Follow TV Tropes


Characters / Cuphead

Go To

The character sheet for the Studio MDHR video game, Cuphead.

Beware unmarked spoilers!

    open/close all folders 

Main Characters

    Cuphead & Mugman
"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. invoked
    • While using their airplane machine guns, their Ex Move, Chomper Missile, launches a large missile with a chomping jaw on it that deals damage with each bite.
  • Action Bomb: In flying stages, their supers turn them into literal bombs that they can ram into their opponents. It's fittingly named Super Bomb Morph.
  • 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 sparednote . 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 isn't really 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.
  • Big Little Brother: Though the brothers may seem to be around the same height, Mugman is noticeably slightly taller than Cuphead.
  • 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.
  • Color-Coded for Your Convenience: Cuphead's red and Mugman's blue. Even their personalities 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 pours a liquid into his head, then transforms into a tank in this 1936 Japanese propaganda cartoon.
  • Face–Heel Turn: In the bad ending, they become the Devil's servants.
  • Finger Gun: They attack by making finger guns and firing shots from them, with the shots apparently being drawn from the liquid in their heads. Comes in six flavors:
  • Fireball Eyeballs: The boys have these when they are turned into the Devil's servants in the bad ending.
  • Forced into Evil: They have no choice but to be the Devil's enforcers; if they don't collect the souls then they too are doomed to live in hell for all eternity.
  • Foolish Sibling, Responsible Sibling: Cuphead and Mugman, respectively. Case in point, Mugman tried to discourage Cuphead from gambling their souls for the Devil's loot, but the latter was so blinded by his own greed that he took the bet and lost.
  • 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.
  • Kid Hero: 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.
  • Limit Break: The boys can collect three super moves during their adventures, granted by the Legendary Chalice at Mausoleums around the island. They can be used once all 5 Ex Cards are filled.
    • I — Energy Beam: The first Super Art they receive allows them to jump into the air and fire a giant stream of liquid, Wave-Motion Gun-style, at their opponent.
    • II — Invincibility: The second Super Art they get is, as stated, an Invincibility Power-Up that lasts for a limited time (after they somehow turn their heads huge and give off a creepy laugh for... some reason).
    • III — Giant Ghost: The third super they can gain allows them to manifest a ghostly, stronger form of themselves which will float and spin around and hit their enemies repeatedly, after which it will vanish and leave behind a pink heart they can parry for extra mana.
  • 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.
  • Macross Missile Massacre: While using their airplane bombs, their Ex Move becomes Magnet Mine/Missile, which launches a missile barrage that homes in on nearby enemies and works great for screen-clearing.
  • Mocky Mouse: Their designs of having mostly black bodies while wearing white gloves, shoes and shorts is clearly evocative of Mickey Mouse.
  • Mr. Vice Guy: Cuphead may be greedy and short-sighted, 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 who got the duo into their nasty situation in the first place by taking a high-stakes game against the Devil and losing, though Mugman was willing to gamble in the Devil's casino at first, only stopping upon realizing the dangers of taking the Devil's gamble, though it was too late by that time. 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 combat, they both get this reaction when the Devil gives them a Death Glare which plays out what he will do to them, and they both let out a terrifying scream in fright. This is the only battle intro where they get scared out of their wits instead of being prepped up for battle, though they quickly recover their Heroic Resolve and fight like it's now or never.
  • Parrying Bullets: A non-sword variant. When being shot at by pink-colored bullets, the two can jump off of them or slap them aside to avoid damage and possibly collect one special charge. The patched version makes this very essential in the final part of Dr. Kahl's stage, where they will be parry-slapping his pink bullets a lot while attacking him and avoiding electric barriers.
  • 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.
  • 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.
  • 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.
  • Sibling Team: See Bash Brothers stated above.
  • Spin to Deflect Stuff. Their Parry move that allows them to deflect pink-coloured attacks has them do a somersault, deflecting the attack with a hand that grows out of the straw on their head.
  • Stone Wall: The Heart charm turns them into this, reducing damage output in exchange for an extra heart. The Double Heart charm nerfs your damage even more in exchange for one more additional heart (two total).
  • 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 to Twitter, Studio MDHR jokingly describes both of them as "kidults". But according to writer Evan Skolnick, Cuphead and Mugman are adolescents, though their exact age is still unknown.
  • Weak, but Skilled: On their own, they are extremely weak and fragile, with three direct hits being enough to shatter them to pieces. However, they are very agile and persistent, capable of constantly dodging their enemies' attacks and firing at them non-stop with their Finger Guns until they are too injured to fight further.
  • 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
"What a fine pickle you boys have gotten yourselves into!"

Cuphead and Mugman's mentor and legal guardian. An anthropomorphic tea kettle who gives them a special potion to defend themselves against the Devil's debtors.

  • Adult Fear: In the bad ending, his apprentices/grandsons become servants of the Devil.
  • Ambiguously Related: Is stated to be the caretaker of Cuphead and Mugman, but it's unclear if he's actually their father, grandfather, foster parent, or otherwise. Considering that he's an anthropomorphic kettle, and they're cup-headed people, they do look somewhat different.
  • 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 and Mugman for gambling in the Devil's Casino.
  • Do Wrong, Right: He gives Cuphead and Mugman a potion that will help them fight the runaway debtors. He also says that ideally Cuphead and Mugman wouldn't have to do it, but the boys have no choice.
  • Mentor Archetype: He acts as a father figure to Cuphead and Mugman, though it's not made clear if they're actually family. On Twitter, writer Evan Skolnick confirmed that the Elder Kettle is Cuphead and Mugman's legal guardian.
  • 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: Implied, as he "passes the torch" down to Cuphead and Mugman by giving them a magic potion for their Peashooter ability. There's also a sword hanging on the wall of his cottage, and just where he got that potion is never clarified, suggesting it came from an adventure in his youth. In the ruins in the Rugged Ridge level, there is a statue of him kneeling with sword in hand.
  • Shout-Out: His design may be based on Mr. Coffeepot from the 1935 Van Beuren cartoon Picnic Panic.
  • So Proud of You: The good ending when the boys free the Inkwell Isles residents of their debts.

