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Season 1

    Carn-Evil 
  • Cuphead's solution to get the fence painting done faster is to dump a bucket of paint into a cannon and open fire, which destroys the fence the second Elder Kettle comes out to check on them.
    • Upon reflection, he insists this idea would have worked with less gunpowder.
  • Mugman insists there's no way they're going to the carnival. The Gilligan Cut to them riding a rollercoaster kicks in before Mugman can even finish his objection.
  • The montage of the boys' day at the park: lots of eating, followed by fast rides. More eating, more rides. Brief stop to vomit, then right back to the rides.
  • Mugman watches the Phone get his soul stolen, notes the odd name of the attraction, sees the crowd of soulless zombies walking around, and takes all of this in with mild bemusement. What finally gets him to panic is seeing that the carnival sign has the word "evil" in it.
  • During the Devil's Villain Song, he starts rattling off his various nicknames, including "The Big D" with a naughty smirk as if he knows exactly what he just said.
  • The Devil is not pleased with Henchman for interrupting his song:
    Henchman: Hey, Boss–
    The Devil: WHAAAAAAAAAT?!! I was singing!
  • The Devil appears to confront Cuphead ruining his scheme, which causes everyone around him to scream in terror and flee.
    The Devil: My fans, they love me.
  • As the brothers tearfully flee from the Devil:
    Mugman: I'm sorry I made you miss! This is all my fault!
    Cuphead: We should've never come here in the foist place! This is all MY fault!
    Mugman: You're right! It IS your fault!
  • When Mugman discovers the destruction of the carnival caused by the Devil, the former suddenly gets an idea on how to destroy the soul-sucking machine:
    Mugman: C'mon, Cuphead! It's time for a double-down!
    Cuphead: [confused] What are you, NUTS?!
    [the boys move closer to the skee-ball machine]
    Mugman: Now pretend like we're cornered!
    Cuphead: [frightened] We ARE cornered!
    [cue the Devil approaching them]
  • After the Devil destroys the skee-ball machine and the souls fly away, he only slaps and pulls at his face in frustration rather than immediately exploding in rage.
  • When the souls are freed, the pig man with the hot dog stares at his lunch in bewilderment... until it, too, gets its soul back, and he happily chows down.
  • Cuphead and Mugman barely escape the ruined CarnEvil with their lives. Instead of chasing after the cups, the Devil just rolls his eyes and petulantly complains "You don't just get to run away!"
  • Cuphead and Mugman reflecting on the day's adventure
    Cuphead: What an amazin' day! We rode rides...
    Mugman: And you owe the devil your soul...
    Cuphead: We played games...
    Mugman: And you owe the devil your soul...
    Cuphead: We're even almost finished with this dumb fence!
    Mugman: AND YOU OWE THE DEVIL YOUR SOUL!
    Cuphead: [already loading another paint cannon] Eh, I ain't too worried about it.
    Elder Kettle: [coming by] Hey, boys, how's that fen- [gets blasted by paint]
    Cuphead: Still too much gunpowder.
    Mugman: And you still owe the devil your soul.

    Baby Bottle 
  • Once the Elder Kettle leaves, the boys immediately get into a Big Ball of Violence, apparently just because he told them not to. But they still take special care to avoid his radio during the brawl.
    • Hearing a knock at the door, the boys pop out with halos on their heads and big grins as if they hadn't literally just been fighting intensely.
      Cuphead & Mugman: (In unison) "Back so soon, dearest Kettle~?"
  • Baby spends the whole episode tormenting Cuphead while Mugman's not looking, and in return Mugman repeatedly chastises Cuphead for getting angry. When Mugman tries to give Baby his prized teddy bear from when he was a kid, the baby rips its head off and destroys its music box without so much as a second thought.
    Mugman: I'M GONNA KILL THAT THING!
    Cuphead: (Pushes Mugman away from the baby) Mugman, no! It's a baby!
    Mugman: IT'S NOT A BABY! It's evil...
    • Prior to ripping off the teddy bear's head, baby looks Mugman dead in the eye before doing it.
  • At one point, Cuphead gets up and yells frantically "Dresser!" Mugman looks on confusedly, asking, "What?" and Cuphead repeats his exclamation, pointing as a dresser gets thrown at them by the Baby.
    • Then the Baby throws a chair at them, and Cuphead exclaims about this too. Mugman tries to learn from his previous mistake by tapping the dresser drawer calmly and saying, "No, dresser". Cuphead has to repeat his exclamation to get Mugman to understand.
  • Cuphead and Mugman have this exchange, making them appear like an old married couple who's about to get divorced:
    Mugman: Not a chance, Cuphead. Baby needs our love!
    Cuphead: What it needs is a leash!
    Mugman: Cuphead! The way you're talking, it's like you never even wanted a baby.
    Cuphead: I didn't!
    Mugman: [gasps] Oh, well, then... I guess I'll do all the parenting myself.
    Cuphead: Be my guest! Hmph!
  • Whenever the baby gets angry, it gives a hilarious Death Glare to whoever it's mad at and says "Mama..." in a threatening voice.
  • At one point, Elder Kettle comes back home, to Cuphead and Mugman's horror, since the baby made a gigantic mess (including several things on fire). However, once he enters the house, he couldn't care less about the mess, simply shrugging and saying "Boys will be boys". But once he sees that his prized radio has been broken, well...
    Elder Kettle: Huh? Door ripped off its hinges? Piano on fire? Fishbowl shattered with fish missing?! Antique China in pieces! Dresser smashed into wall?! More fire?! Eh. Boys will be boys. [chuckles then gasps] MY RADIO!
  • Elder Kettle initially thinks Baby Bottle is really cute... until he rips his mustache clear off. His scream of pain just sells the humor. He gains a bandaid soon after this.

    Ribby and Croaks 
  • The argument that kicks off the episode:
    Cuphead: So let me get this straight, you expect me to believe you sleep-ate an entire container of ice cream without waking up?!
    Mugman: Well you expect me to believe that you did!
  • The start of the pocket lint Running Gag:
    Cuphead: Why does he always get the five bucks?!
    Mugman: And why does he always get the pocket lint?!
  • The pocket lint gets thrown in the water when Cuphead and Mugman get thrown out by Ribby and Croaks, and they stare at it sadly, as if they're losing a loved one. It's even accompanied by sad music.
  • This:
    Ribby: Hey, how did you bozos get in here!? Just kidding! You fine folks are paying customers. You ain't bozos.
    Croaks: Except for this clown!
  • The fact that Ribby and Croaks can't go a few minutes without fighting with each other, but they make sure to stop whenever they see the mayor and his wife and always greet them politely (even at one point when they're chasing Cuphead and Mugman, they still stop to take a picture with them—the wife's less than pleased). They desperately want to be seen as "respectable types" to please their mother.
    • How the Mayor’s wife is always referred to as Mrs. Mr. Mayor.
  • Every time Ribby and Croaks start swinging fists. They actually manage to land a few hits the first time around.
    • When they kick Cuphead and Mugman into the river:
      Ribby: (laughing) Did you see how far I kicked that little punk?
      Croaks: You sayin' you're better than me?
      Ribby: So what if I am?
      (boxing bell rings)
    • When the portrait of their mother catches fire:
      Ribby: Aaaah! Ma's on fire!
      Croaks: You sayin' it's my fault?
      Ribby: So what if I am?
      (boxing bell rings)
    • Finally, when their riverboat is sunk:
      Ribby: Our club! It's ruined!
      Croaks: You sayin' it's my fault?!
      Ribby: So what if I am?
      (boxing bell rings)
      • Bonus points for the fact that it technically WAS indeed Croaks's fault, he was the one who shot the pipe with the firefly's fire which spread to the mother portrait, and he was the first to punch at the wall, causing the water to get through.
  • At one point Ribby and Croaks sing a song about how much they love their mother, complete with a not-so-flattering portrait of her (even pronouncing it "mudda"), but hate their father, who apparently walked out on them.
  • Also, during the song, Cuphead and Mugman have an argument, with Mugman getting ready to shove Cuphead, and it then cuts to an imprint of Mugman's face on the side of the vent. This implies that even though Mugman was the one getting ready to shove Cuphead, Cuphead still managed to overpower him and smash him into the vent.
  • When Cuphead and Mugman get frozen, their faces are hilarious. Also, they get stuck in the kitchen with a chef who is having relationship issues with his significant other, Doris, who pronounces "anniversary" as "anniversiary" for some reason. They escape easily.
    • Also, the chef in question is a big towering bulldog, while his wife is a Dachshund who is about a tenth of his size.
  • After spending an entire episode where Cuphead and Mugman both claim they "sleep ate" each other's ice cream, Mugman decides to finally tell Cuphead the truth... while the riverboat they're in is on fire and filling with water. Sad violin music even begins as Mugman begins his confession, and a random extra on fire runs screaming in the background.

    Handle with Care! 
  • The brothers’ blindfolded pillow fight.
  • Mugman has a comical Freak Out twice when his handle falls off. The second time, he has this to say:
    That does not get any easier.
  • This bit:
    Cuphead: Buddy, relax! We’ll handle it!
    (beat)
    Cuphead: (immediately backpedaling under Mugman’s glare) I mean, take care of it!
  • Cuphead tries increasingly ridiculous ways to stick Mugman's handle back on, including spit, tape, and honey (which leads to them getting mauled by a bear), and Cuphead wistfully wonders if there was just something that could stick one object to another. Eventually it leads to an argument to where Cuphead bursts out:
    Cuphead: I'M the one over here rackin' my brain tryin' to remember what GLUE is!
  • The brothers need to go to Porkrind's to get some glue to fix Mugman's handle, but Mugman is too scared to be seen in public without it. His solution? Dress up as a bride with Cuphead as his flower girl.
    • When the disguise fails, some onlookers are horrified at Mugman's broken handle and run off screaming. All except for one.
      Bowl Boy: Well, I think he looks swell!
      Mugman: Nobody asked you, Bowl Boy! (angrily storms off with a nervous Cuphead following suit)
      Bowl Boy: Gee, what's eatin' him?
  • While Porkrind is out searching for glue, Cuphead thinks of getting a replacement handle for Mugman. He tries all sorts of things, including a candle, a telephone handle, an iron, and a snake.
    Mugman: [in horror at the snake] NOOOOO!
    • One of the things he tries is a toilet flush lever, which is one of two things Mugman actually seems to briefly consider (the other was a half-eaten donut), until Cuphead "flushes" and the whites of his brother's eyes are drained.
  • While comforting Mugman, Elder Kettle drops this gem, which Mugman doesn’t find quite so reassuring:
    Elder Kettle: Mugman, I’m sorry I screamed in horror at the mere sight of you, but it just took me by surprise.
    [Mugman glares at him]
  • As Mugman is successfully cheered up with Elder Kettle’s story, Cuphead declares he wants a “man handle” too and promptly breaks his handle off against the wall.
    Elder Kettle: Well, I suppose that saves the Handle Fairy a trip.
  • The brothers toasting to their new “man handles” with their heads…and shattering them.

