulate the dice enough to only fight just three of them.
  • Quirky Miniboss Squad: They don't even have multiple forms; they're all just stepping stones to get to King Dice.

     Tipsy Troop 
http://static.tvtropes.org/pmwiki/pub/images/21_tipsy_troop.png
"Go sleep *hic* it off...you look a little *hic* rough!"

A martini, a shot glass filled with whiskey, and a bottle of cognac fought on a regular table.
  • Alcohol Hic: These guys hiccup while they talk in their Game Over quotes, due to the alcohol in their bodies.
  • Death from Above: The cognac bottle shoots out streams of booze into the air which then falls on your position.
  • Drunken Master: All of them appear quite tipsy on themselves, and this reflects in their losing animations — the martini becomes dizzy and disoriented, the whiskey gets sentimental and weepy, and the cognac turns raucous and loud.
  • Dual Boss: Taken an extra step since you fight against three here.
  • Flunky Boss: The martini summons flying olives who shoot their eyes at you.
  • Lady Drunk: The martini resembles one.
  • Mook Maker: The martini serves as one of these with the aforementioned flying olives.
  • Stationary Boss: 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...
  • Turns Red: Inverted — as you progress through the battle, the trio will fall one by one, making the fight get progressively easier.

     Chips Bettigan 
http://static.tvtropes.org/pmwiki/pub/images/22_chips_bettigan.png
"Hey short stack! This isn't a place you wanna be hanging 'round."

A stack of poker chips fought on a card table.
  • Attack Its Weak Point: 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 
  • Nice Hat: Wears a nice Stetson on his head.
  • Punny Name: His first name is pretty obvious, given what he is. As for his surname... well, just say it out loud.
  • Shout-Out: His main attack resembles that of the signature move of the Devil series bosses from Mega Man.

     Mr. Wheezy 
http://static.tvtropes.org/pmwiki/pub/images/23_mr_wheezy.png
"Looks like you could use some fresh air."

A giant cigar you fight on two ashtrays over a pit of flames.
  • Battle Amongst the Flames: His fights take place right above a pit of flames.
  • Good Smoking, Evil Smoking: Definitely evil considering he's literally a living cigar under the employ of the Devil's Dragon.
  • Flunky Boss: Smaller winged cigarettes fly in the middle of the stage, making it difficult to jump between platforms.
  • Meaningful Name: Wheezing is one of the natural results of smoking for lengthy periods of time, after all.
  • One to Million to One: Every so often, he'll burn himself up and reform from the ashes on the other ashtray.
  • Playing with Fire: Spits out fireballs during his battle.
  • Shout-Out: To Cab Calloway, especially notable in his picture on the right; it's an expression Cab made and had photographed many times, like so.
  • Vader Breath: He constantly coughs and wheezes during his fight, more so after being defeated.
  • Villain Teleportation: Going hand-in-hand with his ash-regeneration technique.
  • You Have Failed Me: When beaten, King Dice stomps on him for his failure. Also doubles as a Stealth Pun; what's the most common method people use to put out a cigarette?

     Pip and Dot 
http://static.tvtropes.org/pmwiki/pub/images/24_pip_and_dot.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.
  • Conveyor Belt-O-Doom: Their boss battle is set on one leading you toward a wall of spikes, which you must keep running away from while avoiding their attacks and the spiked floor as well.
  • More Teeth than the Osmond Family: Their middle section holds a third mouth that has a lot of fangs in the middle of it.
  • Multiple Head Case: Both the male and female faces have separate personalities.
  • Nice Hat: Pip wears a blue top hat.
  • Punny Name: A "pip" and a "dot" are both terms that refer to the dots on a domino.
  • Tertiary Sexual Characteristics: Cleverly, the bow in the center pulls double duty: it serves as a masculine bow tie for Pip and a feminine bow for Dot.
  • You Have Failed Me: Humorously, not from King Dice, but from Dot, who kicks Pip in the face for losing.