    The Devil

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.
  • Aerith and Bob: Most other bosses have creative (and often alliterative) names, but he is plainly referred to as "The Devil".
  • Antagonist Title: Sorta. His name appears in the game's subtitle, "Don't Deal with 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. He proceeds to unleash his inner Kaiju on the player, to the point that the protagonists are about as big as his pupil.
  • Background Boss: He spends the first phase of the fight on his throne in the background, reaching into the foreground to do various attacks. Taken further during his second phase and onward, where his giant head takes up most of the background.
  • 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 turns 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 Cuphead and Mugman. 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: The opening theme song isn't kidding if you lose to his second phase and onwards!
  • The Devil Is a Loser: The final phase of his boss battle has him crying, 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.
  • 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.
  • Graceful Loser: Well, his display at the end is far from graceful but... He really does stick by his words when he talks about how "a bet is a bet". After his defeat, he pulls no strings or backstabbings and instead, truly frees Cuphead and Mugman and lets them even burn the bosses Soul Contracts.
  • Gruesome Goat: During the first phase of his boss fight. One of his attacks is having his face morph into a goat head (complete with rectangular-shaped pupils) and his hands turn into hooves. Even his Evil Laugh sounds like goat bleats during that attack.
  • 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.
  • Humanoid Abomination: The Devil may be humanoid in appearance, but is so powerful that he is capable of shapeshifting into various terrifying forms.
  • Jerkass: Anyone who loses to him in his casino has to repay him with their soul in eternal servitude. And if that weren't enough... he's the Devil.
  • Losing Your Head: One of his attacks has him remove his head before transforming it into a spider.
  • Nice Job Fixing It, Villain!: Sending the brothers on their quest to collect his wayward debtors bites him big-time: after their Training from Hell, Cuphead and Mugman end up becoming strong enough to defeat him.
  • 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.
  • Reptiles Are Abhorrent: Able to transform his head into a draconic serpent.
  • Satan: He's the Devil himself, of course.
  • Scaled Up: One of his transformation attacks has his head become a draconic serpent.
  • 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: He initially has this reaction when the player decides not to hand over the soul contracts after all, triggering the fight with him. As the second phase of his fight progresses on, he gradually grows angrier and more frustrated. By the final phase, he's lost all composure, is reduced to pitifully crying parryable tears, and no longer has the strength or will to summon anything other than a lone poker chip on the only remaining platform. Upon defeat, his pride is completely shattered and he can only clutch his head in pain.
  • Voluntary Shapeshifting: Pulls a number of these in his fight, turning into a draconic serpent, 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
"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.
  • Crossdressing Voices: His Villain Song, "Die House," is performed by a female singer, Alana Bridgewater.
  • Dastardly Whiplash: His appearance resembles this style of villain. He even has the pencil-mustache.
  • 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: He's the self-described "Devil's right-hand man", his boss' main face and enforcer on the island, and the last boss that needs to be fought to get to the Devil.
  • 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's got to keep a friendly and welcoming attitude up to convince people to come there in the first place. Also goes hand-in-hand with his status as a sort of Anthropomorphic Personification of gambling and games of chance — tempting with the promise of riches, yet deceitful and dangerous.
  • Flunky Boss: King Dice never actually attacks you directly. For most of his boss fight, he instead sends you to a Boss Bonanza of various minibosses, and even when he does fight you himself, he sends lines of cards marching towards you; if you can't parry off the pink heart cards, you'll get hurt.
  • Foil: Seems to be one for Cuphead and Mugman. Both are cartoony people with Non Human 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.
  • Genre Savvy: It's implied King Dice grew privy to the idea that the Devil might just replace him with Cuphead and Mugman should they successfully bring him the contracts, so he decides to fight the boys for them and deliver the contracts himself. Given who his boss is, he has all the reason to be wary of his job security.
  • 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: His Die Houses block the bridges between the isles, and he'll only let you through once you've defeated all the bosses on that island. Even his boss fight is this, as the route to the Devil will only open up once he's played his game with the boys. Referenced in his 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.
  • Secondary Color Nemesis: Wears a purple tux and has green eyes.
  • Sharp-Dressed Man: Wears a purple tux.
  • 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 being based on pure 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.
  • Slasher Smile: He sports a rather potent grin.
  • Stealing the Credit: Implied in his Villain Song. Despite the fact that Cuphead and Mugman have to collect soul contracts for the Devil, King Dice won't let you see him, even if you have all of them. Instead, you have to beat him before facing the Devil.
    Bring me those contracts, pronto!
    Don't you mess with me!
    Bring me those contracts! Come on, bring 'em to the king!
  • Sudden Eye Colour: When he's being particularly menacing, his irises turn green.
  • 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 and unrepentant villain.
    "I'm Mr. King Dice, I'm the gamest in the land.
    "I never play nice, I'm the Devil's right-hand man!"
  • 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

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 separate 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: It's possible to get through all of these levels without killing any enemies. It is not, however, easy.
  • 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: All of the minibosses are skippable in some matter, to facilitate the Pacifist Rank. Some can be smoke bombed past, some can be skipped with clever parries, and sometimes you can just take damage and let your Mercy Invincibility do the rest.

    Forest Follies' Foes
"Nowhere to run, nowhere to go — this forest is yer foe!"

The inhabitants of the woods leading to Goopy le Grande.

  • Blob Monster: The tiny slimes with limbs that run back and forth, and respawn after being defeated.
  • Foul Flower: The most basic enemies on this level are humanoid flowers that run after Cuphead and Mugman to harm them the moment they appear. There are also purple tulips that fire exploding beans.
  • The Goomba: The flower people that parachute from the sky are the most basic enemies on this level and can be defeated in several shots.
  • Incendiary Exponent: The purple tulips fire purple beans that explode into flames when they hit the ground.
  • Invincible Minor Minion: There are Piranha Plant-esque plants that jump from bottomless pits as a stage hazard, which can't be destroyed.
  • Man-Eating Plant: Giant black flytrap-esque plants appear as stage hazards.
  • Mook Maker: The Acorn Maker, a furnace-like machine endlessly cranked by a single flower enemy.
  • Plant Person: With the exception of the slimes and the mechanical Acorn Maker, all of the enemies are animated plants (or animated fungi, or living seeds).
  • Reviving Enemy: The tiny slimes that run about fall into a puddle when shot once, but reform themselves a second later to continue running around.

    Treetop Trouble's Terrors
"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.

  • Airborne Mook: The beetle enemies constantly fly mid-air.
  • Big Creepy-Crawlies: The level is populated with tumbling ladybugs, fanged beetles, helpful mosquitoes, and a giant dragonfly as a miniboss.
  • Dreadful Dragonfly: A giant fire-breathing dragonfly serves as the Mini-Boss in this level.
  • 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.
  • Mosquito Miscreants: Averted; mosquitoes are actually very helpful, providing Cuphead and Mugman the platforms to stand on. In fact, this helpfulness is most likely the reason why they get shot out of the sky by the level's Mini-Boss.
  • 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".
  • Tree Trunk Tour: Their level sees the player climbing up and through a gigantic, hollow tree, facing a variety of insects, living logs and gigantic woodpeckers on the way.
  • Visual Pun: The large dragonfly miniboss spits fireballs like a dragon. It's a dragon-fly.
  • When Trees Attack: Living wood logs appear as enemies in this level.

    Funfair Fever's Fighters
"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.
  • Anthropomorphic Food: A giant dancing hotdog appears as a Mini-Boss at the end of the level. There are also giant pretzels that hop up and down, serving as obstacles.
  • 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 is 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.
  • Spread Shot: The balloons that float past you explode if damaged, shooting out bullets in all directions.
  • 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.

    Funhouse Frazzle's Frights
"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, but then 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 Structure Monster: The living walls that need to be defeated to head deeper into the level.
  • 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
"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.
  • Classical Cyclops: A grey-skinned cyclops with a single centrally-positioned horn appears as an Advancing Boss of Doom, starting to chase the player halfway through and destroying any platform in its way.
  • Death Mountain: Rugged Ridge is a treacherous mountain area featuring plentiful pits and slopes, and home to a variety of enemies based on both actual mountain wildlife and mythical creatures associated with mountainous areas.
  • Evil Living Flames: The animated flames that circle around in the air in the first half of the level, chuckling nastily.
  • 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.
  • Gratuitous Latin: 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").
  • 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.
  • Our Dragons Are Different: During the ancient elevator sequence, tiny dragons constantly appear to spew fireballs at Cuphead and Mugman.
  • Rock Monster: The lion heads made of rocks appear as more dangerous enemies, blowing Cuphead and Mugman back with their roars.
  • 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
"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.

  • Airborne Mook: The flying fish are constantly airborne.
  • Determinator: The lobster mini-boss of the third area will always come back ten seconds later, no matter how many times you beat him, until you get to the boat.
  • Fiendish Fish: The flying fish are some of the most common enemies in this level.
  • 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 buoys that you parry to gain extra distance, and the octopus that takes you to the end of the level. It even spits cannonballs for you!

The Mausoleums

    The Spectre Syndicate
"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.
  • Touch the Intangible: You can only interact with them by parrying. Anything else will just go straight through them.

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...

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

It falls upon both Cuphead and Mugman to get these strange people in strange lands to cough up the contracts in order to save themselves, even as they take on increasingly vile forms and use a variety of weapons against them.

