Characters / Cuphead - The Delicious Last Course

Cuphead | Main character index
Main Characters | Allies and Enemies | The Runaway Debtors | The King's Court | The Delicious Last Course

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The new characters introduced in The Delicious Last Course who populate Inkwell Isle Four. For Ms. Chalice and Chef Saltbaker, see Main Characters.

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In General

• Animation Bump: The animation quality of Inkwell Isle Four's bosses are even more lively and fluid than the original game, and considering the original game, that's saying something.
• Badass Normal: Because they never dealt with the Devil, none of them have any transformations outside the logical scope of their abilities, unlike the main game bosses. Glumstone the Giant, the Moonshine Mob, the Howling Aces, and the King's Champions don't transform at all; Mortimer Freeze can magically control snow, but uses Living Bodysuits instead of transforming himself; and Esther Winchester only gets cooked due to freak accidents. Even Chef Saltbaker only attacks you with his established skill, creating magic food. Despite this, they're still among the more formidable foes in the game.
• Dub Name Change: As per tradition following the original game, most of them have new names in other languages.
• Mook Maker: While this is also true of some of the bosses in the main game, every boss on Isle 4 summons multiple minions. There is actually a Steam achievement for beating an Isle 4 boss without killing any of its minions, and judging by the small percentage of people who have achieved it, it's not an easy task.
• Would Hurt a Child: Comes with the territory of being bosses in a game with kid protagonists, but in the case of the Guardians, the cups are infringing upon their territory with the intent of stealing property, and in the case of the King's Champions, it's all a sporting event anyway.

Wondertart Ingredient Guardians

In General

Baking the Wondertart that Chalice needs to truly come back to life requires 5 mystical ingredients found throughout Inkwell Isle Four. There's just one problem; the ingredients are guarded by exceptionally powerful individuals, and they're not letting go of them without a fight!

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• Edible Ammunition: Every one of the ingredient guardians will try and attack you with food:
  • In Glumstone's third phase, he'll occasionally shoot chicken drumsticks at you. Downplayed in that the real purpose of the drumsticks is to make the skeleton monsters stop acting like platforms.
  • Some of the Mooks in the Moonshine Mob's second phase are dancing barrels of moonshine.
  • In the Howling Aces' secret phase, the puppies will throw literal pineapple grenades at you. These same pineapples are served with the Pineapple Mint you need for the Wondertart.
  • Mortimer's snow golem can throw popsicles at you, and when it turns into a snowflake, it'll occasionally attack you with ice cream missiles.
  • Esther Winchester, aside from becoming quite edible herself, attacks you with T-bone steaks and baked beans in her third phase, and attacks you with sausage strings and chili peppers in her fourth.
• Flunky Boss: All of them employ minions to various degrees in their fights. There's an achievement for defeating one of them without killing any minions.
• Gameplay and Story Segregation: Like with the bosses in the base game, any transformations are entirely contained in their boss battle (such as size changes), and may lead to an Unexplained Recovery or two.
• Leitmotif: Much like the Runaway Debtors in the base game, they all have their own unique boss fight themes named after the level they're in.
• Physical, Mystical, Technological: Three of the five ingredient guardians fit this trope:
  • Glumstone the Giant is the Physical, using either his or his gnomes' physical prowess to fight, including his own stomach lining.
  • Mortimer Freeze is the Mystical, being a wizard who uses ice-themed spells, tarot cards, hammerspace tricks, and summons to fight.
  • The Howling Aces are the Technological, being a squadron of dogs who utilize flying vehicles and gadgets to fight.
• Punch-Clock Villain: The Ingredient Guardians, even more than the Runaway Debtors in the main game; they haven't signed any contracts with the Devil, they're just between the Cups and the Wondertart that will bring Ms. Chalice back to life. Given what Saltbaker plans, one could even make an argument that the Guardians are actually Anti-Villains, just like the Runaway Debtors.

Glumstone the Giant

"You thought you were bold, but I am boulder."

A mountain giant who is faced on a mountaintop in "Gnome Way Out". He's helped by a large group of gnomes who live around and inside his mouth. Defeating him gets you the Gnome Berries.

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• Acid Pool: The third phase of his fight takes place in his acid-filled stomach, touching that will obviously hurt the player. You need to stand on the skeletal reptiles' heads that float over the acid.
• Beard of Evil: Has a massive flowing beard that covers the mountain platform the players are standing on. It also has an army of gnomes living in it. The transition between his first and second phases has him angrily tear it off in a painful fashion, leaving him with only stubble.
• Bears Are Bad News: One of his attacks in the first phase is to pull a bear from...somewhere, and dangle it closer to the player from the left side of the screen.
• Bizarre Alien Biology: Glumstone has irregular ridges of fleshy spikes, like a mountain range, poking through his hair and running down his back, and getting swallowed by him reveals his stomach lining is also sentient. He also seems to have a semi-symbiotic relationship with the colony of gnomes that live on his body.
• Burp of Finality: Emits one after swallowing the player, though given this is the transition to the last phase, the battle's far from over.
• The Cameo: Glumstone uses hand puppets of King Dice and the Devil as part of his second phase.
• Cave Mouth: Glumstone initially appears as a stone mountain, and the gnomes are seen working in a mine that's actually his mouth.
• Dem Bones: In his third phase, skeletal reptiles floating in the stomach acid serve as your only platforms. They submerge after swallowing a chicken drumstick; if one eats a bone instead, you can parry its tongue to bring them all back up to the surface.
• Expy: The Art of Cuphead artbook states that Glumstone is modelled both after the titular character of The Old Man of the Mountain and Gustav the Giant from Brave Little Tailor.
• Flunky Boss: He's assisted by several gnome minions in all three phases, with the gnomes hammering the platforms or shooting from their hats in the first phase, jumping out of his beard in the second, and jumping out of the stomach acid to fire darts in the third.
• Foul Waterfowl: During his battle, he can summon a flock of geese to attack the players.
• Four-Fingered Hands: Averted. Like Captain Brineybeard, Glumstone has five fingers per hand.
• Gag Nose: A huge red one. It actually turns into a whistle used to summon his flock of geese.
• Hand Puppet: Brings out two resembling King Dice and the Devil as part of his second phase.
• Magic Cauldron: Has one in his mouth, which the gnomes use to attack you with clouds of colored steam
• Monster-Shaped Mountain: Apparently a common trait of giants in this universe; much like Glumstone, one can see various other mountain giants in the background of his battle, albeit more benign and docile, or are just dormant.
• Non-Standard Character Design: Glumstone himself averts the game's Four-Fingered Hands standard, while the gnomes have simple lines for limbs, unlike every other character who has Rubberhose Limbs at the skinniest.
• Our Giants Are Bigger: Glumstone (and his kin seen in the background of his fight) are practically living mountains. Glumstone in particular has an almost symbiotic relationship with the colony of gnomes that have taken up residence among his body.
• Our Gnomes Are Weirder: Glumstone appears to have been made the home of an entire community of gnomes living on and around him, like on the rocks, in his beard, on the geese, in his mouth, inside his stomach, etc.
• Perpetual Smiler: The gnomes appear to be a whole race of these — none of them are ever seen not smiling, even when they're attacking you or being blasted away in the battle intro.
• Really 700 Years Old: The 'Art of Cuphead' artbook states that Glumstone is meant to have been resting dormant for so long that the gnomes have built an entire civilization on him.
• Shout-Out: In addition to his inspirations stated above in Expy, he also resembles Willie the Giant from Mickey And The Beanstalk when his beard comes off.
• Swallowed Whole: The final phase of the fight starts with him throwing the player characters into the air and swallowing them. You end up fighting his stomach lining as the last phase.
• That's No Moon: The initial scene of his fight has a bunch of gnomes working in a mine cut into the side of an oddly-shaped mountain. Then one of the gnomes hits a gold deposit, the mountain starts shaking, the stone shatters off to reveal skin, the "snow" is revealed to actually be beard hair, the gold is actually a gold tooth...
• The Tooth Hurts: Glumstone is awakened by a gnome mistaking one of his teeth for gold ore and striking it with a pickaxe.
• Womb Level: The third phase of the fight takes place within Glumstone's stomach.
• You Have Failed Me: One of his attacks involves pulling out a bear to maul you. After deciding that it's not as effective as he'd hoped, he chucks it off into the distance.

Moonshine Mob

^{Click here to see the snail} "Surprise! Forgetting about da boss ain't wise."

"One-two punch, you and da cops are eatin' dirt. Bingo bingo!"
"This dance is over, there's no excuse... you couldn't handle the giggle juice."
"One thing dis nose knows is, youse cups gonna be pushin' up roses!"

A liquor-bootlegging gang consisting primarily of bugs that you fight in an underground distillery by the coastline in "Bootlegger Boogie". The mob includes a spider by the name of Charlie Left Legs, a light bug, and an anteater, as well as a caterpillar and several fly mooks, all of whom are led by a snail. They're accosted by the ant police during the battle, who sometimes get in your way. Defeating them gives you the Distillery Dough.

