Follow TV Tropes

Following

History Characters / CupheadRunawayDebtors

Go To

OR

Added: 191

Changed: 845

Is there an issue? Send a MessageReason:
None


* VisualPun: Her turning into a plane to fight you in the final phase. She's a "Buzz Bomber" "Bee-plane". Or, alternatively, a "[[{{Pun}} Bee]]-17 Flying Fortress"[[note]](which would be era-appropriate, and which she vaguely resembles)[[/note]]. In this phase, she also attacks you by turning one of her wings into a "Buzz Saw."
** The bees work in an office building that's drenched in dripping honey. A sticky business, in other words.
*** The worker bees have a SalaryMan look, in other words: They're office drones.

to:

* VisualPun: StealthPun: She's a bee called Rumor, and she works at an office that's presumably a news building (if the level name "Honeycomb Herald" is any indication). Another word for rumors and news is "the buzz".
* VisualPun:
**
Her turning into a plane to fight you in the final phase. She's a "Buzz Bomber" "Bee-plane". Or, alternatively, a "[[{{Pun}} Bee]]-17 Flying Fortress"[[note]](which would be era-appropriate, and which she vaguely resembles)[[/note]]. In this phase, she also attacks you by turning one of her wings into a "Buzz Saw."
** The bees work in an office building that's drenched in dripping honey. A sticky business, in other words.
***
words. The worker bees have a SalaryMan look, too; in other words: They're words, they're office drones.
Is there an issue? Send a MessageReason:
None


* NonActionGuy: Sally's husband, despite [[TopHeavyGuy looking fairly capable]], runs around uselessly in the background while his wife delivers all the beatings to Cuphead.

to:

* NonActionGuy: Sally's husband, despite [[TopHeavyGuy looking fairly capable]], runs around uselessly in the background while his wife delivers all the beatings to Cuphead.Cuphead and co. He's a more active participant in the third phase should you take the alternate route, but even then, he only adds one attack and takes on a SlouchOfVillainy while Sally remains proactive.

Added: 539

Changed: 1471

Is there an issue? Send a MessageReason:
None


* AnimateInanimateObject: Her parasol seems to have teleportation abilities and can drop pieces of itself and grow them back.
** Sally herself apparently turns into one in the third phase. Despite being a cardboard cutout, she's able to change expressions, clutch her chest in pain when defeated, and taunt you if she beats you.

to:

* AnimateInanimateObject: AnimateInanimateObject:
**
Her parasol seems to have teleportation abilities and can drop pieces of itself and grow them back.
** Sally herself apparently turns into one The cardboard cutout representing her in the third phase. Despite being phase, if not a cardboard cutout, she's literal transformation, is at least one of these. She's able to change expressions, clutch her chest in pain when defeated, and taunt you if she beats you.



* CurtainCall: In the patched version, Sally's co-stars will appear in the background to take a bow for the audience during her final phase.

to:

* CurtainCall: In the patched version, Sally's co-stars will appear in the background to take a bow for the audience during her final phase. The priest appears on both routes, but her husband and children only appear in the normal route, and the nun only appears in the secret route.



* EnfantTerrible: The babies in the second round can drop their bottles on you. And one of them will push out a "fireball" at you in the alternate third round.

to:

* DyingDream: The third phase likely represents one in-universe, with Sally picturing herself as ascending to godhood after her "death" in the second phase. As stated by her game over card, it's a soliloquy, meaning that she's projecting her thoughts to her audience rather than literally becoming divine.
* EnfantTerrible: The babies in the second round can drop their bottles on you. And one of them will If you take the alternate route, they push out a "fireball" "fireballs" at you in the alternate third round.



* HenpeckedHusband: The guy that portrays Sally's husband in the "play" just stands in the background acting cowardly, doing little to contribute to the battle except drive his wife in his car (that is, until you bring down the FallingChandelierOfDoom on him in the post-game update, changing the course of the second and third rounds). That being said, [[AwLookTheyReallyDoLoveEachOther she does reward him with a smooch in the epilogue]].

to:

* HenpeckedHusband: The guy that portrays Sally's husband in the "play" just stands in the background acting cowardly, doing little to contribute to the battle except drive his wife in his car (that is, until you bring down the FallingChandelierOfDoom on him in the post-game update, patched version, changing the course of the second and third rounds). That being said, [[AwLookTheyReallyDoLoveEachOther she does reward him with a smooch in the epilogue]].



* NeutralFemale: Gender inverted by Sally Stageplay's husband during her boss fight; despite [[TopHeavyGuy looking fairly capable]], he runs around uselessly in the background and looks concerned in the manner associated with this trope, while his wife delivers all the beatings to Cuphead. Unused sprites do suggest that he was originally intended to be fought at some point during the battle... and he can be, if you go out of your way to squash him flat as of a post-launch update.
* OneWingedAngel: Also parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the cups, which plays a large part in her BadassNormal status.

to:

* NeutralFemale: Gender inverted by Sally Stageplay's husband during her boss fight; NonActionGuy: Sally's husband, despite [[TopHeavyGuy looking fairly capable]], he runs around uselessly in the background and looks concerned in the manner associated with this trope, while his wife delivers all the beatings to Cuphead. Unused sprites do suggest that he was originally intended to be fought at some point during the battle... and he can be, if you go out of your way to squash him flat as of a post-launch update.
Cuphead.
* OneWingedAngel: Also parodied.Parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the cups, which plays a large part in her BadassNormal status.



* StationaryBoss: The cardboard cutout/s in the third phase don't move ''or'' directly attack; all of their attacks come from other places on the stage.

to:

* SquashedFlat: If you take the secret route in phase 1, you end up crushing her husband with a chandelier. He doesn't show up in the curtain call if this happens, but he does reappear in the ending.
* StationaryBoss: The cardboard cutout/s cutout(s) in the third phase don't move ''or'' directly attack; all of their attacks come from other places on the stage.



* WidowedAtTheWedding: In the Switch and Patch 1.2 versions, if you take the secret route, you end up 'killing' her fiancé/husband by crushing him with the chandelier.

to:

* WidowedAtTheWedding: In the Switch and Patch 1.2 versions, patched version, if you take the secret route, you end up 'killing' "killing" her fiancé/husband by crushing him with the chandelier.

Added: 48

Removed: 48

Is there an issue? Send a MessageReason:
None


* AlliterativeName: '''S'''ally '''S'''tageplay.


Added DiffLines:

* AlliterativeName: '''S'''ally '''S'''tageplay.
Is there an issue? Send a MessageReason:
None


* MsFanservice: She's quite the dish and she knows it. Her Gorgon form doesn't look too bad either. [[GorgeousGorgon As noted above]].

to:

* MsFanservice: She's quite the dish and she knows it. Her Gorgon form doesn't look too bad either. [[GorgeousGorgon As either, as noted above]].in GorgeousGorgon above.

Added: 38

Changed: 28

Is there an issue? Send a MessageReason:
None


[[foldercontrol]]




[[folder:In General]]




[[foldercontrol]]

to:

\n[[foldercontrol]]\n[[/folder]]
Is there an issue? Send a MessageReason:
None


* TacticalSuicideBoss: You'd expect a military-themed boss to be more, ahem, "tactful".
** Werner's first phase have him launching various debris, before sending his tank in a charging tackle. Problem is, those debris include a pair of spring-loaded platforms allowing the cups to leap over his tackling move.

to:

* TacticalSuicideBoss: You'd expect a military-themed boss to be more, ahem, "tactful".
"tactical".
** Werner's first phase have has him launching various debris, random objects, before sending his tank in a charging tackle. Problem is, those debris objects include a pair of spring-loaded platforms allowing the cups to leap over his tackling move.

Added: 427

Changed: 426

Is there an issue? Send a MessageReason:
None


* ShoutOut: The whole fight is based off war cartoons and ''WesternAnimation/TomAndJerry''; not only does Katzenwagen bear a striking resemblance to Tom in his early years (when he was known as Jasper), but Werner's screams sound vaguely like [[https://www.youtube.com/watch?v=4eHCxCLYuE0 Tom's]] too. [[GeniusBonus This also makes sense on another level]]: "Jerry" was a common nickname for German soldiers during UsefulNotes/WorldWarI.

to:

* ShoutOut: ShoutOut:
**
The whole fight is based off war cartoons and ''WesternAnimation/TomAndJerry''; not only does Katzenwagen bear a striking resemblance to Tom in his early years (when he was known as Jasper), but Werner's screams sound vaguely like [[https://www.youtube.com/watch?v=4eHCxCLYuE0 Tom's]] too. [[GeniusBonus [[StealthPun This also makes sense on another level]]: "Jerry" was a common nickname for German soldiers during UsefulNotes/WorldWarI.
Is there an issue? Send a MessageReason:
None


* {{Kaiserreich}}: Werner is based primarily on World War I-era German soldiers, with his Pickelhaube and soup-can tank. He also has war medals and bullet shells hanging around his mouse hole, although a Union Jack flag can be seen near the ceiling, oddly enough, and 2 British medals.
* MacroZone: They are fought in a mouse hole in a giant house.

to:

* {{Kaiserreich}}: Werner is based primarily on World War I-era German soldiers, with his Pickelhaube and soup-can tank. He also has war medals and bullet shells hanging around his mouse hole, although a hole. The designs of the medals and Union Jack flag can be seen near the ceiling, oddly enough, and 2 ceiling suggest that he defected to the British medals.
during the war.
* MacroZone: They are He's fought in a mouse hole in a giant house.



* MegaNeko: Katzenwagen.

to:

* MegaNeko: Katzenwagen.Katzenwagen is huge, but only because you're the size of a mouse yourself.



** Then there's the Katzenwagen, which can attack forward (evidenced when it [[spoiler:collects Werner as its pilot]]) and yet chooses to lunge at the cups from the ''side''.

to:

** Then there's the Katzenwagen, which can attack could clearly just reach forward to attack the cups (evidenced when it [[spoiler:collects Werner as its pilot]]) eats Werner), and yet chooses to lunge at the cups them from the ''side''.
Is there an issue? Send a MessageReason:
None


* PungeonMaster: The vast majority of their game over taunts.

to:

* PungeonMaster: The vast majority of their game over taunts.taunts, often time with some RhymesOnADime.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* {{Determinator}}: If there’s one thing they all have in common it’s that they refuse to give up. They each continue fighting in spite of receiving severe injuries, most of their body being destroyed, and the cups besting their strongest moves. Of special note are Wally Warbles, who fights you with most of his feathers gone and being lifted on a gurney by two medics, and Cala Maria, who keeps trying to kill you despite being reduced to a floating head in her last phase. {{Justified|Trope}} since they all know that losing means serving the Devil for all of eternity.

Added: 160

Changed: 21

Is there an issue? Send a MessageReason:
None


* GameFace: He starts off looking pretty cute before...well, look at his image here. If the ending is any indication, the cute face might be his actual default.



* GreenThumb: Many of his attacks are plant-based.

to:

* GreenThumb: Many of his attacks are plant-based. For obvious reasons.

Added: 138

Removed: 103

Is there an issue? Send a MessageReason:
None


%%zce* {{Expy}}: Of Sindbad's giant Rokh from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''


Added DiffLines:

** Wally's red and blue color scheme is a reference to Sindbad's giant Rokh from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''
Is there an issue? Send a MessageReason:
None


* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this]], his animator Jake Clark has confirmed he's still alive.

to:

* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this]], his animator Jake Clark [[https://twitter.com/JakeClarkDude/status/1040232769975189507 has confirmed he's still alive.alive]].



* FeatherFingers: A slightly more justified bat-winged example. The gesture he makes during the opening is done with his wings and his actual hands.

to:

* FeatherFingers: A slightly more justified bat-winged example. The gesture he makes during the opening is done with his wings and not his actual hands.



* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. Jake Clark, his animator, confirms his survival.

to:

* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. Jake Clark, his animator, [[https://twitter.com/JakeClarkDude/status/1040232769975189507 confirms his survival.survival]].
Is there an issue? Send a MessageReason:
None


* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this]], [[WordOfGod his animator]] Jake Clark has confirmed he's still alive.

to:

* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this]], [[WordOfGod his animator]] animator Jake Clark has confirmed he's still alive.



* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. [[WordOfGod His animator]], Jake Clark, confirms his survival.

to:

* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. [[WordOfGod His animator]], Jake Clark, his animator, confirms his survival.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* BenevolentGenie: Weirdly enough, he's perfectly willing to [[spoiler:give the cups 3 extra hitpoints should they summon him - though he's still gonna mock them if they still lose to him with said extra hitpoints.]]
Is there an issue? Send a MessageReason:
Please see Chained Sinkhole.


* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this,]] [[WordOfGod his animator]] Jake Clark has confirmed he's still alive.

to:

* DeaderThanDead: He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not. [[SubvertedTrope Despite this,]] this]], [[WordOfGod his animator]] Jake Clark has confirmed he's still alive.
Is there an issue? Send a MessageReason:
Jake Clark once confirmed Goopy and Wally's survival.


* DeaderThanDead: He's implied to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies he's dead.

to:

* DeaderThanDead: He's implied He appears to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cups end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies not. [[SubvertedTrope Despite this,]] [[WordOfGod his animator]] Jake Clark has confirmed he's dead.still alive.



* WhatHappenedToTheMouse: He's nowhere to be found during the finale of the good ending, implying that he really is dead.

to:

* WhatHappenedToTheMouse: He's nowhere to be found during the finale of the good ending, implying that he really is dead.ending.



* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. It was never confirmed or denied whether he was eaten or did he manage to survive. If the fact he is absent from the good ending is any indication, his fate might not be a pleasant one.

to:

* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. It was never confirmed or denied whether he was eaten or did he manage to survive. If the fact he is absent from the good ending is any indication, [[WordOfGod His animator]], Jake Clark, confirms his fate might not be a pleasant one.survival.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

----

Added: 223

Changed: 954

Is there an issue? Send a MessageReason:
None


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

to:

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



* AntiVillain: The only reason they're fighting Cuphead and Mugman is because they're acting as the Devil's agents, and throw a big celebration in honor of the duo after they defeat the Devil and destroy the contracts.
* AttackOfThe50FootWhatever: While they vary in size, many of the bosses seen tower over Cuphead and Mugman.
* DealWithTheDevil: All of them likewise have made deals with the Devil, but skipped out on paying them. Cuphead and Mugman's role is to get their soul contracts from them.

to:

* AntiVillain: The only reason they're fighting Cuphead and Mugman the cups is because they're acting as the Devil's agents, and throw a big celebration in honor of the duo after they defeat the Devil and destroy the contracts.
* AttackOfThe50FootWhatever: While they vary in size, many of the bosses seen tower over Cuphead and Mugman.
the cups.
* DealWithTheDevil: All of them likewise have made deals with the Devil, but skipped out on paying them. Cuphead and Mugman's The cups' role is to get their soul contracts from them.



* EvilIsBigger: Downplayed. The Runaway Debtors are {{Anti Villain}}s to various degrees and vary in size; however, many of the bosses seen tower over Cuphead and Mugman.

to:

* EvilIsBigger: Downplayed. The Runaway Debtors are {{Anti Villain}}s to various degrees and vary in size; however, many of the bosses seen tower over Cuphead and Mugman.the cups.



* SmugSmiler: A solid majority of them also flash a big, sinister smile of some sort at least once in their boss fights. Indeed, most of them don't seem to be all that worried that Cuphead and Mugman are trying to collect their soul contracts. [[NintendoHard Granted…]]

to:

* SmugSmiler: A solid majority of them also flash a big, sinister smile of some sort at least once in their boss fights. Indeed, most of them don't seem to be all that worried that Cuphead and Mugman the cups are trying to collect their soul contracts. [[NintendoHard Granted…]]Granted, they're justified in thinking that.]]



* WouldHurtAChild: The bosses are more than willing to fight Cuphead and Mugman, although both of them are adolescents. Granted, it's in self-defense, since the only other option is to give up without a fight and let the Devil claim their souls.
* YourSizeMayVary: When you battle them, many of the Runaway Debtors are gigantic and absolutely tower over Cuphead and Mugman. In the ending cutscene where most of them were there, many of them were only the size of an average person -- even the largest debtor, Grim Matchstick is only twice as tall as one.

to:

* WouldHurtAChild: The bosses are more than willing to fight Cuphead and Mugman, although both of them are adolescents.the cups, despite how young they are. Granted, it's in self-defense, since the only other option is to give up without a fight and let the Devil claim their souls.
* YourSizeMayVary: When you battle them, many of the Runaway Debtors are gigantic and absolutely tower over Cuphead and Mugman. the cups. In the ending cutscene where most of them were are there, many of them were are only the size of an average person -- even the largest debtor, Grim Matchstick Matchstick, is only twice as tall as one.



* AffablyEvil: He might anatognize Cuphead and Mugman, but at least he's well-mannered.

to:

* AffablyEvil: He might anatognize Cuphead and Mugman, the cups, but at least he's well-mannered.