  • Anti-Villain: 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.
  • Evil Is Bigger: Downplayed. The Runaway Debtors are Anti Villains to various degrees and vary in size; however, many of the bosses seen tower over Cuphead and Mugman.
  • 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.
  • Leitmotif: Every boss has their own unique theme named after the level where they are fought, and they get most of the Awesome Music in the game. invoked
  • Noodle Incidents: All of them made deals with The Devil, 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: The vast majority of their game over taunts.
  • Ragtag Bunch of Misfits: The bosses vary wildly in terms of design and species. Their numbers include a sentient pack of vegetables, a gorgon-mermaid, a woman who can turn into a blimp, a human stage actress, a pair of boxing frog brothers, a mouse that pilots a giant tank shaped like a soup can, a ruler of living candies, and an entire haunted train, among others.
  • Riddle for the Ages: We never do find out what they made their deals with the Devil for.
  • 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 on to 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. Granted, it's in self-defense, since the only other option is to give up without a fight and let the Devil claim their souls.

Inkwell Isle One

    The Root Pack
"Buttered, smashed and mashed, it's over for you."
"Hey, little guy, it's okay if you have to cry!"
"I'm lean, mean and full of beta-carotene!"

A group of vegetables whom you fight in a garden in "Botanic Panic". They consist of three main characters; Sal Spudder (a potato), Ollie Bulb (an onion), and Chauncey Chantenay (a carrot). A fourth character, Horace Radiche (a radish), also appears under certain conditions.

  • Alliterative Name: Sal Spudder and Chauncey Chantenay.
  • Anthropomorphic Food: They're all vegetables.
  • Dishing Out Dirt: Sal Spudder starts the battle off by spitting out dirt clods and earthworms at you.
  • Dual Boss: In the secret phase of the fight, Horace and Chauncey attack at the same time, and you can only safely stand on the ground once Horace dies.
  • Edible Ammunition: Chauncey can launch homing carrots at you.
  • Everything's Better with Spinning: Horace, who spins around like a top and dashes across the arena at high speed.
  • Eye Beams: One of Chauncey's attacks has him firing some beams from his Third Eye.
  • Hypnotic Eyes: Chauncey wields these when you fight him, which he uses to send carrots at you or launch psychic beams.
  • Innocently Insensitive: A variant in how Ollie 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: Chauncey Chantenay uses one with homing carrots of all things.
  • Ocular Gushers: Ollie attacks this way by crying, with his tears raining down projectiles at you.
  • Onion Tears: Ollie's attack is a reference to the idea that onions make you cry.
  • Psychic Powers: Chauncey Chantenay wields psychic abilities.
  • Punny Name:
    • Sal Spudder is based on 'spud', a colloquialism for potato.
    • Chauncey Chantenay's last name is taken from a variety of carrot.
    • Ollie Bulb's last name is a synonym for onion
    • Horace Radiche has his name originating from 'horse radish'.
  • Sheathe Your Sword: A post-launch update added an Easter Egg to skip Ollie Bulb's phase. If he isn't hit by any projectiles, he exits without attacking, but Horace Radiche pops out during Chauncey Chantenay's phase, making it slightly more difficult.
  • 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.
  • Skippable Boss: Ollie Bulb and Horace Radiche, interchangeably. If you attack Ollie, you'll battle him normally and Horace will be skipped, but if you instead decide to Sheathe Your Sword, he'll leave without a fight while Horace Radiche pops up to attack you in tandem with Chauncey Chantenay.
  • Stationary Boss: Compounding on the rest of their easiness factors, the main trio can't move from where they're rooted. Averted with Horace, who continuously sweeps across the arena.
  • Terrible Trio: All three of them seem to be the debtors.
  • Third Eye: Chauncey opens his up when he starts firing his Eye Beams.
  • Throw the Dog a Bone: As of the 1.2 update, Ollie will pause after he appears, looking around with a scared expression. If you don't start fighting him, he'll breathe a sigh of relief and disappear back into the ground while smiling, then Horace and Chauncey will both appear instead.
  • Token Good Teammate: Ollie is the only of the three who doesn't mock the heroes in his win quotes, showing him to be nicer than his friends. In fact, he doesn't directly attack at all, and (as of an update) can actually be skipped if he isn't attacked.
  • 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 Chauncey, 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 (although one of Cagney's attack animations turns his stem into legs, so who knows).

    Goopy Le Grande
"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".

  • Alliterative Name: Goopy le Grande.
  • 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. The only real upside is the element of surprise against players who thought the fight was over.
  • 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.
  • Obvious Rule Patch: The pink question marks that appear when he takes the pill exist for the sole purpose of being parried for the A+ rank, since Goopy doesn't use projectiles.
  • 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.
  • Victory Fakeout: The transition from his second to third phase. Goopy gets a dazed look on his face, an Instant Gravestone drops on him and splatters him into a million droplets... and then the gravestone starts moving around trying to squash you!
  • 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.

    Hilda Berg
"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".

  • Ambiguously Human: Is seemingly human, but has bright pink skin and odd powers like being able to transform into a blimp, cloud constellations and a mechanical crescent moon with her face.
  • The Archer: Hilda's Sagittarius form, where she turns into a man on a cloud and shoots arrows at you.
  • Balloon Belly: Her transformation into a blimp starts with her inhaling so deeply, her belly inflates.
  • Blow You Away: She can summon tornados from the weather vane on her head to throw at you.
  • Brutish Bulls: Hilda's Taurus form, which has her turning into a bull made of clouds to ram at you.
  • 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.
  • Gender Bender: Of the three constellation forms fought in her second phase, only Gemini is female, with Taurus and Sagittarius both being male, true to their depictions in reality.
  • The Hyena: Cackles incessantly in her blimp form, with lethal results. She later unleashes a much more impressive, yet non-harmful example upon transforming into her Moon form.
  • The Man in the 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.
  • 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, clenches her eyes, and makes a pained moan, then her body starts spasming uncontrollably.
  • Punny Name: Her name is a pun on the Hindenburg.
  • Ramming Always Works: Tries this during phase 2, both as herself when transforming into one of her Constellations, and when in her Taurus form, in which this is her sole attack.
  • Shout-Out: Her hairstyle was clearly inspired by Betty Boop.
    • Her airship form appears to be a reference to recurring boss Kabula from the Kirby series.
    • Her Dub Name Change in the Portuguese language is Geni Buarque, a reference to the Brazilian song "Geni e o zepelim ("Jenny and the zeppelin", loosely based on Pirate Jenny) and its author, Chico Buarque.
    • The whole boss fight is one big homage to Three Wonders 's Chariot: all the constellation-based minibosses (save for Taurus) apppear in the Capcom title, and the final phase is the spitting image of Hypnos, the second level boss.
  • 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.
  • Star Power: Many of Hilda's attacks are themed after celestial objects, with her initial transformations being based on the western zodiac and her final form resembling a moon and firing star projectiles and flying saucers.
  • 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.
  • Trickster Twins: Hilda's Gemini form, where she turns into two girls on clouds and forms an energy ball to hurl at you.
  • Voluntary Shapeshifting: She begins the fight by turning into a blimp, and then takes two of three different constellation-themed forms. Her final transformation into the moon, however, appears to be involuntary.
  • 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: The 'wicked' part is downplayed, but Hilda certainly seems to have this theme going for her, what with her evil cackles, transformation magic, and the snout. Even her tornado attack might be a reference to 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
"Extreme pollination and total domination!"

A flower boss whom you fight in a forest clearing in "Floral Fury".

