- Right when you start up the game you get a catchy little barbershop tune telling you pretty much what's happening. And the lyrics at the end are so cheery yet morbid you can't help but chuckle. "...and now they're fighting for their lives, on a mission fraught with dread: and if they proceed but don't succeed, well... the devil will take their heads!"
- The tutorial just being a single parchment of paper you travel on to perform actions over sketched objects.
- The game over cards are labelled "MDHR Inc. Death".
- For a Side Quest on the second island, find the missing member of a barbershop quartet. Your reward is another catchy little tune, this time about taking a quick break from the game.
- Beat Baroness Von Bon Bon and she starts crying. What's really funny is her castle starts bawling like a baby too as it beats the ground with its fists.
- Also Bon Bon's absurdly angry facial expressions.
- When Dr. Kahl is beaten, the robot head explodes from underneath him, knocking off his clothes in the process.
- In the first phase of Cala Maria's battle, she has an attack where she briefly goes underwater to grab a giant fish, which she uses like a gun. First of all, her animation when she goes underwater is funny — she does a silly grin and a very trollish laugh while waving her arms. There's also the way in which the attack ends: the fish struggles free from her grasp and flops back into the water, leaving her with a disappointed look.
- For a bit of Black Comedy, there's her transformation into her second stage: a pair of electric eels pop out of the water in front of her and then sink their teeth into her midriff. Cue X-Ray Sparks and a lot of screaming. Also, if one looks closely, they can also see that the octopus in her hair has a skeleton of its own.
- When Cala is beaten in Regular Mode, one of the snakes in her hair plays a small violin.
- Morbid as it is, Goopy being flattened by his own gravestone is pretty funny.
- Bit of Black Comedy, but seeing Wally Warbles still trying to fight you while on a stretcher is both admirable and chuckle-worthy. Likewise, the two medic birds preparing to eat him when he's beaten.
- The first and third phases of Beppi the Clown's battle both end with Beppi falling off the screen with a funny-sounding scream. The guy has such a high-pitched voice!
- Beppi's ridiculous facial expressions while on the bumper cart, and his enthusiasm while on his horse, are also worth a mention. Of all the bosses in the game, he's clearly the one having the most fun. And his final phase's defeat, rather than the usual highly pained screaming, has more of an utterly exhausted "okay, that's all I got" expression.
- When fighting Captain Brineybeard, on the third phase, his ship suddenly turns into a narwhal and throws him off. You can see Brineybeard flying into the background as a result.
- The fact that the cat that ate Werner Werman is really nothing more than a very elaborate mecha to fight you with. Once defeated, the faceplate opens to reveal Werner in the pilot seat.
- Virtually everything about Sally Stageplay's fight. Especially around the third phase (a parody of the final battle against Kefka in Final Fantasy VI) where you're not really fighting her, but rather a cardboard cutout of her and the "attacks" (actually props) she summons. Especially good is her "Big Wave" attack, since it's some clearly overworked stagehand struggling to run at you with the giant prop in question.
- When starting the fight with Rumor Honeybottoms, you have to fight her officer. After you defeat him, he just sulks off rubbing his arm with a look that just screams "Not cool, guys".
- Whilst losing to a boss can be frustrating, the developers were kind enough to compensate for players' shortcomings by providing cheesy taunt lines unique to each boss form. Some highlights include:Hilda Berg: Fitting, isn't it? I'm a blimp — you're a wimp!Sally Stageplay: Break a leg... nah, break two!Djimmi's Puppet: That beating was for free — no strings attached!Chauncey Chantenay: I'm lean, mean, and full of beta-carotene!Brineybeard's Ship: HAW-HAW-HAW-HAW-HAW!
- When you fight King Dice and beat him, his hands look like they're bowing to you.
- A bit of a Stealth Pun in his attacks, too: he marches a row of ace cards out of his arm to attack you, with some pink heart ones in there so you can bounce off. So he literally has an ace up his sleeves (or two, or three...).
- During King Dice's boss rush, Pip and Dot (the domino boss) will not take losing well, with Dot kicking Pip in the eyes repeatedly. And then there's Mr. Wheezy; King Dice puts him out personally when defeated, by grinding him under his foot.
- After the 3 phases of the nightmarish battle against the Devil, what does he do for his final phase? Cry. The Devil starts crying like a baby during his final phase, spilling pink tears that'll allow the protagonist to parry off of them and avoid the falling chip.