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• Aardvark Trunks: The anteater's mouth is placed at the base of the snout rather than at the tip, making the snout a trunk of sorts. Despite this, the tip of the snout still has a tongue come out of it, making him essentially have two mouths! Also, in his game over quote, he still refers to his snout as a nose.
• Alliterative Name: The Moonshine Mob.
• Animal Jingoism: The police in their level are all ants, and the gang deals with them by getting the help of a giant anteater. Averted within the gang itself, where flies have no issues working under a spider.
• Animate Inanimate Object: They're accompanied by living moonshine barrels sprouting arms and legs.
• Attack of the 50-Foot Whatever: The anteater is huge, making its entrance tearing at the platforms and towering over Cuphead, Mugman and Ms. Chalice.
• Background Boss: The anteater fights you from the background.
• Battle Couple: As stated in the code, Charlie Left Legs and the light bug are married. When Charlie is beaten, he drops the light bug and her gramophone onto the stage by his thread.
• Beauty Is Never Tarnished: The light bug makes her entrance like she’s just putting on a dance performance, and when she’s defeated she stumbles backwards while howling in pain and faints, only to promptly get up and make her exit like nothing happened.
• Big Ball of Violence: The anteater will use its tongue to pull a bunch of mob flies and ant police, which causes them to get into one of these as a destructible projectile that bounces all over the area.
• Big Creepy-Crawlies: Played with. While all of the bugs and such in the battle are about the same size as Cuphead and co., they're tiny compared to the other bosses, especially in comparison to the anteater who appears in the battle.
• Chasing Your Tail: The second phase has the gramophone in the middle of the area perform the "fire in a loop" sort, where three of its rotating streams turn hazardous and force you to run around them (or Smoke Bomb dash through them).
• Cigar Chomper: The fly goon almost always have cigars in their mouth when they enter the stage proper.
• Clipped-Wing Angel: The snail's only real combat advantage is the element of surprise — once he loses that, his projectiles are simple to dodge or parry (unless you let your guard down), and he goes down in seconds.
• Combat Pragmatist: As expected of a mob, they don't fight very fairly, with Charlie Left Legs calling in goons to even the numbers, the anteater faking you out a few times with its tongue and especially the snail who tries to let the player's guard down with a false knockout screen.
• Dance Battler: The light bug dances back and forth on middle platform, while dancing moonshine barrels will occasionally appear at the top and bottom.
• Dastardly Dapper Derby: The flies and the anteater wear blue bowler hats; the anteater concealing the snail boss underneath.
• Enemy Summoner: Charlie Left Legs will stop to call for help over his telephone, bringing in several flies each time.
• Expy:
  • The caterpillar that Charlie tosses against you is inspired by Hoppity from Mr. Bug Goes to Town.
  • The light bug that dances is reminiscent of the moth in the Silly Symphonies short "The Moth and the Flame".
  • The anteater is possibly based off of the Anteater from the 1940 Fleischer cartoon Ants in the Plants. He also may be based off the Aardvark from The Ant and the Aardvark.
• Fastball Special: Charlie Left Legs can enter with a caterpillar goon, which he kicks into the area and causes it to bounce around as a destructible projectile.
• Flunky Boss: Charlie Left Legs can call in fly minions, kick in a caterpillar goon, and the local ant police will also pop in from the sides to shoot at him but their bug spray projectiles can also hurt you. The female bug has dancing barrels and ant police move along the top and bottom rows.
• Foreshadowing: When the anteater shows up, he tips his hat for a moment, exposing his snail boss chuckling underneath. You can actually damage the snail a bit while this is happening, hinting that the anteater isn't the last of your worries in this fight.
• Four-Legged Insect: Charlie Left Legs has only 6 limbs instead of 8, and the other bugs have only 4 limbs instead of 6. In a curious non-insect inversion, the snail has a pair of arms.
• Friendly Enemies: Zig-zagged. On the one hand, the ant police are raiding the distillery and the cups are caught in the crossfire. On the other, in the epilogue, the snail is shaking hands with one of the ant detectives putting the defeated Chef Saltbaker to work. The moonshine barrels are relabeled as baking pop soda, but it's unclear if they've truly reformed, or if they're just double-crossing the police.
• Gameplay and Story Integration: The ants are more interested in catching the gang, you just happened to be caught in the crossfire. If any of their bug spray hits Charlie, he'll take damage.
• Giant Spider: The first bug you face, Charlie Left Legs, is one of these. He's actually a retool of the Giant Spider boss shown in press kits submitted to gaming magazines back in the early days of the game's development^* Which, despite popular belief, was never intended to be in the game to begin with and was made just for demonstrative screenshot purposes - though the Moldenhauers did have the idea of making a giant spider boss independently from that. Ironically, he's still much smaller than that boss appeared to be.
• Hazy-Feel Turn: By the epilogue, the snail is seen shaking hands with an ant detective while Chef Saltbaker is undergoing his work for reform, tasked with moving baking soda. Said "baking soda" is being moved by moonshine barrels that are labeled by the flies (or by themselves) as such. It's not clear if they're genuinely helping or if they're simply finding a new way to move their product.
• Hostile Show Takeover: The normal announcer intro sounds different and if you look closely, you'll see the snail is yelling on a megaphone, implying he's taken over the announcer's role for the fight. There's even a fake "Knockout", and when you beat the snail the real announcer can be heard clearing his throat before announcing the real knockout, either implying they somehow held him hostage, or showing just how annoyed he is that some upstart gastropod muscled in on his turf.
• Informed Species: According to notes in the code, the female bug in phase two is a light bug (in American English, a firefly). She doesn't look much like any particular bug.
• Instrument of Murder: The second phase's main source of damage is the gramophone emitting dangerous music from the center of the arena.
• I Surrender, Suckers: The Announcer Snail makes a knockout message appear and announces it with his own voice, as if you have beaten his goons and he surrenders. He doesn't, you have to beat him as well.
• Kaizo Trap:
  • The light bug can still hurt you after she's defeated and running back to the center of the stage. If she kills you this way, the death card will be for the anteater.
  • After defeating the anteater, the victory screen appears. It turns out to be fake; you still have the snail under his hat to worry about.
• Last Breath Bullet: Defeating the anteater causes a "Knock out!" screen to appear... which is a fake made of flypaper. The snail will shortly pop up and fire easy-to-dodge projectiles from his megaphone, and he goes down pretty easily.
• Lovable Rogue: By the end, they are considered friends to Chef Saltbaker and the others.
• Mad Bomber: Charlie Left Legs springs bombs suspended by his webbing, which detonate whenever you pass them by.
• The Mafia: Their fashion sense and manner of speech are meant to evoke the Italian-American mafia as it existed during the Prohibition.
• Mêlée à Trois: There are police officers trying to attack them during the fight, but they're harmful to you as well. You've essentially walked in on a huge police raid. Interestingly, the cops actively target Charlie Left Legs with their bugspray, and it'll do damage if he gets hit. Additionally, it seems like none of the members actively attack the player besides the Snail. Charlie kicks caterpillars and call for flies, but none of them actively pursue the player. The Light Bug doesn't attack at all, with the only attacks in this phase coming from the gramophone and the cops that are only moving in straight lines along the platforms, and the Anteater seems to be aiming at the fight between the flies and cops rather than the player. (Granted, all of their death cards - except maybe the Light Bug's - do directly acknowledge the player character.)
• Mickey Mousing: The music begins to distort when the light bug enters the fight, speeding up and slowing down a bit in places and suffers from skipping if you get hit while she’s on screen.
• Mister Big: The snail is the leader of the operation but is the smallest by far, as well as the most fragile member with least hit points.
• Musical Assassin: The light bug "fights" by placing down a gramophone that fires out six streams of harmless music, three of which periodically turn into deadly sound waves.
• No Name Given: Only Charlie Left Legs has had his name revealed. The light bug, anteater and snail remain unnamed.
• Old-Fashioned Copper: The cops are dressed with old-fashioned hats and old-school batons.
• Painting the Medium: In the second phase, the background music will distort whenever the phonograph uses its sound wave attack. Getting hit during this phase will also cause a horn sting to play.
• Pinball Projectile: The caterpillar and the ant/fly fights will bounce off the edges of the screen until destroyed by the player's attacks.
• Scatting: Vocals by Alana Bridgewater form part of their theme. In-game, it's implied to be coming from the gramophone that the light bug dances to.
• Secret Weapon: The anteater is implied to be the mob's ultimate weapon against the ant cops — he's not shown in the fight intro, is only revealed as the fake final phase after Charlie and the light bug go down, and his very nature as an anteater gives the mob a decisive Weapon of X-Slaying against the ant police.
• Shout-Out: Charlie Left Legs' phase resembles that of the fight against Lololo and Lalala in Kirby's Dream Land, and subsequent derived boss fights in the Dream Land sequels; namely Nelly and Nruff and Pon and Con.
• Skippable Boss: You can actually avoid fighting the anteater if you deal enough damage to the snail when he first appears from under the hat.^note This would most likely require precise use of the Giant Ghost super. However, you’ll still have the snail himself to deal with.
• Speaking Simlish: Charlie speaks in quick gibberish on the phone.
• Super-Scream: The snail's only attack is firing sound waves at you from his megaphone.
• Tertiary Sexual Characteristics: The light bug has feminine eyelashes for female signifiers, and the fly underlings have five o'clock shadow.
• Token Good Teammate: Downplayed with the caterpillar, who clearly doesn't want to be here. Still, if you look closely, he's smiling when Charlie brings him out, as if he's willing to help fight off the cups and ants. He stops smiling when he realizes what role he's playing in this plan.
• Trap Master: Charlie will drop cocoons all over the stage that explode a short window after being touched.
• Underground Level: The entrance to the fight is a cave with stairs heading down, while the level appears to be a city/hive where the mob operate.
• Unholy Matrimony: According to Word of God, Charlie Left Legs and the light bug are married and considering that both seem to be high ranking mob members, the "unholy" part goes without saying.
• Victory Fakeout: After defeating the anteater, you're presented with a fake knockout screen made of flypaper — but a few moments later, the snail pops out from under the anteater's hat and starts yelling sound waves at you. The game over quote from the snail lampshades this should you die to him.
• Visual Pun:
  • One that doubles as a Development Gag. The second phase is repurposed from an unused boss fight which was codenamed "Light" during development. In its finished form, the attacks are brought on by a light bug. invoked
  • The anteater is massive, which makes him a giant anteater.
  • The announcement of the 1.3.3 version of the game on Steam is accompanied by an image of the cup trio treating the injured members of the Moonshine Mob in a hospital. After all, it's about bug fixes.
• Weak Boss, Strong Underlings: The leader of the mob is the snail, and when he comes out to fight you during the Victory Fakeout, he goes down much faster than his underlings and only has a single, easily-avoidable attack.
• Whack-a-Monster: The pre-final phase of the fight has you target the anteater's snout, which is only vulnerable when it comes out of one side of each of the three tiers on the screen.
• With Friends Like These...: Charlie will kick the caterpillar to use him as a projectile against you, and the anteater isn't picky about grabbing mob flies along with ant policemen.

