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A set of nine minibosses that are under the command of King Dice, fought within the myriad games and halls of the Devil's Casino. You have to fight at least a few of these strange fellows in order to finally fight King Dice himself.
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    In General 
  • 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, including Chips Bettigan, Phear Lap and King Dice himself, represent various forms of gambling.
  • Mini-Boss: They're not as powerful as most of the other bosses in the game and only have one phase each, but several of them must be fought before you can get to King Dice.
  • Obviously Evil: Unlike the debtors, who can be classified as Anti-Villains, as King Dice's lackeys they clearly don't have much in the way of a moral compass and are fighting the boys to hinder their progress.
  • Optional Boss: A skilled player can manipulate the dice enough to only fight just three of them, but those seeking a real challenge can battle all nine.
  • 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.
  • Quirky Miniboss Squad: This set of quirky characters are fought in a row (exactly how many of them you fight depends on how good you are at rolling the dice), and all their fights have only one phase.
  • Sequential Boss: Averted, they all have only one pattern, but considering how they are fought in the same level, they are boss phases on their own.

Individuals:

    Tipsy Troop 
https://static.tvtropes.org/pmwiki/pub/images/tipsytroop.png
"Go sleep *hic* it off...you look a little *hic* rough!"
Ginette (a martini), Ol' Ethan (a shot glass filled with whiskey) and Rumulus (a bottle of rum), all fought on a bar table.
  • Alcohol Hic: These guys hiccup while they talk in their Game Over quotes, due to the alcohol in their bodies.
  • The Alcoholic: Being alcohol containers, they are all constantly drunk, presumably on themselves.
  • 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' 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.
  • Edible Theme Naming: All based on alcoholic drinks (gin, rum and ethanol - the actual alcohol in them).
  • Flunky Boss: Ginette summons flying olives who shoot their eyes at you.
  • Grimy Water: Ol' Ethan attacks by spilling booze out of himself across the tabletop 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...
  • Turns Red: Inverted — as you progress through the battle, the trio will fall one by one, making the fight get progressively easier.
  • Wolfpack Boss: The three of them aren't as strong as an average boss when alone, but will work together to overwhelm Cuphead and friends.

    Chips Bettigan 
https://static.tvtropes.org/pmwiki/pub/images/chipsbettigan.png
"Hey short stack! This isn't a place you wanna be hanging 'round."
A stack of poker chips fought on a card table.
  • 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.
  • 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.
  • Yellow Eyes of Sneakiness: He has yellow sclera and is one of the bad guys.

    Mr. Wheezy 
https://static.tvtropes.org/pmwiki/pub/images/mrwheezy.png
"Looks like you could use some fresh air."
A giant cigar you fight on two ashtrays over a pit of flames.

    Pip and Dot 
https://static.tvtropes.org/pmwiki/pub/images/pipanddot.png
"You set them up, I'll knock them down."
A domino with a male half on top and a female half on the bottom. You fight them in a room with a conveyor belt pulling you toward a wall of spikes.
  • Amazing Technicolor Battlefield: Notably one of two bosses in the Dice Palace that fight you in one of these, and the only one where what it's supposed to be is very vague, being some sort of strange void with domino tiles floating, appearing, and disappearing everywhere (although it could be interpreted as a dominoes board).*
  • Arc Number: 4. They have four eyes in total (which are reminiscent of dots on dominos), and they're fought if you land on space number 4 on King Dice's board.
  • Battle Couple: They fight together as one boss, and their designer Tina Nawrocki considers them a married couple.
  • Eyelash Fluttering: Dot starts the battle by looking up at Pip and batting her eyes with a xylophone tinkling sound, while Pip looks down at her and tips his hat.
  • Flunky Boss: Occasionally, Pip will release small domino-bird creatures from his top hat, which will circle around the battlefield before leaving.
  • More Teeth than the Osmond Family: Their middle section holds a third mouth that has many fangs in the middle of it.
  • Multiple Head Case: Both the male and female faces have separate personalities.
  • 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 hair bow for Dot. The latter also has prominent eyelashes.
  • Too Many Mouths: Not only do Pip and Dot each have a mouth of their own, their "midsection" can also open up as a third, fang-lined mouth.
  • You Have Failed Me: Humorously, not from King Dice, but from Dot, who kicks Pip in the face for losing.

    Hopus Pocus 
https://static.tvtropes.org/pmwiki/pub/images/25_hopus_pocus_removebg_preview.png
"...and PRESTO!! The cup has completely disappeared."
A crazed rabbit magician fought in a room with playing cards.
  • Arson, Murder, and Jaywalking: He doesn't seem to represent any particular vice like the other bosses of the King's Court, instead being primarily themed around magic. Given his Playing Card Motifs, it's possible that — like Chips Bettigan — he represents poker as a game of chance. There is also the possibility that he represents the magic shows that can be seen in casinos.
  • Barely-Changed Dub Name: Is named "Hopus Pokus" in both German and Polish.
  • 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.
  • Playing Card Motifs: Similar to King Dice, one of his attacks is a wall of of bubble-like projectiles that advance through the battlefield, shaped like the four card suits. The heart bubbles are colored pink and thus are parry-able. Additionally, an Ace of Spades card is provided on the battlefield as a platform for you to stand on.
  • 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 
https://static.tvtropes.org/pmwiki/pub/images/26_phear_lap_removebg_preview_5.png
"This derby is over and the results are in. Last place... YOU!"
A skeletal racing horse who is fought via planes above a haunted horse racing track.
  • 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.
  • Interface Screw: Phear Lap's racetrack has the most obstructive foreground setting of any arena in the game, and the artbook confirms that this is an intentional design choice in order to disrupt the player's view of the fight.
  • 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.

    Pirouletta 
https://static.tvtropes.org/pmwiki/pub/images/pirouletta.png
"Ah-ha! You've noticed that my style is very Russian!"
A fairly tall roulette wheel who's likewise a ballerina. Fought on a roulette betting table.
  • Barely-Changed Dub Name: Has several of these across the game's localizations:
    • "Piroulette" in Italian.
    • "Pirouetta" in Japanese
    • "Piruletka" in both Polish and Russian.
    • "Piroleta" in Portuguese.
    • "Piruletta" in European Spanish and "Pirruleta" in Latin American Spanish, making it an example between both versions as well.
  • Dance Battler: Dances across the area, which means that you must use the poker chips to jump over her or dash through her (with the Smoke Bomb) to avoid damage. 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.
  • Gag Nose: She's got quite the honker on her face.
  • Punny Name: A portmanteau of the words "pirouette" and "roulette."
  • Statuesque Stunner: Very tall and lanky, yet oddly pretty too.
  • Stealth Pun: She's a roulette wheel who claims to have a "very Russian" style. Think about it.

    Mangosteen 
https://static.tvtropes.org/pmwiki/pub/images/mangosteen_18.png
"Fault, scratch and choke — are you trying to hustle me?"
A giant eight ball fought on an abstract pool table.
  • Amazing Technicolor Battlefield: Where he's fought is less of a pool table and more of a bizarre pool dimension.
  • Arc Number: 8, of course. He is a living eight-ball, and you fight him if you land on space number 8 on King Dice's board.
  • Bad Guys Play Pool: In this case, bad guys are pool.
  • Body Horror: He's just eyes and a mouth over an eight-ball, which looks very disturbing. Even more so in his defeated animation, which reveals his "body" is actually a mass of floating ink. Creepy.
  • Edible Theme Naming: Named after the mangosteen, a round, purplish-black fruit.
  • 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. Indeed, analogous to his inspiration (who's named after a fruit-based food), he's named after a fruit. He even fires a single ball of energy as his sole direct method of attack, just like his inspiration. Additionally, while pool does have some luck elements, he's also based off of the Magic 8-Ball, which is a game of luck as you hope it reveals a good fortune for you when you shake it.
  • 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 
https://static.tvtropes.org/pmwiki/pub/images/mrchimes.png
"Monkey see, monkey doom."
A toy monkey fought via planes in a crane game machine.
  • Anachronism Stew: Despite the game's 1930s setting, Mr. Chimes is based on the cymbal-banging monkey toy, which wasn't invented until the 1950s in real life.
  • Arson, Murder, and Jaywalking: The various members of The King's Court all represent common adult-oriented casino paraphernalia, such as cigars, booze and poker. Mr. Chimes represents a crane game, which is more common in arcades. That said, crane games are often seen as rigged against the player, which fits with the Devil's other rigged games.
  • 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.
  • Ghostly Gape: 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. How long he stays active depends on his current health; the fight is designed so that you'll ultimately have to match all the cards in order to defeat him.
  • Shout-Out: Mr. Chimes himself is a toy monkey, and also seen in the crane game are a Godzilla-like lizard and a wolf. Word of God is that the three are a reference to George, Lizzie, and Ralph, the three main characters from Rampage.
  • Spread Shot: Every time he bangs his cymbals, a spread of 6 projectiles are fired out radially.

Unused

    Pachi-Pachi 
"Cling cling, clang clang, your bell has rang!"
An unused boss (notable for being the farthest in development) that was originally accessible in the earliest version of the game via debugging before later updates removed all assets entirely. A moving tulip catcher fought in a pachinko board, though only after defeating all the other 9 members of King Dice's court.
  • A Day in the Limelight: An odd variation, but Pachi-Pachi is the sole focus of the Deluxe+ mini-artbook that came bundled with the Superdeluxe Games' First Release Physical Edition bundle.
  • Challenge Run: Originally the end result of doing one; they were only fought if you deliberately made low rolls in order to fight every Dice Palace boss.
  • Playing with Fire: Pachi-Pachi breathes fire through the tulip catcher hole on their head.
  • Uniformity Exception: Unlike the other bosses in the set, who are all based on activities and games contemporary to the time the game is set, Pachi-Pachi stands out, in that he's based on a game which did not exist in America at the time (Pachinko didn't appear in the West until around the 1970's, about 40 years after this game's time period), and Pachinko machines with tulip catchers like the one he is based on were first manufactured in the 1960's in Japan, about 30 years later.

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