  • Alliterative Name: Cagney Carnation.
  • Battle Boomerang: One of his early projectiles is a sycamore seed that flies to the left over the platforms, then back across the right over the ground.
  • Bullet Seed: He forms a machine gun that shoots out seeds (one of them pink) into the air before they fall to the ground and become monstrous plants.
  • Evil Laugh: He lets out a manic laugh as he transforms.
  • Eye Scream: When he's beaten, his eyes completely disappear. You can see straight through one eye hole and out the other.
  • Fiery Redhead: Gives the impression of one, with his orange petals and maniacal temperament.
  • 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' short Swing, You Sinners!, who in turn is a reference to Monroe Silver, an actor and comedian of the Depression era known for incorporating similar hand motions into his routine.
    • His name is obviously a pun on 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. For triple points, one of the first great Real Life mobsters was an accomplished florist who often did arrangements for gangland funerals; to this day, flower shops are still a semi-stereotypical 'front' for cartoon mobsters.
    • Intentionally or not, the fact that he's a flower that acts all innocent before quickly revealing his 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. Then again, it's also a play on the Latin American Gangster Lands...
  • 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
"We've had fightin' souls since we've been tiny tadpoles."

Two frog brothers in boxing gloves fought in a showboat club setting (ironically run by flies) in "Clip Joint Calamity". Ribby is in white, Croaks is in red.

  • Amphibian Assault: Two giant frog boxers that are not surrendering their soul contracts without a fight.
  • Amphibian at Large: They tower over Cuphead and Mugman, and appear to be human-sized, if not larger.
  • Bash Brothers: A pair of frogs who've been enjoying brawls since they were tadpoles. While not stated in the game to be related, The Art of Cuphead book confirms them to be brothers.
  • 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, but the pushing wind does make Ribby's projectile claps harder to dodge.
  • Boxing Battler: They are styled after boxers and Ribby fights by using elemental punches.
  • 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 Lollipop Ghouls on the Phantom Express and the Tipsy Troop, the two frogs share health, so it doesn't matter which one is attacked.
  • Frog Men: The pair are frogs who fight for the amusement of the crowd in a showboat club, they made a bet with the devil and have now refused to pay their debts.
  • 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 in the game itself, 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? The artbook does indeed confirm them to be brothers and even states that this relationship is unique only to them and the cup brothers.
  • 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
"I won't sugarcoat it... you never stood a chance!"

The ruler of a candy area and boss of the "Sugarland Shimmy" level. Sends a random assortment of confectionery bosses (Muffsky Chernikov, a cupcake; Sgt. Gumbo Gumbull, a gumball machine; Sir Waffington III, a flying waffle; Lord Gob Packer, a multi-layered jawbreaker; and Kernel Von Pop, a giant candy cornnote ) at you from atop her living castle Whippet Creampup 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.
  • Ambiguously Human: It's unclear if she's meant to be human, or a strange humanoid. Especially since she lacks a nose, has pink skin, and lives in a chiefly candy-inhabited setting.
  • 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 Whippet Creampup certainly does: getting its towers pulled on. In fact, this is how she initiates the final phase of the battle; by pulling on Whippet's towers, sending it into a rage and causing it to chase the boys down.
  • Detachment Combat:
    • Sir Waffington III breaks his 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.
  • Kicking Ass in All Her Finery: Averted. While she does have a stunning appearance, she never engages the boys directly at any point in her battle.
  • 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: Lord Gob Packer is surrounded by several layers of candy shell. Once he's defeated, each shell cracks open to reveal a smaller jawbreaker until the tiny original is exposed, which then floats away.
  • Off with Her Head!: Invoked.
    • The Baroness threatens the duo with this at the start of the battle.
    • She can do this to herself and chuck the severed heads at the boys, regrowing a new one almost immediately.
  • One-Winged Angel: Not her so much as her cake castle, which transforms into an angered beast in the final phase.
  • Overly Long Name: According to a series of tweets, all of her minions have extremely long names.
  • Pimped-Out Dress: Wears one with a peppermint-striped bodice, puff sleeves, and flounces that resemble piped icing, topped off with an ice cream cone hennin hat.
  • Shockwave Stomp: Muffsky Chernikov produces waves made of icing whenever he 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, Lord Gob Packer, 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. invoked
    • Her name is a reference towards Baron Von Blubba from the Bubble Bobble franchise.
    • Design-wise, she was influenced by various actresses from the era of the game's design (such as Betty Grable, Bebe Daniels, and Loretta Young).
  • 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, Whippet also beats the ground in frustration while crying.
  • 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 Muffsky is defeated, the cherry on his head swells up as its stem turns into a fuse and blows itself up along with the cupcake. It turned into a cherry bomb, see.
  • Volumetric Mouth: She breaks down into sobbing in this way upon her defeat.
  • Wheel of Feet: Sgt. Gumbo Gumbull's feet are animated this way.
  • Winged Soul Flies Off at Death: Lord Packer gains a halo when defeated, floating off the screen while Bon Bon prepares for the next phase.
  • Your Head A-Splode: Happens to Sgt. Gumbull in his death animation; his glass head shatters and it scurries off.

    Beppi the Clown
"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 turns.
  • 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: 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
"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.
  • Bald of Evil: A Freeze-Frame Bonus shows that Djimmi is bald under that turban of his.
  • Beat Them at Their Own Game: His fourth phase (third if not counting his Death Course) has him making a Cuphead puppet named Cuppet and sending it at the boys. If you shrink while he's doing this, he instead makes a mini-Cuppet that can't really fight the boys on its own, so Djimmi transitions right to his final phase while the mini-Cuppet backs him up by shooting pellets from the center of the screen.
  • 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.
  • Dual Boss: The miniature Cuppet attacks during Djimmi's final phase if its secret phase is accessed, serving as another obstacle in a very crowded screen until it gets destroyed.
  • Ethnic Magician: Has some elements of the "Arabian stage magician" sort, considering he's found in a carnival area, his title, and the fact that he speaks about needing a new volunteer (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 Cuppet, he even unleashes a slightly-robotic laugh to match his lightbulb turban. The most impressive one of all in his repertoire comes as he enters the final phase of his fight.
  • 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. In fact, the battle opens with Djimmi appearing in a plume of smoke released from the pipe.
  • Homage: The background as you fight him in the sky is drawn in the style of the old Popeye two-reelers.
  • Idea Bulb: Has one while he laughs maliciously to the screen before starting the fourth phase of the battle.
  • 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", referencing the Moldenhauer brothers' father Jim.
  • Pyramid Power: In 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.
  • Skippable Boss: Cuppet in its regular size can be avoided by transforming into a mini-plane while Djimmi is analyzing you, skipping straight to the fifth phase. To compensate, however, a miniature version of Cuppet will appear and attack you alongside the giant Djimmi.
  • Smoking Barrel Blowout: One of the Game Over cards shows Cuppet 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 standing 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 from 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 Cuppet, his turban also acts as an obstacle that attempts to collide with the player and fire out a spread of shots every now and then. In his final phase, he also shoots out beams of energy out of his turban's gem.

    Grim Matchstick
"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.
  • Blood Knight: He is a somewhat ambiguous example of this trope. While he apologies for fighting you and in general, seems like the nicer bunch of the villains, several of his expressions clearly indicate that he enjoys fighting you.
  • 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: In three different flavors, no less. He shoots fireballs in his first phase, spits out living flames in his second, and spews both flaming bubbles and jets of flame, complete with his middle head turning into an actual flamethrower, during Phase 3.
  • Bubbly Clouds: Fought on the clouds surrounding a tower
  • Delightful Dragon: He's endearingly goofy, and even his win quotes make him seem sympathetic. This does not stop him from being one of the hardest bosses the player will have faced up to that point.
  • Energy Ring Attack: In his first phase, Grim Matchstick attacks with Eye Beams that manifest themselves as a short row of rings flying in the player character's direction. The last ring in a row is pink, allowing Cuphead and Mugman to parry-slap it.
  • Evil Living Flames: During one phase of his battle, he opens his mouth and stretches out his tongue, and a marching band of flames walks out.
  • 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 as well as 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. Moreover, they also draw in your Chaser shots.
  • 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, and letting the player keep a healthy distance on the highest clouds to avoid his flamethrower attack.