The Howling Aces

"You thought you were top dog, but you never had a sniff."
"Affirm Roger Fox! Affirm Roger Fox!"
"Looks like your skills have gone AWOL, fleabags."

A team of canine pilots consisting of airship-flying saluki Sergeant O'Fera, her plane-flying bulldog co-pilot, and a group of pups known as the Yankee Yippers. You fight them in "Doggone Dogfight" by riding on the wings of Canteen Hughes' plane. Defeating them gets you the Pineapple Mint.

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• Abnormal Ammo: With the exception of the yarn balls (which are shot out from a cat), and the (literal) pineapple grenades in the secret phase, most of the weapons that the Aces use are dog-themed, such as tennis balls, bones, fire hydrants, dog bowls, and even the letters BOW-WOW.
• Ace Pilot: It's in their title: they all fly their own aircraft while launching their assault at the cups.
• Ambiguously Related: The Howling Aces give off the impression of a nuclear family, with O'Fera and the Bulldog pilot being naturally assumed to be the parents of the Yankee Yippers, but there is no actual confirmation on the relationship between any of them. The beta design for Sergeant O'Fera appears to support a relation between them [1].
• Animal Mecha: The Chinook airship that O'Fera pilots serves as this, capable of opening its mouth for the Howling Aces to enter it, shooting fire hydrants from its back and dog bowls from its eyes, and firing laser rays out of the portholes on its paws, which O'Fera and the Yankee Yippers can also pop out of to attack the Cups in the secret phase.
• Badass Adorable: The Yankee Yippers are a group of puppies and they're all capable of combat. They're also present in all phases of the fight if the secret phase is achieved, which makes them the most active combatants of the squad.
• Badass Crew: The bulldog, O'Fera, and the Yankee Yippers are capable of combat, be it themselves or via the very vehicles they pilot. Should the player manage to activate the secret phase, O'Fera and the Yippers will even fight alongside each other.
• Bait-and-Switch: The level's represented by a biplane on the overworld, next to an aerial hangar, and the level name has 'Dogfight' on it, so surely it's a plane level... except it's not; it's a platform level taking place on a plane.
• Boomerang Comeback: The bulldog's crossbone tattoos will fly to one side of the screen, stick there for a while, before flying backwards.
• Boss-Altering Consequence: If you bring all four of the puppies' HP low without taking any of them out, O'fera will round them up and enter a unique final phase where the five of them will attack with homing fire hydrants and pineapple grenades. This phase also lacks the Interface Screw that the regular final phase has.
• Breaking Old Trends: The Howling Aces are the first and only boss with a secret phase where said secret phase isn't a variation on a preexisting phase, but rather a completely different boss phase and attack pattern.
• Bully Bulldog: The pilot in the first phase is a brutish bulldog who pulls out all the stops to attack you. He even grabs a cat and forces him to spit out yarn balls in one of his attacks.
• Canis Major: The dachshund airship, which appears to be based on a Chinook.
• Captain Smooth and Sergeant Rough: The two adults give off this impression. Sgt. O'Fera is more refined and graceful, flies the much bigger and more powerful vehicle, and is also the one to formally salute the Cups (and Hughes) when the battle begins, while the male bulldog is much more rough and tough, flies the smaller plane, and doesn't bother with the niceties, just immediately attacking.
• Cool Plane: All their vehicles, as might be expected. The plane the bulldog flies for the flight has hatches for the Yankee Yippers to attack from. Once he and the pups are down, the massive airship shaped like a dachshund flies back in, piloted by O'Fera; it appears to be a Chinook. Both come fully equipped with a multitude of weaponry to go after the Cups. In the epilogue, Chef Saltbaker has to help them repair the former as part of his community service.
• Do Well, But Not Perfect: In order to fight the secret alternate final phase, you need to get all four puppies to low health (indicated by their jetpack smoke turning grey) without actually defeating any of them.
• Interesting Situation Duel: Your characters stand on the wings of Canteen Hughes' aircraft during the fight.
• Interface Screw: In the final phase, the warship grabs the camera and the screen rotates ninety degrees every time the warship opens or closes its mouth. This can result in the screen being upside-down for huge chunks of the battle. The secret phase won't do this, but it comes at the cost of having to deal with O'Fera and the Yankee Yippers at the same time. The game includes a control option just for this phase of the fight, which changes how the game controls relative to the shifting camera. Control type A has Cuphead always aim and move relative to his perspective, such that pressing up has Cuphead aim above his head, even if the plane is upside-down. Control type B has Cuphead aim and move relative to the screen's orientation, such that pressing up will aim towards the top of the screen, regardless of how Cuphead is turned.
• Jet Pack: The squadron is fond of these; the bulldog has one in the first phase, and the kids have them in their second phase.
• Lady of War: Sgt. O'Fera is elegant and graceful, even when turned to the side due to the mechanics of her phase of the fight. Even her defeat animation is more shocked and surprised than goofy. Though defeating her during the secret phase or the "outside" phase of her fight leaves her wringing her hat in shame, she's still more composed than a lot of the other bosses are.
• Male Might, Female Finesse: The male bulldog fights in direct combat, even jumping into the fray to do so. Sgt. O'Fera never attacks directly, with all her attacks launched by the airship she pilots and commands with great skill.
• Mama Bear: If the pups are knocked out during the second phase, O'Fera will fight much more aggressively and flip the camera.
• Mercy Rewarded: Downplayed in that you just beat them up again a while later, but choosing not to shoot down any of the Yankee Yippers completely changes the third phase to one with no Interface Screw. Note that this is downplayed even further if you're gunning for an S-rank or speedrun, as getting the secret phase, never mind completing it, takes a lot more time than the regular one.
• Military Alphabet: The Yankee Yippers' quote if you lose to them is "Affirm Roger Fox! Affirm Roger Fox!", or "ARF! ARF!" in UK pre-NATO terms.
• More Deadly Than the Male: Sgt. O'Fera is implied to be in charge; she's the one that salutes the player at the fight's start, she's driving the bigger dachshund Chinook compared to the bulldog's smaller plane, and she's the final opponent in both the normal and secret phases, though in the latter, the puppies assist her like they do the bulldog in the first phase. She overall gives off an impression of being a commanding officer. Tina Nawrocki, their animator, has confirmed on Twitter that O'Fera is indeed the leader of the squadron.
• No Name Given: While the Yippers are named in the files, and O'Fera is named via a figure, we still don’t know the bulldog’s name.
• Oh, Crap!: The bulldog and Yankee Yippers have this reaction when their plane starts going down in the first phase of their fight.
• Recursive Ammo: The pineapple grenades thrown by the pups in the secret phase will explode into a Spread Shot of three shrapnel fragments if shot.
• Shout-Out:
  • The entire fight situation where the player stands on the wings of a propeller aircraft bears resemblance to Sky Chase Zone from Sonic the Hedgehog 2.
  • The bulldog and Sgt. O'Fera are a reference to Rolento and Cammy, respectively, from the Street Fighter series. The bulldog has the same outfit as Rolento, and mimics his Capcom vs. SNK 2◊ art in his death card. O'Fera has Cammy's red beret and blonde "hair"/fur with a single strand sticking out, and mimics Cammy's win pose◊ in her death card.
  • The bulldog is also a reference to Spike from Tom and Jerry, especially when he pulls out a cat that looks almost like Tom.
• Shows Damage: When one of the pups in the second phase is at low health, the smoke trail from their jetpack turns from white to grey. This is useful to know if you're going for the secret phase, when you need to get all four to this state without defeating any of them.
• Spread Shot:
  • In the first phase, the pups will throw a spread of three tennis balls downwards.
  • In the secret phase, shooting any of the pineapple grenades that the pups throw causes them to explode into a 3-way downward spread of shrapnel.
• Testosterone Poisoning: The bulldog is oozing with testosterone, being an absolute beefcake wearing a sleeveless top, fingerless gloves, and is so damn manly that he can attack you with his crossbones tattoos just by flexing!
• Villain Respect: If the pups are spared in their phase, O'Fera will repay your mercy by avoiding the use of her lasers. Knock out any of the pups, however, and she will fight more aggressively with those lasers.
• Visual Pun:
  • They're dogs, and you fight their airships on Hughes' plane. It's a literal dogfight.
  • One of the bulldog's attacks has him use a cat like a gun to shoot yarn balls at you. Said cat bears a distinct resemblance to Tom... so he's got a tommy gun!
  • In the secret phase, the pups will throw pineapple grenades at you... literal pineapples with grenade pins. These same pineapples are served with the Pineapple Mint you get for defeating the Howling Aces.
• Weapons-Grade Vocabulary: The second phase has the pups attack you by shouting the letters BOW-WOW at you.
• Whack-a-Monster: In the secret phase, O'Fera and the Yankee Yippers will pop in and out from five of the 6 holes of the aircraft's paws. While the Yippers can be shot at to be deterred, they pop back into the fight after a short while, and your main target in this phase is O'Fera.
• Wolfpack Boss: In a near-literal example, the four pups will attack you together in the second phase by circling around you and shouting the letters BOW-WOW at you.
• Worthy Opponent: Implied. Sgt. O'Fera will be a lot more respectful to you if you spare the Yankee Yippers, and even smile as you fight her and the pups. Shoot them out of the sky, however, and she will be more aggressive and frantic while controlling the plane.