    Roll the Dice 
  • King Dice's assistants putting lipstick on King Dice...'s pips on the side of his head.
  • King Dice's reflection flirting with him.
    King Dice: [to his mirror] Who's the host with the most, hmm?
    Reflection: You are, you handsome devil. Mwah.
    King Dice: [coyly] Oh! You're terrible!
  • The Phone's trivia question is 'What's the only mammal that can't jump', to which he answers elephants. Cue two unamused elephants in the audience, with one of them angrily muttering "show-offs..." while the rest of the audience jumps for joy.
    • A bit of a Black Comedy at its finest, but after the phone's soul is sucked out, and his zombified body is dumped into an alley with a cushion, there is a neon sign next to a wall of a building to the right of him that says, "Thank you for playing!"
  • Cuphead’s ecstatic reaction to being chosen as the show’s next contestant.
  • Cuphead keeps taking the microphone from King Dice and increasingly annoying him every single time.
    Cuphead: Everyone in town can hear this, right?
    King Dice: That's right, now first—
    Cuphead: (steals the microphone and blows a raspberry into it) That's for you, Jimmy! And you KNOW what for!
    • He takes the mic at one point to tell a joke but blanks on the punchline with an extended 'Uhhhhhhhh', which gives Dice enough time to piece together that this is who the Devil is after.
  • When King Dice realizes he's unintentionally gotten the Devil's most wanted soul on his show, he rigs all of the challenges to be incredibly easy so that Cuphead will win and go into the prize room that contains the soul sucking machine. Yet somehow, Cuphead continually botches two of every challenge (the first "Name That Tune" challenge, and the "Roll the Dice" challenge) to the point where King Dice has to practically hold his hand the entire time.
    • When King Dice goes to commercial to call the Devil, we see him taking a bubble bath with cucumbers over his eyes right before Henchman gives him the phone.
      Henchman: Duuh... hey, boss? Phone call.
      The Devil: Ugh, this better be important.
    • When Cuphead decides to use Mugman as a lifeline, the spotlight lands on him in the audience. Poor Mugsy's stage fright causes him to freeze in shrunken-eyed terror, as shown above.
    • The way Mugman's animated during this moment. The spotlight shines on him. One second he's sitting normally, literally the next he flashes into a scared state with a creaking sound effect. Almost like someone flicked a switch.
    • In the first "Name that Tune" challenge, Cuphead hems and haws for a moment before guessing "Sprinkle, Sprinkle, Mr. Car?" Elder Kettle, listening in at home, is less than pleased.
    Elder Kettle: SPRINKLE, SPRINKLE, MISTER CAR?! (grabs his radio and shakes it) COME OOOOOOON!
  • Dice finally gets Cuphead to the final game that's designed to be impossible to lose. All he has to do is roll some dice and have it land on any number and he wins. Cuphead rolls them so hard, they explode.
  • Cuphead finally realises the show's rigged, and he declares he and Mugman are going to leave with their dignity intact, picking up Mugman, who's still frozen in terror, and marching out with him carried under his arm.
  • How is King Dice defeated? Elder Kettle's lucky tire—which the boys had chased into the studio earlier—rolls over him and scoops the boys back out the door.
  • When the boys return home, the first thing Elder Kettle does before even greeting them is yell at Cuphead about his idiotic answer from earlier.
  • King Dice is forced to have an extremely awkward elevator ride down to the Underworld with Henchman to tell the Devil about how he couldn't get Cuphead's soul. His face is priceless.
    • Henchman also takes the elevator ride as an opportunity to ask King Dice for an autograph.
    King Dice: (flatly, with the aforementioned "I want to die right now" expression) Not. The time.
  • In the Finnish dub, King Dice's scream when the Devil appears behind him is very high pitched.
  • The Devil removes King Dice from his role as show host and instead gives the role to Henchman, who promptly fails at doing the same dance King Dice does.

    Ghosts Ain't Real 
  • Coming from watching a horror movie, we see that Mugman has a new record... he only had to change his pants three times during the movie.
  • When cutting through the graveyard, Cuphead and Mugman boast to themselves how well they're taking it as it slowly gets darker and they become progressively more and more freaked out.
    Cuphead: Wow! Really startin' to get dark now!
    Mugman: Some might find that unsettlin', but not me!
    Cuphead: Good thing we're both so brave!
    Mugman: I can't think of a time I've been LESS scared!
    Cuphead: Nothin's scary about a graveyard!
    Mugman: It's just a yard!
    Cuphead: Yards are for playin'!
    Mugman: Wehaveayardathome!
    Cuphead: Weshouldvacationhere!
    Mugman: WESHOULDLIVEHERE!
    Cuphead: INEVERWANNALEAVE!!!
  • This exchange, after Cuphead tries assuring Mugman "ghosts ain't real" again:
    Duke: [snickering] You hear that? We ain't real.
    Jasper: [confused] We ain't?
    • Duke then proceeds to smack Jasper on the back of his head as Emma facepalms.
  • Cuphead trying to reassure Mugman after opting they briefly split up:
    Cuphead: You think you’re gonna be scared, but then it won’t be so bad. ‘Cause whyyyyy?
    Mugman: ‘Cause I’m a big, strong man?
    Cuphead: Well, suuuuuure? But also because ghosts ain’t real.
  • Mugman, after coming face to face with a ghost for the first time, gets so scared, his nose falls right off his face. He runs off, only to come back for his nose and reattach it with a honking sound effect.
  • When the boys finally make it home, Elder Kettle screams and attacks them as he mistakes them for zombies.

    Root Packed 
  • Elder Kettle throwing out his back mid-song.
  • For some reason, the boys assume dressing as scarecrows will scare the vegetables into leaving. Not only does this fail to cause the intended reaction, but a murder of crows appears out of nowhere to attack them as well.
  • The gobsmacked looks on Cuphead and Mugman's faces when the cops they called give way to the bouncer.
    Eggplant: Ya ain't on the list.
    Cop: Sorry, boys. We gave it a shot.
  • Cuphead, after being told by Sal that the vegetables' party wasn't over "until sunrise", tries to lasso the moon to make the morning come sooner... 'tries' being the operative term.
    Mugman in a rooster costume: ...Cock-a-doodle-doo?
  • Mugman attempts to get all of the partying vegetables' attention by calling to himself on stage... and then freezes in stage fright, complete with the same expression from "Roll the Dice".

    Sweater Off Dead 
  • After Cuphead has a nightmare in which the goat from the front yard transforms into the Devil who devours his soul, Mugman has his brother follow him outside in the middle of the night to do something about the threat of “the Devil thing once and for all”. When Cuphead sees the sleeping goat, he panics and cautiously goes around it, in the hopes that it doesn't transform into the Devil in real life.
  • The Devil practically squealing and skipping with excitement as he surveys the various evildoing projects his imps have been up to.
  • This bits during the middle of the Devil's gloating about his accomplishment.
    Imp Worker 1: What's he talking about?
    Imp Worker 2: I don't know, but we haven't had a break in 3000 years, so just go with it.
  • When the Devil appears in front of Cuphead, the latter is all set to point and scream "THE DEVIL!" Devil, having none of it, just slaps his finger away in annoyance.
    • Cuphead does it the second time he appears as well, before remembering he's wearing the sweater.
  • The Devil offers Cuphead ten bucks to take off the sweater, who almost does so until Mugman stops him, angrily stating that Cuphead's soul is worth more than that. Cuphead agrees with his brother... and then demands that the Devil raise it to $20.
    • The Devil shapeshifing into various things in an attempt to trick the boys and get Cuphead to remove the sweater. By the third time, Mugman is annoyed and blows a raspberry at the Devil for his tricks.
    • There’s also this zinger from Cuphead:
      Cuphead: (smugly) You should try transforming into somebody who doesn't fail all the time!
  • Devil's shapeshifting tantrum when Mugman saves Cuphead is nightmare-worthy... which makes it all the funnier when he abruptly returns to normal and gives up with an exasperated sigh.
  • Stickler—the nebbish downer who keeps nagging the Devil about Cuphead's soul, and therefore ruining the productivity party—gets his just deserts when the Devil destroys his records and makes him go back and recount every one of the millions of souls the Devil's collected.