    Wally Warbles
"I own the air — I fly where eagles dare!"
"My dad's the brawn and I'm all brains! Together, we bring the pain."

A bird who lives within a cuckoo house, and the boss of "Aviary Action". After he takes a beating, his son, Willy Warbles, comes out of the birdhouse to attack you. You fight them in the skies.

  • Alliterative Name: Wally Warbles and Willy Warbles.
  • And Show It to You: A case where Wally literally coughs up his own heart to attack you.
  • Brains and Brawn: A dynamic that Wally shares with Willy, even lampshaded if the latter beats you.
  • Bullet Hell: The second phase of the fight has Wally 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, however, he is no less deadly, being able to unleash an utter onslaught of bullets with the help of his doctors.
  • Deadly Doctor: The paramedics carrying Wally in a stretcher during his final phase will assist him in battle by spitting pills at you.
  • Determinator: Even when you destroy the house around Wally, he still comes back, featherless, being carried by two medic birds, and attacks by not only turning his head into a trash can to spew trash at you, but also kicking his stomach, which shoots his heart out of his mouth to fire projectiles at you. Considering that you just recently defeated his son, no wonder he's pissed.
  • Eaten Alive: Presumed to be Wally's fate when beaten, as the medic birds are seen pouring salt and pepper on him with hungry looks in their eyes. But Wordof God states that he's still alive.
  • Enfant Terrible: Willy is as deadly as his father is, and arguably more malevolent.
  • Feather Flechettes: Wally does this in the second phase of his attack by flapping wildly and sending feathers at you. By the end of the phase, he's run out of feathers.
  • Flunky Boss: Wally's first and second phases has him accompanied by birds with nails on their heads who fly at you. The fourth has the medic birds spit out pills that turn into homing shots and fly at you.
  • Gadgeteer Genius: Willy during the third phase, who presumably built the hovering, spiked invulnerable eggs surrounding him, his raygun, and possibly even the birdhouse that protects his father.
  • High-Pressure Emotion: At the start of the second phase, Wally's anger reaches its tipping point, and he sounds off like a steam whistle, with his head even briefly turning into one for good measure!
  • Humiliation Conga: Hoo boy, Wally took it much worse than other bosses in the game. Over the course of battle, he ends up losing his house, gets defeathered, has his son get beaten up, and then he himself gets beaten unconscious as his own medics decide to eat him alive, while the ones who gave him said beating take his soul contract to deliver it to the Devil who would gladly reclaim his soul.
  • Instantly Defeathered Bird: After beating him in the second phase, Wally ends up losing all his feathers and falls out of his house. Doesn't stop him from coming back in the final phase.
  • Mr. Seahorse: Wally can apparently produce eggs.
  • Orbiting Particle Shield: Willy is surrounded by spiked eggs that constantly circle him, moving closer in then farther away.
  • Overlord Jr.: Willy 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 Willy 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.
  • Proj-egg-tile: Spitting eggs is Wally's main form of attack in the first phase. Later, in the third phase, Willy employs a telekinetic Orbiting Particle Shield variant of the same eggs.
  • Rage Breaking Point: While he almost never looks happy, Wally's second phase is initiated by him turning his head into a steam whistle, and his only attack is to send a storm of his own feathers out while screaming in anger.
  • Ride of the Valkyries: Played briefly during their theme music, 'Aviary Action'.
  • Shout-Out:
    • Wally's temper tantrums during the second phase are reminiscent of Donald Duck's own fits of rage.
    • Wally's color scheme and elongated beak are also similar to Woody Woodpecker. They, along with Willy, all even have alliterative names beginning with W.
  • Spread Shot: Wally has several — during the first phase, the eggs he spits out explode into a spread of three (five on expert) when they hit the left side of the screen, and his 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.
  • Toothy Bird: Both Wally and his son have beaks full of teeth. Willy's are most visible when he grins right before firing his gun.
  • Uncertain Doom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. It was never confirmed or denied whether he was eaten or did he manage to survive. If the fact he is absent from the good ending is any indication, his fate might not be a pleasant one.
  • Visual Pun: Wally's attack in the fourth phase where his head morphs into a trash can and spits out trash to shoot you out of the sky. He's literally talking trash at you.
    • Another attack in his final phase while he's being carried by paramedics has him kick up his own heart to attack you. In other words, it's his heart attack.
  • Voluntary Shapeshifting: Wally 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: Wally is the first shoot-em-up boss that is likely to give players trouble; his attacks are a fair bit harder to avoid, he throws quite a few curveballs with the variety in his projectiles and forms, and has a far higher density of bullets to avoid than Hilda or even Djimmi, making him a test of spacial awareness and quick reaction time. His final phase also highlights the importance of your secondary weapon in plane battles, as the bombs can help you hit targets you can't easily reach or destroy with the default shot.
  • What Happened to the Mouse?: Neither Wally nor Willy are seen in the ending.

Inkwell Isle Three

    Rumor Honeybottoms
"Hey sugar, this honey is off limits. Now scram."

A queen bee fought in an office building for bees (naturally) in "Honeycomb Herald".

  • Animal Stereotypes: She's the Queen Bee and fought in the hive, a company building with exhausted drones who will defend their queen with their lives.
  • The Bad Guys Are Cops: Before the Queen fights you, you have to fight one of her hive's police officers first. If he defeats you, he accuses you of attempting a honey heist.
  • 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. Bob the policeman bee 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 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.
  • A Pig Named "Porkchop": She is a bee named Rumor Honeybottoms, which references honey, the food product that bees make.
  • 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 attack 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" "Bee-plane". 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, reflected in his full name, Bob the Bee.
  • Voluntary Shapeshifting: In her final phase, she uses her powers to turn herself into a plane and attacks from the bottom of the screen. Not only does this shoot out projectiles, but she can turn her arm/wing into a saw to hit you. It should be noted that, unlike almost every other boss in the game, she apparently uses a spell from a book in order to make it happen.

    Captain Brineybeard
"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.
  • Attack the Mouth: To defeat the Brineybeard's ship, the player is required to attack the uvula, located in the ship's mouth.
  • 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, according to a trailer from 2013, he was originally named Captain Silver, averting this trope.
  • Death from Above: An environmental hazard in his level is a large living barrel suspended over the dock, which will drop down on Cuphead if he stays under it for too long.
  • Dressed to Plunder: Hits quite a few of the checks...
  • Eyepatch of Power: Although it's apparently just for show - though it's hard to see in the middle of the battle, he occasionally peeks out of it, revealing a good eye underneath.
This picture helpfully shows that he still has two in-game.
  • Equippable Ally: He fires bullets from an octopus that he grabs and uses as a shotgun.
  • 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.
  • Non-Action Guy: Despite his big physique, the captain doesn't really do any of the fighting himself, instead relying on his ship and the creatures he summons. Even the one attack in the fight that comes directly from him (shooting pellets from the octopus) still has a minion (the octopus, of course) doing most of the work. He doesn't even fight in the final phase, with his ship taking over as the opponent instead.
  • 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.
  • Seadog Beard: Though contrary to his name, it doesn't look very briney.
  • Seadog Peg Leg: Concept art shows both his legs are these, though in the game itself it's hard to see even one.
  • 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.
  • The Unintelligible: The ship does not have any spoken taunts in its Game Over screen; instead, it simply makes gnarling noises.
  • 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
"Stay away from center stage or succumb to the power of a starlet's rage!"