* DeaderThanDead: He's implied to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cup brothers end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies he's dead.

to:

* DeaderThanDead: He's implied to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cup brothers cups end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies he's dead.



* RedBoxingGloves: On his right hand, which he uses to rough up Cuphead and Mugman.

to:

* RedBoxingGloves: On his right hand, which he uses to rough up Cuphead and Mugman.the cups.



* VineTentacles: He can grow thorny vines through the soil when battling Cuphead or Mugman and stick them up to spike the brothers from below.

to:

* VineTentacles: He can grow thorny vines through the soil when battling Cuphead or Mugman and stick the cups, to strike them up to spike the brothers from below.



* AmphibianAtLarge: They tower over Cuphead and Mugman, and appear to be human-sized, if not larger.

to:

* AmphibianAtLarge: They tower over Cuphead and Mugman, the cups, and appear to be human-sized, if not larger.



* AdvancingBossOfDoom: In the final stage of the battle, Whippet Creampup begins to chase Cuphead and Mugman.

to:

* AdvancingBossOfDoom: In the final stage of the battle, Whippet Creampup begins to chase Cuphead and Mugman.the cups.



* BerserkButton: The Baroness herself doesn't have one, but her cake castle Whippet Creampup certainly does: getting its towers pulled on. Indeed, this is how she initiates the final phase of the battle; by pulling on Whippet's towers, sending it into a rage and causing it to chase the boys down.

to:

* BerserkButton: The Baroness herself doesn't have one, but her cake castle Whippet Creampup certainly does: getting its towers pulled on. Indeed, this is how she initiates the final phase of the battle; by pulling on Whippet's towers, sending it into a rage and causing it to chase the boys cups down.



*** Sgt. Gumbo Gumbull: A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.

to:

*** Sgt. Gumbo Gumbull: A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.cups.



** During the minion phase of the battle, jellybean soldiers (referred to as the Jelly Bullies squad) will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging ordering Whippet Creampup to chase the boys down, and sends huge peppermints (named Patsy Menthol) rolling out its mouth.

to:

** During the minion phase of the battle, jellybean soldiers (referred to as the Jelly Bullies squad) will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging ordering Whippet Creampup to chase the boys cups down, and sends huge peppermints (named Patsy Menthol) rolling out its mouth.



* KickingAssInAllHerFinery: Averted. While she does have a stunning appearance, she never engages the boys directly at any point in her battle.

to:

* KickingAssInAllHerFinery: Averted. While she does have a stunning appearance, she never engages the boys cups directly at any point in her battle.



* LosingYourHead: At the beginning of the fight, her head briefly detaches while giving Cuphead and Mugman a ThroatSlittingGesture. Also, she can detach her own head and regrow it, even using the spare heads as projectiles in the last phase!

to:

* LosingYourHead: At the beginning of the fight, her head briefly detaches while giving Cuphead and Mugman the cups a ThroatSlittingGesture. Also, she can detach her own head and regrow it, even using the spare heads as projectiles in the last phase!



* OffWithHisHead: More like, "Off with Their Heads!"; she threatens the duo with this at the start of the battle via giving them a ThroatSlittingGesture, complete with her briefly [[LosingYourHead losing her head]].

to:

* OffWithHisHead: More like, "Off with Their Heads!"; she threatens the duo cups with this at the start of the battle via giving them a ThroatSlittingGesture, complete with her briefly [[LosingYourHead losing her head]].



* ShotgunsAreJustBetter: Her candy cane functions as one in the third phase of her fight, adding additional projectiles for the duo to worry about.

to:

* ShotgunsAreJustBetter: Her candy cane functions as one in the third phase of her fight, adding additional projectiles for the duo cups to worry about.



* BeatThemAtTheirOwnGame: His fourth phase (third if not counting his DeathCourse) has him making a Cuphead puppet named Cuppet and sending it at the boys. If you shrink while he's doing this, he instead makes a mini-Cuppet that can't really fight the boys on its own, so Djimmi transitions right to his final phase while the mini-Cuppet backs him up by shooting pellets from the center of the screen.
* BlowingSmokeRings: Or "a Smoke Teacup", actually: At the beginning of the fight, he blows out some smoke that forms a teacup with [[WingdingEyes X's for eyes]] and a frowning mouth, indicating that the boys have no chance against him.

to:

* BeatThemAtTheirOwnGame: His fourth phase (third if not counting his DeathCourse) has him making a Cuphead puppet named Cuppet and sending it at the boys. cups. If you shrink while he's doing this, he instead makes a mini-Cuppet that can't really fight the boys cups on its own, so Djimmi transitions right to his final phase while the mini-Cuppet backs him up by shooting pellets from the center of the screen.
* BlowingSmokeRings: Or "a Smoke Teacup", actually: At the beginning of the fight, he blows out some smoke that forms a teacup with [[WingdingEyes X's for eyes]] and a frowning mouth, indicating that the boys cups have no chance against him.



* ShoutOut: The way he moves and acts seems to be a villainous version of the Genie from ''WesternAnimation/{{Aladdin}}''. In particular, his fourth phase has him turn into a giant disembodied hand, which was a quirk of the Genie's.

to:

* ShoutOut: ShoutOut:
**
The way he moves and acts seems to be a villainous version of the Genie from ''WesternAnimation/{{Aladdin}}''. In particular, his fourth phase has him turn into a giant disembodied hand, which was a quirk of the Genie's.



* EnergyRingAttack: In his first phase, Grim Matchstick attacks with Eye Beams that manifest themselves as a short row of rings flying in the player character's direction. The last ring in a row is pink, allowing Cuphead and Mugman to parry-slap it.

to:

* EnergyRingAttack: In his first phase, Grim Matchstick attacks with Eye Beams that manifest themselves as a short row of rings flying in the player character's direction. The last ring in a row is pink, allowing Cuphead and Mugman the cups to parry-slap it.



* OneWingedAngel: After taking enough punishment from the boys, he suddenly grows two extra heads.

to:

* OneWingedAngel: After taking enough punishment from the boys, cups, he suddenly grows two extra heads.



* ImAHumanitarian: The start of the battle has her looking hungrily at the boys while rubbing a fork and knife together.

to:

* ImAHumanitarian: The start of the battle has her looking hungrily at the boys cups while rubbing a fork and knife together.



* InterfaceScrew: Brineybeard will sometimes summon a squid minion who throws ink on the camera, causing the screen to darken with each glob that successfully hits the boys and makes seeing any incoming attacks much more difficult for a few seconds.

to:

* InterfaceScrew: Brineybeard will sometimes summon a squid minion who throws ink on the camera, causing the screen to darken with each glob that successfully hits the boys cups and makes seeing any incoming attacks much more difficult for a few seconds.



* BattleCouple: She and her husband were originally intended to be this for their battle with the boys. After a post-game update, they can potentially be this in the third phase if you end the first phase by [[VideoGameCrueltyPotential dropping a light fixture on her husband in the first phase]].

to:

* BattleCouple: She and her husband were originally intended to be this for their battle with the boys.cups. After a post-game update, they can potentially be this in the third phase if you end the first phase by [[VideoGameCrueltyPotential dropping a light fixture on her husband in the first phase]].



* OneWingedAngel: Also parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the boys, which plays a large part in her BadassNormal status.

to:

* OneWingedAngel: Also parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the boys, cups, which plays a large part in her BadassNormal status.



* YouExclamation: Although a bit hard to hear, she does this during the start of the second phase when she sees that Cuphead and Mugman are still on the stage. It makes more sense if the first phase ended with her fiancé's death.

to:

* YouExclamation: Although a bit hard to hear, she does this during the start of the second phase when she sees that Cuphead and Mugman the cups are still on the stage. It makes more sense if the first phase ended with her fiancé's death.



* BadassNormal: Werner is an expert machine pilot, and that's all he really needs to fight the Cup Brothers. As a result, he's notably one of only two examples of this in the entire game, the other being Sally Stageplay.

to:

* BadassNormal: Werner is an expert machine pilot, and that's all he really needs to fight the Cup Brothers. cups. As a result, he's notably one of only two examples of this in the entire base game, the other being Sally Stageplay.



* EatenAlive: After beating Werner's second phase, Katzenwagen suddenly knocks down the wall and eats him. [[spoiler:Or so it appears; it's actually a clever method of him entering the mechanical cat and manually controlling it in a last-ditch effort to put the boys down.]]

to:

* EatenAlive: After beating Werner's second phase, Katzenwagen suddenly knocks down the wall and eats him. [[spoiler:Or so it appears; it's actually a clever method of him entering the mechanical cat and manually controlling it in a last-ditch effort to put the boys cups down.]]



* FakingTheDead: [[spoiler:After the second phase, he's seemingly eaten by Katzenwagen, which forces Cuphead and Mugman to defend themselves from it. However, Katzenwagen is revealed to be a mecha designed to scare off any intruders or give Werner the advantage]].
* {{Foreshadowing}}: When your bullets hit Katzenwagen in the third phase, [[spoiler:it makes a metal clinking sound]]. Additionally, after Katzenwagen bursts in and eats Werner, the brothers don't get the latter's contract, hinting that [[spoiler:he's still alive]]. Speaking of Katzenwagen, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.

to:

* FakingTheDead: [[spoiler:After the second phase, he's seemingly eaten by Katzenwagen, which forces Cuphead and Mugman the cups to defend themselves from it. However, Katzenwagen is revealed to be a mecha designed to scare off any intruders or give Werner the advantage]].
* {{Foreshadowing}}: When your bullets hit Katzenwagen in the third phase, [[spoiler:it makes a metal clinking sound]]. Additionally, after Katzenwagen bursts in and eats Werner, the brothers cups don't get the latter's contract, hinting that [[spoiler:he's still alive]]. Speaking of Katzenwagen, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.



** Werner's first phase have him launching various debris, before sending his tank in a charging tackle. Problem is, those debris include a pair of spring-loaded platofrms allowing Cuphead and Mugman to leap over his tackling move.
** Then there's the Katzenwagen, which can attack forward (evidenced when it [[spoiler:collects Werner as its pilot]]) and yet chooses to lunge at Cuphead and Mugman from the ''side''.

to:

** Werner's first phase have him launching various debris, before sending his tank in a charging tackle. Problem is, those debris include a pair of spring-loaded platofrms platforms allowing Cuphead and Mugman the cups to leap over his tackling move.
** Then there's the Katzenwagen, which can attack forward (evidenced when it [[spoiler:collects Werner as its pilot]]) and yet chooses to lunge at Cuphead and Mugman the cups from the ''side''.



* SelectiveMagnetism: One attack in the first phase after the middle part of the robot is damaged is a magnet that pulls Cuphead and Mugman to the bottom-left of the screen, leaving other objects unaffected.

to:

* SelectiveMagnetism: One attack in the first phase after the middle part of the robot is damaged is a magnet that pulls Cuphead and Mugman the cups to the bottom-left of the screen, leaving other objects unaffected.



* AttackOfTheFiftyFootWhatever: A giant mermaid who basically towers over the two boys and their planes.
* TheBeastmaster: In the first two phases, she fights primarily by summoning sea creatures to attack the two brothers.

to:

* AttackOfTheFiftyFootWhatever: A giant mermaid who basically towers over the two boys cups and their planes.
* TheBeastmaster: In the first two phases, she fights primarily by summoning sea creatures to attack the two brothers.cups.



* TakenForGranite: In her gorgon form, she can fire out a huge beam that'll turn our heroes into stone, which will put them in danger of getting hit by a real bullet if they're not quick to break out of their stoned forms. This eventually gets turned on her in her second-to-third phase transition, where her whole body (sans her head) turns to stone and crumbles into the ocean, forcing her to detach her own head and continue battling the boys. In simple difficulty, her entire body becomes completely petrified after her defeat.
* TheTease: Not only does she pose before the boys in her intro, but her game over card in her first phase definitely has her flirting with them too.

to:

* TakenForGranite: In her gorgon form, she can fire out a huge beam that'll turn our heroes into stone, which will put them in danger of getting hit by a real bullet if they're not quick to break out of their stoned forms. This eventually gets turned on her in her second-to-third phase transition, where her whole body (sans her head) turns to stone and crumbles into the ocean, forcing her to detach her own head and continue battling the boys.cups. In simple difficulty, her entire body becomes completely petrified after her defeat.
* TheTease: Not only does she pose before the boys cups in her intro, but her game over card in her first phase definitely has her flirting with them too.

Added: 485

Changed: 863

Is there an issue? Send a MessageReason:
None


* ShoutOut: Her hairstyle was clearly inspired by ''WesternAnimation/BettyBoop''.

to:

* ShoutOut: ShoutOut:
**
Her hairstyle was clearly inspired by ''WesternAnimation/BettyBoop''.WesternAnimation/BettyBoop.



* AdvancingBossOfDoom: In the final stage of the battle, the castle where she hides in begins to chase Cuphead and Mugman.
* AmbiguouslyHuman: It's unclear if she's meant to be human, or a strange humanoid. Especially since [[TheNoseless she lacks a nose]], has [[AmazingTechnicolorPopulation pink skin]], and lives in a chiefly candy-inhabited setting.

to:

* AdvancingBossOfDoom: In the final stage of the battle, the castle where she hides in Whippet Creampup begins to chase Cuphead and Mugman.
* AmbiguouslyHuman: It's unclear if she's meant to be human, or a strange humanoid. Especially since [[TheNoseless she lacks a nose]], has [[AmazingTechnicolorPopulation pink skin]], can [[LosingYourHead remove her head]], and lives in a chiefly candy-inhabited setting.



*** A candy corn that flies around horizontally or vertically, occasionally spawning smaller candy corns that fly upwards.
*** A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.
*** A cupcake that [[BouncingBattler jumps into the air]] and slams into the ground, unleashing frosting [[ShockwaveStomp shockwaves]].
*** A jawbreaker that slowly chases after Cuphead, trailed by InvincibleMinorMook jawbreakers (none on Simple, one on Regular, and two on Expert).
*** A winged waffle that flies around, [[DetachmentCombat splitting itself apart before putting itself back together]].
** During the minion phase of the battle, jellybean soldiers will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging the castle to chase the boys down, while sending large peppermints rolling out.

to:

*** Kernel von Pop: A candy corn that flies around horizontally or vertically, occasionally spawning smaller candy corns that fly upwards.
*** Sgt. Gumbo Gumbull: A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.
*** Muffsky Chernikov: A cupcake that [[BouncingBattler jumps into the air]] and slams into the ground, unleashing frosting [[ShockwaveStomp shockwaves]].
*** Lord Gob Packer: A jawbreaker that slowly chases after Cuphead, trailed by InvincibleMinorMook jawbreakers (none on Simple, one on Regular, and two on Expert).
*** Sir Waffington III: A winged waffle that flies around, [[DetachmentCombat splitting itself apart before putting itself back together]].
** During the minion phase of the battle, jellybean soldiers (referred to as the Jelly Bullies squad) will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging the castle ordering Whippet Creampup to chase the boys down, while sending large and sends huge peppermints (named Patsy Menthol) rolling out.out its mouth.



* ImprobableWeaponUser: Her candy cane can somehow be used as a ''shotgun''.

to:

* ImprobableWeaponUser: Her candy cane can somehow be used also functions as a ''shotgun''.double-barreled shotgun, firing puffs of harmful sugar.



* OffModel: Her death card shows her with white stripes on her dress instead of red. Like other color inconsistencies in the game, this is likely intentional.



* OneWingedAngel: Not her so much as her cake castle, which transforms into an angered beast in the final phase.
* OverlyLongName: According to a series of tweets, all of her minions have extremely long names.

to:

* OneWingedAngel: Not her so much as Whippet Creampup, her cake castle, which transforms into an angered beast in the final phase.
* OverlyLongName: According to a series of tweets, all All of her minions have extremely long and formal names.



* ShotgunsAreJustBetter: Her cane functions as this in the third phase of her fight, adding additional projectiles for the duo to worry about.
* ShoutOut: The appearance of the Baroness and her barony are inspired by various cartoons' candy kingdoms, but most noticeably Cookietown from "WesternAnimation/TheCookieCarnival". One of her minions, Lord Gob Packer, is also a jawbreaker version of VideoGame/PacMan.

to:

* ShotgunsAreJustBetter: Her candy cane functions as this one in the third phase of her fight, adding additional projectiles for the duo to worry about.
* ShoutOut: ShoutOut:
**
The appearance of the Baroness and her barony are inspired by various cartoons' candy kingdoms, but most noticeably Cookietown from "WesternAnimation/TheCookieCarnival". One of her minions, Lord Gob Packer, is also a jawbreaker version of VideoGame/PacMan.