    Sweater Luck Next Time 
  • The Devil's many failed attempts at trying to take Cuphead's soul, appearing at random hoping Cuphead had taken off the sweater only to get shocked every time to the point that the boys just view him as a mere nuisance than a threat. The Failure Montage with a Conversation Cut makes it better.
    The Devil: [appears at the the cottage front yard as the boys are chasing each other] Give me...
    [gets zapped by the sweater; scene cuts to the bedroom with the cup brothers fast asleep]
    The Devil: ...your...
    [gets zapped by the sweater under Cuphead's pajamas; scene cuts to a clothing store with the boys examining different clothes for them to wear]
    The Devil: ...your soul!
    [gets zapped by the sweater once more before vanishing; Mugman shows the blouse to his brother, who shrugs his shoulder and shakes his head]
    • By the time the Devil arrives at the cups' house, Cuphead's had enough and simply slaps his grabbing hand away. The Devil's little "Oh!" makes it better.
    • The Devil having a fire outburst after getting the door slammed in his face (which also ruins the fence). Cuphead then reopens the door to scold him for making noise.
    • A bit of Fridge Brilliance on this part is that the Devil specifically chooses times to attempt the soul-snatching when it's not normally feasible to wear a sweater, like at the beach.
  • When the Devil appears at the cups' door, Cuphead demands he go around to the back entrance to talk. The Devil grumbles about being bossed around... but does it anyway.
    The Devil: Stupid cup making me go around the back. I’m the DEVIL! Nobody tells me what to–
  • Cuphead slapping the Devil into a bush so that Elder Kettle doesn’t see him, complete with another little "Oh!" There's also the fact that he stays down there until Elder Kettle closes the window.
  • Cuphead tricks the Devil into painting the fence in exchange for removing the magic sweater. The Devil gets so into it that he doesn't notice until hours later that they ran off to the amusement park.
    • Old Scratch is just painting the fence but he does so in his own dramatic fashion. He magically commands a legion of brushes to fly through the air, wielding a rainbow of colors, and all while he conducts it like a maestro giving his command performance in a beautiful spectacle backed up by whimsical orchestral music. And this is all, again…just to paint a fence.
    • And when he finally realizes that they ditched him, he seems more upset that he didn't have an audience for his fence-painting performance.
  • Cuphead’s sweet gesture to buy Mugman a thank-you funnel cake for the protective sweater is somewhat undercut by Cuphead asking his brother for five bucks to buy it with.
  • The Devil, in a rare moment of camaraderie with Cuphead, pats him fondly on the shoulder. Then he has to do it a few more times before realizing Cuphead isn't wearing the sweater anymore.
  • Henchman treating the Devil's wounds from the sweater with iodine, making him wince each time.

    Dangerous Mugman 

    Dirt Nap 
  • The entire premise of the episode: Kettle overhears a conversation between Cuphead and Mugman and becomes convinced they're planning to murder him. They're actually just planning to bury Mugman's (apparently) dead pet worm.
    • The first time Elder Kettle eavesdrops, he's happy because it sounds like the boys are talking well about him. At first.
      Mugman: Don't you just love him?
      Elder Kettle: [Laughs to himself] Mugman.
      Cuphead: Eh. I'm still in the like stage.
      Elder Kettle double takes.
    • Later, as he serves them breakfast.
      Elder Kettle: [To Mugman] Hope you love it! [To Cuphead, glaring] Hope it's in the like stage.
  • The boys walking into the kitchen after Elder Kettle gave himself a generous shining:
    Mugman: MY EYEBALLS ARE ON FIRE!!
    Cuphead: Why's it so BRIGHT!?
  • As the boys go to bury the worm:
    Mugman: Should we say a few words?
    Cuphead: Sure… Shoelace. Mailbox. Slingshot. Octopus. Bagel. Lipstick…
  • Elder Kettle decides to take out the boys first before they take him out and booby-traps his home. One slip, however, and Elder Kettle is thrown back and forth around his house, setting off every trap while the boys watch. The second time he slips, classical music plays as he bounces between explosions in slow motion. Then a piano falls on him.
  • After Elder Kettle finds out the boys were talking about their pet worm, not him, Elder Kettle is so relieved he accidentally walks backwards into the tiger trap he set for them. Then the camera cuts to the inside of the pit looking out, which reveals Elder Kettle lined it with spikes.
    Mugman: [both wince] Yikes! He's not looking so hot.
    Cuphead: I guess we can bury him in the backyard?
    Mugman: [deadpan] I'll get the shovels.

    In Charm's Way 
  • The whole scene with the Elder Kettle becoming blind without the glasses, unaware that the cup boys had accidentally broken them trying to get the cookies. For one thing, he keeps bumping into walls and corners, and when he sees what he thinks are Cuphead and Mugman (they are actually pail-and-flour sack mannequins), he gets relieved before walking over and knocking himself into a wall again.
  • Cuphead and Mugman follow Chalice to try and figure out how she keeps getting things for free when she suddenly corners them.
    Chalice: Alright! Who're you two workin' for?? Spill the beans or you’ll be spillin’ milk!
    Cuphead: Workin'? We don't have jobs!
    Mugman: Yeah! We're just a couple uh... dumb-dumbs!
    Cuphead: Zip it, ding-dong! She don't gotta know we're a couple of dumb-dumbs!
  • Chalice decides to test Cuphead and Mugman by telling them to charm their way past a security guard into a cookie factory. Cuphead and Mugman get the security guard's attention and then awkwardly mimic Chalice's dancing while set to discordant music. The security guard glowers at them and then slowly gets ready to use his truncheon. It's only after Chalice appears behind them that he raises a Fascinating Eyebrow and is charmed enough to let them into the factory.
  • As much of a bad sign as it was, the "silent alarm" switch briefly coming alive to point its function out to the audience can be considered funny.
  • Right after the Sudden Downer Ending with Ms. Chalice escaping and Cuphand Mugman being thrown in jail... cue happy credits music as if nothing happened.

Season 2

    Jailbroken 
  • Cuphead and Mugman arguing about how they wound up in prison because of Ms. Chalice.
    Mugman: I told you we shouldn't have hung out with her.
    Cuphead: No you didn't!
    Mugman: [surprised] I didn't?! That sounds like something I should've said.
  • It's apparently been weeks since Cuphead and Mugman have been locked up. And Elder Kettle is still wandering around the house and crashing into things while he looks for his glasses. He finally turns to Cuphead and Mugman (really two dummies made of trash) for help, only for the dummies' heads to fall off, causing Elder Kettle to scream in terror.
  • The montage of Cuphead and Mugman's attempts to break out of prison. Each time they end up chased by dogs then punished by the warden.
    Warden: [first attempt] You boys just bought yourself a day of breaking rocks!
    Warden: [second attempt] You boys just bought yourself a night in the box!
    Warden: [third attempt] You boys just bought yourself a night in the box breaking rocks!
  • Cuphead and Mugman's argument after their failed prison breaks. Mugman just wants to serve his sentence while Cuphead wants to keep trying to escape.
    Mugman: Well I'm not doing it that way.
    Cuphead: Well I am!
    Mugman: Oh, you're doing it that way? Well good for you!
    Guard: Hey! Quiet down in there!
    Cuphead: [whispering] Good for me? Great for me!
    Mugman: [also whispering] I'm happy for you!
    Cuphead: [still whispering] I'm happy you're happy for me!
    Mugman: [also still whispering] Good!
    Cuphead: [still whispering again] Great!
    • When the two argue again later on, the guard complains he can still hear their "whispering", causing them both to keep arguing even quieter.

    Charmed and Dangerous 
  • Mugman is skeptical Chalice is really their friend, while Cuphead keeps trying to defend her.
    Mugman: We know nothing about her! Except she abandoned us and never came to visit us in prison!
    Cuphead: See? That's two things we know about her already!
    Mugman: [audibly deflates] I really thought she was gonna be our friend. It was nice not being on our own.
    Cuphead: Hey, Chalice is a great friend!
    Mugman: Well if she's so great, how come we never heard from her again, hm? [knock at the door] Ooh! Maybe that's your dear friend Chalice now! [opens door]
    Chalice: Hey! It's me, Chalice!
    [Mugman slams door in her face.]
  • The Hurricane of Euphemisms to describe jail.
    Chalice: Gosh, fellas. I'm sorry I got you tossed in the hoosegow.
    Mugman: "Sorry" won't bring us back so many cold, cold nights in the slammer.
    Cuphead: The crowbar hotel.
    Chalice: The pokey.
    Mugman: The clink.
    Chalice: The stoney lonesome.
    Cuphead: The convict condo!
    Mugman: The zoo for criminals.
    Chalice: The ol' hooba-dooba.
    Cuphead: Yeah! The old... hooba... dooba...?
    Mugman: The old hooba-dooba? That's not even a thing!
    Chalice: Well, if you never heard of it, that's your problem.
  • When Elder Kettle tries to throw Ms. Chalice out of the cottage after hearing an angry mob's after her, a quick dance is enough to convince him to let her stay. Then he gives her a cookie which he refused to do for Cuphead and Mugman after they performed the exact same dance in the episode's opening, much to their shock.
  • Ms. Chalice asks Cuphead and Mugman what they do for fun around the cottage. Cut to Cuphead riding the goat! Then Mugman riding the goat. Then Cuphead riding Mugman. Then the goat riding Cuphead and Mugman.
  • The goat is included when Ms. Chalice orders everyone to huddle up. Then quickly scrams once he realizes Ms. Chalice wants him to carry the three of them to their dance contest.
  • Ms. Chalice tells the boys she was lying about an angry mob being after her and that the true reason she wanted to hang out with them was because she really did miss them. Then the doorbell rings.
    Cuphead: Who could that be?
    Mugman: Oh, I don't know. Maybe that's your angry mob now. [opens door]
    Angry Mob: Give us Chalice! Give us Chalice! Give us—
    [Mugman slams the door in their faces]
    Mugman: [Beat] Chalice, it's for you.
  • Chalice disappears while Mugman appeals to the mob's sense of decency. The mob decides they should beat up the Mugs since they came all this way.