An actress you fight on a stage in front of an live audience in "Dramatic Fanatic".

  • Alliterative Name: Sally Stageplay.
  • 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 1930s 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? 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. After a post-game update, they can potentially be this in the third phase if you end the first phase by dropping a light fixture on her husband in the first phase.
  • 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 either the actor portraying her husband crying tears of sorrow or a priest bowing down in agonizing prayer if you squished the husband earlier. Then she goes One-Winged Angel, as detailed below.
  • Curtain Call: In the patched version, Sally's co-stars will appear in the background to take a bow for the audience during her final phase.
  • 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!).
  • Dual Boss: If the secret path of the fight is taken, Sally's third phase will have a cardboard cutout of her husband participating alongside her cutout. Unlike the other secret double-bosses, both of them share the same health and the only thing added is an reoccurring new attack during that phase.
  • Enfant Terrible: The babies in the second round can drop their bottles on you. And one of them will push out a "fireball" at you in the alternate third round.
  • 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.
  • Falling Chandelier of Doom: In the post-game update, during the first phase of Sally Stageplay's battle, you can stand on the two floating cherubs to lower them down and bring down the chandelier on her husband and squish him, shocking Sally so much that she'll cut the first round short to mourn over him and change the course of the second and third rounds.
  • 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. Jump on both of the platforms, and a light fixture will crush him, causing Sally to cut the first phase short to mourn for him and the second phase to take place at a nunnery.
  • Giggling Villain: She's constantly cackling and clearly having fun with her battle. Her babies also giggle as they drop bottles on you.
  • 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 is, until you bring down the Falling Chandelier of Doom on him in the post-game update, changing the course of the second and third rounds). That being said, she does reward him with a smooch in the epilogue.
  • Imagine Spot: The third phase of the fight can be taken as this.
  • Large Ham: Her mannerisms really come off as over the top. She is a stage actress, after all.
  • 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... and he can be, if you go out of your way to squash him flat as of a post-launch update.
  • 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, which 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".
  • Pietà Plagiarism: During her third phase, the cardboard cutout of her husband (if you squished him via Falling Chandelier of Doom) parodies the Pieta by striking a pose similar to that of the "Rest" part of the Statue of the Gods in Final Fantasy VI (see Shout-Out below).
  • 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. In the post-game update, the cardboard cutout of her husband you've squished earlier (complete with Holy Halo) also bears a striking pose similar to that of the "Rest" part of the Statue of the Gods in that game. There's even cards in the upper-left corner that display her next attacks.
    • Her battle may be a stylistic reference to Dynamite Headdy. Whereas that game's setting is a puppet show, Sally fights Cuphead during her vaudeville act.
  • Slouch of Villainy: Not done by Sally herself, but her husband is seen leaning on a bed and eating grapes (invoking the Greek god Dionysus) in the alternate path for the third phase, while otherwise contributing little in terms of new attacks.
  • Smooch of Victory: In the ending, Sally can be seen triumphantly planting a kiss on her husband as Cuphead and Mugman announce that they are free from the Devil's debt.
  • 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/s in the third phase don't move or directly attack; all of their attacks come from other places on the stage.
  • Stern Nun: In the alternate second round, there's a nun who appears from window to window at St. Timothy's Nunnery, intending to drop cardboard crosses at you, some of which are pink and parryable.
  • Together in Death: A strange sort of in-universe take. She mourns her husband's death on the secret route, and once she is also "killed" at the end of her second phase both of them return as cardboard cut out angels you have to fight.
  • 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.
  • Widowed at the Wedding: In the Switch and Patch 1.2 versions, if you take the secret route, you end up 'killing' her fiancé/husband by crushing him with the chandelier.
  • Winged Soul Flies Off at Death: When Sally's second phase is defeated (thus dying in her play), she instantly switches into an angel outfit and "flies" off the stage on wires.
  • "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. It makes more sense if the first phase ended with her fiancé's death.

    Werner Werman
"Zis tank is ze ultimate veapon! You vill not vin!"

A giant rat that controls a mechanical soup can to fight you. Meanwhile, a massive cat by the name of Katzenwagen watches the battle, and eventually intervenes in the final stretch. You encounter them in "Murine Corps".

  • Alliterative Name: Werner Werman.
  • Accent Depundent: Werner's 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 Katzenwagen suddenly decides to have Werner for a snack and goes on to attack you.
  • Badass Normal: Werner is an expert machine pilot, and that's all he really needs to fight the Cup Brothers. As a result, he's notably one of only two examples of this in the entire game, the other being Sally Stageplay.
  • Bamboo Technology: Katzenwagen aside, Werner uses a tank made out of a soup can and simple machines which shoots bottlecaps and chewed gum. His second phase also has bottlecaps that act like circular saws.
  • Car Fu: One of his first phase's attacks is simply running you down with his tank. Fortunately, he's also kind enough to give you two bounce pads that you can use to jump over.
  • Cats Are Mean: Katzenwagen, who seemingly eats Werner and then sets its sights on you. In this case, it's a mecha-kitty that's piloted by Werner himself.
  • Cigar Chomper: Werner starts his battle off by lighting a cigar and keeps it in his mouth through the entire fight.
  • Cool Helmet: Werner sports a Pickelhaube.
  • Defector from Decadence: The medals in the background of the fight indicates that Werner was born in Austria and he defected to the British during the first world war. The third medal is harder to determine but the dark blue edges of his ribbon indicate that he spent the remainder of his service in the Royal and Merchant Navies (also evident by the ghosts in the 3rd phase of the battle, they either fought alongside him in the war or were prisoners of war). The light blue center of his ribbon indicates that he served in the air force, likely referencing the Battle of Jutland 1916 since it involved Naval Aviation.
  • Eaten Alive: After beating Werner's second phase, Katzenwagen 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.
  • Epic Fail: The transition from Werner's first phase to his second involves his can tank bringing out a firework, only for the mechanical arm carrying to fail and drop it inside the can, causing it to blow up.
  • Expy: Katzenwagen resembles a pre-Art Evolution Tom quite a bit. Werner himself resembles Mortimer Mouse.
  • Faking the Dead: After the second phase, he's seemingly eaten by Katzenwagen, which forces Cuphead and Mugman to defend themselves from it. However, Katzenwagen is revealed to be a mecha designed to scare off any intruders or give Werner the advantage.
  • Foreshadowing: When your bullets hit Katzenwagen in the third phase, it makes a metal clinking sound. In addition, after Katzenwagen bursts in and eats Werner, the brothers don't get the latter's contract, hinting that he's still alive.
    • Speaking of Katzenwagen, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.
  • Funetik Aksent: Werner's game over quotes have him speak in an exaggerated German accent.
  • Humongous Mecha: It's not very obvious at first, but Katzenwagen serves as Werner's trump card in the final phase of the fight, and is revealed to be one upon his defeat.
  • Hurricane of Puns: Nearly everything about Werner is a pun in some way: his name, who he's based off of, the name of his level...
  • Kaiserreich: Werner is based primarily on World War I-era German soldiers, with his Pickelhaube and soup-can tank. He also has war medals and bullet shells hanging around his mouse hole, although a Union Jack flag can be seen near the ceiling, oddly enough, as well as 2 British medals.
  • Macro Zone: They are fought in a mouse hole in a giant house.
  • The Man Behind the Curtain: Werner is revealed to be the one controlling the mecha-cat Katzenwagen, once you beat the third phase.
  • Meaningful Name:
    • Katzenwagen means "Cat Cart" and it is Werner's last resort in the fight.
    • Werner means "soldier" and he's a veteran of World War 1. Wermin is a German pronunciation of "vermin".
  • Mega Neko: Katzenwagen.
  • 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 Katzenwagen's mouth and shoot out parryable projectiles. These are actually spirits who were left trapped inside Katzenwagen's stomach.
  • Perpetual Frowner: Werner lapses into this unlike most of the other bosses, though this may just be an animation quirk from the cigar in his mouth.
  • Playing with Fire: Werner's second phase has him using chair-mounted flamethrowers.
  • Pun-Based Title: The title of their stage is "Murine Corps". "Murine" is an adjective that pertains to the subfamily of old world rats and mice.
  • Punny Name: In addition to the Accent Depundent entry above, Werner's last name also sounds like the German word "Wehrmann" which is an old way to address soldiers, fitting well with his Pickelhaube helmet. invoked
  • Resourceful Rodent: Werner fights by using a tank that's been made from various household junk (a tin can, rubber bands, and wood) and he was able to turn a bottlecap into a buzz saw.
  • Robotic Reveal: When beaten, Katzenwagen's face falls off and is revealed to be actually a mecha piloted by Werner.
  • Rodents of Unusual Size: Werner is shown to be roughly the same size as other humans in the ending.
  • Screams Like a Little Girl: When Werner can't seem to control his tank anymore and when he gets eaten by Katzenwagen.
  • Shout-Out: The whole fight is based off war cartoons and Tom and Jerry; not only does Katzenwagen bear a striking resemblance to Tom in his early years (when he was known as Jasper), but Werner's screams sound vaguely like Tom's as well. This also makes sense on another level: "Jerry" was a common nickname for German soldiers during World War I.
  • Spread Shot: In Werner's first phase, the tank can catapult a spread of random garbage at the heroes.
  • Tank Goodness: Werner pilots a makeshift tank made from a giant soup can in his first two phases.
  • Visual Pun: The cannon on Werner's tank shoots literal cherry bombs.
  • The Unintelligible: Katzenwagen does not have any spoken taunts in its Game Over screen; instead, it simply hisses and meows.
  • Wartime Cartoon: Being a rat with a German accent and pickelhaube helmet, which were often shown in WW1 depictions, it can be assumed Werner came from one of these.
  • You Dirty Rat!: He fights with a homemade tank, he also created Katzenwagen as a mobile tank. Since he's in debt to the devil, it's suggested by the background of his home that the Devil may have assisted him in defecting to the British army during WW1.