Mortimer Freeze

"It'll be a hot December before I let you be a member."

A snow wizard whom you face in an ice palace in "Snow Cult Scuffle". He controls a cult of snowlems who assist him in battle. Defeating him gets you the Icy Sugar Cubes.

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• Adorable Evil Minions: The little icicles Mortimer summons. Some of them even have bows in their hair!
• Alliterative Name: The Walloping Winter Whale, one of his attacks.
• Ambiguously Human: He looks nearly human aside from his blue skin. It's unclear if he is a being made of ice or a regular human who gained ice powers.
• Arc Symbol: Moons, snowflakes, celestial objects like stars and planets, and buckets, with moons decorating his colosseum and a prominent snowflake with a face sitting in the center. His final phase has him turn into a massive snowflake that occasionally shoots out buckets which bursts into moon-shaped projectiles. Given that his final form descends from the night sky before attacking the cups, it could be that this form is meant to be evocative to a moon or a star of some sort. As for the buckets? Who knows besides Mortimer himself, but regardless of what they mean they do make for distinct hats for his cult members.
• Ascend to a Higher Plane of Existence: This seems to be what's happening to him during his second and final phase, where he incubates himself inside Jupiter and eventually bursts out of his body in a new snowflake-form that ascends to the night sky, to which the audience in the background beckon upwards in glee and reveration. Given that he thaws right out back to normal when defeated, and that you can still see his normal hands and 'normal' spirit poke and spew out of the snowflakes mouth, this is probably another wizards trick than an actual ascension.
• Asteroids Monster: One of his attacks is to throw a big ice cube that, if it hits the floor, breaks into two smaller ice cubes that can still hurt you. And if they touch the floor, these also break in two even smaller ones.
• Bad Boss: It's subtle, but he doesn't seem to mind hitting his own icicle minions with his Walloping Winter Whale, which sends them flying off-screen.
• Big Fun: He's a notably plump fellow, who ice-skates into the arena before fighting you and generally looks like he's enjoying every second of it.
• Cult: Leads one consisting of snowmen, if his level title's any indication. Their beliefs are unclear, but it seems to have something to do with buckets.
• Evil Is Deathly Cold: He's an Evil Sorcerer who resides in an ice castle, has a legion of snowmen, and uses snow-based magic.
• Evil Sorcerer: A wicked cryomancer who uses Tarot cards and snowlems to attack. Though somewhat downplayed as he seems to be an otherwise decent fellow (weird snowman bucket cult notwithstanding), as evidenced by him having a part in Chef Saltbaker's community service and being pals with the other Inkwell Isle 4 denizens in the epilogue.
• Expy: Ice wizard? Check. Lives in an ice palace? Check. Blue skin? Check. Long white beard and a long pointed nose? Check. Just switch out his legion of snowmen for penguins and his hat for a magic crown and you have the Ice King from Adventure Time. His game over card also harkens back to the show's phrase "Wizards only, fools".
  • He also bears a striking resemblance to Old Man Winter from the 1934 ComiColor cartoon Jack Frost, as well as the Snow Miser from The Year Without a Santa Claus.
• Eye Scream: One of his attacks in his third phase has him launch out his own eyeball by wringing his own face until it pops out. And then he eats it...
• Flunky Boss: He's capable of summoning little icicle minions in his first phase that drop down, get stuck in the ground, and walk away. Amusingly, they're also vulnerable to being crushed by the Walloping Winter Whale. In his second phase, his snowman bodysuit can release a swarm of flying ice lollies that will swoop down and harass you during the boss' attacks, with one of these being pink.
• Half the Man He Used to Be: Mortimer's snowflake form bursts out of Jupiter the Snow Monster, leaving only its legs. Said legs will waddle off to the other side of the screen, damaging the player if they haven't jumped up the ice platforms yet.
• Hulk Speak: Jupiter's death quote has poor grammar and is in all caps, the latter of which is something he only shares with Dr. Kahl's Robot.
  Jupiter: ICED ALREADY? WHERE PUNY CUPS GO?
• Ice Palace: He's fought in one of these.
• An Ice Person: He's a wizard with snow-based magic, and he attacks the cups with just about anything related to ice — snow, ice cubes, ice cream...
• Living Bodysuit:
  • Mortimer uses a snowman as a bodysuit in his second phase (which animator Jake Clark calls the "Snow Monster" - later material gives him the name "Jupiter"), but the epilogue reveals that it's actually sentient even without him inside. This is also implied by its death quote, which uses a different speaking style than the other two phases.
  • The snowflake phase also melts away when defeated, revealing that Mortimer was piloting it. He occasionally sticks his hands out to cast a spell.
• Monster Whale: His Winter Whale that he brings out to smash the Cups with.
• Portal Cut: A variation of this. Jupiter will teleport its limbs and only its limbs to the other side of the screen, leaving it as a giant snowball who will either roll or jump across the arena and merge back with its arms and legs.
• Shamu Fu: One of his attacks involves slamming the heroes with his giant Walloping Winter Whale.
• Shout-Out:
  • Both Mortimer and Jupiter the Snow Monster contain elements of the titular villain from the 1932 Ted Eshbaugh cartoon The Snow Man◊.
  • According to notes in the game's code, the level as a whole is intended to reference the cult in Bimbo's Initiation. Mortimer's death quote is an inversion of the well-known "Wanna be a member? Wanna be a member?" refrain in said short.
  • The Walloping Winter Whale that Mortimer uses to attack the players bears a passing resemblance to Monstro from Pinocchio.
• Snowlems: He encases himself in a giant, living snowman in his second phase, which becomes a huge snowflake for the third.
• Spread Shot: In his final phase, Mortimer's hands can throw bucket kettle bombs that explode into a spread of three crescent moons upon hitting the far wall.
• Squishy Wizard: Averted; at 1850 Hitpoints in Expert Mode, he is one of the tankiest platformer bosses in the whole game.
• Tarot Motifs: His first phase has him summon Tarot cards from a crystal ball to attack you, which likely explains the "cult" part of his level name.
• Tarot Troubles: The cards themselves can be seen as foreshadowing for the DLC's plot. The Sun can mean new friendships, which seems in line with Ms. Chalice being a new playable character. The Moon can represent mystery and hidden paths, which seems to conect to story elements such as the Broken Relic and the hidden boss. The Three of Swords can indicate a betrayal of trust, relating to Chef Saltbaker being a Treacherous Quest Giver. In this case, the trope name also doubles as a Literal Metaphor, since the cards warn you of dangers but are themselves dangerous bullets you have to dodge.
• Tertiary Sexual Characteristics: When he summons his living icicle minions, two have noticeable bows on their head.
• Voluntary Shapeshifting: Jupiter, being made of snow, can take the shape of a refrigerator and a snowflake at will.
• Wintry Auroral Sky: The Aurora borealis is clearly visible in the background of his final phase.
• Wizard Classic: Aside from wearing pants instead of a robe and lacking a Magic Staff, he fits the bill quite nicely.

Esther Winchester

"Y'all took quite the fall... I s'pose it's last call!"