    A High Seas Adventure! 
  • Mugman initially refuses to board the ship without permission.
    Cuphead: Mugman, you’re missing out! You could be having a high seas adventure right now!
    Mugman: Don’t you think I want that?! I need permission!
    Cuphead: Well then, permission to come aboard!
    Mugman: YAAAAAAAAY!!
  • Cuphead and Mugman having a sword fight while tearing up the ship.
    • This sword fight then directly leading into cutting the ship from port and them sailing off to sea. Cue Mugman freaking out upon realization.
  • Brineybeard mistakenly using Cuphead’s head for his coffee mug.
  • Brineybeard's pretty upfront about the dangers of their mission.
    Brineybeard: But I'll be honest with ye, our chances of survival are slim to none. And Slim just drowned.
    Mugman opens his mouth to object and Cuphead shuts him up by covering his mouth with his hand
    Cuphead: I like those odds. We're in!
  • Brineybeard's sword inexplicably coming to life to sass Cuphead.
    Cuphead: Yuck! Keep that mushy stuff out of my high seas adventure, will ya?
    Brineybeard: [draws his sword] Bite your tongue! Or me sword will bite it for ye.
    Sword: You can bite it or I can bite it, but either way it's gon' get bit. [pokes Cuphead's nose]
  • Captain Brineybeard remains in love with Cala Maria, even after she tries to kill him with her Deadly Gaze.
    Brineybeard: I'll never give up on love!
    Mugman: Your love wants you dead!
    Brineybeard: Relationships are a series of peaks and valleys.
    • Becomes more amusing coming from Mugman considering Mugman also becomes somewhat smitten by her towards the end of the episode and this crush is carried over into “The I Scream Man”.
  • Brineybeard telling the boys to step back while he talks to Cala Maria, that it is something that is strictly “between a man and the woman he loves”. Cue Brineybeard jumping around, flapping his arms like a big goof, with his voice all high pitched and giddy.
    • Cala Maria promptly turning him to stone because he “talked too much”.
  • Mugman accidentally breaking off Brineybeard’s (as a stone statue) legs is dark comedy at its finest. First, it happens because Mugman got distracted by a starfish, leading him to trip and lose his hold on the pirate’s petrified legs. Then the tide drags the broken feet into the sea. Leading Mugman to improvise two peg legs from some nearby salvage.
    • When Brineybeard returns to normal, he’s surprised at first by his new legs, but takes it in stride, thinking he's twice the pirate as anyone else now since he has 2 peg legs.
  • Cuphead and Mugman play the blame game.
    Cuphead: If we end up eaten or turned to stone, we'll all know whose fault it is.
    Mugman: Look, you're the one who wanted a "high seas adventure."
    Cuphead: This is no time for the blame game.
    Mugman: You started the blame game!
    Cuphead: It takes two to blame game!
    Mugman: Yeah, and you started it.
    • In the middle of the argument a large shadow falls over the two.
      Cuphead: Who cares who—[notices shadow] Is it... her?
      [Mugman turns his head and sees a giant crab who roars at them]
      Mugman: It's just a giant crab monster.
      Cuphead: Oh, is that all?
      [Beat]
      Both: GIANT CRAB MONSTER?!
    • Mugman gets into a sword fight with the giant crab after it steals the box of treats Brineybeard was going to give Cala Maria. After Mugman disarms the crab, the crab is intimidated into putting the box of treats back and then scuttling away into its cave on twinkling toes.
  • Cala Maria has a song that's extremely funny due entirely to set-up. The entire episode is about Brineybeard's clearly doomed love for Cala Maria, who is a homicidal Sea Monster, but when the boys drag his petrified (and now peg-legged) body to the lair, she gets a Villain Song. The slow start, the fact she starts it by singing about her Half-Human Hybrid origins, even mentioning how lonely her life is, and the fact that the episode is mostly about romance make the entire thing a clear reference to other sad villainous songs, leading the viewer to think that Cala Maria will turn out to be a Tragic Monster whom Brineybeard can save through Love Redeems... except Cala Maria loves what she is, deliberately set out to be the fiercest Sea Monster in the world, and she's outright proud of all she's done! Even the part about being lonely she admits, but then further states it's the only life for her- she'll take the loneliness if she can continue to prey upon the sea! It's probably the funniest thing in the entire episode simply for the sudden left turn it takes from where any watcher would expect.
  • Mugman meets Cala Maria.
    Mugman: Wow, you have a beautiful voice. Hi, Miss Cala Maria, ma'am. My name is—
    Cala Maria: [unimpressed] Dinner. Your name is dinner.
    Mugman: Actually, my name is [dawning realization]... Oh. You're gonna eat us.
    Cala Maria gives him a deadpan look
  • While Mugman tries to convince Cala Maria that the petrified Brineybeard loves her, Cuphead chips in with this gem.
    Mugman: This stone loves you!
    Cuphead: [knocks on stone Brineybeard] Yeah. It's love on the rocks. Get it?
    Mugman: Not helping.
  • Cala Maria is impressed Brineybeard is the first person to ever turn back into a person after being turned to stone.
    Brineybeard: It's cause I love ya, Baby!
    Cala Maria immediately turns him back to stone
    Cala Maria: Don't call me "Baby."
    Brineybeard: [breaks free again] Understood!
  • As Cala Maria goes on to let Brineybeard down easy and explain how it won’t work between them, one of the "sweet treats", an octopus egg, hatches and the octopus then lunges itself at Cuphead, who then fights to get it off.
  • After their little chat, Cala Maria just casually inform that she gonna eat them and give 10 seconds headstart to escape. And Cuphead would ask about it to Mugman as soon as he get the octopus off his face.
    Cuphead: What did she say?
    Mugman: Ah, she said she gonna eat us.
    Cuphead: Ohhh...
    [Beat]
    Both: EAT US?!
  • Cuphead falling off the pirate ship at the end of the episode.

    Another Brother 
  • While Cuphead looks for another brother, he scopes out several pairs at the park, including a cameo by Ribby and Croaks dressed in their suits, playing on the seesaw.
    Ribby: Whee!
    Croaks: Yay!
    Ribby: Whee!
    Croaks: Yay!
  • Cuphead picking up supplies.
    Cuphead: Hey, where do we keep the gunpowder?
    Mugman: Between the flour and the sugar, where it's always been.
  • Mugman trying to convince the Mailman to be his new brother.
    Mugman: Just listen to how good this sounds. Mugman, Mailman. Mailman, Mugman. Mugman, Mailman. Mailman, Mugman. Mugman, Mailman. Mailman, Mugman. Mugman, Mailman. Mailman, Mugman. [Mailman runs to his truck. Mugman's in the passenger seat.] Mugman, Mailman. Mailman, Mugman. Mugman, Mailman. Mailm—[gets kicked out the window]
  • Mugman's priceless reaction to finding out Cuphead's "new brother" is Bowlboy. Dramatic music plays, then the camera zooms in on Cuphead and Bowlboy holding hands, then to their faces, then back to their hands, then it focuses on Mugman as the picture goes black-and-white and he speaks in slow-motion.
    Mugman: BOOOWLBOY?!
  • As Bowlboy and Cuphead are strapped to a rocket they plan to use as a jetpack, Bowlboy decides to let Cuphead in on a real "Bowlboy doozy" of a secret.
    Bowlboy: I've never done any of this crazy stuff before.
    Cuphead: Wait. But all day, you've been irresponsible, careless, and simply unhinged.
    Bowlboy: Well, I was just doing what I thought you would do. [Bowlboy's face becomes more and more unhinged] I want to learn from you, Cuphead, and be just like you, Cuphead, and become you, Cuphead!
    Cuphead: [horrified] ... What was that last part?
    Bowlboy: [back to normal] Nothing! [lights rocket]

    Sweet Temptation 
  • Mugman sure takes his time enjoying his one piece of candy, slicing into it with the care and precision of one enjoying a fine steak... Compared to Cuphead who's chowing Mugman's entire candy stash like a maniac.
  • The debut of Baroness Von Bon Bon. Not only does Cuphead immediately see the red flags in the Baroness offering to let him have a literal taste of what Sugarland’s got to offer, but he still almost falls for the obvious trap!
    Baroness Von Bon Bon: My name is Baroness Von Bon Bon and today is your lucky day! You get to eat all the sweet treats you desire!
    Cuphead: [Beat] ...Aaaaaand goodbye. [marches away]
    • Just the impulsive and kind of dim Cuphead being Genre Savvy about the whole mess. He's so annoyed and matter of fact about the whole thing.
    • The animators must’ve been challenged to have the not-so-sweet baroness make as many goofy faces and chew the scenery as much as possible in her debut scene.
    • Cuphead apologizes to "The Baroness" for misjudging her.
      Baroness: Oh please, we're friends now! Call me The.
    • Cuphead continues to inexplicably trust her despite picking up on her bizarre mannerisms.
      Cuphead: You got a real creepy way about you, lady.
      Baroness: I don't get out much! In fact, I can't leave Sugarland on account of an [face contorts, music distorts] ancient curse... but that's a story for another time.
  • After Cuphead and Mugman both break the rules of Sugarland, the Baroness appears on her castle. Mugman doesn't think she seems as creepy as Cuphead said. Then she breaks into a truly unhinged villainous laugh.
    Mugman: Oh. Yeah, I see it now.
  • Mugman is unable to get off the ground after being turned into gingerbread.
    Mugman: Cuphead, leave me. Save yourself.
    Cuphead: Uh, okay! [bounces away]
    Mugman: CUPHEAD!
    Cuphead: Alright, alright, I'm coming back.

    The I Scream Man 
  • The fact that errands are actually something everyone in the cottage actually loves doing.
    Cuphead: Poor, Mugman. He loves errands.
    Elder Kettle: Errands are pretty great. Maybe we could save just one errand for Mugman?
    Both: Hmm... NAH! [both drive away cheering] Errands! Whoo!
  • Mugman’s pirate fantasy. This leads to him dreaming about Cala Maria as his lover.
    • On a meta note, it’s almost like this dream sequence was made in response to the fans who like to ship Mugman and Cala.
    • Another meta note, Mugbeard’s facial hair resembles that of Frank Todaro himself.
    • Mugbeard's compliments to Cala Maria start off strong.
      Mugbeard: Oh, sea beast! Your eyes are glowing stars. Your voice? A symphony! And your hair—well, let's face it, your hair is a dead octopus.
    • If you look at the pages for 'Romance on the High Seas', you'll see mentions of characters such as "Rib-beard", "Croak-beard", "Cup-beard", "Kettle-beard", and "Chalice-beard, beard".
  • When the ice cream man drives off sad after being told off by Mugman, his truck's rendition of "Pop Goes the Weasel" plays in a minor key.
  • The Cala Maria from the book goes off script due to Mugman's guilt over yelling at the Ice Cream Man.
    Cala Maria: No! I refuse your kiss!
    Mugbeard: B-b-but it's in the story! We're supposed to kiss.
    Cala Maria: I cannot be with someone so very cruel to the ice cream man.
  • After a tense chase where it looks like the ice cream man is trying to run down Mugman in a psychotic act of vengeance, it turns out he was just chasing after Mugman to thank him for the "inspiration" to get a new hat. A hat which looks exactly the same as the last one just imperceptibly smaller. He then casually spoils that Mugbeard dies at the end of the book Mugman's been trying to read. Cue Mugman breaking out into a psychotic laugh and lunging at the ice cream man in a blind fury, as well as the implication that Mugbeard probably does actually look like Mugman's self-inserted imagination.
    • Even funnier is how his punches don't even do anything to the ice cream man, who is just left confused at why Mugman hates him.