    Dr. Kahl and his Robot
"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.
  • Early-Bird Cameo: While the robot's an Isle 3 boss, a miniature version can be seen in mobile form during Djimmi's fight in Isle 2 if you trigger the alternate route.
  • Eating Machine: The robot is seen chewing bubblegum in his intro, blowing a bubble before the match starts.
  • Energy Weapon: 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.
  • 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.
  • Four Eyes, Zero Soul: Downplayed for Dr. Kahl. Even though he wears glasses and uses the power of the gems to attack you, he's more of an Anti-Villain, as he and his robot still have souls, but though the robot's Soul Contract is destroyed in the good ending, the two of them are absent, but at least they are still grateful that they won't have to work for the Devil anymore.
  • Giant Scrap Robot: Dr. Kahl's robot is presumably this, if their stage is any indication.
  • 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.
  • Oh, Crap!: The Knockout animation has the doctor making this expression, upon realizing his robot is about to blow.
  • 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?
  • Robo Speak: Both of the robot's death screen quotes are robotic messages.
  • 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: His name is a shout-out to legendary animator Milt Kahl. Design-wise, he's 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 magical, multi-colored 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 - Ted Hughes' The Iron Man -on the Giant's design, not the 1999 movie based on it), as well as being very close to the boxing robot from Mickey's Mechanical Man. His intro also has him waggling his eyebrows in a similar manner to Dr. Wily.
  • Smart People Build Robots: 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.
  • Stealth Pun: The robot's weak point in the first phase is a large, metal heart. Looks like the tin man has a heart, after all.
  • Tin-Can Robot: The robot has the classic old-fashioned clunky robot look.
  • What Happened to the Mouse?: Neither he nor his robot are seen in the ending.
  • You Gotta Have Blue Hair: Has purple hair.

    Cala Maria
"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".

  • 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 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 Monster Girl: She's a giant mermaid/gorgon hybrid, as well as a complete Ms. Fanservice.
  • 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.
  • Equippable Ally: Can obtain two different coloured fish that spit different elemental projectiles at you. The red fish spit fireballs, while the yellow fish spits a homing electrified dolphin.
  • 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, and they're in constant motion too!
  • Losing Your Head: The final phase of her fight has her detaching her head from 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 female characters, like Sally Stageplay and Baroness von Bon Bon, Cala Maria 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: About fifty feet tall, wears an octopus, can turn into a gorgon...
  • Painful Pointy Pufferfish: She can summon 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.
    • The sea turtle she summons in her first phase looks like a very angry Toby Tortoise from Disney's Silly Symphonies (specifically "The Tortoise and the Hare"), and his fisticuffs pose alludes to the boxing match held in "Toby Tortoise Returns".
  • 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!"
  • Throat-Slitting Gesture: Shown doing this in her first phase game over card, as seen in her page image.
  • 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
"I can... see... into the future. You... will be... counting worms."
"All aboard!! Next stop — your funeral."
"Sorry! This train is only for the dead... but we can help you with that."
"What a glorious night for me to bring the fright!"

A haunted train comprised of the Blind Specter, an eyeless ghost; the Conductor, a skeletal conductor; the Lollipop Ghouls, two giant animate pistons; and finally, the train's living engine, the Head of the Train. You fight them on a rail cart in "Railroad Wrath".

  • 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 the Conductor and the Lollipop Ghouls 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 Lollipop Ghouls in the third phase attack you by breathing columns of lightning.
  • Death from Above: The Head of the Train has many of these attacks, since he's galloping after you on stilt legs. Not only can he drop rings made of bone on you, but if you open his boiler core, the hot coals inside will also start dropping on your head.
  • Dem Bones: The second phase sends out the Conductor, 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.
  • Everyone Calls Him "Barkeep": The Conductor has no official name aside from...well, the Conductor.
  • 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: The Blind Specter's one eye socket is completely empty at all times.
  • Ghost Train: The Phantom Express is a creepy living train who carries a ghost, a skeleton conductor, and two lightning-shooting creatures through a dark forest.
  • High-Speed Battle: You spend the whole fight racing alongside them in a rail cart with parryable controls, while continually-appearing minions try to mess with your positioning.
  • 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 Tank: 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 can block shots and spawning pumpkin enemies that can parry the pink handles at the end of your cart, either yanking it out from under you while you're in mid-air, or sending it straight towards the Specter itself.
  • What Happened to the Mouse?: The Head of the Train, the Conductor, and the Lollipop Ghouls aren't seen in the epilogue (indeed, the latter are seen melting upon defeat). The Blind Specter from the first phase does, though, perhaps on behalf of the entire train.
  • Wrong Side of the Tracks: Their tracks, that is - Inkwell Hell is just on the other side on the map.
  • Youkai: All of the ghosts inhabiting the Phantom Express are subtly based on different types of youkai. The Blind Specter is based on tenome, an eyeless old man with eyeballs on his hands; the Conductor is based on gashadokuro, a giant skeleton; the Lollipop Ghouls appear to be based on rokurokubi, women that have long serpentine necks; and the Head of the Train is based on oboroguruma, oxcarts with faces found on roads late at night.

The King's Court

A set of nine minibosses that are under the command of King Dice. You have to fight a few of them in order to finally fight King Dice himself.