- When Conan O'Brien played the game for his "Clueless Gamer" segment, Studio MDHR created a special selection screen with his head floating in the middle of it!
- Someone got Deedee Magno Hall to say Hilda Berg's phase 1 death quote.
- At The Game Awards 2017, when Hideo Kojima and Guillermo del Toro prepared to announce the winner for Best Art Direction, del Toro opened the envelope... then looked at the name of this game on it and cracked up, giggling a bit before joking at Kojima's name and blurting out, "CUPHEAD!" As a bonus, del Toro had never seen the name of a game on the envelope like this one, let alone that said name like Cuphead looked a bit silly-sounding to the director. Heck, this whole Best Art Direction speech by the Moldenhauer brothers is pretty funny and a Heartwarming Moment.
- The Nindies Spring Showcase 2019 had an ad opening up about drinking milk instead of coffee. The man in the commercial comes from the "Ministry of Drink and Health Regulation". Why does that sound familiar...?
- This animatic based off "Carnival Kerfuffle" demonstrates that Charlie Adler's voice work of The Red Guy, the antagonist from Cow and Chicken and I Am Weasel, fits remarkably well with Beppi the Clown. Highlights include:
Beppi: *in a deadpan voice* "It leaks."
- Beppi using Cuphead's head as a coffee mug, to audio from "101 Uses For Cow and Chicken". And all Mugman can do is watch in horror.
Beppi: "Well, it all started when I was about ni-en. I was just a boy, I didn't know pants were required at school." *grabs Cuphead's collar, startling him into dropping the notepad* "WHO WOULD HAVE GUESSED?!"
- When Cuphead acts as Beppi's therapist (to the audio from the I Am Weasel episode "He Said, She Said"), he doesn't write any notes at all, instead doodling on his notepad. It's a picture of him firing his finger gun at Beppi over the words "Go to Hell".
Beppi: *singsong voice* "Mr. Sackless isn't very happy heeeere..."
- The audio from another I Am Weasel episode ("The Sackless Games") sees Beppi in his balloon-man form from the second stage of his boss fight, trying to get the brothers to shoot an apple sitting on his (ridiculously large) head. Whereas Weasel and Baboon end up nailing the Red Guy's bottom in the episode itself, the animatic has the spread-shot bullets the brothers fire end up hitting Beppi's chest instead.
- From the fanmade song "Greedy":
- There's something darkly humorous about how the song goes straight from Elder Kettle warning Cuphead and Mugman not to gamble at the Devil's Casino to the Devil welcoming them into the casino. It's like the musical version of a Gilligan Cut:Elder Kettle: (speaking) Listen to my advice, boys. If you come upon a casino, don't deal with the de-de-de-devil.
The Devil: (singing) Welcome to my casino, lads!
- Later in the song, the Devil starts singing scat! It can be seen as a reminder that, as evil as he is, he's still a toon, and no less a part of the colorful world of Cuphead than any other character.
- There's something darkly humorous about how the song goes straight from Elder Kettle warning Cuphead and Mugman not to gamble at the Devil's Casino to the Devil welcoming them into the casino. It's like the musical version of a Gilligan Cut:
- "Devil's in the Details" is much more upbeat and lighthearted than most other fan songs, and it contains quite a few funny moments. Special mention goes to one section where it shows live-action footage of two people tap dancing, with Cuphead and Mugman's heads superimposed over the peoples' heads.
- "King of Dice" has a hilarious exchange between Cuphead and Mugman halfway through:Cuphead: What do you think, Mug, is [King Dice] for real?
Mugman: Uh-whah... what do you mean "do you think he's for real?" Are you kidding me?!
Cuphead: Well, I don't know,note the guy's got a big dice for a head! Who knows?!
Mugman: I'M A TALKING MUG! AND YOU'RE A TALKING CUP! WHO CARES IF HIS HEAD IS A DICE?!
Cuphead: CALM DOWN! You're always freaking out, just CHILL!
Mugman: WE'RE ABOUT TO SPEND THE REST OF OUR LIVES IN HELL! HOW CAN YOU BE CHILL?!
(An Evil Laugh is heard, apparently from the Devil.)
Mugman: See, se... see what you've done?!
