11 disturbing vintage cartoons that were TOO dark to be Cuphead bosses

You’d be excused for thinking the creators of Cuphead have let their imagination run a little too wild while designing their bosses. I mean, come on: there’s a potato that spits worms at you and transforms into a giant, psychic carrot; an anthropomorphic blimp/starsign belle; even a starlet that becomes a cardboard prop for one section. Mind you, it turns out that they actually reigned it in quite a bit, as most of the cartoons doing the rounds in the 30s (the period Cuphead draws inspiration from) didn’t have the same kind of reservations about mentally scarring children that we tend to have today. Thankfully. In case you don’t believe me, here are 11 of the creepiest vintage cartoons I could find, all of which could easily be Cuphead bosses in an alternate universe. Where watching cartoons is a punishment and children go to bed screaming. 

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1. Suspiciously scary scientist

What their level would look like: Obviously it would have to be a decrepit laboratory, with test subjects wriggling in vats and an Igor-like figure appearing every so often to chuck his master some syringes. Or something equally sharp and unsanitized. 

What attacks they’d have: Where do we even begin here? Hurling atoms, using Cuphead’s chopped-up shadow as a puppet, sending the poor results of their experiments marching after Cuphead, and probably transforming into Frankenstein’s monster for their final form. Complete with chuckable nuts and bolts that fire out from the neck. Oh, and buckets of electricity (not literally). 

2. Worryingly warped walrus

What their level would look like: I’m assuming this… thing is meant to be a walrus - but honestly, its features are so nightmarishly odd that it could be an unholy spliced creature made from multiple subjects (to spawn this oddity a dancer was rotoscoped, and the real footage was then traced over to create a cartoon). Behind it would be a San Francisco-esque Pier 39, filled with apprehensive seals who don’t dare to stand up to this horrific abomination.

What attacks they’d have: An almighty bodyslam wouldn’t go amiss, nor would throwing copious amounts of fish and possibly the odd unlucky chap whose job it is to feed the seals. I bet the tusks would detach and fire out torpedoes too. Don’t think I haven’t noticed how bulbous that belly is either… the final form could have the tummy unzipped to reveal it’s being piloted by a seal bouncing a rubber ball, which would be fired at you with intense enthusiasm. Or deadly force, depending on your point of view. 

3. Candle-headed cultists

What their level would look like: Figures in dark robes would be swaying from side to side, with flaming braziers at either end. Plus an altar. That would be conspicuously clean. As if someone had scrubbed it recently...

What attacks they’d have: Obviously the whole head-on-fire thing would be a gamechanger. I’m imagining it’d fire lit candles Cuphead’s way, culminating in a massive flamethrower attack. Hot wax falling from the sky would need to be dodged, plus you have to try and avoid the initiation rituals… in the full-length cartoon that involves its main character dodging blades with teeth. Think of it as hazing gone overboard. 

4. Several-headed shed

What their level would look like: God, I don’t want to imagine what farm this building came from. But I have to. So I’m thinking some poor farmer bought land but he wasn’t told it was an ancient burial ground, and all his things began to be possessed. Tractors have teeth instead of grills, cows walk on their hind legs, and all the crops prance around. Reeeeal spooky stuff. 

What attacks they’d have: Like the hydra that grew two heads whenever one was cut off, each head emerging from the barn would multiply, with each one having its own attacks. The one with the hat would use its headwear like a boomerang, all while firing out chickens from the doors and having the barn jump around on its stubby little legs to try and squish Cuphead. 

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5. Hairy hermit

What their level would look like: This creep is basically a giant with a beard and some missing teeth. A very long, prehensile beard at that - but I’ll get onto that later. As he’s got a hideout in a cave there would be treasure and various other giants’ skulls strung up behind him, like you can see in the gif. 

What attacks they’d have: Considering it’s prehensile (basically meaning it can grab and move like a hairy tentacle), you can bet his beard is going to be snaking its way towards Cuphead. If only our hero had a clipper as a special attack… he’d have to jump over the beard and avoid the treasure the hermit pulls out from under his raggedy tunic and throws your way. Just don’t ask where those bits of glittering gold have been. 