    Piano Lesson 
  • Nearly everything Ludwig says and does.
  • The way Ludwig mispronounces Mugman's name as "Moog Maan":
    Mugman: Yep! That's my name!
    Cuphead: (from off screen) No, it's not!
    • Ludwig later doing the same with Cuphead's name as "Coop Haad".
  • Mugman tries to ask Ludwig something, only for Ludwig to interrupt him by saying he needs to remove his driving gloves. Seconds after Ludwig gives Mugman permission to speak, he interrupts Mugman again so he can put on his non-driving gloves. By the time he's finished, Mugman forgets what he wanted to ask.
    Ludwig: Such is the power of watching a man remove and then put on various pairs of gloves.
  • Ludwig telling Mugman that he loathes him... because Mugman's musical talent is at its dawn while Ludwig's is at its dusk.
  • After Cuphead shows off his amazing talent for playing the piano, leaving his brother, Elder Kettle and Ludwig staring dumbfounded at him:
    Cuphead: What are you weirdos looking at? Eh, I got crawdads to eat.
    • As Ludwig lays on his praises for Cuphead’s natural talent.
    Cuphead: Mister, you’re starting to creep me out.
    • Cuphead repeatedly turning down Ludwig to learn and perform at the piano recital until Ludwig mentions the $10,000 cash prize.
  • Elder Kettle encourages Mugman to practice the piano with an old saying.
    Elder Kettle: You know the old saying. Practice all day and you might get better, but don't practice and you certainly won't.
    Mugman: [sniffles] Nobody says that.
  • People who hear Mugman playing the piano suggesting he tries water colors instead.
  • Mugman comes to the conclusion that Cuphead can't play the recital if he doesn't have any hands!
    Elder Kettle: [stops Mugman] What have I told you about using my hedge trimmers to mutilate your brother?!
  • This from the boy’s nighttime argument:
    Cuphead: You want me to give it up? Just say the word and I’ll give it up.
    Mugman: (no hesitation) Give it up.
    Cuphead: WHAT?! No way!
  • The brothers are rightfully upset by Ludwig’s plagiarism, wanting to teach him a lesson. Cue the piano Mugman had rigged on stage the night before crushing the phony.
    [audience screaming]
    Announcer: Oh dear! Ludwig has been crushed by a falling piano! Who would do such a–
    [Mugman cutting the radio off with an embarrassed grimace]
    Cuphead: So. You were going to crush me with a piano, huh?
    Mugman: …Just a little?
    Cuphead: [Beat] Eh, don't sweat it! I would've done the same thing if I were you.
  • Both Cuphead and Mugman decide to snack on crawdads at the end of the episode. The former comes to realization that simple crawdads can be considered tiny lobsters. Mugman agrees... but suddenly, a giant musclebound crawdad appears behind them.
    Crawdad: Who you're callin' tiny, punk?

    Release the Demons! 
  • The Devil reads a book called "Controlling your Rage". He's sitting composed in his chair, licks his thumb and grabs the page titled "Chapter 3: Turn That Frown Upside Down"—and immediately begins ripping out the pages.
    • If you look at the page preceding Chapter 3, it appears the last bit of the preceding chapter spends a while on an elongated, highly-specific hypothetical about an invisible, impenetrable sweater made out of brotherly love, as well as touting how someone being affected by this situation while somehow harboring a hatred for the word 'cup' is very statistically unlikely.
  • Big D getting so worked up over his hatred for Cuphead that the flames he generates accidentally annihilate his finest demons. He then orders his second finest demons be summoned! And does the exact same thing. His third finest are so pathetic the only reason he doesn't incinerate them is because he's worried what the fourth finest would look like.
    • The only reason King Dice was spared the first time it happened was because he was fashionably late. And his horrified reaction upon seeing the piles of ashes.
      King Dice: WHAT DID YOU DO?!?
    • Both times The Devil’s about to let loose his flames of fury, Henchman takes cover. The second time he drags King Dice behind cover.
    • The Devil's less than impressed reaction to his third-finest demons. Included in this pathetic group are a wheezing giant turtle, a goofy-looking vulture, and an eyeball with wildly mismatched wings.
      The Devil: A cyclops with an eyepatch. And how does that work exactly? [Cyclops growls, charges and runs face first into a stalactite] Ah. It doesn't.
    • The demon Burpy shows off his fire breath by using it to destroy one of his fellow demons.
    • As the Devil keeps talking in terms of third and fourth finest demons, Henchman helpfully corrects him that since the original finest and second finest were killed by him, the third and fourth finest demons are now respectively the finest and second finest by default.
      The Devil: Thank you, Henchman.
  • After the Devil cries out "Release the demons!" it cuts to the gates of the Underworld opening up and the C-list demons pouring out all set to Verdi's Requiem. King Dice compliments the Devil on watching him work. Until he realizes he's also ordered to go after Cuphead. Cue the even less impressive shot of the gates opening, ''Requiem'' playing and a minuscule King Dice running across the screen.
    King Dice: (Laughing) Big D, Big D. It is a pleasure to watch you in action. Nobody works a room like you.
    The Devil: (Not even looking at him.) Are you still here?
    King Dice: You mean, Number One's got to do it too?
    The Devil: (Simply looks at him.)
    • The moment it leaves the gates, the cyclops with an eyepatch immediately turns in the wrong direction and wanders off into the forest, no longer seen again in the episode.
  • The snapping turtle demon trying to scare the cups but he’s so pathetic they literally walk all over him.
  • The Four Horsemen’s horses getting scared by the stuffed horse head. The horsemen don’t mind since that means they get the day off. One minute they’re built up as the Devil’s ultimate enforcers, primordial beings whose very presence inspire frozen terror, the next they’re merry fair goers excited about pie.
  • It turns out the "undisclosed location" that the invisible sweater Mugman knitted that makes one impervious to the Devil's attacks is on Stickler. When the Devil tries to vaporize him only to find out he can't, he can only throws the most childish temper tantrum and unable to do anything about it.
    Devil: Take it off this instant, so I can obliterate you!!
    Stickler: I do not believe that would be in my best interest.
    Devil: I WILL EAT YOUR SOOOUL!!
    (Beat)
    Stickler: Not possible, because of this impenetrable—
    Devil: SWEATEEEEEEER...!! AAAUUUGHH... Forget it...
    • The end of the episode, Stickler and the Devil get stuck in the Hellevator. And Stickler decides to pass the time singing. The Devil is reduced to sobbing.
      999 million souls in the vault
      999 million souls
      Take one out, do a recount
      998,999,999 souls in the vault
  • The unusually detailed appearance of the horsemen is hilarous for just out of brazenly out of place it is in a franchise that in every other instance attempts to imataite the stlye of 30s and 40s animataion as closely as possible.

    Dead Broke 
  • Cuphead complaining about draft while fighting with Mugman.
  • The brothers exchanging a dollar around from their bet on whether Chalice was a real ghost. Only for Chalice to con them into giving it to her in exchange for telling them about her ghost powers.
    • Chalice possessing each of the brothers and making them mock themselves.
      Chalice!Mugman: My name is Mugman. I'm a weenie who's afraid of everything. Honk! Honk!
      Chalice!Cuphead: My name is Cuphead. My straw is bent, and I ain't too worried about aaaaaaanything...
  • When the trio isn’t able to pay for their ice cream, the Ice Cream Man takes their cones, tosses them aside and drives off.
    Ice Cream Man: I'm afraid the flavor of the day is... GOODBYE!!!
  • Sally Stageplay cutting off her dramatic screaming to answer the door.
  • The Birnbaum Quadruplets really disliked their imprisonment:
    Bedelia: Do you have ANY idea what it’s like to be trapped in the same house with your sibling day in and day out?!
    (beat)
    Cuphead and Mugman: (deadpan) …Yes.
    Bedelia: Good! Then you’ll be used to it!
  • The final battle with the quadruplets. It gets to a point where it becomes a complete back-and-forth as everyone keeps switching painting.
  • The piggy bank also getting trapped in the painting with the Birnbaum quadruplets reveal.

    Rat's All, Folks 
  • Elder Kettle overhears Cuphead and Mugman making a racket in the kitchen. They convince him not to investigate by telling him they're working on a surprise for him.
    Cuphead: Phew, he bought it!
    Camera pans to show Mugman is preparing to frost a cake.
    Mugman: Bought what? We really are making him a surprise.
    Cuphead: Oh yeah!
  • The slapstick in this episode is a sight to behold. It is physical comedy of the likes of a Tom and Jerry episode.
    • Doubly so, since Jerry is the inspiration for Werner.
  • Cuphead and Mugman argue over whether they should tell Elder Kettle about the rat.
    Mugman: But we deserve the blame. We left the door open.
    Cuphead: We don't know that's how it got in!
    Werner: [pokes out head] Zat is how I got in.
  • Elder Kettle growing suspicious when he sees "pain stars" floating over Cuphead and Mugman's heads.
  • When Cuphead and Mugman go after Werner with a rolling pin and frying pan, Werner teleports back and forth from their heads to trick the brothers into bludgeoning each other.
  • Mugman puts a wedge of cheese on his glove and "walks" into Werner's mouse hole to "seduce" him. Werner immediately sees through it and smashes his hand with a mallet.
  • When Werner is tricked into having a stick of dynamite go off in his face, he drops the German accent, adopts an American one and gives up on taking over the cottage. Elder Kettle tells him to scram and not come back, then sits down in his chair and reads his newspaper, which is on fire, and asks Cuphead and Mugman to close the door to keep the varmints out. The camera then pans out to reveal Elder Kettle is oblivious that his dynamite destroyed the entire cottage except for two walls and a chimney.

