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10 Of The Best And Coolest Cuphead Bosses

Cuphead is a run and gun video game developed and published by the Canadian video game developer StudioMDHR in 2017. The game was inspired by the rubber hose style of animation used in cartoons of the 1930s, such as the work of Fleischer Studios and Walt Disney Animation Studios, and sought to emulate their subversive and surrealist qualities.

Cuphead features one or two players taking control of animated characters Cuphead and his brother Mugman to fight through several levels that culminate in boss fights, in order to repay their debt to the devil. The game was praised for its art style and noted for its challenging difficulty. It was both a critical and commercial success, winning several awards and selling over five million copies within two years. An animated series based on the game is in production by Netflix.

Take a look below for our list of the 10 best and coolest Cuphead bosses.

1. Cala Maria

Cala Maria has a physical appearance reminiscent of a typical humanoid female character. She is a slender mermaid with fairly wide hips. She has pale lavender-pigmented skin, an exposed midriff, a small button-nose, and two scar-like markings on the bicep of her left arm (though how or why she got them is unknown).

On her head, she has a dead, purple octopus with pale lavender eyelids over X-crossed eyes, with a lighter purple coloring and pale pink suckers under the tentacles. The octopus clearly acts as her hair since the three tentacles in front of Cala’s face are flipped back over her head, resembling curly hair-bangs in a pompadour, while the octopus’s head vaguely resembles a hair bun. Although it appears to be dead, the octopus’s eyes clearly open during Cala’s “summoning” animation, revealing simple, black pupils.

Cala has big, pale turquoise eyes with sea-green eyeshadow and three short, black, triangular eye-lashes each. She also has thin, black eyebrows and light, rose-pink lips.

As a sign of her mermaid status, Cala wears a sky-blue sea-shell bra with no shoulder straps, and her lower body is replaced with a sea-green, fish-like tail with round scales, connected with a water-ripple-like pattern below the waist line. Because only her upper body is seen, it is unknown what the tail-fins look like.

However, in her second phase, Cala Maria gets bitten on her belly and shocked by two eels, resulting in a much more menacing appearance—a gorgon-mermaid hybrid, greatly resembling the famous mythology figure, Medusa.

Her once pale-lavender skin turns to a mint-green color. Her fingers become longer due to her fingernails becoming claw-like. Her lips turn an emerald-green color, her tongue becomes forked and reptilian, and her teeth are now quite sharp, forming an eerie, Cheshire Cat-esque grin. The markings on her arm remain unchanged.

Her eyes become menacingly cat-like with yellow sclera and black, slit-shaped pupils, losing the irises completely.

Her tail takes on a more forest-green hue and the scales become sharper and more triangular. Her once sky-blue sea-shell bra is now a green bikini top made from either seaweed, moss, or grass.

The most distinctive part of her new form is the octopus on her head, which has now seemingly fused onto her head and has become a marginally different shade of purple. The tentacles each transform into menacing-looking snakes with lavender, segmented underbellies, yellow, cat-like eyes, and small fangs in their mouths. Only the snakes acting as her bangs are active, while the rest are asleep.

Cala Maria is said to be playful, but not to be trifled with. Cala Maria seems to be a flirty and vivacious being. She appears to have some interest in Cuphead and Mugman, as seen in her intro where she makes a sweet “yoo-hoo!” sound while fluttering her eyelashes and making a pose, and in the ending sequence in which she is staring at the brothers (although, as a siren, she could only be doing it to catch them off-guard as well).

Her first phase death message only helps support this. However, she seems to become more cruel after she is forcefully transformed into a gorgon-mermaid, due to electric eels biting her hips and shocking her. Cala also seems to have a strong connection with fish and aquatic animals, as she can summon them at will to help her, and also use the fish as weapons without them apparently caring much.