* SoreLoser: She bursts into angry tears upon defeat (complete with a VolumetricMouth). In Regular mode, Whippet also beats the ground in frustration while crying.
* StationaryBoss: She stays on top of her castle for most of the fight, but can't be damaged until the end. On Simple difficulty, she stays still and keeps firing cotton candy blasts when her third minion is defeated. On Regular and higher, she instead progresses the fight by turning into an AdvancingBossOfDoom.
* VaudevilleHook: Blink and you'll miss it, but her candy cane functions as this at the very start of her level, implying her candy castle may have some control over it.

to:

* SoreLoser: She bursts into angry tears upon defeat (complete with a VolumetricMouth). In Regular and Expert mode, Whippet also beats the ground in frustration while crying.
* StationaryBoss: She stays inside or on top of her castle Whippet Creampup for most of the fight, but can't be damaged until the end. On Simple difficulty, she stays still and keeps firing cotton candy sugar blasts when her third minion is defeated. On Regular and higher, she instead progresses the fight by turning into an AdvancingBossOfDoom.
* VaudevilleHook: Blink and you'll miss it, but her candy cane functions as this at the very start of her level, implying her candy castle Whippet Creampup may have some control over it.



* YourHeadASplode: Happens to Sgt. Gumbull in his death animation; his glass head shatters and it scurries off.

to:

* YourHeadASplode: Happens to Sgt. Gumbull in his death animation; his glass head shatters shatters, and it the rest of him scurries off.
Is there an issue? Send a MessageReason:
None


!In general

to:

!In !!In general



!Inkwell Isle One

to:

!Inkwell !!Inkwell Isle One



!Inkwell Isle Two

to:

!Inkwell !!Inkwell Isle Two



!Inkwell Isle Three

to:

!Inkwell !!Inkwell Isle Three
Is there an issue? Send a MessageReason:
None

Added DiffLines:

[[WMG:[[center:[-''VideoGame/{{Cuphead}}'' | [[Characters/{{Cuphead}} Main character index]]\\
[[Characters/CupheadMainCharacters Main Characters]] | [[Characters/CupheadAlliesAndEnemies Allies and Enemies]] | '''The Runaway Debtors''' | [[Characters/CupheadTheKingsCourt The King's Court]] | ''[[Characters/CupheadTheDeliciousLastCourse The Delicious Last Course]]''-]]]]]
Is there an issue? Send a MessageReason:
None


* BaldOfEvil: He's one of the debtors that sold his soul to {{Satan}}, and the little tip on his head is tipped like a hat before the fight.

to:

* BaldOfEvil: He's one of the debtors that sold his soul to {{Satan}}, TheDevil, and the little tip on his head is tipped like a hat before the fight.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* DegradedBoss: In a weird sense, but Katzenwagen goes from being the final phase of a boss fight to being a yarn gun for the Howling Aces in "Doggone Dogfight". Or maybe it's just a cat that looks like it, who knows.
Is there an issue? Send a MessageReason:
None


!!In general

to:

!!In !In general



!!Inkwell Isle One

to:

!!Inkwell !Inkwell Isle One



!!Inkwell Isle Two

to:

!!Inkwell !Inkwell Isle Two



!!Inkwell Isle Three

to:

!!Inkwell !Inkwell Isle Three

Added: 12

Changed: 28

Removed: 65

Is there an issue? Send a MessageReason:
None


[[foldercontrol]]

!The Runaway Debtors
[[folder:Bosses in general]]



!!In general



[[/folder]]

to:

[[/folder]]

[[foldercontrol]]
Is there an issue? Send a MessageReason:
None


!!!Inkwell Isle One

to:

!!!Inkwell !!Inkwell Isle One



!!!Inkwell Isle Two

to:

!!!Inkwell !!Inkwell Isle Two



!!!Inkwell Isle Three

to:

!!!Inkwell !!Inkwell Isle Three
Is there an issue? Send a MessageReason:
None

Added DiffLines:

[[foldercontrol]]
Is there an issue? Send a MessageReason:
None

Added DiffLines:

!The Runaway Debtors
[[folder:Bosses in general]]
A veritable RoguesGallery of toons who owe the Devil their souls for one reason or another. As part of the deals they made, they own soul contracts — which, as the name suggests, signify that the Devil owns their souls...

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

It falls upon both Cuphead and Mugman to get these strange people in strange lands to cough up the contracts in order to save themselves, even as they take on increasingly vile forms and use a variety of weapons against them.
----
* AntiVillain: The only reason they're fighting Cuphead and Mugman is because they're acting as the Devil's agents, and throw a big celebration in honor of the duo after they defeat the Devil and destroy the contracts.
* AttackOfThe50FootWhatever: While they vary in size, many of the bosses seen tower over Cuphead and Mugman.
* DealWithTheDevil: All of them likewise have made deals with the Devil, but skipped out on paying them. Cuphead and Mugman's role is to get their soul contracts from them.
* EveryoneHasStandards: They all ''refused'' to work for the Devil [[ScrewThisImOuttaHere and ran off with their own contracts]]. Needless to say, it doesn't look good on the player [[spoiler:if they decide to [[YouBastard pick the bad ending]]]].
* EvilIsBigger: Downplayed. The Runaway Debtors are {{Anti Villain}}s to various degrees and vary in size; however, many of the bosses seen tower over Cuphead and Mugman.
* FlunkyBoss: Almost all of them have at least one phase where they send out {{Mooks}} to do their dirty work. Some of them do nothing ''but''.
* GameOverMan: If they beat you, you get a card with their face on it [[HaveANiceDeath mocking you with a pun related to your defeat]]. To really rub it in, there's a little chart at the bottom showing how close (or far) you were to beating them.
* {{Leitmotif}}: Every boss has their own unique theme named after the level where they are fought, and they get most of the SugarWiki/AwesomeMusic in the game. [[invoked]]
* NoodleIncidents: All of them made deals with The Devil, and managed to get away with it somehow.
* OneWingedAngel:
** Considering the theme of the game, you can bet that most if not all the bosses are gonna transform or change shape at least once in their respective fights. The real fun is seeing how or what they'll transform into.
** Elder Kettle actually {{Lampshade|Hanging}}s all the shape-shifting when you first talk to him, stating that they will turn into beasts to confront the two. It's subtly implied that the Soul Contracts give them this ability.
* PungeonMaster: The vast majority of their game over taunts.
* RiddleForTheAges: We never do find out what they made their deals with the Devil for.
* SequentialBoss: So many of them, enough [[SequentialBoss/{{Cuphead}} for its own page]].
* SmugSmiler: A solid majority of them also flash a big, sinister smile of some sort at least once in their boss fights. Indeed, most of them don't seem to be all that worried that Cuphead and Mugman are trying to collect their soul contracts. [[NintendoHard Granted…]]
* TheUnreveal: The deals they made with the Devil are never fully addressed beyond being PlotCoupons. If they simply had lost to the Devil at the casino, they probably wouldn't be on the run from his influence, so the Contracts must be for other desires the Devil promised them in the past. Possibly {{Subverted|Trope}} in that it's implied during battle what they got from the Devil (like Rumor rifling through a spell book to transform and move on to her third phase).
* WouldHurtAChild: The bosses are more than willing to fight Cuphead and Mugman, although both of them are adolescents. Granted, it's in self-defense, since the only other option is to give up without a fight and let the Devil claim their souls.
* YourSizeMayVary: When you battle them, many of the Runaway Debtors are gigantic and absolutely tower over Cuphead and Mugman. In the ending cutscene where most of them were there, many of them were only the size of an average person -- even the largest debtor, Grim Matchstick is only twice as tall as one.
[[/folder]]

!!!Inkwell Isle One
[[folder:The Root Pack]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/rootpack.png]]
->''"Buttered, smashed and mashed, it's over for you."''\\
''"Hey, little guy, it's okay if you have to cry!"''\\
''"I'm lean, mean and full of beta-carotene!"''
A group of vegetables whom you fight in a garden in "Botanic Panic". They consist of three main characters; Sal Spudder (a potato), Ollie Bulb (an onion), and Chauncey Chantenay (a carrot). A fourth character, Horace Radiche (a radish), also appears under certain conditions.
----
* AlliterativeName: '''S'''al '''S'''pudder and '''C'''hauncey '''C'''hantenay.
* AnthropomorphicFood: They're all vegetables.
* CardCarryingVillain: Judging from his win quote, Chauncey Chantenay knows he's a villain and he's proud of it.
* DishingOutDirt: Sal Spudder starts the battle off by spitting out dirt clods and earthworms at you.
* DualBoss: In the secret phase of the fight, Horace and Chauncey attack at the same time, and you can only safely stand on the ground once Horace dies.
* EdibleAmmunition: Chauncey can launch {{homing|Projectile}} carrots at you.
* EverythingsBetterWithSpinning: Horace, who spins around like a top and dashes across the arena at high speed.
* EyeBeams: One of Chauncey's attacks has him firing some beams from his ThirdEye.
* HypnoticEyes: Chauncey wields these when you fight him, which he uses to send carrots at you or launch psychic beams.
* InnocentlyInsensitive: A variant in how Ollie is definitely the most benevolent of the trio, but his defeat card can be taken as accidental TrashTalk.
-->''"Hey, little guy, it's okay if you have to cry!"''
* MacrossMissileMassacre: Chauncey Chantenay uses one with homing carrots of all things.
* OcularGushers: Ollie attacks this way by crying, with his tears raining down projectiles at you.
* OnionTears: Ollie's attack is a reference to the idea that onions make you cry.
* PsychicPowers: Chauncey Chantenay wields psychic abilities.
* PunnyName:
** Sal Spudder is based on 'spud', a colloquialism for potato.
** Chauncey Chantenay's last name is taken from a variety of carrot.
** Ollie Bulb's last name is a synonym for onion
** Horace Radiche has his name originating from 'horse radish'.
* SheatheYourSword: A post-launch update added an EasterEgg to skip Ollie Bulb's phase. If he isn't hit by any projectiles, he exits without attacking, but Horace Radiche pops out during Chauncey Chantenay's phase, making it slightly more difficult.
* ShoutOut:
** Their name references the Creator/RatPack.
** A subtle one, but if you look in the background of the fight, you'll see the root pack was grown using a bag of [[WesternAnimation/LooneyTunes ACME Grow]].
* SkippableBoss: Ollie Bulb and Horace Radiche, interchangeably. If you attack Ollie, you'll battle him normally and Horace will be skipped, but if you instead decide to SheatheYourSword, he'll leave without a fight while Horace Radiche pops up to attack you in tandem with Chauncey Chantenay.
* StationaryBoss: Compounding on the rest of their easiness factors, the main trio can't move from where they're rooted. Averted with Horace, who continuously sweeps across the arena.
* TerribleTrio: All three of them seem to be the debtors.
* ThirdEye: Chauncey opens his up when he starts firing his EyeBeams.
* ThrowTheDogABone: As of the 1.2 update, Ollie will pause after he appears, looking around with a scared expression. If you don't start fighting him, he'll breathe a sigh of relief and disappear back into the ground while smiling, then Horace and Chauncey will both appear instead.
* TokenGoodTeammate: Ollie is the only of the three who doesn't mock the heroes in his win quotes, showing him to be nicer than his friends. Indeed, he doesn't directly attack at all, and (as of an update) can actually be skipped if he isn't attacked.
* WarmUpBoss: One of the first few bosses in the game (if not ''the'' first), and definitely one of the easiest; all three have incredibly obvious tells to their attacks and their projectiles don't have anywhere near high enough density to be a big threat to you. The only member of the trio that might give someone a rough time would be Chauncey, but even then, he's pretty [[{{Pun}} small potatoes]] compared to some of the bosses you'll be facing later.
* WhatHappenedToTheMouse: None of the trio are seen in the ending. Of course, being {{Stationary Boss}}es, it's unlikely that they could leave the garden they were planted in, though by that logic, Cagney Carnation would be the same way, and yet he's one of the bosses that appear in the ending (although one of Cagney's attack animations turns his stem into legs, so who knows).
[[/folder]]

[[folder:Goopy Le Grande]]
[[quoteright:258:https://static.tvtropes.org/pmwiki/pub/images/goopylegrande.png]]
->''"I'm a handsome slime bringing pain — one bounce at a time!"''
A blue slime-like boss you fight in a forest in "Ruse of an Ooze".
----
* AffablyEvil: He might anatognize Cuphead and Mugman, but at least he's well-mannered.
* AlliterativeName: '''G'''oopy le '''G'''rande.
* AttackItsWeakPoint: Shooting his portrait on the tombstone is the only way to hurt him in his final phase.
* BaldOfEvil: He's one of the debtors that sold his soul to {{Satan}}, and the little tip on his head is tipped like a hat before the fight.
* BlobMonster: He's a blue slime monster, if the name of the boss and level didn't tip you off.
* BoxingBattler: His attacks in the first two phases consist largely of devastating punches complete with boxing gloves.
* ClippedWingAngel: His Tombstone has only one attack (as opposed to the two his other forms have), and it's pretty easy to dodge if you stand still until he uses it. The only real upside is the element of surprise against players who thought the fight was over.
* CloseRangeCombatant: Out of all the bosses in the entire game, he's the only one that lacks any ranged attacks or even helpers, instead preferring to crush the player characters or punch them.
* ConMan: The title and the stunt he pulls with the gravestone implies it.
* DeaderThanDead: He's implied to have died after his second phase, where he's dazed into unconsciousness before being crushed by a falling sentient tombstone. It's ambiguous whether the living gravestone -- which the cup brothers end up destroying anyway -- is an extension of Goopy's consciousness or not, but either way, the fact that he is absent from the finale implies he's dead.
* {{Determinator}}: The third phase of his fight involves his ''gravestone'' attacking you.
* DoesThisRemindYouOfAnything: He's a boxer who takes a special pill that turns him bigger and stronger, which gives off implications of steroid use (and the fact that [[DrugsAreBad he's implied to have died by the end of the second phase]] pushes it further.)
* TheFightingNarcissist: Each one of his win quotes talks about how handsome he is. [[RhymesOnADime Some of them are even in rhyme!]]
* GuideDangIt: Getting the parry bonus for this fight is not immediately obvious, since he does not have any projectile attacks. In order to get it, you need to parry the three pink question marks that appear when he shifts into his second phase.
* HalfTheManHeUsedToBe: Upon being knocked out in his third phase, his gravestone form cracks vertically into half.
* InstantGravestone: His third phase has one drop onto him. Then ''the gravestone'' attacks you, complete with taunting you as though it's still him if it kills you.
* KingMook: Basically, a larger version of the slime enemies from Forest Follies. Indeed, a piece of DummiedOut code reveals that, upon being smashed by his tombstone, Goopy was once supposed to [[AsteroidsMonster split off]] into [[FlunkyBoss two of the slime enemies]].
* LetsFightLikeGentlemen: Tips his "slime hat" to you before the brawl commences.
* TheLostWoods: Fought in a forest clearing.
* MakeMyMonsterGrow: His second phase has him eating a pill and getting much bigger.
* MeaningfulName: His surname means "the great" in French and refers not only to his ego but also his size (although the grammar is incorrect; "le" is masculine, but "grande" is feminine, so technically speaking, it should be "Le Grand" or "La Grande").
* MegatonPunch: His first phase has him forming his body into a boxing glove to hit you. His second form has him literally donning a boxing glove to punch at you.
* NinjaProp: The pink question marks that surround him when he transitions to his second phase are actually parryable. You'll want to remember this if you want that A+ rank.
* ObviousRulePatch: The pink question marks that appear when he takes the pill exist for the sole purpose of being parried for the A+ rank, since Goopy doesn't use projectiles.
* OneWingedAngel: After swallowing an unknown pill-like object, he becomes bigger and tougher-looking. His tombstone form may also count, although it's doubtful he intended to take the form of the tombstone in the first place.
* RedBoxingGloves: On his right hand, which he uses to rough up Cuphead and Mugman.
* ShoutOut: His blue appearance and pointed top allude to the famous Slimes from ''VideoGame/DragonQuest''. When he transitions from his first phase to his second phase, he changes shape similar to how [[VideoGame/ABoyAndHisBlob the blob shapeshifts]]. Likewise, his final form is, [[StealthPun literally]], a [[Music/TheLivingTombstone Living Tombstone]].
* UnskilledButStrong: His attacks are insanely telegraphed (even by the standards of games of this nature), but they cover a wide area.
* VictoryFakeout: The transition from his second to third phase. Goopy gets a dazed look on his face, an InstantGravestone drops on him and splatters him into a million droplets… and then the ''gravestone'' starts moving around trying to squash you!
* WarmUpBoss: One of the first bosses in the game that you'll face, his attacks have incredibly obvious tells and are fairly easy to avoid, plus they have fairly simple patterns. Also, he's the only boss with no projectile attack to speak of.
* WhatHappenedToTheMouse: He's nowhere to be found during the finale of the good ending, implying that he really is dead.
[[/folder]]