    Say Cheese! 
  • In order to get Cuphead and Mugman to stop fighting so he can get a family portrait, Elder Kettle promises to take them to both the amusement park and the movies if they behave. The brothers cheer briefly, then remember something.
    Cuphead: Wait a minute! You're always promising to take us places, then when it's time to go, you say you can't remember.
    Elder Kettle: ... I don't remember that.
  • Elder Kettle's flashback of using a flamethrower to burn down all the billboards showing him as the Diaper Baby mascot.
  • When Elder Kettle overhears that Cuphead and Mugman plan on keeping the embarrassing photo of him to laugh over forever, he falls over when he makes an attempt to snatch the camera away, Family Guy death pose style, before chasing the boys by crab-walking over the walls and ceiling like he's been demonically possessed. It's equal parts hilarious and horrifying.
  • Elder Kettle's attempts to bribe Mugman into handing over the camera with his embarrassing picture in it.
    Elder Kettle: Let's face it, Mugman. This whole you and Cuphead thing? It's getting old. Try this on for size! Kettle, Mugman. Mugman, Kettle. Kettle, Mugman. Mugman, Kettle. Kettle—[Cuphead pulls Mugman aside while Kettle keeps going]
  • Cuphead and Mugman have been arguing all episode about whether they should go to the amusement park or the movies. When their plan to blackmail Elder Kettle fails, they resume the argument, only for Elder Kettle to interrupt.
    Mugman: Now we'll never get to the [shoves Cuphead] movies!
    Cuphead: [shoves Mugman] Amusement park!
    Mugman: [shoves Cuphead] Movies!
    Cuphead: [shoves Mugman] Amusement park!
    Elder Kettle: FIRE POKER!
    Brothers stop, look up then run as Elder Kettle starts chasing them with a fire poker
  • Cuphead and Mugman land on the windshield of a cop car while trying to escape an enraged Elder Kettle.
    Cop: Requesting backup. We got two escaped cookie convicts from the cookie factory caper. [The boys escape and Elder Kettle smashes the cop car with his fire poker] We also have the Diaper Baby billboard burner. He's armed and insane.
  • Elder Kettle is happy to finally get the family portrait he's wanted. Even though it's a group mugshot of him, Cuphead and Mugman.

    Lost in the Woods 
  • Cuphead's pleasant dream of Mugman showing up at the cottage doorstep, dying because he "worried too much," and Elder Kettle cradling his body while crying, "He learned it from me!" All the while Cuphead is lounging by a roaring fire, laughing.
  • Three squirrels beating up Cuphead and throwing him off a cliff for trying to steal their acorns.
  • Mugman's complete lack of sympathy toward Cuphead after the latter stumbles on his cottage in the middle of a blizzard since he got them lost in the first place.
    Cuphead: Mugsy? What are you doing out here?
    Mugman: Well, someone I once knew lost our only compass. Then the harsh winter set it and I was forced to build this cabin and lodge here until spring. Now if you'll excuse me, it's quite cold and I'm baking a pie.
    Cuphead: [stops him from closing door] Wait, Mugsy! I'll freeze to death! I'll starve!
    Mugman: I ain't too worried about it.

    The Devil's Pitchfork 
  • The table read for “The Devil’s Pitchfork”. Not only do the voice actors recite the lines for the upcoming episode, they get so into it they emote and do a little physical acting!
  • Henchman tries to cheer up the Devil by pointing out what a beautiful day it is, throwing back the curtain to reveal souls being tortured in a lake of fire.
    • When that doesn't work, he tries reading some sad newspaper headlines.
    Henchman: "Invasive Beetles Devastate Crops", "Meteor Hurdling Towards Orphanage"—Ooh! Meteor!—"Four Horses of Apoca-ba-lypse On the Loose". What a time to be the Devil, huh? [wiggles eyebrows]
  • The thought of someone actually caring about Mr. S up topside enough to write a review of him in the newspaper.
  • Mugman's surprise for Cuphead.
    Cuphead: You mutilated our bikes!
    Mugman: It's a present! I made our bikes into a tandem bike. Now we can ride bikes together!
    Cuphead: We already did ride bikes together separately.
    Mugman: But now we can ride out bikes together together!
  • When the Devil loses his pitchfork and starts to frantically look around the underworld, Henchman is trying his best to calm him down. "Trying" is the keyword here.
    Devil: It's not under here. It's not back here. Where is it? Did I have it in the elevator...?
    Henchman: Uhh, I don't know.
    Devil: Well, look around. Find it!
    Henchman: Daah, calm down-
    Devil: YOU CALM DOWN!!
  • The titular weapon, a famous symbol of the Devil himself and weapon of terrible dark forces... being used as a fork for spaghetti.
  • The return of Sherman and Doris, the latter of whom gets jealous when their spaghetti is brought to life by the Devil's pitchfork and latches onto her husband's face.
  • Cuphead being sincere to Mugman.
    Cuphead: Mugsy, old boy, earlier today, when you mutilated our bikes, you did something nice for me. Now, I want to mutilate something nice for you.
  • Cuphead zapping Big D with his own weapon. It starts off accidental, but after the second time it happens, Cuphead breaks out into the most mischievous smile and starts doing it on purpose. And yes, it happens over and over.
    • The table read of the episode has Luke Millington-Drake going so over-the-top with the Devil's screams whenever he's zapped that he makes the entire cast start Corpsing.
    • Cuphead finally finds out the Devil no longer has any claim on his soul and feels so sorry for the Devil that he offers him his pitchfork back... only to zap him again.

Season 3

    The Devil's Revenge! 
  • At the beginning of the episode, Cuphead is shown to be taking Mugman's fate...very poorly, with him having a Thousand-Yard Stare and only able to say "Mugman" over and over again. When he finally gets home and Elder Kettle asks what's wrong, Cuphead lies and says he lost his pocket knife. Elder Kettle somehow believes it.
    Elder Kettle: [comforting] Aw, is that all? That's easily replaceable. It's not like you lost [grins in a way that's meant to be reassuring but instead looks incredibly sinister] Mugman!
    [Cuphead gasps and runs out of the cottage, sobbing hysterically. Elder Kettle watches in concern...before smiling as if nothing happened.]
    Elder Kettle: ...They're so emotional at this age.
    • Elder Kettle doesn't even bat an eye that a child has a pocket knife. Also, of all the things Cuphead could lie about losing instead of Mugman, it was a lethal weapon.
  • Down in the Underworld, it looks like Mug ain't too worried about his capture while he's waiting for Cuphead to come to the rescue. While he's hanging around, he's got a fellow prisoner to talk to. Except that prisoner has clearly been down there so long that all he can do is scream, that or he's reacting to Mugman's yammering, not that it bothers Mugman.
    Mugman: [cheerfully] So, how long have you been here?
    Prisoner: AHHHHHHHHHHH!
    Mugman: [still cheerful] Ya don't say! Well, I'm only here till my brother comes and gets me.
  • One of the hulking demonic torturers catches Mugman trying to talk with the prisoner and orders him not to talk. Mugman's too curious about the guard's Scary Teeth to listen to him and instead asks questions about them that clearly make the demon feel self-conscious.
    Guard: Prisoner, don't talk to the inhabitants!
    Mugman: Wow! Look at them chompers! Can you even close your mouth all the way?
    Guard: [looks surprisingly wounded] Don't talk to me either!
    Mugman: Just one more question. Is it hard for you to eat pasghetti with those?
    Guard: [clearly insecure] Not if I... cut it up.
    Mugman: Ew! You cut up pasghetti? Gross!
    Guard: I said don't talk to me!
  • Mugman can not only free his arm from the restraints, but he also demonstrates it by pulling a lever and accidentally killing the demon guarding him.
    Mugman: Oops. Well, on the bright side, now we can keep talking!
    [prisoner screams without stopping as Mugman begins telling him a story about finding a shoe on the side of the road]
  • The Devil laments losing his pitchfork because he was so expressive with it, but now he has no idea what to do with his hands, which he displays by making awkward gestures and poses with them.
  • It turns out Old Scratch got his pitchfork as part of a utensil set alongside a giant golden spoon. The Devil tells Henchman to put it away before someone sees it.
  • The Devil talks about how easy it'll be to crush Mugman's spirit. While outside the window, Mugman is happily swinging from his chains singing "la-la" over and over again, while the prisoner next to him screams again.
  • Quadratus on vacation. Hey, even all-knowing mysterious oracles who dwell in reflective pools need to take some R&R.
  • Quadratus gives Cuphead vital information on how to get to the Underworld to rescue Mugman, only for him to miss all of it because an "operator" tells him to insert another fizzy jawbreaker to keep the call going.
  • The Devil's first attempt to break Mugman is by literally turning up the heat in the Underworld. The increased flames cause a ghoul to melt and even the Devil to start sweating profusely, but Mugman doesn't even notice as he entertains himself with marbles. Eventually the Devil breaks and runs off to turn off the fire.
  • The Devil laughs at Mugman's claim that Cuphead will save him but has to force his ghoul prisoners to laugh along with him. There's a montage of various ghouls in various cells who all start laughing uncomfortably. Then it cuts to the prisoner chained next to Mugman who just keeps screaming.
  • The Devil tries to convince Mugman it's actually been 80 years and Cuphead is dead.
    Mugman: Great. So he's here, then.
    Devil: What? No. He's dead, but he's not here. He's... (points upward)
    Mugman: (Beat) Not buying it.
    Devil: What?! Oh! Not buying it?
    Mugman: Listen, I know my brother, and if he's not down here, then he's not dead. Which means, he's coming to save me.
    • The implication that the Devil considers "Heaven" a bad word.
    • Mugman with no hesitation declaring that if his brother isn’t down in the Devil’s domain, than there’s no way that he’s actually dead.
    • Devil, now irked at Mugman's unwavering cheerfulness, glances up towards his office window. Henchman, dressed as a hula dancer (complete with wide eyes and long lashes), dances and hums island music, much to the Devil's further irritation.
  • The Devil tries to adjust the clock when he sees the clock is ten to twelve, but Henchman catches him with a look of disapproval. The Devil proceeds to explain that he's dusting the clock and then "daylight savings". Henchman is not buying it, and even talks back to his boss.
    Henchman: You ought to be ashamed.
    • The argument continues in the background as the cups escape.
  • Despite his whining that he just got his throne reupholstered, the Devil immediately poofs it back after it was turned completely to ash. Implying that, in Hell, reupholstering a throne is harder than poofing one back into existence.
  • After saving Mugman and getting out of the Underworld, Mugman hopes Cuphead learnt something from all that happened, to which Cuphead said he'll be on the straight and narrow. He then asked what Cuphead will do after he no longer owes his debt to the Devil, which the latter decides to... play another round of Soul Ball at Carn-Evil. Looks like some people will never learn...