2. Cagney Carnation

Cagney Carnation, like his last name implies, is a tall, sentient carnation flower. His thorn-covered stem is a dark green color (The thorns do not appear when Cuphead and Mugman encounter him, but appear when Cagney reveals his true colors.), while his petals are two different shades of orange. His face is yellow, with a long, pointy nose and black eyes, and he is usually seen grinning in an evil way. He has long arms that can shift into leaves that a flower would normally have. There are small green leaves surrounding his stem as well. In his final phase, Cagney will have his hands planted into the ground, and his usually round teeth and petals will have a sharper shape. He also seems to have vines come out of his bottom petal.

Cagney is sneaky. He seems to delight in catching his enemies off guard with his appearance, posing as a harmless and adorable flower before roaring loudly and showing his true colors. His constant maniacal smile during battle also implies that he’s either too overconfident about winning or he enjoys the fight more than he should, considering that his soul and life are on the line. Also, it seems Cagney is easily angered by losing and may have apoplexy since he appears to pass out from anger in his knockout animation. His innocent smile at the beginning of the battle implies that he is innocent and caring when not confronted.

3. Grim Matchstick

Grim Matchstick bears an appearance similar to a typical dragon character from the game’s time period.

He is a large, slightly chubby, European dragon with a very simple design. He has lime-green scales and a light-amber underbelly (lacking segments) that starts of at his distinct, beak-like muzzle. He has large pie eyes, no visible eyebrows (minus an indentation) and featureless ears on his head.

Grim has two large fangs resembling buck teeth and has a tongue that can extend like that of a frog, allowing his flame minions to walk across (similar to the famous red carpet method).

On his shoulder blades, he has average-sized, bat-like wings, the same color as his scales, that are flexible and can shape into arms (similar to actual bats), as seen in his intro, where he forms them into hands with fingers. His limbs are rather small and stubby, with four fingers on each hand, two toes on each foot, and silver claws/talons. He also has solid-white spikes running all the way down his spine (like many other dragons in popular culture), and he has a very long tail, which he uses like a baseball bat to swat his victims away.

When Grim reaches his third phase, he grows two more heads on his shoulders that look exactly the same as the original’s head, which morphs into a red flame-thrower with a gold gas sprayer and lighter just in front.

Grim Matchstick is quirky and goofy, being more like a giant, overly playful dog, just as likely to hurt you while trying to play as he would be apologetic after his folly. He strives to spook people, making “ghostly” motions whenever the battle commences. He also stutters when speaking, as shown by his death screen lines.

Interestingly, Grim is one of the only two bosses (the other being Ollie Bulb) in the game that doesn’t actually want to hurt Cuphead and Mugman. He views himself as misunderstood and apologizes for being forced into putting the brothers in a hot seat if they lose to him in his second phase. He even suggests that the brothers should run away from him after he turns into a hydra in his third phase.

4. King Dice

King Dice is a six foot tall humanoid being with a dice for a head, with each side of his head showing the number of pips that would be on a die, with the “One” side acting as his face (the dot being his nose). He wears white gloves, purple shoes and tailcoat, a lavender waistcoat, and dark purple pants and bow tie. He also has a mustache, purple eyelids, and seafoam green eyes that are only shown whenever he acts seriously in a wicked manner. His head floats due to not having a neck.

King Dice is an extremely sleazy, deceitful, untrustworthy, and manipulative individual. While normally relaxed and cheerful in a sadistic way, he can be as cruel as his master if he wants to be. He also tends to speak using stereotypical New York Gangster slang, saying phrases such as “Scram”, or “Big cheese”.

Very arrogant and overconfident in himself, King Dice believes that no one is allowed to mess with him and that he can easily triumph over anyone who tries to, which ultimately leads to his defeat. However, it seems like King Dice does have a heart, as shown when he congratulates Cuphead and Mugman every time they are let through to the next isle, and during the cutscene in the beginning of the game, where it is shown that he is proud of them for not being able to lose.

King Dice also takes his own bets very seriously, going as far as to attempt to kill the brothers when they succeed in getting all of the soul contracts after he made a bet that they would fail their mission, though given who his boss is, the stakes were likely to be extremely high for him.