A literal cowgirl who is faced in a desert canyon in "High-Noon Hoopla". She's an outlaw who travels in a saloon on wheels. Defeating her gives you the Desert Limes.

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• Abnormal Ammo: Uses bottles of snake oil as guns to fire oil snakes.
• All Deserts Have Cacti: One of her attacks is throwing a rope and pulling in a cactus as it tries to break free.
• Anvil on Head: Her second phase has her launching safes into the air after using her vacuum gun to suck gold bars and money bags.
• Barely-Changed Dub Name: Named "Estera Winchester" in the Polish localization.
• Blowing a Raspberry: Transitioning to the second phase of her fight, Esther does this as she pulls off the roof of her saloon and sucks up the rest if it with her vacuum gun.
• Cool Car: Esther's first phase starts off with her inside her saloon, which has wheels under it like a horse-drawn carriage.
• Cowgirl: Quite literally, as she's a cow who's also a cowgirl outlaw. In her second phase she appears in a full cowgirl getup, complete with the hat, boots and spurs.
• Determinator: Esther might be the biggest Determinator of all the bosses. While continuing to fight despite taking massive damage is fairly common in Cuphead, it still takes a special kind of stubborn to continue fighting after being turned into sausages by one's own malfunctioning equipment. Esther not only does that, but takes it one step further: once her sausage-body is packed away into a tin for convenient eating, she keeps fighting, bursting out of the tin with her sausage-link body and spitting chili peppers from the advertising on the tin containing her remains- in effect, she dies twice during the fight, yet returns from the dead to keep up the battle! One might say she's quite bull-headed.
• Edible Ammunition: In her phase 3, she spits out T-bone steaks that fly in a loopy, circular pattern, while tins of ACME beans fly past, spilling upwards or downwards to catch the player. Her phase 4 has sausages sweep across the screen, forcing the player to move through the thinner casings to avoid damage, while Esther's image on the tin spits out flaming jalapenos.
• Expy: Clearly modeled after Clarabelle Cow.
• Flunky Boss: In her first phase, vulture outlaws and literal horse fly outlaws will assist her by spitting shots at you and dropping a Recursive Ammo Spread Shot dynamite respectively.
• Forced Transformation: In her third phase, she gets sucked into her vacuum gun and processed into sausages. In the final phase, she turns into a tin can, with sausage strings bursting right out of it.
• Furry Reminder: She occasionally moos like a real cow, saying "Moooo-haw!" instead of "Yee-haw!" and her laughter starts off with a moo, i.e. "Moo-ha-ha!". In her third phase, she gives a downright bestial moo when she uses her steak attack.
• Gun Twirling: Does this with her bottles of snake oil during the first phase of her fight.
• Hoist by His Own Petard: Her own vacuum gun sucks her into it when her third phase starts, turning her into a living string of sausages.
• Let's Meet the Meat:
  • Played for Black Comedy when in her third phase she is sucked into her own vacuum gun, which turns into a cooker that processes her into a living string of sausages. It's still not enough to stop her.
  • The fourth phase as well has her sausage form encased in a tin can with her own regular face on it, happily serving two sausages on a platter.
• Living Drawing: In her fourth phase, the tin can she's stuffed into has a picture of her own face on it, which comes to life and spits out flaming peppers as Edible Ammunition.
• Lovable Rogue: She's an outlaw with a wanted poster on the side of her saloon, and her attacks imply she's a thief and a Snake Oil Salesman. Despite this, she still runs a saloon with a lot of customers, has vultures and horseflies helping her in her fight, is willing to accept Chef Saltbaker's community service, and pals around with everyone else in the ending, indicating she's a pretty friendly gal (outside of battle, anyway).
• Mirror Reveal: She pulls out a hand mirror and looks shocked at her new sausage form when she enters her third phase.
• Mobile Kiosk: Esther's saloon doubles as a carriage, complete with wheels.
• Money Mauling: An interesting and indirect variant comes up in her second phase where she takes out a vacuum, the gold bars, coins, and money bags being sucked in can damage the player. A more straightforward example is when she fires winged safes up into the air that will explode into damaging gold bars, coins, and wads of cash when they hit the ground.
• Never Trust a Trailer: A minor case, but the DLC's Game Awards 2021 trailer introduced her as Sheriff Winchester. In the actual game, she's the exact opposite and doesn't even pretend to be any kind of lawman.
• Oh, Crap!: As her second phase ends she gets this expression right before getting sucked into her own vacuum gun. She does this again after her third phase.
• Outlaw: She's a cowgirl who has a wanted poster of her on her own saloon, bottles of snake oil, as well as a vacuum gun that sucks up gold, money, and sheriff stars.
• Painting the Medium: The death screen for Esther's second phase shows her sucking up part of the card with her vacuum.
• A Pig Named "Porkchop": A cow named after a brand of beef. Taken even further when she actually gets turned into beef sausages partway through her fight.
• Production Foreshadowing: She makes a very small cameo appearance in Zack Keller's Cuphead: Cartoon Chronicles & Calamities, released 3 months before she made her first official appearance as a DLC boss in the Game Awards trailer (though her hair curl is colored differently in the comic).
• Recursive Ammo: The vulture that flies in during the first phase drops dynamite that explodes into a spread of three, then two smaller sticks in a vertical Spread Shot upon hitting the ground. In Expert mode, it explodes into a spread of four, then three.
• Rhyming Name: Esther Winchester.
• Rollerblade Good: She manages this trope with just the spurs of her boots.
• Saloon Owner: Esther is confirmed to be one the minute her fight begins, as the first phase of her battle has her lurking inside her saloon on wheels. In the epilogue, Chef Saltbaker has to help Esther in the saloon as a waiter amidst a hootenanny, as part of his community service.
• Sausage String Silliness: Esther becomes a string of sausages for her third phase, and in her fourth phase she shoots two endless strings of sausages at you.
• Shed Armor, Gain Speed: For a certain definition of "armor". In her normal form, Esther is huge and very telegraphed in her movement; after she gets cooked into sausages, she becomes smaller and more agile, even being able to float through the air. Once she gets canned, though, she goes back to being pretty much stationary.
• Snake Oil Salesman: Esther is implied to be one, as one of her attacks has her fire snake oil at you that takes on the shape of snakes.
• Sizeshifter: An implied example. During her boss fight, Esther is gigantic compared to Cuphead. However, during the comic strip seen after beating the DLC, she's closer in height to Chef Saltbaker.
• Spread Shot:
  • The dynamite that the vulture drops in the first phase explodes twice into a spread of three, then two smaller fragments upwards. On expert, it instead explodes into four, then three.
  • The Living Drawing of Esther's face on the can in the final phase spits out a spread of flaming pepper projectiles, with more projectiles in the spread on Expert mode.
• Tertiary Sexual Characteristics: There's nothing really effeminate about her Cowgirl outfit or overall design except for her long, visible eyelashes and her pastel-colored cowboy hat with a flower on it.
• Unexplained Recovery: She gets transformed into a living string of sausages and then stuffed into a can which is shown releasing sausage angels after being defeated, yet the ending credits shows her having turned back to normal.
• Vile Vulture: A vulture wearing a cowboy hat will occasionally fly by in the first phase to drop a bundle of dynamite.
• Visual Pun: Winchester is named after both a type of beef and a type of gun. And she's a cow who wields a vacuum gun. Then there's the fact that she's a cowgirl who is also a cow. She also has guns that shoot snake oil that takes the shape of snakes, and horsefly minions that are horses with fly wings.
• "Wanted!" Poster: Being an outlaw, a wanted poster of Esther's face is on the side of her saloon during the first phase of the fight.
• Weapons That Suck: She pulls out a vacuum gun for the second phase of her battle. With it, she sucks up various objects for blowing them out.
• Winged Soul Flies Off at Death: Her defeat animation has sausage angels coming out of her tin can form, with the typical harps replaced by banjos.
• Your Size May Vary: When she's fought as a boss, she's as big as her own saloon. However, in the epilogue, she's shown to be around the same size as Chef Saltbaker. She's the only boss besides Mortimer and Chef Saltbaker to experience a change in size to this degree throughout the Delicious Last Course.