Cuphead: It's all good bro, got it handled, 'bout to go kill all these demons while you sit around and complain!
Mugman: Oh, whatever!
- This entire animatic, superimposing the game's characters over the audio of "The Salt and Pepper Diner".
- Special note goes to Wally Warbles' son, who is seen crying and shooting his blaster everywhere... only to stop dead in his tracks and mutter "Dad swore..." in shock after Wally goes "GOD DAMMIT!" and pounds his table.
- After Mugman suggests adding "It's Not Unusual" after seven plays of "What's New Pussycat" to lull everyone into a false sense of security, you can see Cuphead's eyes light up like a Christmas tree as he says "Mug, you monster." (This is while Mulaney's narration says "And that is when the afternoon went from good to great...")
- This is followed by a shot of Cala Maria sporting light-up eyes and a wide grin of ecstatic relief... Only, if you look closely, you can see the incisions on the table that she presumably made a few moments before.
- When yet another play of "What's New Pussycat" starts up after the one "It's Not Unusual", everyone except the brothers completely loses it, including Cagney turning into his wilted, wailing husk from his defeat animation, Beppi's head becoming the balloon-like form of his second stage, the Blind Specter's eyes in his palms emitting Ocular Gushers, and Cala Maria transforming into her second-stage gorgon form.
- The "homeless schizophrenic" is played by Werner Werman, and while everyone else throws a collective fit during the above scene, he and one of the prisoner rat ghosts from the third stage of his boss fight enact the part where Mulaney wishes one of the schizophrenics stands up and says "Now you know. Now you know what it's like to live in my brain."
- And to top it all off, King Dice of all people is the one playing the diner staff's Unfazed Everyman, mopping the floor with the mop facing the wrong way and having the most deadpan expression while Mulaney narrates the staff thinking "Yep, same shit as always."
- And to top that off, The Devil plays the role of the guy who finally unplugs the jukebox.
- And another animatic (swear warning) featuring the audio from a John Mulaney skit (this time it's "The One Thing You Can't Replace"), starring Mugman in the role of Mulaney.
The Policeman Bee: *speaking into his walkie-talkie* "Get the paddywagon."
- Mr. McNamara and his son are, respectively, played by Wally Warbles and his son. The Asshole Victim teacher's departure ("which you should never do IF YOURE AN ASSHOLE") is shown as Wally simply flying off to who-knows-where, followed by Wally Jr. inviting the rest of the characters to a party at the birds' house... whereupon everyone else gets the most deliciously evil expressions while Mulaney narrates them all thinking "Okay, lets go over there and destroy the place."
- When Mulaney notes that "everyone was drinking like it was the end of the world", Cuphead can be seen among the party-goers pouring his drink into his own head (with the same tipsy expression as the rest of them).
- Naturally, it's The Devil who leaps onto the pool table in the basement and breaks it in half. The looks on everyone else's faces are priceless.
- Special mention to Mugman's response when either Cagney and the Blind Specter, in Mulaney's words, "took a shit on [Wally's] computer". (Though it isn't shown which one does it, nor how they manage to do it, since we only see Mugman's Reaction Shot.)
- When Mugman himself gets drunk, there are several split-second close-ups showing the plastic cup he's holding having first Cuphead's face, and then Master Shake's.
- The police officers who show up at the house are, naturally, played by Rumor Honeybottoms and her officer. There's also their reaction when they find everyone (prompted by Mugman himself) drunkenly yelling "FUCK THE POLICE" in their faces.
- Just before The Devil smashes a bottle on the floor and yells for everyone to "SCATTER!", Mulaney's narration mentions that the character he's playing is now a father ("he has a baby"), and at the word "baby", another Freeze-Frame Bonus has The Devil holding up a certain other toony demon.
- The following Monday, Wally Jr. frantically reveals that "someone stole these old antique photos of my grandmother and my parents are freaking out about it" (sic), whereupon Mugman wonders in horror if he was the perpetrator. It isn't until two years later that he discovers the real culprit: his own brother, Cuphead (playing Alex, the guilty party from Mulaney's skit) who's been stealing antique photos from people's parties for years. And where does he keep the stolen photos? In, to quote Mulaney's narration, "a side room off of his bedroom. Never a good thing to have."
- See what happens when Cuphead and Mugman drink themselves.
- The Devil has evil laughter envy.