5. The Devil

The Devil has black fur, yellow eyes with red pupils (which are only seen in close-ups), two horns on his head, gray hands and feet and large, pointed ears. He also appears to be very tall and huge. He has a tail with a pointed end in artworks, but does not have one in the game.

Much like many depictions of Satan, the Devil is a cruel and malevolent being that grants deals to anyone who asks in exchange for their souls and servitude. He can be a manipulative and deceitful trickster as well, turning Cuphead and Mugman into his slaves despite agreeing to spare them if they hand over all of the soul contracts. He also lacks empathy towards everyone, including his own minions, as evident by him calling King Dice a “good-for-nothing lackey” after he has been beaten.

The Devil’s main trait is that he is incredibly prideful of himself, believing he’ll always win in the end as he brushes King Dice off when the latter tries to warn him about the brothers becoming stronger.

Being the owner of the casino, the Devil resided in Inkwell Hell, making deals with anyone who wanted their wishes granted for the price of their souls. One day, after being impressed by the winning streak of Cuphead and Mugman at the Craps table, he approached the pair and offered them all the loot in the casino if they won the next roll. If they lost, he would claim their souls.

Cuphead, blinded by greed, threw the dice before Mugman, who was fully aware of the risks, could stop him. Be it by sheer coincidence or the game being rigged, the dice landed on snake eyes, resulting in the Devil’s victory. Having lost, the brothers begged him not to take their souls and asked if there was anything else they could give him in exchange. After pondering, the Devil told them that if they can gather the soul contracts from his other debtors before tomorrow at midnight, he would spare their lives and rudely boot them out of his casino. He then sent King Dice to make sure the pair fulfill their end of the bargain.

Later, in a conversation with King Dice, the Devil proclaims that he knew there was something special about the pair after Dice reports their growing progress in collecting the contracts of the other debtors. In response to Dice’s concern about Cuphead and Mugman being up to something, he assures him that he’ll be waiting in case they try anything.

Eventually, Cuphead and Mugman obtain all the contracts and confront the Devil once again in his throne room. The Devil congratulated the pair for defeating King Dice and offers the choice to join him if they give him the soul contracts. If the brothers agree, he will happily turn them into demonic beings (possibly as his replacement henchmen for King Dice), revealing that he had deceived them.

If the brothers refuse, the Devil will become angry and battle them for not holding their end of the bargain. In the end, the Devil is defeated and forced to finally surrender, and all the soul contracts are destroyed by Cuphead and Mugman, thus freeing Inkwell Isles and its inhabitants from his clutches.

6. Beppi The Clown

Beppi is a tall clown with a red and blue clown suit, as well as a collar that has blue and red triangles on the sides with the top of the collar being white. He also seems to have red and white face paint as well as a small black top hat. He also has yellow eyes with black pupils, a long red nose, and short eyelashes.

His second form resembles his first form, but portrays him as made out of balloons. His head is a giant balloon.

His third form, which is faced during his fourth phase (His first form is used in phase 3 as well, except with a horse instead of a car.), transforms him into a carousel.

True to his nature a clown, Beppi is a fun-loving and joke-cracking character, as shown by his habit of making puns whenever the brothers lose to him and constantly smiling and laughing throughout his battle. He is shown to use many carnival tools at his disposal, from bumper cars and balloon animals to carousel horses and roller coasters, which solidifies his fun-loving nature.

Beppi also appears to have a dramatic side, as seen when he throws a fit upon his defeat in the third phase.

In his fourth phase, Beppi is shown to be psychotic and overconfident as evident by the maniacal laughter and the fact that he is constantly smiling.

7. Phantom Express

The Phantom Express is a train for the dead. Blind Specter is a light blue ghost with one large empty eye socket on his head, and his eyes coming out of his palms.

T-Bone is a very large skeleton, with his most notable feature being the conductor hat he wears. He also appears to be missing a tooth.

The Blaze Brothers look similar to the pistons of a train. They have large round heads being held on very thin tubes. They also have knives as teeth set.

