History Characters / CupheadRunawayDebtors

* 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 the cups are trying to collect their soul contracts. [[NintendoHard Granted, they're justified in thinking that.]]

* AuthorityGrantsAsskicking: Although most of the time she sends her mooks to do the bidding, she can also attack using a sugar cane as a shotgun.

* KamehameHadouken: Ribby fires these off in his first phase.

* 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.

* TheArcher: Hilda's Sagittarius form, where she turns into [[GenderBender a man on a cloud]] and shoots arrows at you.

* BattleCouple: She and her husband were originally intended to be this for their battle with the 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]].

* SmugSnake: Downplayed. He's an AntiVillain just like the rest of the Runaway Debtors, and he really is quite powerful and impressive. However, he has a smug and confident attitude throughout the entire fight up until his defeat. His character designer, Jake Clark, stated in [[https://youtu.be/ZFzqxEYvSk0?si=NQN0uw1YRLXGSJk0 this lecture]] that Djimmi was intentionally made to be as smug as possible so that players would "want to kill him."

* TechnicalPacifist: Ollie seems to be the only boss in the game who ''really'' doesn't want to fight. If the player starts shooting him, Ollie does nothing but burst into tears, though he doesn't seem to realize that his tears can hurt the player character. Chalice. If the player spares Ollie, he seems relieved.

* RiseToTheChallenge: Her stage features a constantly-ascending vat of honey.

!!In general

* 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.

* 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]].

* 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.