[[folder:Hilda Berg]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/hildaberg.png]]
->"''You won't get too far... it's been foretold in the stars."''
A woman that can turn her body into a blimp whom you fight in the skies in "Threatenin' Zeppelin".
----
* AmbiguouslyHuman: Is seemingly human, but has [[AmazingTechnicolorPopulation bright pink skin]] and odd powers like being able to transform into a blimp, cloud constellations and a mechanical crescent moon with her face.
* TheArcher: Hilda's Sagittarius form, where she turns into [[GenderBender a man on a cloud]] and shoots arrows at you.
* BalloonBelly: Her transformation into a blimp starts with her inhaling so deeply, her belly inflates.
* BlowYouAway: She can summon tornados from the weather vane on her head to throw at you.
* BrutishBulls: Hilda's Taurus form, which has her turning into a bull made of clouds to ram at you.
* EvilLaugh: [[WordsCanBreakMyBones Weaponised in her standard form]], no less! In her first phase and between her Zodiac forms, Hilda can attack you by sending "HA HA HA"s your way. When she transforms into her final form, this attack's gone, but she still opens the phase with a more menacing "HEH HEH HEH..."
* {{Faceship}}: Played with, she turns into a ship and her face happens to be at the front.
* FlunkyBoss: Little planes aid her in the fight in the first two phases. In the third phase, she can summon {{Flying Saucer}}s.
* FlyingSaucer: She summons these in her final phase. Red ones will prepare to fire as soon as they're above you, so you'll have to move forward to avoid their beams, while brown ones will prepare to fire as they approach you, so it's best to move back away from them as soon as they prepare to fire.
* GenderBender: Of the three constellation forms fought in her second phase, only Gemini is female, with Taurus and Sagittarius both being male, true to their depictions in reality.
* TheHyena: Cackles incessantly in her blimp form, with [[WordsCanBreakMyBones lethal results]]. She later unleashes a much more impressive, yet non-harmful example upon transforming into her Moon form.
* TheManInTheMoon: Her final phase has her shifting into a huge crescent moon form where she can not only attack you with her face, but summon [=UFOs=] to hit you with their beams.
* MoreDakka: The energy balls summoned from her Gemini form shoots a stream of bullets in rotating motion.
* OneWheeledWonder: While the top half of her body (before going OneWingedAngel, anyway) is merged with a blimp, the bottom half is a pair of perfectly human legs riding a unicycle — in all likelihood, [[HamsterWheelPower the thing's power-source]].
* OneWingedAngel: Her "[[NinjaPirateZombieRobot Alien Clockwork Crescent Moon]]" phase.
* PainfulTransformation: Before she changes into her final phase, she holds her head, clenches her eyes, and makes a pained moan, then her body starts spasming uncontrollably.
* PunnyName: Her name is Hilda Berg and it's a pun on the [[https://en.wikipedia.org/wiki/LZ_129_Hindenburg Hindenburg]].
* RammingAlwaysWorks: Tries this during phase 2, both as herself when transforming into one of her UsefulNotes/{{Constellations}}, and when in her Taurus form, in which this is her sole attack.
* ShoutOut: Her hairstyle was clearly inspired by ''WesternAnimation/BettyBoop''.
** Her airship form appears to be a reference to recurring boss Kabula from the ''{{Franchise/Kirby}}'' series.
** Her DubNameChange in the Portuguese language is Geni Buarque, a reference to the Brazilian song "Geni e o zepelim ("Jenny and the zeppelin", loosely based on Music/PirateJenny) and its author, Chico Buarque.
** The whole boss fight is one big homage to ''VideoGame/ThreeWonders'' 's Chariot: all the constellation-based minibosses (save for Taurus) apppear in the Capcom title, and the final phase is the spitting image of [[ThatsNoMoon Hypnos]], the second level boss.
* SinisterSchnoz: Has a very long nose, and when she shifts into her moon form, it gets even longer.
* SpreadShot: The green flunky blimps during her battle fire a spread[[note]]the number of shots is dependent on difficulty[[/note]], while her Sagittarius phase fires a spread of blue homing stars.
* StarPower: Many of Hilda's attacks are themed after celestial objects, with her initial transformations being based on the western zodiac and her final form resembling a moon and firing star projectiles and flying saucers. Each of the Zodiac forms are introduced with an illustration of their respective constellation upon Hilda transforming into them.
* StationaryBoss: She takes up enough of the screen in her moon form to prevent her from moving, other than popping her face out to signal her UFO attack.
* TricksterTwins: Hilda's Gemini form, where she turns into two girls on clouds and forms an energy ball to hurl at you.
* VoluntaryShapeshifting: She begins the fight by turning into a blimp, and then takes two of three different constellation-themed forms. Her final transformation into the moon, however, appears to be involuntary.
* WarmUpBoss: As the first shoot-em-up boss, she mostly serves to introduce you to the new mechanics. Much like a lot of the other early bosses, her attack tells are fairly easy to read, any gimmicks she throws out are not very difficult to manage, and even when she goes OneWingedAngel in her final phase, the bullet density is ''nowhere near'' as bad as later shoot-em-up bosses.
* WickedWitch: The 'wicked' part is [[AntiVillain downplayed]], but Hilda certainly seems to have this theme going for her, what with her evil cackles, transformation magic, and the snout. Even her tornado attack might be a reference to [[Film/TheWizardOfOz the trope codifier]].
* WingdingEyes: All her constellation forms have stars for pupils; this extends to her second-phase Game Over card.
* WordsCanBreakMyBones: Her starting phase has her shooting out "[=HAs=]" at you.
[[/folder]]

[[folder:Cagney Carnation]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/cagneycarnation.png]]
->''"Extreme pollination and total domination!"''
A flower boss whom you fight in a forest clearing in "Floral Fury".
----
* AlliterativeName: '''C'''agney '''C'''arnation.
* BattleBoomerang: One of his early projectiles is a sycamore seed that flies to the left over the platforms, then back across the right over the ground.
* BossArenaIdiocy: Cagney's arena contains tons and tons of obstacles on ground level... and three floating platforms which makes those obstacles avoidable. Granted, every now and then Cagney will use his vines to cover one of the platforms, but how about picking a platformless arena instead (Assuming he isn't rooted into the ground like a normal flower is and has a choice of where he can fight, of course)?
* BulletSeed: He forms a machine gun that shoots out seeds (one of them pink) into the air before they fall to the ground and become monstrous plants.
* EvilLaugh: He lets out a manic laugh as he transforms.
* EyeScream: When he's beaten, his eyes completely disappear. You can see straight through one eye hole and out the other.
* FieryRedhead: Gives the impression of one, with his orange petals and maniacal temperament.
* FlunkyBoss: In his first two stages, he occasionally launches seeds that sprout into enemies.
* FoulFlower: A giant flower boss who acts innocent before quickly revealing his true, AxCrazy colors.
* GRatedDrug: Cagney's fuzzies are the quickie type in the patched version.
* GreenThumb: Many of his attacks are plant-based.
* InterfaceScrew: In the patched version, if you get hit by one of the fuzzies Cagney spits at you, the screen will get blurry and distorted for a second or two.
* KingMook: Looks like a much larger, thorn-covered, and malicious version of the flower people you fight in Forest Follies.
* NightmareFace: Starts his fight off by giving an innocent smile, then suddenly roars at you, stretching his mouth open. He can even stretch his face to attack you. It gets even ''more'' nightmarish-looking in his final phase. And when beaten, his face ''completely loses its eyeballs'' and his mouth hangs agape in a soundless despair wail.
* OneWingedAngel: Becomes slightly bigger and [[SpikesOfVillainy spikier-looking]] in his final phase.
* ShoutOut:
** The way Cagney moves his hands is similar to the animation of a ghost character from Fleischer Studios' short ''WesternAnimation/SwingYouSinners'', who in turn is a reference to Monroe Silver, an actor and comedian of the Depression era known for incorporating similar hand motions into his routine.
** His name is obviously a pun on Creator/JamesCagney. The fact that one of his moves involves turning ''his own head'' into a crank-driven Tommy Gun (because of some of James' most memorable roles being gangsters) says a lot. For triple points, one of the first great [[https://en.wikipedia.org/wiki/Dean_O%27Banion Real Life mobsters]] was an accomplished florist who often did arrangements for gangland funerals; to this day, flower shops are still a semi-stereotypical 'front' for cartoon mobsters.
** His pre-fight adorable-looking design is a homage to the sentient flora from ''WesternAnimation/FlowersAndTrees'', a 1932 ''WesternAnimation/SillySymphonies'' animation, and the background is also inspired by the background artwork of the same short.
* SlasherSmile: Wears a maniacal grin through his boss battle, with him really ratcheting it up in the final phase.
* SoundtrackDissonance: His battle theme, "[[https://studiomdhr.bandcamp.com/track/floral-fury Floral Fury]]", appropriately spices up the battle with adrenaline-pumping fast Latin/samba music, which is a fine tune to go along with getting yourself killed by a psychopathic flower. Then again, it's also a play on the Latin American {{Gangster Land}}s, which fits with his aforementioned gangster theme.
* StationaryBoss: After spreading spiky vines along the ground, Cagney stays in a hunched position for the rest of the battle. His first phase isn't quite stationary because he can occasionally shoot his face out on the upper or lower halves of the screen (his face lunges are much faster in the patched version).
* VineTentacles: He can grow thorny vines through the soil when battling Cuphead or Mugman and stick them up to spike the brothers from below.
* WakeUpCallBoss: Unlike the Root Pack and Goopy, Cagney is the first ground boss to start invoking BulletHell and will force you to pay attention to not only where the attacks come from, but also stay cognizant of his distinct wind-ups and whatever follows after; things that you'll ''need'' to learn if you're going to get far in the game. Fittingly, he's the final boss unlocked for the first world.
[[/folder]]

[[folder:Ribby and Croaks]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/ribbyandcroaks.png]]
->''"We've had fightin' souls since we've been tiny tadpoles."''
Two frog brothers in boxing gloves fought in a showboat club setting (ironically run by flies) in "Clip Joint Calamity". Ribby is the shorter one and wears white trunks, while Croaks is taller and wears red.
----
* AmphibianAssault: Two giant frog boxers that are not surrendering their soul contracts without a fight.
* AmphibianAtLarge: They tower over Cuphead and Mugman, and appear to be human-sized, if not larger.
* BashBrothers: A pair of frogs who've been enjoying brawls since they were tadpoles. While not stated in the game to be related, ''The Art of Cuphead'' book confirms them to be brothers.
* BlowYouAway: Croaks can turn himself into an electric fan in the 2nd phase of the battle. This attack doesn't do any damage, but the pushing wind does make Ribby's [[ShockwaveClap projectile claps]] harder to dodge.
* BoxingBattler: They are styled after boxers and Ribby fights by using [[ElementalPunch elemental punches]].
* DualBoss: You have to fight them both at the same time, with Ribby going to the opposite side of the screen in the 2nd phase and Croaks turning into a makeshift fan to blow you into him while Ribby sends sonic blasts at you. However, unlike the Lollipop Ghouls on the Phantom Express and the Tipsy Troop, the two frogs share health, so it doesn't matter which one is attacked.
* FrogMen: The pair are frogs who fight for the amusement of the crowd in a showboat club, they made a bet with the devil and have now refused to pay their debts.
* FusionDance: Their final phases on normal mode has Croaks swallow Ribby whole and suddenly combine into a [[FusionDissonance slot machine]] that's only vulnerable when it starts attacking after you parry-slap the handle.
* KamehameHadouken: Ribby fires these off in his first phase.
* MirrorCharacter: Not explicitly stated in the game itself, but they're a pair of BashBrothers who got in trouble with the Devil, and who are now fighting for their lives to avoid having to pay up on the bargain they made. That's not very far removed from Cuphead and Mugman, is it? The artbook does indeed confirm them to be brothers and even states that this relationship is unique only to them and the cup brothers.
* OcularGushers: Ribby will be left gushing with tears with Croaks pounding the floor when they are defeated in Simple difficulty.
* OneWingedAngel: Their slot machine form, the result of a FusionDance as seen above.
* PlayingWithFire: In the first phase, Croaks will sometimes spit out burning fireflies that fly towards you.
* RapidFireFisticuffs: Ribby starts his attacking by punching rapidly, which produces projectiles that zip toward you.
* ShoutOut:
** The characters and their color scheme are very similar to the ones from the series ''Literature/FrogAndToad'' by Arnold Lobel.
** To Ryu and Ken from ''Franchise/StreetFighter'', made apparent by their boxing gloves and karate gi. They even do their more well-known taunts before battle (Croaks does Ken's BringIt, while Ribby lets out a {{Kiai}} as he gets into a fighting stance). In their final phase, they turn into a slot machine that includes tigers (which result in uppercuts) and bison (which result in psycho power) as part of its roulette.
** Additionally, the background featuring a cheering audience is another ''Street Fighter'' reference.
* StationaryBoss: While Ribby rolls across the screen to start the second phase (and then returns to Croaks for the final phase), neither frog moves around while attacking during each phase, and the slot machine is obviously immobile.
* VisualPun:
** Croaks spits out glowing bugs on fire that fly at you. They're literal fireflies.
** The flies watching the fight in the background are literal barflies.
* WhatHappenedToTheMouse: Croaks doesn't show up for the ending, probably because he has to stay at home. Ribby, however, does appear along with the remaining debtors on behalf of his brother.
* WrongSideOfTheTracks: According to their second phase's game over card, they're from the wrong side of the lily pad, [[RhymesOnADime which is why they're crude and bad]].
[[/folder]]

!!!Inkwell Isle Two
[[folder:Baroness Von Bon Bon]]
[[quoteright:231:https://static.tvtropes.org/pmwiki/pub/images/baronessvonbonbon.png]]
->''"I won't sugarcoat it… you never stood a chance!"''
The ruler of a candy area and boss of the "Sugarland Shimmy" level. Sends a random assortment of confectionery bosses (Muffsky Chernikov, a cupcake; Sgt. Gumbo Gumbull, a gumball machine; Sir Waffington III, a flying waffle; Lord Gob Packer, a multi-layered jawbreaker; and Kernel Von Pop, a giant candy corn[[note]]all unnamed in the game itself, but given pet names by [[WordOfSaintPaul animator Tina Nawrocki]][[/note]]) at you from atop her living castle Whippet Creampup before you are able to attack her directly.
----
* AdvancingBossOfDoom: In the final stage of the battle, the castle where she hides in begins to chase Cuphead and Mugman.
* AmbiguouslyHuman: It's unclear if she's meant to be human, or a strange humanoid. Especially since [[TheNoseless she lacks a nose]], has [[AmazingTechnicolorPopulation pink skin]], and lives in a chiefly candy-inhabited setting.
* AngryFistShake: She ''frequently'' angrily shakes her fist at you whenever you defeat one of her minions.
* AnthropomorphicFood: Among her minions are a living cupcake, a sentient waffle, an animate jawbreaker, a monster candy corn, and a mobile gum ball dispenser. Her castle is a living cake monster, which can dispense jelly bean soldiers and rolling peppermints with faces. It's hard to notice except for [[LosingYourHead in the game over quote for her final phase]], but Bon Bon herself is actually a bottle of soda, with her head functioning as the cap.
* AuthorityEqualsAsskicking: Although most of the time she sends her mooks to do the bidding, she can also attack using a sugar cane as a shotgun.
* TheBaroness: That's her title, after all.
* BerserkButton: The Baroness herself doesn't have one, but her cake castle Whippet Creampup certainly does: getting its towers pulled on. Indeed, this is how she initiates the final phase of the battle; by pulling on Whippet's towers, sending it into a rage and causing it to chase the boys down.
* BossArenaIdiocy: The arena she's fought contains a floating green candy platform right in its very middle, which can be jumped on to avoid most of her attacks.
* DetachmentCombat:
** Sir Waffington III breaks his body apart and launches the pieces in a SpreadShot attack.
** The Baroness will throw her head during the final phase.
* FlunkyBoss:
** The first part of her boss battle is fighting three randomly-chosen minions, each with their own game over screen:
*** A candy corn that flies around horizontally or vertically, occasionally spawning smaller candy corns that fly upwards.
*** A gumball machine that [[BulletHell fires out gumballs that rain down]] on the boys.
*** A cupcake that [[BouncingBattler jumps into the air]] and slams into the ground, unleashing frosting [[ShockwaveStomp shockwaves]].
*** A jawbreaker that slowly chases after Cuphead, trailed by InvincibleMinorMook jawbreakers (none on Simple, one on Regular, and two on Expert).
*** A winged waffle that flies around, [[DetachmentCombat splitting itself apart before putting itself back together]].
** During the minion phase of the battle, jellybean soldiers will occasionally charge out of the castle. The final phase of the battle has the Baroness enraging the castle to chase the boys down, while sending large peppermints rolling out.
* HighClassGloves: Wears a pair of pink opera gloves.
* HomingProjectile: Her own head acts as one, chasing down the player character to try to damage them.
* ImprobableWeaponUser: Her candy cane can somehow be used as a ''shotgun''.
* KickingAssInAllHerFinery: Averted. While she does have a stunning appearance, she never engages the boys directly at any point in her battle.
* LevelAte: Fought in a kingdom of candy.
* LosingYourHead: At the beginning of the fight, her head briefly detaches while giving Cuphead and Mugman a ThroatSlittingGesture. Also, she can detach her own head and regrow it, even using the spare heads as projectiles in the last phase!
* MatryoshkaObject: Lord Gob Packer is surrounded by several layers of candy shell. Once he's defeated, each shell cracks open to reveal a smaller jawbreaker until the tiny original is exposed, [[WingedSoulFliesOffAtDeath which then floats away]].
* OffWithHisHead: More like, "Off with Their Heads!"; she threatens the duo with this at the start of the battle via giving them a ThroatSlittingGesture, complete with her briefly [[LosingYourHead losing her head]].
* OneWingedAngel: Not her so much as her cake castle, which transforms into an angered beast in the final phase.
* OverlyLongName: According to a series of tweets, all of her minions have extremely long names.
* PimpedOutDress: Wears one with a peppermint-striped bodice, puff sleeves, and flounces that resemble piped icing, topped off with an ice cream cone hennin hat.
* ShockwaveStomp: Muffsky Chernikov produces waves made of icing whenever he slams onto the floor.
* ShotgunsAreJustBetter: Her cane functions as this in the third phase of her fight, adding additional projectiles for the duo to worry about.
* ShoutOut: The appearance of the Baroness and her barony are inspired by various cartoons' candy kingdoms, but most noticeably Cookietown from "WesternAnimation/TheCookieCarnival". One of her minions, Lord Gob Packer, is also a jawbreaker version of VideoGame/PacMan.
** Marie Antoinette may be also a strong contender, due to the infamous quote often (but [[BeamMeUpScotty incorrectly]]) attributed to her, ''"let them eat cake"'', and the fact that she indeed [[LosingYourHead loses her head]]. [[invoked]]
** Her name is a reference towards Baron Von Blubba from the ''[[VideoGame/BubbleBobble Bubble Bobble]]'' franchise.
** Design-wise, she was influenced by various actresses from the era of the game's design (like Betty Grable, Bebe Daniels, and Loretta Young).
* SlasherSmile: [[https://68.media.tumblr.com/a04f9e10845bfda98e4ef84b650b66db/tumblr_oxeln7w6hH1wnrdtzo1_1280.png Makes a wide, unstable-looking smile]] just before she initiates the final stage of the battle.
* SoreLoser: She bursts into angry tears upon defeat (complete with a VolumetricMouth). In Regular mode, Whippet also beats the ground in frustration while crying.
* StationaryBoss: She stays on top of her castle for most of the fight, but can't be damaged until the end. On Simple difficulty, she stays still and keeps firing cotton candy blasts when her third minion is defeated. On Regular and higher, she instead progresses the fight by turning into an AdvancingBossOfDoom.
* VaudevilleHook: Blink and you'll miss it, but her candy cane functions as this at the very start of her level, implying her candy castle may have some control over it.
* VisualPun: When Muffsky is defeated, the cherry on his head swells up as its stem turns into a fuse and blows itself up along with the cupcake. It turned into a cherry bomb, see.
* VolumetricMouth: She breaks down into sobbing in this way upon her defeat.
* WheelOfFeet: Sgt. Gumbo Gumbull's feet are animated this way.
* WingedSoulFliesOffAtDeath: Lord Packer gains a halo when defeated, floating off the screen while Bon Bon prepares for the next phase.
* YourHeadASplode: Happens to Sgt. Gumbull in his death animation; his glass head shatters and it scurries off.
[[/folder]]