The King's Leap

In General

• Chess Motifs: The whole lot of them are based upon pieces in chess.
  • The eight Pawns are individually weak, but attack as a group to overwhelm you, similarly to pawns' behavior in actual chess.
  • The best way to avoid the Knight's charge is to roll under him, and to hit him you have to jump on his mane, referencing how knights can jump over pieces. The Knight is also a horse, which is how the piece is typically shaped. The way he holds his sword horizontally above him as well as the way his arm and sword move during his upward stab attack resembles the "L" shape that knights move in, and his quote when you lose against him also mentions the letter "L".
  • The Bishop's head moves in a diagonal manner, and if he gets the better of you, he'll comment on how he has you beat from every angle, alluding to how the bishops move diagonally.
  • The Rook sends out spark attacks that move directly forward, and says that beating you is straightforward, which references the fact that rooks can only move in a straight line. He's also the only Champion who's completely stationary; rooks can't move if another piece is blocking them.
  • The Queen is the only Champion who attacks from the background since the queen has the strongest movement options in chess. She mentions that she has you in checkmate when she beats you; one of the most common checkmate scenarios occurs when a pawn promotes to a queen.
  • The Champions are faced in the order that pieces are usually valued in chess; pawns are worth 1 point, knights and bishops are both worth 3, rooks are worth 5, queens are worth 9, and the king is the win condition.
  • After all five of the Champions go down, the King congratulates you and concedes without a fight. After all, he's got no one else left — you put him in checkmate, and it's well-known that the King is the weakest piece in chess.
  • Even the name of his stage, "The King's Leap," refers to an old chess rule that evolved into what we now know as "castling."
• Color Motif: Every member of the King's Leap wears a red outfit with a yellow diamond pattern, except for the Queen, who wears a red and blue dress with white diamonds (so she at least keeps the same idea).
• Dub Name Change: In this case, the translations will just give them the names of the chess pieces they are based on in another language.
• Everyone Calls Them Barkeep: The Champions are only referred to by the names of the chess pieces they represent, instead of actual names.
• Floating Limbs: Both the King and Queen have heads that float above their torsos, with no neck in sight. Each of the other bosses except for the Knight (an anthropomorphic horse) also have detachable heads.
• Leitmotif: "King of Games' Castle", which is remixed into "Bourree on the Board" for the Champions, and "The Queen's Riguadon" for the Queen herself. Furthermore, each Champion has unique instruments for their version of "Bourree on the Board": xylophone for the Pawns, recorder for the Knight, acoustic guitar for the Bishop, oboe and trombone for the Rook. The Knight's variation also has the violin take a more prominent role, as it performs the two solos of the theme.
• Losing Your Head: All the Champions but the Knight have this trope in some way.
  • The Pawns are defeated by knocking all eight of their heads off — but until then, the headless bodies still chase after you.
  • The Bishop removes his head and sends it after you.
  • The Rook takes the cake, though - he's almost entirely themed around this concept! He's not only an executioner with an axe who is introduced daydreaming about a Betty Boop-style guillotine, the central mechanic of his fight is based on the fact he sometimes attacks with severed heads. Some of those heads are parryable; knocking them back into the Rook is the only way to hurt him. And, of course, when you defeat him, his head falls right off his neck and into his own hands.
  • The Queen's death animation has her spinning her disembodied head on top of her scepter, and she is defeated by getting repeatedly shot in the face with cannonballs.
• No-Gear Level: All of them are fought without weapons or charms. Parrying is the only method of beating them.
• Non-Human Head: The King of Games and the Queen both have crowns for heads.
• Off with His Head!:
  • Parrying the head of one of the Pawns knocks it off, and you have to repeat that for all 8 of them to win.
  • The Rook attacks you with the disembodied heads he's cut off before. Both his and the Queen's heads fall off upon their defeat.
• Optional Boss: Fighting on the King's Leap isn't necessary to complete the DLC content, though it does reward you with coins.
• Punch-Clock Villain: They only fight you as part of a friendly competition. Indeed, the Queen that looked positively mad in her fight is seen palling around with the King and Saltbaker in the ending, indicating that she, and likely the others, aren't as hostile as they appeared.
• Puzzle Boss: Direct attacks don't hurt the Champions; you have to use your parry to do so (either directly hitting them with the parry or using it in other ways).
• Quirky Miniboss Squad: While they're not villains, they do fit the trope fairly well, being a group of subordinates for the King of Games that you fight one by one.
• Red Is Violent: Downplayed. They all wear red outfits, and all except the King of Games will fight you, although it's implied that this is more of an in-universe game as opposed to the bosses actually wanting to kill you.
• Sequential Boss: Averted, mostly. Though some of them have poles on their progression bars hinting at a phase transition, they all have only one true phase with some attacks becoming harder over time but no actual transformations or pattern changes.

The King of Games

"Hail, ye cups! I bid thee welcome to my floating palace."

A king who rules over a court consisting of five champions, each based upon a piece in chess, faced aboard his airship, the King's Leap. He places the Cups in his tournament after recognizing their fighting skill.

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• A Winner Is You: Complete his Gauntlet, and he will give you the best reward he can give you...a king's admiration! And that's about it.
• Cool Old Guy: The King of Games is a friendly and jovial fellow who recognizes Cuphead and co.'s fighting skill, rewards them for doing well in his tournament, and sticks around after their victory to help them (and the player) polish their parry skills afterward. He even helps in Chef Saltbaker's rehabilitation!
• Go-Karting with Bowser: In the epilogue, the King is seen enjoying a friendly game of checkers with Chef Saltbaker, as part of his community service. The Queen is shown watching the match, too, and seems to be having as much fun as the King.
• Good Counterpart: Not only a good counterpart, the King of Games acts as a complete thematic inversion of King Dice. Both are 'kings' who lead a Boss Bonanza found in a secondary area on their respective Inkwell Isles, which you challenge in palaces with chess theming, but nearly every other element is in total contrast:
  • While King Dice and his Dice Palace are located deep underground (as Hell tends to be), The King's Leap is an airship found high in the sky.
  • King Dice, despite his aplomb and bombast, is merely a king In Name Only, and is subservient to the Devil. The King of Games, on the other hand, is a true sovereign (as far as we know).
  • While both are associated with a vocal theme, King Dice's theme is based on the jazz stylings of Cab Calloway, while The King of Games' theme has a classical-styled choral sound.
  • King Dice is described as a 'sleazy manager' and shares his boss's infamy throughout the Inkwell Isles (his portrayal in adaptations notwithstanding). Meanwhile, judging from the epilogue, the King of Games is a well-respected member of the community.
  • King Dice and his court are themed on vices, gambling, and games of chance, while the King of Games and his champions are themed around chess, a highly-celebrated and respectable game of strategy.^note Granted, in medieval times and even as late as the early 1800s, chess was as synonymous with gambling as cards and dice; Inkwell Hell's casino even has towers shaped like chessmen!
    • Playing into this, the feel of their entire game segments reflects their game of origin: King Dice's boss rush basically boils down to "Go in guns blazing and hope you don't get hit by bad RNG". With the King and his Champions, you can't shoot and you need to find the specific strategy to beat all the bosses.
  • King Dice is a mandatory encounter and the penultimate boss in the base game, while the King of Games challenges are entirely optional and are mainly just a means to earn more coins.
  • King Dice challenges Cuphead out of petty revenge when he lost a bet (after Cuphead successfully acquires the Soul Contracts) and forces him to participate, while the King of Games simply challenges Cuphead and co. in friendly sporting terms after he recognizes their skill in combat, and always gives them a choice to back out if they so choose.
  • In King Dice's game, losing at any point forces you to start over again from the beginning. You fight each of the King of Games' champions separately, and you can retry each fight as many times as it takes to win...however, he does offer you the option to fight all of his champions Boss Rush style, but only if you so choose it, and only after you've beaten all of his champions.
  • Once you make it to the end of King Dice's game, he takes over center stage and tries to deal with Cuphead himself, and is humiliated and ousted from his position once he's beaten. Defeating all of the King of Games' champions just simply makes him give you money and congratulatory remarks, letting you fight any of his champions if you so wish to when you visit him afterwards.
• King of Games: It's in the name. In this case, he literally rules over the game of chess, though like the chess piece he's based on, he's a Non-Action Guy by nature.
• Leitmotif: "King of Games' Castle", which also comes in a Rococo form after fighting all of his champions.
• The Unfought: Once you beat all of his Champions, the King willingly concedes - fitting since you took down all his champions, so it's checkmate.
• Ye Olde Butcherede Englishe: Uses many archaic words like "forsooth" and "unto" and often uses "thou" and "ye" interchangably.

The Pawns

"One by one by one by one, your chance at victory is done!"

A group of eight pawns that ambush you from the rafters in the library of The King's Leap.

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• I Can Still Fight!: Even if their head is removed, a headless Pawn will still carry on fighting. For them to truly die you need to knock off the heads of all eight.
• The Pawns Go First: Quite literally; the Pawns are the first of the King's champions you get to face, and the Cups work their way up the ranks from there. Though, the King and his court are far from villainous.
• Shout-Out: In the Latin American Spanish translation, the Pawns reference Despacito in their death quote.
  "Pasito a pasito, suave suavecito, me llevo la victoria, poquito a poquito."^translation(literally) Step by Step, softly, I take the victory, little by little.
• Winged Soul Flies Off at Death: Happens to all of them at once when they're beaten.
• Wolfpack Boss: The Pawns. There are eight of them - parrying all of them wins the fight.

The Knight

"A 'W' for me and an 'L' for you!"

A horse in knight's armor that you duel in the foyer of The King's Leap.