    Don't Answer the Door 
  • While hiding in a closet, Cuphead makes some observations on some of the dangers they've faced.
    Mugman: Baby Bottle sounds bigger and scarier! How did it get bigger and scarier??
    Cuphead: How should I know? Everything around here is always trying to steal our souls or transform into monsters or trying to eat us or shoot bullets out of its fingertips!
    Mugman: ...I've never seen fingertip bullets.
    Cuphead: [laughs knowingly] Oh-ho-ho, it's happenin' somewhere! Believe you me!
  • Cuphead's reaction to seeing a bear stealing Baby Bottle from their porch.
    Cuphead: [dusts off hands] Well, I guess that solves that problem!
  • Cuphead is wandering around looking for Baby Bottle when his shirt gets caught on a shrub. Instinctively, he beats it flat with his bat... and the shrub slaps him back then pulls up its fallen leaves.
  • When Cuphead and Mugman find the bear, their straws squirt milk like they were peeing themselves.
  • Just the simple fact that the bear they’ve been terrified of for half the episode ends up being quite civil. He tells everyone to calm down and apologizes for consuming everything in the basket Elder Kettle put out as a prank. He even ends up giving them their basket back.
    Bear: Yeah, yeah, yeah... Alright. Look, I feel bad for stealing your basket and drinking your milk. But guys, I'm a bear! Don't leave your basket sittin' out.
    • And then when the doorbell rings again, he ends up screaming with fear with everyone else, only to ask, with confusion, who “Baby Bottle” even is.

    Cupstaged 
  • The episode opens with the Devil performing classical opera for his imps, and Henchman, only for all of them, save Henchman, to fall asleep during his performance. The Devil is somewhat annoyed.
    The Devil: Don't any of you appreciate the theater?
    Imp: I appreciated the nap! [chuckles and gets immediately incinerated by the Devil]
  • The Devil, tired of the imps not appreciating his performance, angrily tells them that today's performance will be his last. This gets a standing ovation.
  • The Devil wants the role of the hero in Sally Stageplay's play because he believes it's the only way the audience will adore him.
    Devil: And I need to be adored!
    Henchman: [sweetly] D'uh, I adore ya, boss.
    Devil: [pushes him away] Not you. Strangers!
  • Sally Stageplay is introduced barging into the theater acting like a rabid dog, even foaming at the mouth. She is then revealed to have been acting the whole time. Someone just needs to have a Big Entrance.
  • Mugman's trick to get over his stage fright? Wear a blindfold while performing. Sally sees absolutely no problem with it.
  • Even after he is relegated to stagehand along with Cuphead and the Devil, Mugman still freezes up backstage, even though the audience can't see him.

    Roadkill 
  • Since the Devil hasn't collected any souls in months, "Bubbles of Failure" appear to entomb everything he cherishes. Stickler tells him he won't be able to access any of his belongings without bringing in new souls. The Devil demands to know who came up with such a stupid idea.
    Devil: This is an outrage! Who instituted this miserable policy?
    Stickler: You did.
    Devil: I did?
    Stickler: Yes.
    Devil: [points at himself] I did?
    Stickler: Yes.
    Devil: I did?
    Stickler: Yes.
    Devil: ... Oh. Well, you have to admit, that is pretty evil.
  • While Stickler tells the Devil he only has one business day to collect a new soul, Henchman has been bubbled and is floating in the background, visibly confused.
  • Due to the bubbles, the Devil doesn't have access to his pitchfork or his Hellevator. So how does he get to the mortal world? By taking the stairs. Apparently there's an entrance to the Underworld in the forest near Cuphead's cottage which resembles a subway entrance.
  • The Devil jumps out of the bushes after Cuphead runs by to steal his soul. He's then immediately run over by Elder Kettle.
  • Elder Kettle mistakes the Devil for a stray cat and takes him back to the cottage to adopt him. The Devil decides to play along for the sake of ambushing Cuphead and stealing his soul, but ends up getting really absorbed in the role of "Mrs. Meow Meow". For example, yowling, hissing and clawing when Elder Kettle gives him a bath.
  • The family portrait Elder Kettle has by his bed is the mugshot of him, Cuphead and Mugman taken in "Say Cheese".
  • The family's goat jealously watching as Elder Kettle is petting the Devil, who's curled up on his lap. Sad, melodramatic string music plays as the goat watches. And then it starts raining.
  • Cuphead and Mugman walk in to find the Devil resting on Kettle's lap, with a bow on his head, licking one of his hands like a cat grooming itself. There's a long pause as the Devil slowly realizes what he's doing. The brothers share a look. Then burst out laughing.
  • The Devil is so lost in the role that he attacks the brothers by clawing at them, gets bashed by a broom by Elder Kettle, and ends up so completely enamored with playing with a ball of yarn that he completely forgets about attacking the brothers.
    Cuphead: [watching the Devil bat the barn of yarn between his hands] D'aw, ain't he cute?

    Holiday Tree-dition 
  • Elder Kettle leads Cuphead and Mugman in a song about the importance of getting a big ol Christmas tree, only to sneak back to the cottage during the song, sticking the boys with all the work.
  • Elder Kettle being very insistent that Mugman not pay asking price for one of Porkrind's trees.
    Elder Kettle: He'll ask for ten, [suddenly intense] but don't offer more than five. Given half a chance, old Porkbutt will take you for all you've got. [cheerful again] But, if you stick to your guns, you might even come home with change in your pocket. [intense again] It's very important that you come home with change in your pocket.
  • Mugman's attempts at haggling with Porkrind. He starts off as very confident, only to grow increasingly desperate as Porkrind doesn't budge.
    Mugman: Nice trees you got here, Porkrind. How much ya askin'?
    Porkrind: Ten bucks.
    Mugman: I'll give ya five. Firm.
    Porkrind: Price this year is ten bucks. Price last year was ten bucks. Price next year? Ten bucks.
    Mugman: [chuckles] Listen, Porkrind. How about I give you a crisp five, you give me a tree, and then me and the kid get out of your hair?
    Cuphead: I'm the kid!
    Mugman: What do you say, Porkrind? Let's close it up at five.
    Porkrind: Ten.
    Mugman: [looks nervous] Okay, okay. Six. [Porkrind snorts and walks away]
    Cuphead: [whispering at Mugman] You're doing great!
    Mugman: [panicking] Seven! I'll give you seven bucks!
    Porkrind: Did you say... ten?
    Mugman: [wincing] Eight?
    Porkrind: Tell you what, here's my final offer... Fifteen.
    • Each time Mugman made Porkrind an offer, he'd hold up the same number of fingers, causing them to rip out of his mittens. When Porkrind raises the price to fifteen, Mugman grows 7 extra fingers.
    • Mugman and Cuphead spent so long haggling on the price that all of Porkrind's trees are bought up. Porkrind goes back into his shop while Cuphead and Mugman start crying, only for Porkrind to come out and give them the idea to cut down their own tree.
      Mugman: But we don't have an axe.
      Porkrind: You could have this one.
      Mugman and Cuphead: [smiling] Really?
      Porkrind: For ten bucks.
      [Sad-sounding trombone sting plays over the brothers frowning.]
  • Mugman finds flaws with every tree they come across. Most are complaints like too small, too short, too fat, etc. Then they pass one that's juggling.
    Mugman: Too... desperate.
  • When Cuphead and Mugman find the perfect Christmas tree, a light shines on it from the heavens and Handel's "Messiah" starts playing. It continues to do so even after being chopped down and sliding downhill, with the light continuing to track it and "Messiah" abruptly cutting out whenever the tree's out of sight, only to come back fainter as it rockets further away.