[[folder:Beppi the Clown]]
[[quoteright:222:https://static.tvtropes.org/pmwiki/pub/images/beppitheclown.png]]
->''"What do you call a cup that falls off a swing? A tumbler!"''
An evil clown you fight on the roller coaster in "Carnival Kerfuffle".
----
* AmbidextrousSprite: Since he's the only character with an asymmetrical design. It's moot in his second and fourth phases, where he directly faces the player, but in his first and third phases, the red half of his face is dominant no matter which way he turns. The artbook states [[StylisticSuck this was an intentional design choice]] to harken back to past examples of ambidextrous sprites in retro games.
* AmusementParkOfDoom: Seemingly fights you in one; the rides he [[VoluntaryShapeshifting becomes]] are certainly killer, and the rollercoaster he fights you on is a constant, deadly stage hazard.
* BaldOfEvil: Completely bald, even underneath that little top hat of his, as shown in the ending.
* BalloonOfDoom: Has a stretchy, balloon-like body, most noticeable with his bulbous head. In phase 2 of his battle, his body is attached to a giant helium pump, and his head inflates into a giant balloon tied to his body with a string. The pump also shoots out balloon dog heads that [[FlunkyBoss swarm the arena to attack you]].
* BerserkerTears: Has an ''absolute tantrum'' if you shoot down his merry-go-round horse.
* CarFu: Leaps into a bumper car for the first phase of the fight and tries to ram you.
* CheshireCatGrin: Has a creepy wide, toothy grin.
* CircusOfFear: Fought on a roller coaster in a rather bleak-looking amusement park.
* EverythingsBetterWithPenguins: Nope. In his final phase, he spawns penguin enemies that throw baseballs at you.
* FlunkyBoss: His final phase has him summoning penguins who [[IKnowMaddenKombat throw baseballs at you]].
* FunPersonified: Really seems to be having a blast throughout the fight, particularly when he's riding a horse and is actually ''bouncing'' and cheering with excitement.
* GravityIsAHarshMistress: Falls off the roller-coaster ''twice'' during the fight, yet refuses to give up.
* KnockKnockJoke: One of his death quotes falls under this if you get killed by his horse; see "PungeonMaster".
* MagicalClown: A clown who can transform into and summon amusement park rides and other objects.
* MonsterClown: A clown boss who will not hesitate to fight you.
* NiceHat: Wears a tiny top hat on his head.
* NonIronicClown: During the ending, he has a genuinely pleasant smile on his face.
* OneWingedAngel: While he transforms into a balloon pump for his second phase, his transformation into a chair swing ride in the final one fits the trope better.
* PungeonMaster: All of his death lines are jokes at Cuphead's expense:
-->'''Beppi:''' [''Bumper Car Phase''] Why did the clown drive over the cup? He wanted to crack him up!\\
'''Beppi:''' [''Balloon Phase''] What did the balloon animals think of the cup? Quite the gob-let-down!\\
'''Beppi:''' [''Horses Phase''] Knock-knock! Who's there? Charlie. Charlie who? ''Charlie horse!''\\
'''Beppi:''' [''Swing Ride Phase''] What do you call a cup that falls off of a swing? A tumbler!
* ShoutOut: According to [[http://studiomdhr.com/surprise-cuphead-is-coming-to-playstation-4-and-its-out-today/ a post on the Studio MDHR blog]], Beppi's design is based on a character from ''[[VideoGame/BubbleBobble Super Bust-A-Move 2]]'' (most likely Katze, who is also split into a red side and a blue side).
* StationaryBoss: He can't move while he's a balloon pump/swing ride, which isn't a problem since he relies on minions and arena hazards for those phases.
* VillainousHarlequin: A clown with terrifying transformations and DerangedAnimation, though he isn't outright evil and is mainly just trying to avoid paying up to his end of a DealWithTheDevil. The ending shows he is nice otherwise.
* VoluntaryShapeshifting: Sure, the DerangedAnimation allows everyone to get transformations going on, but Beppi stands out due to how much use he gets out of them; the man can apparently play the whole damn carnival if he wants to, and has no problem becoming a balloon pump or even a giant, spinning, and laughing chair swing ride if pushed.
* YellowEyesOfSneakiness: Has yellow sclerae, and is definitely sinister.
[[/folder]]

[[folder:Djimmi the Great]]
[[quoteright:238:https://static.tvtropes.org/pmwiki/pub/images/djimmithegreat.png]]
->''"You look the fool, falling for the first trick I learnt at genie school."''
A genie fought above the desert in "Pyramid Peril".
----
* AmazingTechnicolorPopulation: Probably because he's been in the desert too long, but his skin is red as a tomato.
* AsideGlance: Performs one complete with an EvilLaugh and IdeaBulb replacing his turban when he decides to create the marionette.
* BadWithTheBone: During the first stage, one of his methods to attack is shooting out his own skull ''[[BodyHorror right from his face]]''.
* BagOfHolding: The first phase of his fight — he rummages around in a treasure chest, tossing out three possible types of projectiles:
** [[CatsAreMagic Cat mummies]]: Lowest density, but the only one of the bunch [[HomingProjectile that can home in on you]], and considered the worst of the bunch because of this.
** [[GemstoneAssault Jewelry]]: [[MoreDakka Highest density]], but not too hard to navigate as long as you keep one finger on the Shrink button at all times.
** {{S|tormOfBlades}}words: Probably the scariest-looking, but universally considered the easiest to dodge.
* BaldOfEvil: A FreezeFrameBonus shows that Djimmi is bald under that turban of his.
* BeatThemAtTheirOwnGame: His fourth phase (third if not counting his DeathCourse) has him making a Cuphead puppet named Cuppet and sending it at the boys. If you shrink while he's doing this, he instead makes a mini-Cuppet that can't really fight the boys on its own, so Djimmi transitions right to his final phase while the mini-Cuppet backs him up by shooting pellets from the center of the screen.
* BlowingSmokeRings: Or "a Smoke Teacup", actually: At the beginning of the fight, he blows out some smoke that forms a teacup with [[WingdingEyes X's for eyes]] and a frowning mouth, indicating that the boys have no chance against him.
* CheatCode: [[spoiler:Spinning around three times on the overworld summons him (as '[[UsefulNotes/GameGenie Game Djimmi]]'), granting you 3 extra health (4 if you have the Twin Heart charm equipped) on Simple and Regular mode until you win a fight, [[NoFairCheating though you can't get an A+ grade while the effect is active]]. Dying to his final phase in his boss fight with the cheat on even gives you a new unique death quote!]]
* DeathCourse: The second phase of the fight has him turn into a death trap obstacle course consisting of advancing pillars with vulnerable faces for the players to destroy for bypassing, and sawblade traps in between.
* DualBoss: The miniature Cuppet attacks during Djimmi's final phase if its secret phase is accessed, serving as another obstacle in a very crowded screen until it gets destroyed.
* EthnicMagician: Has some elements of the "Arabian stage magician" sort, considering he's found in a carnival area, his title, and the fact that he speaks about needing a new volunteer ([[RhymesOnADime because this one has collapsed in fear]]) if you die to him on his final phase.
* EvilLaugh: A [[EvilSoundsDeep pretty deep one]] he belts out whenever he's unleashing something new on you. When he decides to create Cuppet, he even unleashes a slightly-robotic laugh to match his [[IdeaBulb lightbulb turban]]. The most impressive one of all in his repertoire comes as he enters the final phase of his fight.
* GoodSmokingEvilSmoking: Constantly smokes a pipe throughout the fight, even making smoke shapes to taunt you at the beginning and having a bad coughing fit when defeated. Indeed, the battle opens with Djimmi appearing in a plume of smoke released from the pipe.
* {{Homage}}: The background as you fight him in the sky is drawn in the style of [[WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor the old Popeye two-reelers]].
* IdeaBulb: Has one while he [[AsideGlance laughs maliciously to the screen]] before starting the fourth phase of the battle.
* JackassGenie: He fits this down to a T, although he is kind of an AntiVillain himself.
* NiceShoes: Wears ''magic lamps'' as shoes.
* OneWingedAngel: Becomes so huge in his final phase that only his head fits onscreen.
* OurGeniesAreDifferent: He's not here to give any wishes, and he attacks with several summoning and shapeshifting methods. And apparently there's a school for them, if the game over quote from his first phase is of any indication.
* PunnyName: His name is a pun on "djinni" (the formal romanization of "genie") and "Jimmy", referencing the Moldenhauer brothers' father Jim.
* PyramidPower: In the final stage of the fight, he summons three floating pyramids with eyes encircling a half of the stage while firing cross-shaped [[EyeBeam beams from them]].
* ShoutOut: The way he moves and acts seems to be a villainous version of the Genie from ''WesternAnimation/{{Aladdin}}''. In particular, his fourth phase has him turn into a giant disembodied hand, which was a quirk of the Genie's.
** During his first phase, he also does the [[Series/IDreamOfJeannie Jeannie dance]] while his treasure chest takes care of all the actual attacking.
* SinisterScimitar: Used in the StormOfBlades up there, natch. Also, if you try to sneak behind him during the fight, [[NoFairCheating one of these immediately descends from the top of the screen and shish-kebobs you]].
* SkippableBoss: Cuppet in its regular size can be avoided by transforming into a mini-plane while Djimmi is analyzing you, skipping straight to the fifth phase. To compensate, however, a miniature version of Cuppet will appear and attack you alongside the giant Djimmi.
* SmokingBarrelBlowout: One of the Game Over cards shows Cuppet blowing smoke from the tip of his finger gun after he has beaten you.
* SpreadShot: The treasure chest he summons in his first phase fires out a stream of shots in a spread pattern, while his hat in his third phase will also fire out spreads of shots. The last phase, the pyramids, fire cross-shaped beams that span throughout the stage.
* StationaryBoss: Only in his first phase (where he's standing still as his treasure chest attacks) and his last phase (where he takes up the entire right side of the screen).
* WeaksauceWeakness: Well, "weaksauce" is over-stating it, but the bomb upgrade you get before fighting him makes his death course significantly easier, as a direct hit with one shot breaks the vulnerable parts. It also lets you find a quite comfortable position to bomb him from during the Sarcophagus phase, where any ghost that'd hit you will get nuked and the eyeball projectiles fall short.
* WeaponizedHeadgear: During his fourth phase where he attacks you with Cuppet, his turban also acts as an obstacle that attempts to collide with the player and fire out a spread of shots every now and then. In his final phase, he also shoots out beams of energy out of his turban's gem.
[[/folder]]

[[folder:Grim Matchstick]]
[[quoteright:254:https://static.tvtropes.org/pmwiki/pub/images/grimmatchstick.png]]
->''"Don't m-m-misunderstand my flames — I just meant fun and games."''
A dragon fought in the clouds circling a tower in "Fiery Frolic".
----
* AdvancingBossOfDoom: In the second half of the fight, he begins to chase you while he spouts out the walking flames on his tongue in the second phase, and when he becomes three-headed in the final phase.
* ApologeticAttacker: Losing to him in his first has him saying he's misunderstood, and losing to him in the second phase has him apologizing for being forced to put the players in a hot seat. Even his third phase has him suggesting the player run away.
* BattleInTheRain: The moment he enters his third phase and grows two extra heads, the weather goes from pleasant and sunny to stormy and violent.
* BigFun: He's clearly enjoying fighting you more than he should, considering the contract for his soul is on the line — trying to do the spooky fingers routine at the beginning, and going LaughingMad at [[BreakingTheFourthWall the player]] when he grows two extra heads.
* BloodKnight: He is a somewhat ambiguous example of this trope. While he apologies for fighting you and in general, seems like the nicer bunch of the villains, several of his expressions clearly indicate that he enjoys fighting you.
* BreakingTheFourthWall: He makes a "Boo!" motion toward the player at the start of his battle, and his two extra heads are seen glancing at the screen moments after the second to third phase transition.
* BreathWeapon: In three different flavors, no less. He shoots {{fireballs}} in his first phase, spits out living flames in his second, and spews both flaming bubbles and jets of flame, complete with his middle head ''[[VoluntaryShapeshifting turning into an actual flamethrower]]'', during Phase 3.
* DelightfulDragon: He's endearingly goofy, and even his win quotes make him seem sympathetic. This does not stop him from being one of the hardest bosses the player will have faced up to that point.
* EnergyRingAttack: In his first phase, Grim Matchstick attacks with Eye Beams that manifest themselves as a short row of rings flying in the player character's direction. The last ring in a row is pink, allowing Cuphead and Mugman to parry-slap it.
* EvilLivingFlames: During one phase of his battle, he opens his mouth and stretches out his tongue, and a marching band of flames walks out.
* EyeBeams: His first phase has him firing rings from his eyes at you.
* FatFlex: In his first phase, he breathes {{fireballs}} by lifting his gut while inhaling and releasing it when he spits the flame.
* FeatherFingers: A slightly more justified bat-winged example. The gesture he makes during the opening is done with his wings and his actual hands.
* LaughingMad: He unleashes a bellowing laugh once he transforms into his final phase, and all three heads perform various comical smiles.
* MultipleHeadCase: He grows two extra heads for the final phase of the fight.
* OneWingedAngel: After taking enough punishment from the boys, he suddenly grows two extra heads.
* PlatformBattle: His fight consists of you shooting him while jumping from one moving cloud to the next.
* PlayingWithFire: Aside from [[BreathWeapon the obvious]], which he uses in his first and third phase, his second phase has him opening his mouth and sending out fire soldiers along his tongue, creating a makeshift pit of death below you as you keep hopping from cloud to cloud. What's more, a few of the soldiers will jump toward you, which you must likewise dodge.
* PorkyPigPronunciation: All of his win quotes have him stuttering.
* ShoutOut: His first form's design and moveset resembles the Mecha Dragon from ''VideoGame/MegaMan2'', with his final three-headed form adding in aspects of [[Franchise/{{Godzilla}} King Ghidorah]] for good measure, while his name itself is an homage to legendary Fleischer animator Creator/GrimNatwick; he even has a pronounced stutter in his game-over quotes, [[https://twitter.com/AtroxChobatsu/status/914206756665884672 much like the real Grim did]].
* SpeechImpediment: As you can tell with all his quotes, he has a stutter.
* SpreadShot: In the third phase, his flame projectiles explode into a cross-shaped 4-way spread if they're damaged. Moreover, they also draw in your Chaser shots.
* StationaryBoss: He doesn't move during any of his phases, though he shifts to the left side of the screen after the first.
* TailSlap: He will sometimes try to stab you with his tail in the first phase.
* VictoryFakeout: An especially nasty one. Made it through the flame-soldier phase with 1 HP? Watch him cough and wheeze and cringe and... [[OhCrap grow two extra heads that make faces at you while the sky itself darkens in utter terror]].
* WeaksauceWeakness: Very downplayed, but the Lobber weapon is probably the best to use against him. Grim is massive enough that the curve of the projectiles is no issue in the first phase, and becomes a blessing during the second phase (where you want to stay on the highest clouds to avoid his flaming minions, but if you're too high up, you cannot damage him with the Peashooter). The curve also helps in his last phase, making it less likely to accidentally detonate his fire bubbles, and letting the player keep a healthy distance on the highest clouds to avoid his flamethrower attack.
[[/folder]]

[[folder:Wally Warbles]]
[[quoteright:224:https://static.tvtropes.org/pmwiki/pub/images/wallywarbles.png]]
->''"I own the air — I fly where eagles dare!"''\\
''"My dad's the brawn and I'm all brains! Together, we bring the pain."''
A bird who lives within a cuckoo house, and the boss of "Aviary Action". After he takes a beating, his son, Willy Warbles, comes out of the birdhouse to attack you. You fight them in the skies.
----
* AlliterativeName: '''W'''ally '''W'''arbles and '''W'''illy '''W'''arbles.
* AndShowItToYou: A case where Wally literally coughs up his own heart to attack you.
* BrainsAndBrawn: A dynamic that Wally shares with Willy, even lampshaded if the latter beats you.
* BulletHell: The second phase of the fight has Wally flap wildly and send his feathers all over in a spread, everywhere.
* ClippedWingAngel: Played with. Most of the debtors turn into fearsome abominations for their last stand... but Wally instead arrives flightless and featherless in a stretcher. Gameplay-wise, however, he is no less deadly, being able to unleash an utter onslaught of bullets with the help of his doctors.
* DeadlyDoctor: The paramedics carrying Wally in a stretcher during his final phase will assist him in battle by spitting pills at you.
* {{Determinator}}: Even when you destroy the house around Wally, he ''still'' comes back, featherless, being carried by two medic birds, and attacks by not only turning his head into a trash can to spew trash at you, but also ''kicking his stomach, which shoots his heart out of his mouth'' to fire projectiles at you. Considering that you just recently defeated his son, [[PapaWolf no wonder he's pissed]].
* EatenAlive: Presumed to be Wally's fate when beaten, as the medic birds are seen pouring salt and pepper on him with hungry looks in their eyes, and that he is among the few characters not present in the game's closing scene. But WordOfGod states that he's still alive.
* EggLayingMale: Despite being a male bird, spits out eggs as a main weapon.
* EnfantTerrible: Willy is as deadly as his father is, and arguably more malevolent.
%%zce* {{Expy}}: Of Sindbad's giant Rokh from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''
* FeatherFlechettes: Wally does this in the second phase of his attack by flapping wildly and sending feathers at you. By the end of the phase, he's run out of feathers.
* FlunkyBoss: Wally's first and second phases has him accompanied by birds with nails on their heads who fly at you. The fourth has the medic birds spit out pills that turn into homing shots and fly at you.
* GadgeteerGenius: Willy during the third phase, who presumably built the hovering, spiked invulnerable eggs surrounding him, his raygun, and possibly even the birdhouse that protects his father.
* HighPressureEmotion: At the start of the second phase, Wally's anger [[RageBreakingPoint reaches its tipping point]], and he sounds off like a steam whistle, with his head even briefly turning into one for good measure!
* HumiliationConga: Hoo boy, Wally took it much worse than other bosses in the game. Over the course of battle, he ends up losing his house, gets defeathered, has his son get beaten up, and then he himself gets beaten unconscious as his own medics decide to eat him alive, while the ones who gave him said beating take his soul contract to deliver it to the Devil who would gladly reclaim his soul.
* InstantlyDefeatheredBird: After beating him in the second phase, Wally ends up losing all his feathers and falls out of his house. Doesn't stop him from coming back in the final phase.
* MisterSeahorse: Wally can apparently produce eggs.
* OrbitingParticleShield: Willy is surrounded by spiked eggs that constantly circle him, moving closer in then farther away.
* OverlordJr: Willy takes over for the third phase and attacks you with a ray gun and orbiting spiked eggs.
* PapaWolf: Despite being left injured and naked from the first two stages of the fight, hearing Willy cry for help gets Wally to confront Cuphead while two medic birds carry him on a stretcher.
* PerpetualFrowner: In contrast to most of the other bosses, Wally spends basically the entire battle angrily scowling. The closest thing to a smile he's seen with is if you lose to his final phase.
* {{Projeggtile}}: Spitting eggs is Wally's main form of attack in the first phase. Later, in the third phase, Willy employs a telekinetic OrbitingParticleShield variant of the same eggs.
* RageBreakingPoint: While he almost never looks happy, Wally's second phase is initiated by him turning his head into a steam whistle, and his only attack is to send a storm of his own feathers out while screaming in anger.
* Music/RideOfTheValkyries: Played briefly during their theme music, 'Aviary Action'.
* ShoutOut:
** Wally's temper tantrums during the second phase are reminiscent of Donald Duck's own fits of rage.
** Wally's color scheme and elongated beak are also similar to Woody Woodpecker. They, and Willy, all even have alliterative names beginning with W.
* SpreadShot: Wally has ''several'' — during the first phase, the eggs he spits out explode into a spread of three (five on expert) when they hit the left side of the screen, and his FingerGun head transformation can fire out a spread of two to three bullets. His second phase uses a massive spread of FeatherFlechettes on the player characters.
* ToothyBird: Both Wally and his son have beaks full of teeth. Willy's are most visible when he grins right before firing his gun.
* UncertainDoom: The last we've seen of Wally, the medic birds were planning to eat him after his defeat. It was never confirmed or denied whether he was eaten or did he manage to survive. If the fact he is absent from the good ending is any indication, his fate might not be a pleasant one.
* VisualPun: Wally's attack in the fourth phase where his head morphs into a trash can and spits out trash to shoot you out of the sky. He's literally talking trash at you.
** Another attack in his final phase while he's being carried by paramedics has him kick up his own heart to attack you. In other words, it's his heart attack.
* VoluntaryShapeshifting: Wally can turn his head into [[FingerGun a hand to fire out bullets at you]]. In the final phase, he turns his head into a trash can to spew trash projectiles at you.
* WakeUpCallBoss: Wally is the first shoot-em-up boss that is likely to give players trouble; his attacks are a fair bit harder to avoid, he throws quite a few curveballs with the variety in his projectiles and forms, and has a far higher density of bullets to avoid than Hilda or even Djimmi, making him a test of spacial awareness and quick reaction time. His final phase also highlights the importance of your secondary weapon in plane battles, as the bombs can help you hit targets you can't easily reach or destroy with the default shot.
* WhatHappenedToTheMouse: Neither Wally nor Willy are seen in the ending.
[[/folder]]

!!!Inkwell Isle Three
[[folder:Rumor Honeybottoms]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/rumorhoneybottoms.png]]
->''"Hey sugar, this honey is off limits. Now scram."''
A queen bee fought in an office building for bees (naturally) in "Honeycomb Herald".
----
* AnimalStereotypes: She's the Queen Bee and fought in the hive, a company building with exhausted drones who will defend their queen with their lives.
* TheBadGuysAreCops: Before the Queen fights you, you have to fight one of her hive's police officers first. If he defeats you, he accuses you of attempting a honey heist.
* BeeAfraid: She's very dangerous and is not handing over her Soul Contract without a fight... especially when her [[RiseToTheChallenge flooding honey attempts to drown you]].
* BeeBeeGun: One of her attacks consists of spitting bees that look like bullets... or are they bullets that look like bees?
* BigCreepyCrawlies: A honeybee and one of the larger bosses not fought in a plane in the game. The security bee is also roughly human-sized too. [[AllThereInTheManual Concept art shows]] that her bottom half is even more human-like, with legs in high-heels, and her "abdomen" is, indeed, a very flouncy dress.
* ChainsawGood: Her circular saw attack late in the game.
* EvilLaugh: One in her plane phase, when she uses her buzzsaw attack.
* FingerWag: Does this from off-screen during the second phase (in other words, the first phase where she takes an active role). Pay attention to where her finger pops out from — the rest of her will follow a moment later.
* FlunkyBoss: Her first phase has her summoning a police officer to take you on and some regular bee employees that fly across the screen.
* HornetHole: Fought in a beehive-themed office building.
* ImAHumanitarian: The start of the battle has her looking hungrily at the boys while rubbing a fork and knife together.
* InsectQueen: She's a queen bee. [[GodSaveUsFromTheQueen A dangerous one, too.]]
* LosingYourHead: Sorta. In the second phase, she lowers her head from her body via a chain and dangles it in the middle of the screen to spit projectiles at you.
* MagicStaff: Her giant honey dipper that she wields. She also has a [[SpellBook spell book]] she uses to transform.
* NoblewomansLaugh: In her second phase, fitting for a queen bee. In her final phase, it turns into a deeper EvilLaugh.
* OneWingedAngel: Transforms into a bomber plane in her final phase.
* APigNamedPorkchop: She is a bee named Rumor Honeybottoms, which references honey, the food product that bees make.
* PlatformBattle: A vertical one where you have to keep jumping up on honeycombs to stay ahead of the [[RiseToTheChallenge rising honey]] in the first few phases. The last one has her fly to the bottom of the screen in a plane form and attack you from there.
* RocketPunch: One of her later attacks have her launching fist-shaped missiles.
* ShoutOut:
** She starts the battle rubbing a knife and fork together in hunger, just like [[VideoGame/{{Darkstalkers}} Q-Bee]].
** The bee/bullet projectiles she spits look and move an awful lot like [[Franchise/SuperMarioBros Bullet Bills]].
* SpreadShot: The police officer bee plants bombs that explode into spreads of spiked shots. During the second phase, she may also summon a triangular energy thing that fires shots in 3 directions.
* VisualPun: Her turning into a plane to fight you in the final phase. She's a "Buzz Bomber" "Bee-plane". Or, alternatively, a "[[{{Pun}} Bee]]-17 Flying Fortress"[[note]](which would be era-appropriate, and which she vaguely resembles)[[/note]]. In this phase, she also attacks you by turning one of her wings into a "Buzz Saw."
** The bees work in an office building that's drenched in dripping honey. A sticky business, in other words.
*** The worker bees have a SalaryMan look, in other words: They're office drones.
** The bee police officer that attacks you, if you use period-appropriate British slang, is a [[https://www.britannica.com/topic/bobby Bob]]-[[{{Pun}} bee]].
* VoluntaryShapeshifting: In her final phase, she uses her powers to turn herself into a plane and attacks from the bottom of the screen. Not only does this shoot out projectiles, but she can turn her arm[=/=]wing into a saw to hit you. It should be noted that, unlike almost every other boss in the game, she apparently uses a spell from a book in order to make it happen.
[[/folder]]

[[folder:Captain Brineybeard]]
[[quoteright:232:https://static.tvtropes.org/pmwiki/pub/images/captainbrineybeard_removebg_preview.png]]
->''"Yer skills be like me buried treasure... just a myth!"''
A pirate fought on the docks that can summon sea creatures to help him. The boss of "Shootin' n' Lootin'".
----
* AnimateInanimateObject: The barrel that looms over the player, and the ship itself.
* AttackTheMouth: To defeat the Brineybeard's ship, the player is required to attack the uvula, located in the ship's mouth.
* BaitAndSwitchBoss: Basically the only straight example in the game. The final phase isn't against him, but instead his ship.
* TheBeastmaster: Similar to Cala Maria, he can call in a variety of sea creatures to assist him.
* CaptainColorbeard: Though, according to a trailer from 2013, he was originally named Captain Silver, averting this trope.
* DeathFromAbove: An environmental hazard in his level is a large living barrel suspended over the dock, which will drop down on Cuphead if he stays under it for too long.
* DressedToPlunder: Hits quite a few of the checks, between his eyepatch, bandana, single hoop earring, and two peglegs.
* EyepatchOfPower: Although it's apparently just for show - though it's hard to see in the middle of the battle, he occasionally peeks out of it, revealing a good eye underneath.
* EquippableAlly: He fires bullets from an octopus that he grabs and uses as a shotgun.
* EvilLaugh: The Captain himself has a pretty hearty one, and the narwhal-boat's final phase laughs at you in its game over card.
* {{Expy}}: Inspired by Sindbad from ''WesternAnimation/PopeyeTheSailorMeetsSindbadTheSailor''.
* FourFingeredHands: Averted. He's the only character in the game, human or otherwise, to have five fingers on each hand.
* FlunkyBoss: For the most part, it's his ship, barrel, and sea creatures that really attack you, with Brineybeard taking potshots at you on occasion.
* InterfaceScrew: Brineybeard will sometimes summon a squid minion who throws ink on the camera, causing the screen to darken with each glob that successfully hits the boys and makes seeing any incoming attacks much more difficult for a few seconds.
* MakeMeWannaShout: Once Brineybeard's ship takes over in the final phase, it will occasionally [[WaveMotionGun scream out a massive laser]] that engulfs most of the screen.
* NonActionGuy: Despite his big physique, the captain doesn't really do any of the fighting himself, instead relying on his ship and the creatures he summons. Even the one attack in the fight that comes directly from him (shooting pellets from the octopus) still has a minion (the octopus, of course) doing most of the work. He doesn't even fight in the final phase, with his ship taking over as the opponent instead.
* OneWingedAngel: Not the captain himself, but his ship inexplicably turns into a narwhal-whale creature in the final phase of the battle.
* {{Pirate}}: Goes without saying.
* PirateBooty: His Game Over taunt states he ''doesn't'' actually have any buried treasure. It's just a myth, [[TrashTalk just like Cuphead's skills]].
* SeadogBeard: Though contrary to his name, it doesn't look very briney.
* SeadogPegLeg: Concept art shows ''both'' his legs are these, though in the game itself it's hard to see even one, [[https://78.media.tumblr.com/e61bf9a033a3e260d416c516bae2079e/tumblr_oym1m4dIAm1wnrdtzo1_400.png though they're still there]].
* SentientVehicle: The ship itself is sentient and spits out cannonballs in the first phase. In the final phase, it even takes over as the boss.
* SpearCounterpart: As stated above, his attacks and affiliation to the sea are very similar to Cala Maria's.
* StationaryBoss: The captain is stuck on the deck of his ship for most of the fight. Once he gets knocked off, the weak point moves to the ship's uvula but otherwise stays motionless.
* ThreateningShark: He can summon small dogfishes that act as tiny sharks in front of him to attack, and a bigger, more traditional one that will try to bite you if you try to cheese the fight by sitting on the left side of the arena.
* VisualPun: The small brown sharks with chains he summons are ''dogfishes''. Or, put another way, they're ''seadogs''.
* TheUnintelligible: The ship does not have any spoken taunts in its Game Over screen; instead, it simply makes gnarling noises.
-->'''Ship:''' ''"HAW-HAW-HAW-HAW-HAW!"''
* WaveMotionGun: In the final phase, the ship itself can fire one of these from the mouth on its uvula.
* WhatHappenedToTheMouse: In the third phase, the ship turns into a narwhal and throws Brineybeard off of it into the ocean. That's the last you see of him for the rest of the battle. He still shows up in the epilogue, though.
[[/folder]]

[[folder:Sally Stageplay]]
[[quoteright:219:https://static.tvtropes.org/pmwiki/pub/images/sallystageplay.png]]
->''"Stay away from center stage or succumb to the power of a starlet's rage!"''
An actress you fight on a stage in front of an live audience in "Dramatic Fanatic".
----
* AlliterativeName: '''S'''ally '''S'''tageplay.
* ActionDressRip: Bursts out of her wedding dress before the battle, though she's wearing a different dress underneath.
* ActionMom: Assuming the babies in her second phase are her actual children (which is likely, as they resemble her and her husband).
* AllPartOfTheShow: The whole battle is treated as just part of the play she's in. Her third phase even has her sending out cardboard props at you.
* AnachronismStew: The "play" in her battle starts out rather normally for the time period, but in her third phase, she "transforms" into what is essentially a [[EasternRPG JRPG]] final boss. So despite the game taking place in a 1930s cartoon, her play manages to reference games that would come out about six decades later.
* AnimateInanimateObject: Her parasol seems to have teleportation abilities and can drop pieces of itself and grow them back.
** Sally herself apparently turns into one in the third phase. Despite being a cardboard cutout, she's able to change expressions, clutch her chest in pain when defeated, and taunt you if she beats you.
* ArtShift: In the third phase of her battle, she appears as a cardboard prop, which is drawn with watercolors and LimitedAnimation rather than the usual fluid ink animation.
* AscendedExtra: Not Sally herself so much as her husband; if you take the secret route where you drop the chandelier on him, he goes from being a background element into being an active hazard in the third phase of the fight, blocking off a significant part of the stage floor and sending cherubim to push flame-colored pinwheels across the stage.
* AttentionWhore: Sally certainly seems like this, doesn't she? She calls herself a starlet, tells you not to get in the way of her performance, and in the final phase of her fight, she doesn't even focus on Cuphead; she's too busy drinking up the applause from the audience.
* BadassNormal: Basically the only boss who fights without being assisted by or transforming into some sort of giant monster (or being one to begin with). Additionally, her final form is perhaps the most mundane in the game.
* BattleCouple: She and her husband were originally intended to be this for their battle with the boys. After a post-game update, they can potentially be this in the third phase if you end the first phase by [[VideoGameCrueltyPotential dropping a light fixture on her husband in the first phase]].
* CameBackStrong: Parodied. As part of the play, she "dies" after the second phase, complete with a costume change into an angel outfit and either the actor portraying her husband crying tears of sorrow or a priest bowing down in agonizing prayer if you squished the husband earlier. Then she goes OneWingedAngel, as detailed below.
* CurtainCall: In the patched version, Sally's co-stars will appear in the background to take a bow for the audience during her final phase.
* DramaticWind: At the beginning of the boss battle, you notice that the wind is blowing on her wedding dress and veil as she looks at you with disdain before she makes the ActionDressRip mentioned above (although the battle takes place in a ''stage!'').
* DualBoss: If the secret path of the fight is taken, Sally's third phase will have a cardboard cutout of her husband participating alongside her cutout. Unlike the other secret double-bosses, both of them share the same health and the only thing added is an reoccurring new attack during that phase.
* EnfantTerrible: The babies in the second round can drop their bottles on you. And one of them will push out a "fireball" at you in the alternate third round.
* EverythingsBetterWithSpinning: She'll do a spin dive kick for most of her attacks and send out a spinning parasol in the final phase.
* FallingChandelierOfDoom: In the post-game update, during the first phase of Sally Stageplay's battle, you can stand on the two floating cherubs to lower them down and bring down the chandelier on her husband and squish him, shocking Sally so much that she'll cut the first round short to mourn over him and change the course of the second and third rounds.
* FieryRedhead: While her hair is usually blonde, the valkyrie cardboard cutout of her that serves as the third phase has red hair (and so does she in the death cards when you lose, where she's costumed as one).
* FunnyBackgroundEvent: Get hit in the first phase and her fiancé will do a little heel click. Hit Sally, and he'll tug on his hat. Jump on both of the platforms, and a light fixture will crush him, causing Sally to cut the first phase short to mourn for him and the second phase to take place at a nunnery.
* GigglingVillain: She's constantly cackling and clearly having fun with her battle. [[{{Mooks}} Her babies]] also giggle as they drop bottles on you.
* HenpeckedHusband: The guy that portrays Sally's husband in the "play" just stands in the background acting cowardly, doing little to contribute to the battle except drive his wife in his car (that is, until you bring down the FallingChandelierOfDoom on him in the post-game update, changing the course of the second and third rounds). That being said, [[AwLookTheyReallyDoLoveEachOther she does reward him with a smooch in the epilogue]].
* ImagineSpot: The third phase of the fight can be taken as this.
* LargeHam: Her mannerisms really come off as over the top. She is a stage actress, after all.
* NeutralFemale: Gender inverted by Sally Stageplay's husband during her boss fight; despite [[TopHeavyGuy looking fairly capable]], he runs around uselessly in the background and looks concerned in the manner associated with this trope, while his wife delivers all the beatings to Cuphead. Unused sprites do suggest that he was originally intended to be fought at some point during the battle... and he can be, if you go out of your way to squash him flat as of a post-launch update.
* OneWingedAngel: Also parodied. She doesn't actually transform in her third phase. It's just a cardboard prop that resembles her wearing something you would expect from an EasternRPG FinalBoss (thus, the reason it's a parody). In her final phase, she's literally dressed as an angel, but doesn't do any attacking herself and lets her spinning umbrella do the work. Leaving aside the parody elements, this is actually an aversion, as Sally herself never once undergoes a transformation in order to up her game against the boys, which plays a large part in her BadassNormal status.
* ParasolOfPain: One that's tremendously versatile at that, playing roles like "MookMaker", "teleporter", and "spinning top of death".
* PietaPlagiarism: During her third phase, the cardboard cutout of her husband (if you squished him via FallingChandelierOfDoom) parodies the ''Pieta'' by striking a pose similar to that of the "Rest" part of the Statue of the Gods in ''VideoGame/FinalFantasyVI'' (see ShoutOut below).
* ShoutOut:
** Like the final boss battle in ''VideoGame/FinalFantasyVI'', Sally's third stage begins in the clouds, where she descends from the rafters as a painted angel backdrop sporting multiple purple wings. In the post-game update, the cardboard cutout of her husband you've squished earlier (complete with HolyHalo) also bears [[https://vignette.wikia.nocookie.net/finalfantasy/images/2/23/FFVI_iOS_Rest.png/revision/latest/scale-to-width-down/350?cb=20140815010558 a striking pose similar to that of]] the "[[https://finalfantasy.fandom.com/wiki/Rest Rest]]" part of the [[https://finalfantasy.fandom.com/wiki/Statue_of_the_Gods Statue of the Gods]] in that game. There's even cards in the upper-left corner that display her next attacks.
** Her battle may be a stylistic reference to ''VideoGame/DynamiteHeaddy''. Whereas that game's setting is a puppet show, Sally fights Cuphead during her vaudeville act.
* SlouchOfVillainy: Not done by Sally herself, but her husband is seen leaning on a bed and eating grapes (invoking the Greek god Dionysus) in the alternate path for the third phase, while otherwise contributing little in terms of new attacks.
* SmoochOfVictory: In the ending, Sally can be seen triumphantly planting a kiss on her husband as Cuphead and Mugman announce that they are free from the Devil's debt.
* SmugSnake: Spends the entirety of her final phase smiling smugly as she takes in the audience's applause. Even before that, most of her death-quotes are self-aggrandizement or telling Cuphead to [[GreenEyedMonster get out of her spotlight]].
* StationaryBoss: The cardboard cutout/s in the third phase don't move ''or'' directly attack; all of their attacks come from other places on the stage.
* SternNun: In the alternate second round, there's a nun who appears from window to window at St. Timothy's Nunnery, intending to drop cardboard crosses at you, some of which are pink and parryable.
* TogetherInDeath: A strange sort of in-universe take. She mourns her husband's death on the secret route, and once she is also "killed" at the end of her second phase both of them return as cardboard cut out angels you have to fight.
* TokenHuman: One of only three human bosses, and notably the only battle in the game where you ''only'' fight a human.
* TrashTheSet: Quite literally; in the final phase, the stage is basically a mess as she sends her umbrella after you.
* {{Valkyries}}: She "transforms" into one in the third phase of her battle. We say "transforms" in quotes because it's not actually her; it's a cardboard prop that "casts" spells and is meant to stand in for her as Sally herself recovers for an encore performance. Though, given the sorts of transformations other bosses undergo, it may well be the case that she literally transformed into a cardboard cutout.
* WidowedAtTheWedding: In the Switch and Patch 1.2 versions, if you take the secret route, you end up 'killing' her fiancé/husband by crushing him with the chandelier.
* WingedSoulFliesOffAtDeath: When Sally's second phase is defeated (thus dying in her play), she [[InstantCostumeChange instantly switches into an angel outfit]] and "flies" off the stage on wires.
* YouExclamation: Although a bit hard to hear, she does this during the start of the second phase when she sees that Cuphead and Mugman are still on the stage. It makes more sense if the first phase ended with her fiancé's death.
[[/folder]]

[[folder:Werner Werman]]
[[quoteright:220:https://static.tvtropes.org/pmwiki/pub/images/wernerwerman.png]]
->''"Zis tank is ze ultimate veapon! You vill not vin!"''
A giant rat that controls a tank built from a soup can to fight you. Meanwhile, a massive cat by the name of Katzenwagen watches the battle, and eventually intervenes in the final stretch. You encounter them in "Murine Corps".
----
* AlliterativeName: '''W'''erner '''W'''erman.
* BackgroundBoss: The third phase turns the battle into this once Katzenwagen suddenly decides to have Werner for a snack and goes on to attack you.
* BadassNormal: Werner is an expert machine pilot, and that's all he really needs to fight the Cup Brothers. As a result, he's notably one of only two examples of this in the entire game, the other being Sally Stageplay.
* BambooTechnology: [[spoiler:Katzenwagen aside]], Werner uses a tank made out of a soup can and simple machines which shoots bottlecaps and chewed gum. His second phase also has bottlecaps that act like circular saws.
* CarFu: One of his first phase's attacks is simply running you down with his tank. You can avoid him by using the springboards he tosses out, or with the Smoke Bomb if you have it equipped.
* CatsAreMean: Katzenwagen, who seemingly eats Werner and then sets its sights on you. [[spoiler:In this case, it's a mecha-kitty that's piloted by Werner himself.]]
* CavalryOfTheDead: The third phase has ghost mice backing the Katzenwagen.
* CigarChomper: Werner starts his battle off by lighting a cigar and keeps it in his mouth through the entire fight.
* CoolHelmet: Werner sports a [[https://en.wikipedia.org/wiki/Pickelhaube Pickelhaube]].
* DefectorFromDecadence: The medals in the background of the fight indicate that Werner was born in Austria and he defected to the British during the first world war. The third medal is harder to determine but the dark blue edges of his ribbon indicate that he spent the remainder of his service in the Royal and Merchant Navies (also evident by the ghosts in the 3rd phase of the battle, they either fought alongside him in the war or were ''prisoners of war''). The light blue center of his ribbon indicates that he served in the air force, likely referencing the Battle of Jutland 1916 since it involved Naval Aviation.
* EatenAlive: After beating Werner's second phase, Katzenwagen suddenly knocks down the wall and eats him. [[spoiler:Or so it appears; it's actually a clever method of him entering the mechanical cat and manually controlling it in a last-ditch effort to put the boys down.]]
* EpicFail: The transition from Werner's first phase to his second involves his can tank bringing out a firework, only for the mechanical arm carrying to fail and drop it inside the can, causing it to blow up.
* {{Expy}}: Katzenwagen resembles a pre-ArtEvolution WesternAnimation/{{Tom|AndJerry}} quite a bit. Werner himself resembles [[Characters/ClassicDisneyShorts Mortimer Mouse]].
* FakingTheDead: [[spoiler:After the second phase, he's seemingly eaten by Katzenwagen, which forces Cuphead and Mugman to defend themselves from it. However, Katzenwagen is revealed to be a mecha designed to scare off any intruders or give Werner the advantage]].
* {{Foreshadowing}}: When your bullets hit Katzenwagen in the third phase, [[spoiler:it makes a metal clinking sound]]. Additionally, after Katzenwagen bursts in and eats Werner, the brothers don't get the latter's contract, hinting that [[spoiler:he's still alive]]. Speaking of Katzenwagen, you can occasionally see it peeking through the cracks and mouse hole in the wall into the battle before it shows up in person.
* FunetikAksent: Werner's game over quotes have him speak in an exaggerated German accent.
* GadgeteerGenius: That tank looks like just a soup can on treads, but it's equipped with a cigar lighter, bomb cannon, catapult, firework launcher, and flamethrower. The house is rigged with bottlecap buzzsaws. [[spoiler:And did we mention the giant mechanical cat Werner's got on standby just outside?]]
* HumongousMecha: [[spoiler:It's not very obvious at first, but Katzenwagen serves as Werner's trump card in the final phase of the fight, and is revealed to be one upon his defeat.]]
* HurricaneOfPuns: Nearly everything about Werner is a pun in some way: his name, who he's based off of, the name of his level...
* {{Kaiserreich}}: Werner is based primarily on World War I-era German soldiers, with his Pickelhaube and soup-can tank. He also has war medals and bullet shells hanging around his mouse hole, although a Union Jack flag can be seen near the ceiling, oddly enough, and 2 British medals.
* MacroZone: They are fought in a mouse hole in a giant house.
* TheManBehindTheCurtain: [[spoiler:Werner is revealed to be the one controlling the mecha-cat Katzenwagen, once you beat the third phase.]]
* MeaningfulName:
** [[spoiler:Katzenwagen means "Cat Cart" and it is Werner's last resort in the fight]].
** Werner means "soldier" and he's a veteran of World War 1. Wermin is a German pronunciation of "vermin".
* MegaNeko: Katzenwagen.
* OneWingedAngel: Double Subverted. [[spoiler:What initially appears to be a BaitAndSwitchBoss in the final phase turns out to actually be this.]]
* OurGhostsAreDifferent: Ghost mice that fly out of Katzenwagen's mouth and shoot out parryable projectiles. These are actually spirits who were left trapped inside Katzenwagen's stomach.
* PerpetualFrowner: Werner lapses into this unlike most of the other bosses, though this may just be an animation quirk from the cigar in his mouth. He does, however, smile in the good ending.
* PlayingWithFire: Werner's second phase has him using chair-mounted {{f|ireBreathingWeapon}}lamethrowers.
* PunBasedTitle: The title of their stage is "Murine Corps". "Murine" is an adjective that pertains to the subfamily of old world rats and mice.
* PunnyName: Along with having a case of AccentDepundent, Werner's last name also sounds like the German word "Wehrmann" which is an old way to address soldiers, fitting well with his Pickelhaube helmet. [[invoked]]
* ResourcefulRodent: Werner fights by using a tank that's been made from various household junk (a tin can, rubber bands, and wood) and he was able to turn a bottlecap into a buzz saw.
* RoboticReveal: [[spoiler:When beaten, Katzenwagen's face falls off and is revealed to be actually a mecha piloted by Werner.]]
* RodentsOfUnusualSize: Werner is shown to be roughly the same size as other humans in the ending.
* ScreamsLikeALittleGirl: When Werner can't seem to control his tank anymore and when he gets eaten by Katzenwagen.
* ShoutOut: The whole fight is based off war cartoons and ''WesternAnimation/TomAndJerry''; not only does Katzenwagen bear a striking resemblance to Tom in his early years (when he was known as Jasper), but Werner's screams sound vaguely like [[https://www.youtube.com/watch?v=4eHCxCLYuE0 Tom's]] too. [[GeniusBonus This also makes sense on another level]]: "Jerry" was a common nickname for German soldiers during UsefulNotes/WorldWarI.
** His physical appearance is partially based on [[WesternAnimation/ClassicDisneyShorts Mortimer Mouse]].
** Katzenwagen's attack patterns and Main/RoboticReveal are taken straight from the [[https://www.youtube.com/watch?v=FcmSxIUbVLE Cheshire Cat]] in ''VideoGame/TheAdventuresOfBatmanAndRobin''.
** Katzenwagon's preferred attack method, being a stationary body in the background while using his arms to attack in the foreground, is borrowed from the giant gorilla boss from ''VideoGame/TecmoKnight''.
* SpreadShot: In Werner's first phase, the tank can catapult a spread of random garbage at the heroes.
* TacticalSuicideBoss: You'd expect a military-themed boss to be more, ahem, "tactful".
** Werner's first phase have him launching various debris, before sending his tank in a charging tackle. Problem is, those debris include a pair of spring-loaded platofrms allowing Cuphead and Mugman to leap over his tackling move.
** Then there's the Katzenwagen, which can attack forward (evidenced when it [[spoiler:collects Werner as its pilot]]) and yet chooses to lunge at Cuphead and Mugman from the ''side''.
* TankGoodness: Werner pilots a makeshift tank made from a giant soup can in his first two phases.
* VisualPun: The cannon on Werner's tank shoots literal cherry bombs.
* TheUnintelligible: Katzenwagen does not have any spoken taunts in its Game Over screen; instead, it simply hisses and meows.
* WartimeCartoon: Being a rat with a German accent and pickelhaube helmet, which were often shown in [[UsefulNotes/WorldWarI WW1 depictions]], it can be assumed Werner came from one of these.
* YouDirtyRat: He fights with a homemade tank, [[spoiler:he also created Katzenwagen as a mobile tank]]. Since he's in debt to the devil, it's suggested by the background of his home that the Devil may have assisted him in defecting to the British army during [=WW1=].
[[/folder]]

[[folder:Dr. Kahl and his Robot]]
[[quoteright:223:https://static.tvtropes.org/pmwiki/pub/images/drkahl.png]]
->''"OBJECTIVE COMPLETED. TARGET SCRAPPED."''\\
''"I've got the perfect equation to hinder yer evasion!"''
A mad scientist piloting a giant robot (which is named as the debtor) that fights you in the junkyard in "Junkyard Jive".
----
* AfterTheEnd: His level looks like a utter warzone. Justified, in that the fight takes place in a junkyard.
* AndroidsArePeopleToo: The contract specifies Dr. Kahl's robot specifically, so it is not only autonomous but capable of signing into contracts and ''has a soul''.
* AttackItsWeakpoint: The robot has several of them, its main weakpoint being its own heart.
* BattleshipRaid: His robot's first phase is the only boss in the game with destructible "parts" on its body.
* BulletHell: The final phase has Dr. Kahl take out the gems, which fire massive spreads of bullets ''everywhere''. Thankfully, some of these bullets are pink and parryable among the death-inducing ones in the patched version, so that's a bit of a relief.
* ClothingDamage: After defeating Dr. Kahl in his final phase, the resulting explosion blows all of his clothes off.
* DownInTheDumps: Fought in the junkyard.
* DroneDeployer: One of the first attacks.
* EarlyBirdCameo: While the robot's an Isle 3 boss, a miniature version can be seen in mobile form during Djimmi's fight in Isle 2 if you trigger the alternate route.
* EatingMachine: The robot is seen chewing bubblegum in his intro, blowing a bubble before the match starts.
* EnergyWeapon: Uses two in the first phase against you, one that fires at the last spot you were flying in, and another that takes the whole screen but can be deactivated with a parry to the device emitting it. The gems Dr. Kahl himself has at the last phase also shoot these out on a [[BulletHell smaller but more frequent scale]].
* EvilLaugh: Dr. Kahl delivers a huge one in his final phase when using the gems. The robot itself also lets out some short ones in the first phase.
* FourEyesZeroSoul: Downplayed for Dr. Kahl. Although he wears glasses and uses the power of the gems to attack you, he's more of an AntiVillain, as he and his robot still have souls, [[spoiler:but though the robot's Soul Contract is destroyed in the good ending, the two of them are absent, but at least they are still grateful that they won't have to work for the Devil anymore]].
* GiantScrapRobot: Dr. Kahl's robot is presumably this, if their stage is any indication.
* HumongousMecha: Dr. Kahl's robot itself is a huge robot that he pilots to attack you.
* MadScientist: Looks the part with glasses, a lab coat, wild hair, mustache and beard, and crazy expressions.
* MorallyAmbiguousDoctorate: Unknown what he's a doctor of, but clearly the evil kind.
* NoCelebritiesWereHarmed: His design may reference a caricature of [[Creator/MarxBrothers Groucho Marx]] that was frequently used in late '30s and early '40s cartoons.
* OhCrap: The Knockout animation has the doctor making this expression, upon realizing his robot is about to blow.
* OneWingedAngel: The robot becomes just a head in the final phase, with Kahl now being visible and using magical gems to fight.
* PetTheDog: His ''robot'' is the debtor, not him; he still helps it fight.
* PapaWolf: Implied to be the reason why Dr. Kahl is helping his robot fight against you, he doesn't want his creation face you alone.
* PurpleIsPowerful: A genius scientist with purple hair.
* RidiculouslyHumanRobots: Let's see... it has a heart, a soul, emotions, chews bubblegum, and can feel/express pain. Who knows what else of its personality this war machine is hiding?
* RoboSpeak: Both of the robot's death screen quotes are robotic messages.
-->''"OBJECTIVE COMPLETE. TARGET SCRAPPED."''\\
''"MALFUNCTION. MALFUNCTION."''
* SelectiveMagnetism: One attack in the first phase after the middle part of the robot is damaged is a magnet that pulls Cuphead and Mugman to the bottom-left of the screen, leaving other objects unaffected.
* ShoutOut: His name is a shout-out to legendary animator [[Creator/DisneysNineOldMen Milt Kahl]]. Design-wise, he's a clear one to both [[Franchise/MegaMan Dr. Wily]] and [[VideoGame/SonicTheHedgehog Dr. Robotnik]] — a spiky-haired mad scientist who uses robots and has his own flying capsule (what remains of his robot's head in the final phase even resembles a Wily Capsule), but later uses the power of magical, multi-colored gems and skull-motif bombs to attack you. His robot's design clearly takes after ''WesternAnimation/TheIronGiant'' (as in, the original book's take - Ted Hughes' ''The Iron Man'' -on the Giant's design, not the 1999 movie based on it), and being very close to the boxing robot from ''[[WesternAnimation/ClassicDisneyShorts Mickey's Mechanical Man]]''. His intro also has him [[EyebrowWaggle waggling his eyebrows]] in a similar manner to Dr. Wily.
* SmartPeopleBuildRobots: Dr. Kahl himself, of course.
* SmartPeopleWearGlasses: Wears a pair of lime green glasses.
* SpreadShot: Once the laser on his head in the first phase is beaten, the robot gets the ability to spit out a spread of nuts and bolts. In the third phase, the boss attacks with a BulletHell version of this (whose load is at least lightened a bit in the patched version).
* StationaryBoss: The robot doesn't move in its first phase, but unlike other shoot-em-up bosses, you can't just open fire on it, since it has three weak spots on its body to destroy.
* StealthPun: The robot's weak point in the first phase is a large, metal heart. Looks like the tin man has a heart, after all.
* TinCanRobot: The robot has the classic old-fashioned clunky robot look.
* WhatHappenedToTheMouse: Neither he nor his robot are seen in the ending.
[[/folder]]

[[folder:Cala Maria]]
[[quoteright:221:https://static.tvtropes.org/pmwiki/pub/images/calamaria.png]]
->''"You are a cutie... I am not sure if I should catch and release!"''
A gigantic mermaid fought over the ocean in "High-Seas Hijinx".
----
* AttackOfTheFiftyFootWhatever: A giant mermaid who basically towers over the two boys and their planes.
* TheBeastmaster: In the first two phases, she fights primarily by summoning sea creatures to attack the two brothers.
* BodyHorror: When using her petrifying gaze, two of the snakes on her loop around to the back of her skull and [[EyeScream emerge from her eye sockets with both her eyes in their mouths.]]
* BreathWeapon: In her first phase, she exhales ghosts that target Cuphead and/or Mugman's position(s).
* CuteMonsterGirl: She's a giant mermaid/gorgon hybrid, and a complete MsFanservice.
* CuteGiant: A gigantic mermaid with large eyes and an adorable smile. Somehow, she still manages to retain some cuteness after turning into a gorgon.
* EquippableAlly: Can obtain two different coloured fish that spit different elemental projectiles at you. The red fish spit {{fireballs}}, while the yellow fish spits a {{homing|Projectile}} [[ShockAndAwe electrified]] dolphin.
* EyeScream: From a distance, Cala Maria's petrifying gaze can look like she's using binoculars to focus the beams it produces. Look closer, and you'll see that two of her snakes are halfway out of her eye sockets, holding her eyes in their mouths.
* EyelashFluttering: Starts her battle by adjusting the octopus on her head and batting her eyes with a xylophone "doink doink!" sound.
* FlunkyBoss: She summons all manner of aquatic life to attack you with.
* {{Gasshole}}: She belches out pirates ghosts as an attack.
* GiantWoman: Well, giant mermaid, but she's one of the most human-like characters of the game.
* GigglingVillain: Lets out a high-pitched giggle everytime she dives underwater to weaponize a giant fish. She outright cackles after transforming into a gorgon.
* GoodScarsEvilScars: Averted. She has what looks like some type of scar on her left arm if you look. It doesn't really make her any less attractive or look like any sinister markings. And as for the evil part, well, as noted above, she and the other bosses aren't necessarily evil, just trying to save their souls.
* GorgeousGorgon: Turns into a gorgon after taking enough damage, yet still doesn't look that bad despite the scary upgrade.
* HartmanHips: She's got some nice wide hips, and they're in constant motion too!
* LosingYourHead: The final phase of her fight has her detaching her head from her body and floating though a spiked cave.
* MsFanservice: She's quite the dish and she knows it. Her Gorgon form doesn't look too bad either. [[GorgeousGorgon As noted above]].
* NonStandardCharacterDesign: Compared to the other female characters, like Sally Stageplay and Baroness von Bon Bon, Cala Maria has a figure and flaunts it.
* OhCrap: When she uses a giant fish to send projectiles at you (some of which are pink and parryable in the patched version), she reacts in this way when it slips out of her hands. A more pronounced such reaction follows just before her eels shock her and trigger her second phase.
* OneWingedAngel: As mentioned several times, her gorgon form. Her floating head phase is more of a ClippedWingAngel due to not being as powerful and relying more on the surrounding environment to hurt you.
* OurMermaidsAreDifferent: About fifty feet tall, wears an octopus, can turn into a gorgon...
* PainfulPointyPufferfish: She can summon them to damage the players.
* PsychoElectricEel: Two of them appear during the 2nd phase, turning Cala Maria into a gorgon. More show up to assist her in battle too. And they shoot many bullets, some of which are pink and parryable in the patched version.
* PunnyName: Besides the obvious "calamari" pun, Calamaria is a species of snake, and Cala Maria is a beach in Spain, so it's a pileup of puns!
* PurpleIsPowerful: She's got purple "hair", lavender-tinted skin, and she's a powerful foe.
* SeashellBra: Befitting a mermaid.
* ShoutOut:
** One to ''VideoGame/{{Parodius}}'', which likewise featured a giant mermaid with a green tail as a boss in ''Gokujyo Parodius''. And a giant gorgon boss in a later game, ''Sexy Parodius'', which itself was a shout out to ''Franchise/{{Castlevania}}'', since it was virtually a giant Medusa Head[[note]]both ''Parodius'' and ''Castlevania'' were made by Creator/{{Konami}}[[/note]].
** Additionally, when her body turns to stone in her last phase, her head breaks off first, and then her arms. This causes the resulting torso to resemble the famous incomplete statue of Venus de Milo.
** The sea turtle she summons in her first phase looks like a very angry Toby Tortoise from Disney's ''WesternAnimation/SillySymphonies'' (specifically "WesternAnimation/TheTortoiseAndTheHare"), and his fisticuffs pose alludes to the boxing match held in "Toby Tortoise Returns".
* SnakePeople: She takes on some serpentine features once she turns into a gorgon, gaining fangs, snake-like eyes, and a forked tongue. Even in her first phase, her undulating movements evoke the spirit of the trope.
* SpreadShot: Her first phase can use a spread shot via a red fish "weapon" (some of whose bullets are pink in the patched version), and can also call in a turtle that fires mines into the air that explode into 8-way spikes. Her second phase has the respawning electric eels that fire spreads of 5 (some of which, again, are also pink via patch).
* StationaryBoss: Only during the second phase, where she loses the ability to retreat underwater.
* SwallowedWhole: Implied. She uses ghosts of dead sailors as a BreathWeapon.
* TakenForGranite: In her gorgon form, she can fire out a huge beam that'll turn our heroes into stone, which will put them in danger of getting hit by a real bullet if they're not quick to break out of their stoned forms. This eventually gets turned on her in her second-to-third phase transition, where her whole body (sans her head) turns to stone and crumbles into the ocean, forcing her to detach her own head and continue battling the boys. In simple difficulty, her entire body becomes completely petrified after her defeat.
* TheTease: Not only does she pose before the boys in her intro, but her game over card in her first phase definitely has her flirting with them too.
-->"You are a cutie... I am not sure if I should catch and release!"
* TentacleHair: She has an entire octopus adorning her head, its tentacles forming her hair. When she transforms into her [[{{Medusa}} gorgon]] OneWingedAngel form, though, these tentacles become live snakes.
* ThroatSlittingGesture: Shown doing this in her first phase game over card, as seen in her page image.
* UnexplainedRecovery: By the time you get to her third phase, her body has been completely shattered aside from her head, which is now floating. And this is not even taking in an account her gorgon transformation. The ending shows that she's fine, back to her initial appearance, and also much smaller, [[YourSizeMayVary apparently no taller than Cuphead and Mugman]].
* WorldsSmallestViolin: When she's beaten in Regular Mode, one of her snake hairs plays a tiny violin.
* XRaySparks: When being electrocuted by the eels during the transition into the second phase.
* YourSizeMayVary: She's absolutely enormous during her battle, but relatively normal-sized in the ending.
[[/folder]]

[[folder:Phantom Express]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/phantomexpress.png]]
->''"I can... see... into the future. You... will be... counting worms."''\\
''"All aboard!! Next stop — your funeral."''\\
''"Sorry! This train is only for the dead... but we can help you with that."''\\
''"What a glorious night for me to bring the fright!"''
A haunted train comprised of the Blind Specter, an eyeless ghost; the Conductor, a skeletal conductor; the Lollipop Ghouls, two giant animate pistons; and finally, the train's living engine, the Head of the Train. You fight them on a rail cart in "Railroad Wrath".
----
* AfterlifeExpress: Inhabited by many spectral beings who attack you.
* AnimateInanimateObject: In the third phase, the heroes fight against a pair of train pistons with faces protruding from the wagons, and during the final phase, they fight the train's engine.
* AttackItsWeakPoint: In the final phase, you must parry off the engine's tail to expose his boiler core and shoot at that.
* BiggerOnTheInside: It must be, considering the Conductor and the Lollipop Ghouls only partially emerge from the train cars.
* BlindSeer: The Blind Spectre's game-over quote invokes this, though it's not clear if this is just his way of trash-talking our heroes.
* BreathWeapon: The Lollipop Ghouls in the third phase attack you by breathing columns of [[ShockAndAwe lightning]].
* DeathFromAbove: The Head of the Train has many of these attacks, since he's galloping after you on stilt legs. Not only can he drop [[BadWithTheBone rings made of bone]] on you, but if you open his boiler core, the hot coals inside will also start dropping on your head.
* DemBones: The second phase sends out the Conductor, a giant skeleton conductor to try and crush you.
* DiscOneFinalBoss: The final runaway debtor that you need to get a contract from, but the game isn't over just yet.
* EveryoneCallsHimBarkeep: The Conductor has no official name aside from...well, the Conductor.
* EyesDoNotBelongThere: The Blind Specter in the first phase has eyes it can shoot out from its palms... and yet ironically, it never has an eye in its actual socket.
* EyelessFace: The Blind Specter's one eye socket is completely empty at all times.
* GhostTrain: The Phantom Express is a creepy living train who carries a ghost, a skeleton conductor, and two lightning-shooting creatures through a dark forest.
* HighSpeedBattle: You spend the whole fight racing alongside them in a rail cart with parryable controls, while continually-appearing minions try to mess with your positioning.
* ImpliedDeathThreat: Every phase except the final does this in their respective game over quotes.
* SentientVehicle: Aside from the fact that the train ''owes the Devil its soul'', the train engine itself attacks the heroes in the final phase.
* ShoutOut: The final phase could be one to Sleeper Brakeman's fight from ''VideoGame/NoituLove 2'', involving a train engine on legs with an object at its back which has to be hit in order to make the boss vulnerable. Doom Train from ''VideoGame/FinalFantasyVI'' may also have been an inspiration, since you start fighting the "guests", then the conductor and finally the train itself. Even the Game Over text claiming it is meant only for the dead is something said once in Final Fantasy 6 when the group arrives at the train station.
* SpiderTank: At the final phase, the engine stops the train to reappear galloping like a horse with [[RubberHoseLimbs spindly legs]].
* StationaryBoss: Unlike the other parts of the boss, the Blind Specter stays on the right side of the screen and doesn't require moving the handcart to hit it. It compensates by tossing eyeballs that can block shots and spawning pumpkin enemies that can ''parry'' the pink handles at the end of your cart, either yanking it out from under you while you're in mid-air, or sending it straight towards the Specter itself.
* WhatHappenedToTheMouse: The Head of the Train, the Conductor, and the Lollipop Ghouls aren't seen in the epilogue (indeed, the latter are seen melting upon defeat). The Blind Specter from the first phase does, though, perhaps on behalf of the entire train.
* WrongSideOfTheTracks: Their tracks, that is - Inkwell Hell is just on the other side on the map.
* {{Youkai}}: All of the ghosts inhabiting the Phantom Express are subtly based on different types of youkai. The Blind Specter is based on ''tenome'', an eyeless old man with eyeballs on his hands; the Conductor is based on ''{{gashadokuro}}'', a giant skeleton; the Lollipop Ghouls appear to be based on ''rokurokubi'', women that have long serpentine necks; and the Head of the Train is based on ''oboroguruma'', oxcarts with faces found on roads late at night.
[[/folder]]
----

Top