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• Achilles' Heel: Downplayed, his parry-coded weak spot is his mane but it takes multiple parries on the mane to defeat him.
• Bring It: The Knight will occasionally make this gesture towards the player character. It's actually a clue on how to beat him; he'll only attack the player (and thereby expose his weak spot) if they approach close enough.
• Bullfight Boss: The Knight has his weak spot (his mane) in an awkward place; however, when he charges across the screen, he collapses to catch his breath, putting it in an easier spot for Cuphead and Mugman to hit. (Ms. Chalice, on the other hand, can dash into it after every attack due to how her parry works.)
• Duel Boss: The Knight stands out amongst all the other fights for having no minions or even any form of Bullet Hell; it's simply a melee battle between your parry skills and his sword.
• Eye-Obscuring Hat: The visor of his helmet covers only his eyes, with his big horse snout sticking out. Watch for when he exposes his eyes- he'll do a wide swing at the air above him.
• Furry Reminder: The Knight is a bipedal horse who fights with a sword and shield, but when defeated he immediately gets on all fours and starts kicking around like a bucking bronco.
• "Get Back Here!" Boss: Inverted. The Knight will only attack if you get close to him and will even gesture at you to get closer and fight if you move too far away from him. Stay away for too long, and he'll belt out an attack with very little wind-up that's likely to catch you off guard.
• Homage: The knight's moveset is a reference to 2D fighting games. His fighting style specifically is akin to that of player using a cheesy zoning playstyle: he hangs back and pokes at you with safe anti-air moves and taunts constantly to bait you closer, and only situationally tries to play offensively with his charge. The way that the knight moves (he can sidestep in either direction but always faces you), the way the foyer is laid out (you both stand on a carpet laid between two windows, like the "walls" on the edges of fighting game stages) and the emphasis on reading his move's windups and punishing him during his recovery time also brings to mind standard fighting game tropes.
• I Shall Taunt You: As a close ranged combatant, the Knight tends to stop and make a beckoning "come-closer" hand sign should you move too far away during his fight. Ignore this, and he'll eventually lose his patience and do a charge with a much smaller windup than he normally has.
• Knightly Sword and Shield: The Knight, appropriately enough, uses a sword and shield.
• Stealth Pun: His death quote serves as both an anachronistic insult based on fighting game slang and a reference to the L-shaped moves that knights make in chess.

The Bishop

"I've got you beat from every angle!"

A bishop (both in the sense that he's a priest and also a chess piece) that you duel in the cathedral of The King's Leap.

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• Deranged Dance: While the Bishop sends his head (or heads) to attack you, his body dances frantically to the fast-paced battle music.
• Finger Extinguisher: In a sense with the Bishop. To make his head vulnerable to attack, you must put out all the candles in the room by walking over them.
• Holy Pipe Organ: Played for Laughs. He is a bishop who makes the sound of someone banging on a pipe organ's keys when you put out all the candles, thus making him vulnerable to attacks. When you defeat him, his headdress turns into organ pipes that spew smoke, while his teeth turn into organ keys.
• Multiple Head Case: The Bishop grows three more heads before he starts dueling you.
• Shielded Core Boss: The Bishop's main weakpoint, his head, is only rendered vulnerable once every candle in the arena is snuffed out; a set will get re-ignited after every parry. For the final attack, every candle must be snuffed out.
• Sinister Minister: Downplayed with the Bishop, who has a rather creepy ability to remove his head and looks rather scheming in his defeat portrait, but otherwise doesn't seem malicious.
• Stealth Pun: He attacks by spitting out censers. In other words, he's a religious figure that censers violent cartoons.

The Rook

"Beating you was pretty straightforward!"

An executioner that you duel in the dungeons of The King's Leap.

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• Black Comedy: In spades with the Rook, who is an executioner...who throws heads of Marie-Antoinette and Louis XVI at you as his Tennis Boss schtick...and is introduced daydreaming about a female guillotine.
• Death by Irony: Well, defeat by irony, but when he's defeated, his own head falls off into his hands.
• The Dog Bites Back: Implied in the Rook's encounter; When you parry the heads he sends out, they sneer gleefully as they're sent flying back at him, implying that the Rook has beheaded a lot of people, and they are all looking to return the favor.
• The Executioner: The Rook is based off one — he wears an executioner's hood, his daydream at the start of the fight references a female guillotine, he wields an executioner's axe, and his attacks consist of shooting severed heads and skulls from his axe sharpening wheel.
• I Was Having Such a Nice Dream: His battle intro. He starts off with his head in the clouds, smiling to himself as he daydreams about a sexy guillotine...until he notices the player's presence, angrily snaps out of it, and gears up to fight.
• Shout-Out: The guillotine lady the Rook daydreams of in his intro is just Betty Boop in the form of an execution device; specifically, it's Betty with red hair and green eyes, referencing the royal-themed two-strip-color short Poor Cinderella.
• Stationary Boss: The Rook is the only Champion who doesn’t move from his place, possibly referring to the rule that a rook can't be moved prior to castling.
• Tennis Boss: The Rook throws severed heads out of his axe grinder, which must be parried to send them flying back into him. Considering that you may need to parry the heads several times to make them reach the Rook though, perhaps "Volleyball Boss" is a more apt descriptor.

The Queen

"Too little, too late, I dare say that's checkmate!"

The Queen of Games, whom you duel in the throne room of The King's Leap.

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• Background Boss: The Queen is out of reach of interaction, and can only be hit by parrying cannons to fire cannonballs at her.
• Boom, Headshot!: In order to damage her, the cannonballs must hit her head. Anywhere else and it won't connect.
• Excessive Evil Eyeshadow: She isn't evil, but she is your final foe in the tournament, and her heavy blue eyeshadow reflects her ruthless demeanor.
• Flipping the Table: Does this to the table with the adding machine she was clacking away on just before the fight.
• Gemstone Assault: The Queen attacks by whipping out two jewellery boxes and scattering faberge eggs onto you.
• God Save Us from the Queen!: Maybe. On the one hand, she's a merciless fighter and the strongest of the Champions, and the cannon-loading mice cheer when she's defeated. On the other hand, she's quite jovial in the epilogue while she's watching the King play against Chef Saltbaker, suggesting there was a level of Kayfabe at play during the tournament.
• Just Like Robin Hood: The mice in the Queen's battle are dressed like Merry Men, and seem to be invading the royal treasury while you battle her. They also celebrate when the Cups come out on top.
• More Deadly Than the Male: Despite being the second to the King, she is actually the toughest of the bunch. Fitting since she is based on chess, a game in which the queen is the most powerful piece.
• Nice Mice: During the fight with the Queen, a group of mice — who seem to be dressed like Robin Hood's famous Men of Sherwood — load the cannons and assist the Cups in taking down the Queen, cheering when they eventually do.
• Non-Standard Character Design: Like the gnomes in Gnome Way Out, the mice in the Queen's battle have simple lines for limbs rather than proper arms and legs.
• Rank Scales with Asskicking: Much like in real chess, the Queen is the most powerful fighter out of all of the King of Games' Champions.
• Shout-Out: She's fought inside a room filled with gold and treasure. Presumably this is a reference to the nursery rhyme "Sing A Song of Sixpence": "The queen was in the counting-house, counting out her money" (although in the original poem it's the king who is in the counting-house).
• Tiny Guy, Huge Girl: Altough her size is inconsistent (see below), she is usually depicted as taller than the King, fitting since she is the strongest of the court.
• Your Size May Vary: She appears rather huge in her fight, but in the epilogue she appears to be just taller than the King.

Other Characters

Secret Boss (Unmarked spoilers)

The Nightmare

"Wish you may, wish you might, your soul is now trapped in the night."

Acquiring the Broken Relic from Porkrind and solving a puzzle in the graveyard will cause a well of astral energy to appear in the graveyard. Once the cups take a nap in this spot, they have a rather interesting nightmare...

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• Amazing Technicolor Battlefield: The battle takes place in a revolving starfield, on a glowing platform of clouds being carried by what appears to be the Devil's skeleton. From what the ghost detective states about how there's 'potent astral energy' being carried by the three elements of the graveyard puzzle, it's implied that the Cups have entered the Astral Plane through their dreams after taking a nap on the gravestone.
• Ambiguously Evil: The Angel. On one hand, it's modeled after the Devil. On the other hand, its attacks can't harm you, it literally seems to have your back, and it looks remorseful on the game over screen if you die. Either way, it reacts in shock when you win the fight, and is seen praying for mercy when being sucked into the devilish skull with its evil counterpart, who is simply trying to grab onto something to avoid getting sucked in, showing neither of them are happy about getting sucked into the devilish skull.
• Ambiguous Situation: The exact nature of the fight is never explained - Where exactly are the cups? A nightmare? The astral plane? Some type of purgatory? Just what are the angel and the demon? Why do they get pulled into the skeleton in the background when they're defeated? Are they even normal angels/demons by the standards of the Cuphead world? And what does the Relic have to do with all this?
• Big Red Devil: The Demon appears as one.
• Breaking Old Trends: The only boss in the game to not be a Sequential Boss, though notes in the code indicate that the fight used to be a phase for the Devil's boss fight, which Jared Moldenhauer later confirmed to be the case; this was the original second phase of the fight before being cut, and the later three phases were moved ahead afterwards.
• Can't Move While Being Watched: A strange inversion; the attacks of the dream devil you turn your back to become harmless ghost attacks. However, the instant you turn around, the attacks (and the 'alignments' of the devils) shift, so don't move in the opposite direction while you're in the middle of a ghost attack, or you'll be instantly hit.
• Challenge Run: Beating the Nightmare turns the Broken Relic into the Cursed Relic. While the Cursed Relic is equipped, you're turned into a One-Hit-Point Wonder^note Although this can be subverted if you trigger the Game Djimmi cheat, which bumps your hitpoints up to a whopping 2 HP. and your equipment randomly switches every time you dash or use an EX move, though to compensate you receive additional health after parrying enough objects. Attaining 16 points in a secret point system by defeating bosses (a maximum of 8 regular bosses, specifically) throughout the Inkwell Isles (Main Game bosses included but not counting the King's Leap bosses) with the Cursed Relic equipped turns it into the Divine Relic, which allows you to freely switch between all of your guns and activates the positive effect of every charm you have at the same time.
• Dual Boss: Subverted. The fight is against an angel and a demon, but only the demon will actually damage you (and can be damaged in return). The angel's attacks do nothing to you, and they switch places every time you turn around.
• Eldritch Abomination: Whatever the Nightmare is, it's far worse than a mere bad dream. Its game over quote and the effect its deaths have on the Broken Relic hint at it being some kind of unknowable horror that lurks within the Astral Plane. Not helping matters is its resemblance to the Devil, himself a bonafide Humanoid Abomination.
• Evil Is Burning Hot: The Demon is a snarling, fire-spewing monstrosity that is hellbent on killing the cups.
• Good Angel, Bad Angel: The boss' design has an angel and a demon next to the shoulders of what appears to be a huge skeleton statue of the Devil himself, with the Angel having tiny horns and a friendly-looking demeanor and the Demon looking even more demonic than the Devil himself.
• Good Hurts Evil: The Cursed Relic is stated to 'despise bravery', and indeed, battling tougher bosses with it equipped purifies it faster.
• Guide Dang It!:
  • You reach this boss by talking to three NPCs on the map, making note of what they say, and then examining the proper gravestones in the graveyard near the Howling Aces fight location. Not only is this never made clear, but the dialogue that indicates the right gravestones is different on every playthrough. Oh, and make sure you bought and equipped the Broken Relic, or you still can't trigger the fight. Even more than that, it can be difficult to figure out what exactly the proper gravestone is: The player is supposed to treat the center gravestone as the default and pick the correct stone based on the orthogonal movements: If one of the NPCs says "left" then pick the gravestone to the left, but if they say "down" and "right" in the same line, then pick the gravestone in the bottom right corner.
  • Likewise, the method to unlock the Divine Relic involves a secret point system that is not elaborated to the player in any manner - the only hint to its existence is a cryptic statement relating to the Relic: "The greater the foe, the more evil shall go", which is meant to be taken that harder bosses awards more points. Datamining reveals that Isle 1 bosses reward 2 points, Isle 2 bosses reward 2.5 points, the bosses of Isles 3 and 4 reward 3 points, and the final bosses (The Devil and Chef Saltbaker) reward 4 points, with King Dice and his minions rewarding 1 point each. Fortunately you only need to fight a maximum of eight regular bosses to get the 16 points required to get the Divine Relic, and the Cursed Relic gets upgraded at 4, 8 and 12 points respectively, making it easier to get over the One-Hit-Point Wonder aspect with fewer parries to gain health.
• Harmless Enemy: The angel's attacks won't hurt you at all. This is a key element of the fight - because the angel and demon swap places every time you turn around, and their attacks switch qualities in the process, you can escape seemingly-unavoidable attacks by turning around.
• Leitmotif: "One Hell of a Dream", a mysterious and creepy rearrangement of "Admission to Perdition".
• Light Is Good: It's hard to tell just what the Angel's deal is, but at the very least it isn't dangerous. Creepy singing aside, it's a holy being whose attacks harmlessly phase through the cups.
• Optional Boss: The entirety of the Broken Relic quest, and by extension this fight, is entirely optional.
• Red Oni, Blue Oni: The red colored Demon is vicious and aggressive, while the blue-colored Angel is passive and calm.
• Sequential Boss: A rare aversion in Cuphead. The boss only has a single phase, and it doesn't have any other difficulty settings either.
• Shout-Out: Befitting Cuphead being a invokedSpiritual Successor to it, the fight is highly evocative of Silhouette Mirage - a fight with a red enemy and a blue enemy where the direction the player's facing affects which projectiles they get hit by.
• Video Game Randomizer: The effect of the Cursed Relic and, to a lesser extent, the Divine Relic. The Cursed Relic fully randomizes weapons every dash, EX Move, Super, and even when you stop firing, while certain charm effects happen after a number of dashes or parries, depending on what upgrade level the Relic is in. The Divine Relic keeps the same effects for the weapons, but gives you every positive charm effect at the same time instead.
• Visual Pun: Because of the nature of the boss, you'll always be looking at the demon side, and the angel side is always behind you. In other words, you need to face your demons, but the angel's got your back.

The Boatman

A compass-headed boatman who appears to deliver Cuphead and Mugman a message from the Legendary Chalice. He appears on all four Inkwell Isles as of The Delicious Last Course, acting as a link to the DLC content and a way to quickly travel across the isles.

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• The Ferryman: He ferries the cups across the isles, and seems to be mystical, as he wears a robe and appears to have a close connection to Chalice. Unlike most examples, he doesn't have a toll and he's clearly benevolent, if a bit aloof.
• No Name Given: He isn't named in-game, but notes in the code simply call him the Boatman.
• Non-Human Head: His head is a compass, with the arrow serving as a mustache. Notably, this means it always points west rather than north.
• Terse Talker: His lines of dialogue are very short and blunt, adding to his mystique.
• Warp Whistle: In addition to being the gateway to the DLC content, he also functions as the game's fast travel system.

Honorable Judge Wise

An owl judge who presides over the courts of the Inkwell Isles.

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• Expy: He resembles the owl from A Day at the Zoo.
• Mouthy Bird: His beak acts like a nose, and he has a regular mouth underneath.
• The Owl-Knowing One: His name and role as a judge references the common portrayal of owls as wise figures of authority.
• Reasonable Authority Figure: Though he is rather harsh in berating Chef Saltbaker, his sentence is community service, a fairly lenient punishment under the circumstances. True to his name, this punishment is wise; it brings restitution to the victims, and helps Saltbaker see the error of his ways and reform for good.

The Ant Squad

A group of ant detectives who serve as the law on the Inkwell Isles. They raid the Moonshine Mob when the cups come looking for the distillery dough.

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• Big Ball of Violence: The ants get sucked into the anteater's mouth, along with some of the flies, and get shot around the room as they fight each other.
• Cartoon Bug-Sprayer: The ants use these against the flies during the raid.
• Friendly Enemy: In the game, they're enemies of the Moonshine Mob; raiding the place when the cups show up for the dough. In the epilogue, one of the detectives is happy to work with the boss snail to put the defeated Chef Saltbaker to work.
• Lawman Baton: Some of the ant police that appear in their boss fight complete their Old-Fashioned Copper look by arming themselves with old-fashioned police batons. Specifically, they do this during the light bug's portion of the battle.
• Pinball Projectile: They get subjected to this when the anteater sucks them into his mouth and gloms them all together into a ball to attack the cups.
• Sickly Green Glow: Their Cartoon Bug-Sprayer sends out green plumes of toxic smoke, except if the smoke is pink to signify a parry.
• Tertiary Sexual Characteristics: The detective in the epilogue has a much rounder thorax, looking more like a bust. The other ants during the raid have flatter thoraxes.

Inkwell Isle 4 Villagers

The NPCs that you meet in the fourth Inkwell Isle introduced in the DLC. They consist of a cat who hawks newspapers; a lantern, shovel, and pickaxe who entered a climbing competition; a ghostly detective investigating some potent astral energy; and a cactus girl who enjoys campfire stories.

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• And Your Reward Is Clothes: The cactus girl in the south-west of the isle loves to hear ghost stories around campfires, and likes to keep track of "a ghostly gal roughin' up no-good varmints". Defeat every boss as Ms. Chalice, and the cactus girl will give the player a special "Chalice" filter that gives her white skin and a yellow skirt.
• Graceful Loser: The pickaxe in third place can be rather accepting of their loss depending on how the graveyard puzzle is randomly selected. Most of the other times, they're a Sore Loser.
• Pun: The three mountain climbing tools will talk about how they feel in first, second, and third place respectively with directional phrases thrown in, saying things like "I am downright awesome!", "I think I did all right" or "I guess things can only go up from here!". These directional phrases hint to you about the correct gravestones in the gravestone puzzle for the Broken Relic.
• Shout-Out: The ghost detective uses the phrase "order and method" as a reference to Hercule Poirot.
• Sore Loser: The pickaxe in third place will often angrily complain about their placement depending on how the graveyard puzzle is randomly selected. Rarely, however, they might be a Graceful Loser.
• Stop Poking Me!: If approached enough times in a row, the newsie cat will replace their standard dialog with "Extry! Extry! Troublesome Cups Bother Newsie!".
• Unsportsmanlike Gloating: The lantern in first place of the mountain-climbing competition can be doing this depending on how the graveyard puzzle is randomly selected. Other times, they might be a humble winner.

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