  • 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.
  • Anthropomorphic Vice: The Tipsy Troop and Mr. Wheezy represent drinking and smoking, respectively, whereas the others, inluding Chips Bettigan, Phear Lap and King Dice himself, represent various forms of gambling.
  • 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.
  • Punch-Clock Villain: Seeing as how many of them seem to be animate forms of various aspects of gambling, it's probable that for these nine minibosses, they're simply doing their job.
  • 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
"Go sleep *hic* it look a little *hic* rough!"

Ginette (a martini), Ol' Ethan (a shot glass filled with whiskey) and Rumulus (a bottle of cognac), all 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.
  • Alliterative Name: The Tipsy Troop.
  • Big, Thin, Short Trio: Rumulus is big, Ginette is thin, and Ol' Ethan is short.
  • Death from Above: Rumulus 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 — Ginette becomes dizzy and disoriented, Ol' Ethan gets sentimental and weepy, and Rumulus turns raucous and loud. In spite of this, they can be one of the trickier fights to deal with thanks to the density of the amount of things waiting to hurt the player (Rumulus's Death from Above, Ol' Ethan's ground-sweep, and Ginette's endless flying olives taking up airspace).
  • Dual Boss: Taken an extra step since you fight against three here.
  • Flunky Boss: Ginette summons flying olives who shoot their eyes at you.
  • Lady Drunk: Ginette resembles one.
  • Mook Maker: Ginette 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...
  • Theme Naming: All based on alcoholic drinks (gin, rum, and ethanol - the actual alcohol in them).
  • Turns Red: Inverted — as you progress through the battle, the trio will fall one by one, making the fight get progressively easier.

    Chips Bettigan
"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 
  • Detachment Combat: Separates his body into different segments that you then have to dodge.
  • 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
"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.
  • Evil Sounds Raspy: Due to being a living cigar, his voice is as coarse and raspy as a frequent smoker's voice would sound.
  • 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
"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.

  • Battle Couple: They fight together as one boss, and their designer Tina Nawrocki considers them a married couple.
  • 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.
  • Henpecked Husband: Pip gets kicked in the face by Dot when they lose the battle.
  • 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, which he tips to you before the battle begins.
  • Punny Name: A "pip" and a "dot" are both terms that refer to the dots on a domino.
  • Scary Teeth: Their middle section opens up to reveal a mouthful of razor-sharp teeth, from which they spit d20-die-shaped projectiles at you.
  • Shout-Out: The Conveyor Belt o' Doom in their boss battle that pulls you toward a spiked wall is a reference to the 1931 cartoon Bimbo's Initiation, in which Bimbo was faced with a similar trap.
  • 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
"...and PRESTO!! The cup has completely disappeared."

A crazed rabbit magician fought in a room with playing cards.

  • Expy: Based on the Bugs Bunny prototype from the cartoon Prest-o Change-o.
  • Hair-Raising Hare: He's an evil rabbit magician. Interestingly, he averts Killer Rabbit in all but the most literal sense; he's at least twice the size of our heroes, and makes absolutely no effort to look cute.
  • Laughing Mad: Begins laughing as soon as the battle begins, and won't stop until either himself or you are defeated.
  • Magicians Are Wizards: A magician rabbit that can use magic to attack.
  • More Teeth than the Osmond Family: And far, far more teeth than any rabbit should have, let alone sharp ones.
  • Pull a Rabbit out of My Hat: How King Dice "summons" him at the start of the battle.
  • Punny Name: Based on the words "Hocus Pocus" and "hop."
  • Rabbit Magician: He's a magician rabbit that can use magic tricks to attack.
  • 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
"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.

  • Dem Bones: Again, he's a skeleton horse.
  • Expy: Despite being skeletal, he bears quite a resemblance to Horace Horsecollar.
  • Flunky Boss: Pay attention to the skeletal jockeys at the bottom of the screen - the cloaked ones will fly up at you once they get underneath.
  • Hellish Horse: A skeletal racehorse.
  • Shout-Out: His name is one to the famous racehorse, Phar Lap.
  • Spread Shot: The giftboxes he fires out explode into an 8-way spread of horseshoe projectiles.
  • Stationary Boss: While his bucking affects the position of his hitbox, he is otherwise the least mobile plane boss in the game.
  • Visual Pun: Attacks by launching giftwrapped boxes that explode into horseshoes from his mouth, in a play on the phrase "Looking a Gift Horse in the Mouth". Additionally, this fight has you literally beating a dead horse.

"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.

"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 blocks of cue chalk 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: The cue chalks 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
"Monkey see, monkey doom."

A toy monkey fought via 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.
  • Everything's Better with Monkeys: Not in this instance.
  • 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

"You gots to equip those new purchases if you want to use them. Look at your equip card, ya bums!"

A pig who runs the shop where you can buy power ups.

  • Expy:
  • Eyepatch of Power: He has an eyepatch, and although we never see him get in on the action, he does look pretty tough and burly.
  • Guttural Growler: Has a very deep, growly voice.
  • Jerk with a Heart of Gold: He rather rudely tells Mugman and Cuphead off for not immediately equipping what they bought from him when you exit his shop for the first time, but he only does it once and he's an indispensable ally for the rest of the game, seeing as he sells the boys their weapons and gear.
  • Pig Man: An anthropomorphic pig.
  • A Pig Named "Porkchop"
  • Shout-Out: His gravelly "Welcome!" is one to the shopkeep from Resident Evil 4.
  • What the Hell Is That Accent?: In his voice lines, he seems to have a German or Russian accent. However, his written dialogue after you leave his shop for the first time gives him more of a Bronx accent.

    Legendary Chalice/Ms. Chalice
As Ms. Chalice
"Speaking of magic... please accept this gift, it should help!"

A spiritual beverage-holder investigating magic. Grants a super move each time the players protect the urn imprisoning her at a mausoleum in the Inkwell Isles (three in all).

She'll become playable in the DLC, ''The Delicious Last Course", going under the name "Ms. Chalice".

  • Action Girl: She will be a playable character in the DLC campaign.
  • And Starring: Her appearance in the trailer for "The Delicious Last Course" implies that she plays the role of Ms. Chalice as herself.
  • Back from the Dead: Seems to be the case in "The Delicious Last Course".
  • Badass Adorable: As Ms. Chalice, she's just as adorable as Cuphead and Mugman, and just as badass.
  • 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).
  • Double Jump: Has one as Ms. Chalice, according to the trailer for "The Delicious Last Course".
  • Fountain of Youth: She seems around Cuphead and Mugman's age in the DLC, compared to in the base game where she looked considerably older than them as a ghost.
  • 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.
  • Promoted to Playable: Made playable in "The Delicious Last Course", both for the new DLC and on the original Isles.
  • 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 every Mausoleum she visits, she keeps hunting for Super Arts to give to Cuphead and Mugman.

The Delicious Last Course

    Chef Saltbaker 

A new character who will be introduced in the DLC update. Not much is known about him, but he will presumably be integral to the DLC add-on's plot.

  • Big Fun: He's rather portly, and is described as "jolly".
  • Chubby Chef: A pudgy-looking chef.
  • Gag Nose: His nose is noticeably long and pointy.
  • Non-Human Head: His head is a big salt shaker with a humanlike face, similar to Cuphead, Mugman, Ms. Chalice, and King Dice.
  • Punny Name: His name is a portmanteau of "salt shaker", "salt bake" and "baker".

    Glumstone the Giant 
A mountain giant who is faced on a mountaintop.
  • Beard of Evil: Has a massive flowing beard that covers the mountain platform the players are standing on.
  • Expy: Clearly modelled after the titular character of The Old Man of the Mountain.
  • Monster-Shaped Mountain: A trait of giants in this universe; much like Glumstone, one can see various other mountain giants in the background of his battle, albeit more benign and docile.

    Snow Monster 
An evil snowman who is faced in an ice palace.


How well does it match the trope?

Example of:


Media sources: