How to Draw Cuphead Bosses

This is a list of bosses from Cuphead. In the game, the battle bosses take place in the form of debtors, whose souls Cuphead and Mugman must steal to win The Devil's bet, and in The Delicious Last Course, the keepers of ingredients that are used to create the Wondertart to bring Ms. Chalice back to life. They are one of the main points of the game and they occur in several stages. Bosses can have just one phase (such as the minibosses fought in All Bets Are Off! and some bosses played on Simple Mode.) or as many as five (such as Djimmi The Great) but more commonly just have 3 or 4. Whenever the player starts a boss battle, the announcer utters one of the following lines:

"A brawl is surely brewing!"
"Here's a real high class bout!"
"A great slam and then some!"
"This match will get red hot!"
"Good day for a swell battle!"

Followed by one of the following, accompanied by "WALLOP!"

"Now go!"
"You're up!"
"Here goes!"
"It's on!"
"And begin!"

Once the boss is defeated, the announcer will shout "Knockout!", which is followed by the bosses' defeat pose.

However, if the player dies, they will be greeted with a screen that simply says "YOU DIED!" which precedes a "Death Card" which contains a quote of the boss mocking player, often with them rhyming.

There is a total of 28 bosses in the first Cuphead game (footage of each below). There are five bosses each in Inkwell Isles 1 and 2, seven in Isle 3, ten in the showdown with King Dice (nine mini-bosses plus King Dice), and finally, The Devil himself.

Footage_of_all_Cuphead_bosses — Footage of all Cuphead bosses

Boss Name	Preview	Description
Inkwell Isle One
The Root Pack		One of the two bosses initially available, the Root Pack are aptly enough a gang of root vegetables, named (in phase order) Sal Spudder, Ollie Bulb, Chauncey Chantenay. Their level is titled Botanic Panic! Defeating them unlocks access to Clip Joint Calamity. This boss has three phases (two on Simple Mode), and has a secret phase.
Goopy Le Grande		One of the two bosses initially available, Goopy Le Grande is a gigantic, narcissistic slime. His level is titled Ruse of an Ooze. Defeating him unlocks access to Threatenin' Zeppelin. This boss has three phases (two on Simple Mode).
Hilda Berg		Fought in Threatenin' Zeppelin. Beating her unlocks Floral Fury for the player. This boss has two phases (one on Simple Mode), not counting her transformations.
Cagney Carnation		Fought in Floral Fury, which is unlocked upon beating Hilda Berg, or taking a shortcut. Beating him unlocks the Die House for the player. This boss has two phases (one on Simple Mode).
Ribby and Croaks		Ribby and Croaks are a duo of fighting hooligans with "hearts of gold". They are unlocked after beating The Root Pack, and their level is titled Clip Joint Calamity. This boss has three phases (two on Simple Mode).
Inkwell Isle Two
Baroness Von Bon Bon		Baroness Von Bon Bon is one of the three bosses initially available after entering this isle. Defeating her grants the player access to Wally Warbles. Her level is titled Sugarland Shimmy. This boss has four phases, with five (four on simple mode) randomized bosses before the final phase.
Beppi the Clown		Beppi The Clown is one of the three bosses initially available after entering this isle. Once defeated, Wally Warbles and Grim Matchstick are unlocked. His level is titled Carnival Kerfuffle. This boss has four phases (three on Simple Mode).
Djimmi the Great		Djimmi The Great is one of the three bosses initially available after entering this isle. His level is titled Pyramid Peril. This boss has the most phases out of any of the bosses in the game, with a total of five phases (four on Simple Mode).
Grim Matchstick		Grim Matchstick is unlocked after defeating Beppi The Clown, or by taking a shortcut. His level is titled Fiery Frolic. This boss has three phases (two on Simple Mode).
Wally Warbles		Wally Warbles is unlocked after defeating Baroness Von Bon Bon, or taking a shortcut. His level is titled Aviary Action. This boss has three phases (two on Simple Mode).
Inkwell Isle Three
Rumor Honeybottoms		Rumor Honeybottoms is one of two initially available bosses after entering this isle. Defeating her grants access to Dr. Kahl's Robot. Her level is titled Honeycomb Herald. This boss has three phases (two on Simple Mode).
Captain Brineybeard		Captain Brineybeard is the second of two initially available bosses after entering this isle. Defeating him grants access to Cala Maria. His level is titled Shootin N' Lootin. This boss has two phases (one on Simple Mode).
Sally Stageplay		Sally Stageplay is a boss which can be accessed after beating either Cala Maria, Dr. Kahl's Robot, or taking a shortcut. Defeating her grants access to Phantom Express and Werner Werman. Her level is titled Dramatic Fanatic. This boss has four phases (three on Simple Mode).
Werner Werman		Werner Werman is a boss unlocked after defeating Sally Stageplay or completing either of the Run n' Gun levels Perilous Piers and Rugged Ridge. His level is titled Murine Corps. This boss has three phases (two on Simple Mode).
Dr. Kahl's Robot		Dr. Kahl's Robot is unlocked after defeating Rumor Honeybottoms, controlled by Dr. Kahl. Defeating him grants access to Sally Stageplay. His level is titled Junkyard Jive!. This boss has three phases (one on Simple Mode).
Cala Maria		Cala Maria is unlocked after defeating Captain Brineybeard. Defeating her grants access to Sally Stageplay. Her level is titled High Seas Hi-Jinx!. This boss has three phases (two on Simple Mode).
Phantom Express		The Phantom Express is unlocked after defeating Sally Stageplay. Defeating them grants access to Inkwell Hell. Their level is titled Railroad Wrath. This boss has four phases (three on Simple Mode).
Inkwell Hell
Tipsy Troop		The first of nine mini-bosses fought before King Dice.
Chips Bettigan		The second of nine mini-bosses fought before King Dice.
Mr. Wheezy		The third of nine mini-bosses fought before King Dice.
Pip and Dot		The fourth of nine mini-bosses fought before King Dice.
Hopus Pocus		The fifth of nine mini-bosses fought before King Dice.
Phear Lap		The sixth of nine mini-bosses fought before King Dice.
Pirouletta		The seventh of nine mini-bosses fought before King Dice.
Mangosteen		The eighth of nine mini-bosses fought before King Dice.
Mr. Chimes		The ninth and final mini-boss fought before King Dice.
King Dice		The Devil's assistant in running their casino. His level is titled All Bets Are Off!. The player determines the amount of phases this boss has. This level can't be played in Simple Mode, unless a patched-out glitch is used, in where the fight is completely broken.
The Devil		The Devil, the one who Cuphead and Mugman are collecting the soul contracts for, and serves as the main antagonist and final boss of the game. His level is titled One Hell Of A Time, and is accessed after defeating King Dice. This level has four phases, and cannot be played in Simple Mode.
DLC Island
Glumstone The Giant		Not much is known about Glumstone The Giant at the moment, aside from the fact he uses a lot of gnomes for his fight.
Mortimer Freeze		Mortimer Freeze is a wizard cult leader fought in Snow Cult Scuffle.
Esther Winchester		Not much is known about Sheriff Esther Winchester at the moment, aside from the fact that she guards the desert in the south.
The Howling Aces		Two bulldogs with a massive airplane themed after them.

Bug-Themed Gang		Not much is known about them at the moment, aside from the fact that this boss fight may contain more than one member, judging from the anteater on the EDGE cover's hat. They may be based off of animals that prey on bugs.
Unnamed chess knight		One of the King of Games's associates.