    A Very Devil Christmas 
  • The Devil learns about the naughty and nice lists from a sandwich boy who was on the naughty list last year. The reason why? He glued his sister's face to the floor. Permanently. The Devil's impressed by the kid's evil.
  • Santa asks for The Devil's name, which leads to the following exchange:
    Santa: [splutters] What is your last name?
    Devil: Devil.
    Santa: Devil, Devil... I'm not seeing anything. What's your first name?
    Devil: ...The?
  • The Devil makes a deal with Santa that if he can be nice until the stroke of midnight, Santa will put him on the nice list and give him a choo choo. The Devil eagerly accepts and returns to the Inkwell Isles.
    Devil: [confidently] Okay. I can do this. Nice. Gotta be nice. Gotta get on the nice list.
    Old Woman: Spare some change for the less fortunate?
    Devil: Ew! [incinerates old woman]
    [Gilligan Cut to Santa at the North Pole]
    Santa: What happened?!
    Devil: Well, I was off to a good start.
    Santa: Yeah, for, like, ten seconds! Ugh... Santa needs a drink.
  • Santa tells the Devil at the rate he's going, he'll be on the naughty list forever.
    Devil: Forever? [erupts into flames] I WILL ROAST YOU FOREVER!
    Santa: [unimpressed] Tsk, tsk, tsk. [takes out naughty list and writes] "Threatened Santa."
    Devil gasps in horror and begins groveling
  • The whole eldritch ritual to have the Devil replace Santa. Santa and the elves are all dressed in robes, while the Devil is taken to a circle made of candy canes.
    Elves: Decanus Seasonem Holly Jollyum!
  • Doubles as Nightmare Fuel but the Devil's painful transformation into Santa Claus has "Carol of the Bells" playing over Body Horror.
    The Devil: [as Santa Claus] Ho ho hoooooohh nooooooo!
  • The fact that one of Santa's elves is an Identical Stranger to Stickler and the Devil's and Henchman's reaction to that.
    Devil and Henchman: Santa has one too?!
  • Stickler-Elf tells the Devil he has to deliver presents to all the children on the nice list. When the Devil refuses:
    Stickler-Elf: ...Plus, if you do not succeed, you'll stay Santa Claus for all eternity.
    (Camera zooms in on the Devil's increasingly-panicked face as Stickler-Elf's voice echoes)
    Stickler-Elf: [echoing] Eternity... Eternity... Eternity... Eternity...
    (Camera pans out and reveals the echoes are literally just Stickler-Elf repeating himself)
    Stickler-Elf: Eternity, eternity—
    Devil: Would you stop that? You're freaking me out!
  • Stickler-Elf tells the Devil that one of the rules of being Santa is remaining jolly at all times and never losing his temper. The Devil incinerates him for wagging his finger in his face. He resurrects the elf when Henchman tells him that's an example of something Santa can't do and Stickler-Elf goes on to the next rule without missing a beat.
  • The Devil's attempt at doing the reindeer roll call.
    Devil: On Sleazy, on Stinky, on Larry, and Fatso!
  • The Devil as Santa drops off presents at the sandwich boy's house, giving the sleeping boy the rocket he always wanted. And giving his sister glue remover.
    • During the montage, when Devil Claus finishes one house, he climbs down the rooftop, but gets his foot caught in the Christmas light wire and gets electrocuted. And then, when he falls down to the ground, his crash causes the icicles to fall on him, piercing him offscreen. That had to hurt.
  • While eating Stickler's sandwich, the Devil whimpers a little as his stomach makes a churning sound. All that milk and cookies really did him dirty.

    Special Delivery 
  • In order to get their baseball back after breaking one of Porkrind's windows, Cuphead, Mugman and Ms. Chalice to tasked to deliver a package to the Flytrap. When the brothers say they can't go because Ribby and Croaks want to kill them, Porkrind gives them disguises. Disappointed at just being given the disguise of "Peter the Delivery Boy", Porkrind tells Cuphead he's also a secret assassin. This causes Mugman to get really excited about what his disguise will be.
    Mugman: Hey, Porkrind. Porkrind. Hey, hey, Porkrind. Who am I gonna be, Porkrind? Porkrind? Hey, hey. Who am I gonna be? Porkrind, huh, huh, huh? Porkrind?
    [Porkrind skips Mugman and gives Chalice a disguise.]
    Porkrind: And you, you're Biff Macintosh, a handyman.
    Chalice: [expectantly] And?
    Porkrind: [sighs] And you're also a secret assassin.
    Chalice: Now you're talkin'!
    Mugman: Aw, I wanna be someone. Come on, Porkrind. Who am I, Porkrind? Jeez, Porkrind. Will you tell me who I am, Porkrind? Please, Porkrind. Tell me who I am!
    Porkrind: YOU are Tallulah Piccolo.
    Mugman: Oh boy! [hopeful] Am I... am I also a secret assassin?
    Porkrind: No. You're a washed-up dancer.
    [He drops a flapper dress on a visibly disappointed Mugman.]
  • As soon as the cups go outside to deliver the package, Porkrind warns them to not peek into its content. But not too long after that...
    Chalice: Hey! Wanna peek in the package?
    Cuphead & Mugman: Ye-ye-ye-ye-yeah!
  • Porkrind starts to feel guilty after finding out the package he told the cups to deliver is actually exploding shoes. To keep his mind off things, he listens to a horserace on the radio. It doesn't help.
    Announcer: Coming down the track is Baby Go Boom! Followed by Flaming Limbs! And in third is Blown to Bits! Behind him is Horribly Disfigured! And Charred Carcass is pulling up the rear!
    Porkrind switches off the radio.
  • It turns out the person who sent the exploding shoes to Ribby... was Croaks!
    Ribby: Why would you send me exploding shoes?
    Croaks: 'Cause youse tried to bury me alive that time, remember?
    Ribby: [chuckles] Always tryin' to bump each other off. When did this become our thing, huh?
    Croaks: Come here, you.
    Both: [hugging] Aw.
    Cuphead, Mugman and Chalice: Aww...
  • After Ribby rejects the backage, Cuphead, Mugman and Ms. Chalice have to return it to Porkrind. Porkrind, thinking that the cups actually delivered the bomb and not wanting to deal with the aftermath himself, angrily takes the package back, returns the ball to them and shoos the cups off. What he doesn't realise is that the exploding shoes are still in the package.
    Porkrind: [sighs] That was a close one...
    (The timer in the shoes rings)
    Porkrind: Uh oh.
    (The shoes explode, blowing up his shop, causing it to fall apart once again.)
    Porkrind: I hate those cups.

    Down and Out 
  • Mugman's ventriloquist doll seems to have a mind of its own, as it keeps cracking bad jokes and laughing obnoxiously while Mugman tries to shush it.
    Cuphead: I'm already managing this guy and his dummy.
    Dummy: In case you're wondering, he's the dummy.
    Mugman: Hey!
    Dummy: Ah-ha-ha-ha.
  • Elder Kettle using the pet goat as a dress-fitting mannequin during the rags-to-riches dress-up montage is pure gold.
  • King Dice's plan to get back into the Devil's good graces is by tricking Cuphead, who's working as Dice's "manager," into signing a contract that will grant the Devil possession of Cuphead's soul. Everything's falling into place. Until Cuphead begins acting like a slimy showbiz agent.
    Cuphead: I'm touched. What a beautiful gesture. But sorry, kid. [rips up contract] It's over!
    King Dice's jaw drops.
    Cuphead: Listen, I hate to break it to ya, but music's out. Comedy's in! [points at the stage]
    Mugman: You know, Dummy, sometimes you're a little too smart for your own good.
    Dummy: Well, that makes one of us. [crowd laughs]
    Mugman: Hey! Are you sayin' I'm dumb?
    Dummy: Why state the obvious? Ah-ha-ha-ha!

    JoyRide 
  • Elder Kettle's reaction when he first wakes up after Ms. Chalice stops possessing him.
    Elder Kettle: Waking up in the city with no memory of how I got here? Empty gas tank? [checks wallet] Money gone? [Beat] Kettle, you old rascal. You still got it! [Kettle and goat put on sunglasses]
  • Cuphead's fortune.
    Cuphead: [reading] "Your lack of common sense will be your undoing." Huh. Well, that's no help.

    Dance with Danger 
  • Ms. Chalice makes a deal with the Devil after her death so that she can change back into her living form. The first thing she does? Steal the Devil's wallet. When the Devil asks for it back, she sheepishly returns it then goes back to the living world. Henchman then realizes his own wallet's missing.

    The Devil and Ms. Chalice 
  • Ms. Chalice and the Devil are introduced performing a tap-dancing routine. As soon as they're finished, the Devil remembers his plan to have Chalice betray Cuphead and Mugman, only to be distracted as Chalice charms him into doing "one more" dance. She's been successfully distracting him like this for months.
  • The Devil's plan to have Chalice betray Cuphead and Mugman literally amounts to forcing her to ask the brothers to sign a random contract. It works.
    Cuphead: Sure. Why not?
    Mugman: Anything you say, Chalice. Normally we'd inquire about such a thing, but we won't even question it.
    Cuphead: You always have our best interests at heart.
  • Cuphead challenges the Devil to a contest to save Chalice's life.
    Cuphead: Play me in a game, and if I win, her debt is cleared. But if I lose, you can turn her to dust. And you can have my soul... and Mugman's.
    Mugman: Wait. What?
  • The game Cuphead challenges the Devil to is Rock–Paper–Scissors.
    Mugman: Cuphead, are you sure you know what you're doin'?
    Cuphead: Relax. It's rock-paper-scissors, which means I have at least an 85% chance of winning.
    Mugman: ...No? You both have an equal shot at winning.
    Cuphead: Huh? What do you mean?
    Chalice: The odds are 50/50, you ding-dong.
    Cuphead: Ohh... WELL, THAT'S INFORMATION I COULD'VE USED YESTERDAY!
    • Both Mugman and Chalice trying their best to give their faith to Cuphead before facing the Devil. "Trying" is the keyword here.
      Chalice: Don't worry, Cuphead.
      Mugman: We have complete confidence in you! [Cuphead walks away] ...We're dead.
  • Cuphead winning his game of rock paper scissors against the Devil. Mugman and Chalice hug, the crowd cheers, then...
    Devil: Best two out of three!
    Cuphead: Okay!
    Mugman and Chalice: WHAT?!
    • The Devil keeps challenging Cuphead to another round but Cuphead manages to win every single time.
      Devil: Best three out of five. Best five out of seven! Seven out of nine? Best out of eleven!
    • Mugman eventually gets sick of this and drags Cuphead away since he's won enough times and to avoid risking things further.
      Devil: Play me again!
      Mugman: Oh, no, NOO! That's enough!
      Devil: Just one more!
      Mugman: It's over! He won, you lost, that's it, we're done! [pushes Cuphead away from the scene]
      Devil: But—
      Mugman: Nope!
  • Henchman comforting the Devil after his defeat.
    Henchman: Come on, boss. I'll draw you a bath.
    Devil: [like a sad child] With bubbles?
    Henchman: Sure.
    Devil: Thank you, Henchman.
  • The final scene of the season is set a month later, with Cuphead, Mugman and Chalice eating ice cream and swearing to never get involved with the Devil again. Then the three see the grand opening of the Devil's Casino.
    Mugman: No way we're goin' near that place.
    Chalice: Yep. I think we all learned our lesson. Right, Cuphead?
    [A smoke outline of Cuphead is left holding his ice cream as the real Cuphead gleefully runs towards the casino.]
    Mugman and Chalice: Oh no. [they chase after him] CUPHEAD...!!

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