The Head of the Train is a steam locomotive with a blue face and greyish-purple body, with his heart inside of his boiler. He is always seen with his teeth showing. After uncoupling from the rest of the train, he looks similar to a horse, with his body raised above his wheels by four legs and a tail that ends in a light-bulb.

Everyone on the train seems to take enjoyment in poking fun at the brothers dying. Blind Specter says that Cuphead and Mugman shall count the worms that go through their corpses, T-Bone says the train’s next destination is their funeral, the Blaze Brothers state that the train is exclusive to dead people, but now that the brothers are dead, they can ride the train, and the Head of the Train states that he has enjoyed the battle and “bringing the fright”.

8. Werner Werman

Werner is a long-snouted brown rat who operates a dented tin soup can that bears 3 gold stars perched on a wooden cart that he uses as a battle tank. He wears white gloves, blue shoes, and light brown pants (with a tan stripe running down each side of the pants) held up by a single suspender strap. His most notable feature is his metal Pickelhaube helmet strapped to his head. He also smokes a cigar.

The Cat, named Katzenwagen, is a mechanical feline that has navy blue fur, light grayish-blue skin, yellow eyes, salmon paws and inner ears.

Werner Werman is cantankerous and a military master in his own mind. Werner Werman acts like a stereotypical German soldier from World War I, speaking in a thick and exaggerated German accent and making a salute whenever he charges forward to attack with his tank. He appears to be interested in the late 1700- early 1900 military as he is wearing a Prussian soldier helmet (Pickelhaube) and owns a Colonial British soldier figurine.

Werner is also an incredibly skilled technician, having the talent to create both a realistic mechanical cat and a tank with multiple uses out of wood and a soup can. He doesn’t seem to mind boasting about his own technology, as evident by his 2nd phase’s death screen. However, he becomes completely irrational in the face of failure, since instead of giving up in the 2nd phase when his tank is demolished, he chooses to continue fighting while screaming wildly.

Katzenwagen has no real personality, being an automaton created by Werner, although it is capable of expressing emotion as evidenced by the territorial and angry meowing noises that the Cat makes, and by the final phase death screen.

9. Wally Warbles

Wally is a red-headed, blue-feathered bird of unknown species who wears a birdhouse that hides most of his body save for his legs, wings, and head. His legs are disguised as a pendulum before the battle with him begins. He has red and blue feathers and an orange beak and feet. Inside the house resides his son.

Judging by how aggressive he appears and his son’s death screen line, Wally acts as the brawn of the Warbles family. He appears to be a protective father to his son, having a cuckoo house for him to be kept safe in while Wally deals with his own enemies. Wally is even determined enough to fight until the end, no matter what happens to him in the process, as evident by the fact that he continues the battle featherless and on a stretcher. He also seems to have a boastful side, as suggested by the death screens from phases 1 and 3.

10. Djimmi The Great

Djimmi The Great is a muscular red genie wearing a turquoise vest with a yellow inside, and a turban the same color as his vest that has a red gem and large white feather on it. Djimmi is almost always seen with his cob pipe clenched between his teeth. He also wears black and cream arm bands and light blue pants. In official art for the Switch version of Cuphead, he has a tail that matches his body. His shoes appear to be magic genie lamps.

Puphead is a Pinnochio-esque marionette sharing the same color scheme as Djimmi, while also bearing a striking resemblance to Mugman, as evident by the puppet’s eye width and positioning.

Djimmi The Great is said to have vivacious personality. In the game, he seems to treat battling in a playful way like a manipulative trickster, as he has a near-constant grin on his face throughout the fight. He possibly also views Cuphead and Mugman as The Devil’s puppets for doing his bidding, as he appears to mock them by using a marionette version of their species during his fourth phase. He might have gone to “genie school”, judging by his Phase 1 Death Quote.

Despite being capable of normal speech, as evident by the 4th phase death screen, Puphead has no real personality, being a puppet created by Djimmi for the sole purpose of fending off Cuphead and Mugman.

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