6. Pirouetting phantom

What their level would look like: Another rotoscoped dancer, this ghost is certainly no longer of the material world, or his leg bones would be protesting rather strongly. Behind him would be other dancing apparitions, with a disco ball high above whose coloured lights would shine through the jivers. 

What attacks they’d have: Obviously those long legs would be used to kick over large distances, and it’d be a crime against music if he wasn’t able to transform into various objects. How about a jukebox that spits out vinyl records? Or a set of drums that project sentient musical notes? Bonus points if Cuphead jumps to the musical rhythm to unleash an almighty combo cabaret attack. 

7. Centaur cadaver

What their level would look like: A graveyard. Simple. Or maybe not, because by the looks of it the bones have got muddled up. So there’d be skeletons with eight legs like a spider, or a game of piggy-in-the-middle going on with a poor sod’s skull being chucked back and forth. 

What attacks they’d have: Bowling skulls like someone out of The Big Lebowski wouldn’t be enough for this skeleton. It’d snatch bones from the ground to change what it looked like, adding limbs, ribs, and pelvises to turn into other various (boned) mythological creatures. A unicorn, using a pointy rib as a horn and charging forward, or a satyr playing a flute made of… yeah, you guessed it. Bones. 

8. Tarantula’s tavern 

What their level would look like: The actual name of this cartoon is ‘The Cobweb Hotel’, so the background would feature its unlucky guests. God knows why the insects wouldn’t be suspicious about an inn filled with sticky webs, but they’d certainly know their mistake by the time Cuphead is frolicking in front of them. 

What attacks they’d have: Mercifully our arachnid friend would at least free some of their residents by throwing the wrapped-up insects at Cuphead, which would have to be avoided as they broke free and fled from the spider. Mr. Spider would also use his sticky, stretchy webs to pull platforms towards him and attempt to ensnare Cuphead. Hopefully the spider would encounter a massive flyswatter at the end for some poetic justice.

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9. Musician magician and his mystified mummy

What their level would look like: On a stage, the magician (god knows what’s going on with his face, by the way) would be sitting at a piano with an enraptured audience behind him, watching the show eagerly. I can’t guarantee magic wasn’t used to make them so attentive, but they’d cheer and applaud whenever the boss hit Cuphead. 

What attacks they’d have: Monsieur Magician would slam his hands on a keyboard to get the mummy to dance around the stage, whose pirouettes Cuphead would have to avoid (obviously). Piano keys would bounce off of the piano and scatter across the stage while our hero dodges the magic hopping out of his hat and from the top of the instrument, probably in the form of snaking piano wires.

10. Sinister snowman

What their level would look like: Cold, snowy, and full of icicles. Frozen polar explorers would be suspended behind, trying to hack themselves out of the pillars of ice or idly licking snowcones (not yellow ones). Pet polar bears chained up at either side would be acting generally adorable, with happily panting tongues. 

What attacks they’d have: Cold winds blowing from the North would spout from the Abominable Snowman’s fingertips, along with a periodic avalanche and flurries of snow. Frozen creatures would fly Cuphead’s way, with their attempts to escape from the ice sending shards of it spiralling his way. I doubt even a thick fur coat would help Cuphead against the Snowman...

11. Enterprising extra-terrestrials

What their level would look like: Set inside a flying saucer, I’m imagining some artistic sketches for new crop circles as well as some bewildered-looking abductees. Along with futuristic weapons and star charts plastered everywhere, of course. Maybe with a sneaky millennium falcon tucked away in a corner. 

What attacks they’d have: Firing out mini flying saucers (duh) is a must. I’m not ruling out probing tools, although that might be a little inappropriate for Cuphead. Intrepid aspiring astronauts would be thrown out on their airlines like yo-yos, before the two aliens pair up to transform into a massive ringed planet that sends out comets like boomerangs. 

Zoe Delahunty-Light

While here at GamesRadar, Zoe was a features writer and video presenter for us. She's since flown the coop and gone on to work at Eurogamer where she's a video producer, and also runs her own Twitch and YouTube channels. She specialises in huge open-world games, true crime, and lore deep-dives.