History Funny / Cuphead

** Speaking of Esther, her later transformations delve into [[BlackComedy comedy blacker than the snake oil she's shooting at you.]] She gets sucked into her own vacuum, which ''cooks'' her. Into sausage. Living sausage. [[CrossesTheLineTwice That still fights you.]] And if that's not enough, she turns into ''a grocery store tin can of sausage.'' And yes, you fight that too. And here you thought Goopy and Wally were [[WhyWontYouDie persistent.]]

*** And then there's the snail's quote: "Surprise! Forgettin' about the boss ain't wise." Yes, [[LeaningOnTheFourthWall he's basically telling you that you failed]] because you forgot about the damn Snail.

** The surreal nature of the Sergeant O'Fera's wiener-dog airship just makes the third phase. First off, it's actually wearing ribbons on its propellers just like how real dogs wear bows. Throughout the fight, you can see it flying through the background, bending and stretching like a noodle. Then comes the third phase, where they actually break the fourth wall by grabbing the camera and twisting it 90 degrees. The defeat animation involves knocking the airship's teeth out and its ribbons getting frayed. And O'Fera starts whimpering like real dogs do.

** After you beat the Anteater, you get a [[VictoryFakeout fake "KNOCKOUT!" screen]] made of flypaper (with two fly enemies stuck to it). Then when the snail mob leader (who impersonated the announcer at the beginning of the fight and the fake knockout) is defeated and the actual "A KNOCKOUT!" screen appears, the real announcer can be heard clearing his throat just before delivering the line, implying he didn't appreciate the snail stealing his bit.

** The fact that the giant Anteater that is fully ready to eat or just beat up both children and the local police is [[AffablyEvil polite enough to tip his hat first]] is pretty amusing as well.

** Just how far they go with the dog-theming of the Howling Aces. It's not enough the bulldog sends crossbones and weaponizes a cat, their pups spend the first phase popping out of his plane tossing tennis balls everywhere, while the airship flying in the background shoots fire hydrant missiles. And in the third phase, the Saluki actually launches doggy bowls at you!
** The puppies' death quote. "Affirm Roger Fox! Affirm Roger Fox!" What's the abbreviation of that? ARF! ARF!
** The surreal nature of the Saluki's wiener-dog airship just makes the third phase. First off, it's actually wearing ribbons on its propellers just like how real dogs wear bows. Throughout the fight, you can see it flying through the background, bending and stretching like a noodle. Then comes the third phase, where they actually break the fourth wall by grabbing the camera and twisting it 90 degrees. The defeat animation involves knocking the airship's teeth out and its ribbons getting frayed. And the Saluki starts whimpering like real dogs do.
** If one makes it to the secret phase of the fight, the puppies fly into the airship's mouth and it licks its lips like it just ate a tasty treat. Then the airship grabs the camera like before, but instead of twisting the screen, both the Saluki and the pups pop out of the hatches in the paws to continue their assault. This includes them actually using the Pineapple Mint against you! Bear in mind the Pineapple Mint looks like a [[StealthPun grenade.]] The defeat animation this time includes the airship making the silliest face, the Saluki wringing her hat crying like she has to hang up her wings, and the puppies making various silly faces of their own.

** The Spider Mobster has an attack where he kicks a caterpillar goon around the stage. That's amusing on it's own, but it gets funnier because [[FreezeFrameBonus if you look closely,]] you can see the caterpillar smiling as he's carried out, only to [[ThisIsGonnaSuck panic]] when he realizes that the spider is reeling up to kick him, as if he's thinking "Okay, what's the plan! Wait... [[OhCrap CRAP!]]"

*** And then there's the snail's quote, "Surprise, forgettin' about the boss ain't wise!" Yes, [[LeaningOnTheFourthWall he's basically telling you that you failed]] because you forgot about the damn Snail.
** The fact that the giant Anteater that is fully ready to eat or just beat up both children and the local police is [[AffablyEvil polite enough to tip his hat]] is pretty amusing as well.

** For a bit of BlackComedy, there's her transformation into her [[GorgeousGorgon second stage]]: a pair of [[PsychoElectricEel electric eels]] pop out of the water in front of her and then sink their teeth into her midriff. Cue XRaySparks [[SlapstickKnowsNoGender and a lot of screaming]]. Also, if one looks closely, they can also see that ''[[ArtisticLicenseBiology the octopus in her hair]] [[RuleOfFunny has a skeleton of its own.]]''