     Hopus Pocus 
http://static.tvtropes.org/pmwiki/pub/images/25_hopus_pocus.png
"...and PRESTO!! The cup has completely disappeared."

A crazed rabbit magician fought in a room with playing cards.
  • Hair-Raising Hare: He's an evil rabbit magician.
  • Laughing Mad: Begins laughing as soon as the battle begins, and won't stop until either himself or you are defeated.
  • More Teeth than the Osmond Family: And far, far more teeth than any rabbit should have, let alone sharp ones.
  • Punny Name: Based on the words "Hocus Pocus" and "hop."
  • Slasher Smile: 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.
  • Stage Magician: His motif; he uses his magic to send projectiles at you.
  • Stationary Boss: Sits in his top hat for the entire fight.

     Phear Lap 
http://static.tvtropes.org/pmwiki/pub/images/26_phear_lap.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.

     Pirouletta 
http://static.tvtropes.org/pmwiki/pub/images/27_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.
  • Dance Battler: 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.
  • Death from Above: As mentioned above, said roulette balls fall from the top of the screen.
  • Getting Crap Past the Radar: Her game over quote states that her style is "very Russian".
  • Punny Name: A portmanteau of the words "pirouette" and "roulette".
  • Statuesque Stunner: Very tall and lanky, yet oddly pretty too.

     Mangosteen 
http://static.tvtropes.org/pmwiki/pub/images/28_mangosteen.png
"Fault, scratch and choke — are you trying to hustle me?"

A giant eight ball fought on a pool table.
  • Bad Guys Play Pool: In this case, bad guys are pool.
  • Body Horror: He's just eyes and a mouth over a 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.
  • Flunky Boss: He is aided by pool cubes which drop down from the side of the screen and bounce across the area.
  • Shout-Out: His design is a reference to Melon Bread from Gunstar Heroes and other Treasure games, which inspired Cuphead. In fact, 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.
    • In addition, 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.
  • Stationary Boss: His pool cubes handle the ground for him; he just floats still above the table, occasionally firing energy blasts.
  • Waterfall Puke: 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.

     Mr. Chimes 
http://static.tvtropes.org/pmwiki/pub/images/29_mr_chimes.png
"Monkey see, monkey doom."

A toy monkey fought via bi-planes in a crane game machine.
  • Cymbal-Banging Monkey: 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.
  • Eyeless Face: His eye sockets are completely hollow.
  • Hoist by His Own Petard: When defeated, the crane holding him starts to move its front two claws to start slamming his cymbals together into his face.
  • Puzzle Boss: 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.
  • Spread Shot: Every time he bangs his cymbals, a spread of 6 projectiles are fired out radially.

Other Characters

     Porkrind 
http://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.

    Legendary Chalice 
http://static.tvtropes.org/pmwiki/pub/images/chalice.png
"Speaking of magic... please accept this gift, it should help!"

A spiritual beverage-holder investigating magic. Gives new Special Abilities after being protected at Mausoleums across the Inkwell Isles.
  • Damsel in Distress: In all three mausoleums, she's always found stuck inside an urn and needing rescue from the ghosts within. That said, she always rewards the boys with a new powerup (A wave gun, limited invincibility and finally making Fighting Spirit corporeal to attack enemies).
  • Greater-Scope Paragon: An angelic ghost, patterned after the Holy Grail, who gives the boys valuable tools to help in their quest in exchange for their aid. As revealed in the castle ruins of Rugged Ridge, before she died, she was one of the land's heroes.
  • Leitmotif: The xylophone tune serves as her theme.
  • Speaking Simlish: She's one of the few characters with voiced dialogue, and it's done in this way.
  • Too Dumb to Live: Subverted. Despite being captured in the first Mausoleum, she keeps looking for them so she can give Cuphead and Mugman new Super Arts.

http://tvtropes.org/pmwiki/pmwiki.php/Characters/Cuphead