The Top 7 Spookiest Cartoons From The Era That Inspired Cuphead!

Decades before masters of horror like Wes Craven, Tobe Hooper, and John Carpenter hit the scene and even before the Hayes Code, theater goers were watching some jacked up stuff in their pre-show cartoons. Read on to see seven of the spookiest and creepiest cartoons from the early 20th century and learn where Cuphead gets its weirdness!

Betty Boop in Snow White (1933) – dir. Dave Fleischer

Four years before Walt Disney adapted the Brothers Grimm tale, the Fleischers beat him to the punch with their iconic character Betty Boop. In the short, Betty as Snow White (but still called Betty Boop) goes to visit her evil step mother, the queen. The queen’s magic looking glass declares Betty the fairest in the land, and in a much less roundabout way than the Disney evil queen’s plan, she’s condemned to a beheading.
The queen’s guards, played by Bimbo and Koko, dig a grave so deep that they fall hundreds of yards deep allowing Betty to escape. She trips down a mountain, which causes her to become trapped in a giant snowball and then entombed in a coffin made of ice. She’s then found by the seven dwarves who mournfully take the obviously still alive Betty to a “mystery cave”.

We’re then treated to a recurring theme in this period of Fleischer cartoons — a Cab Calloway performance. Thanks to a deal with Paramount, Cab Calloway and his orchestra were featured in three shorts by the Fleischers. Snow White was the last of the three with the song St. James Infirmary Blues. In each of the shorts, Calloway was rotoscoped into a character featured in the cartoon. Rotoscoping is an animation method in which artists actually draw over live action footage. This creates a horrifying cognitive dissonance as the style suddenly changes and the characters longer move like cartoons. The effect is super amplified by Calloway’s otherworldly wail of a singing voice.

Shedding their fairytale costumes for their regular outfits, Bimbo and Koko follow the dwarves and Snow in the most unsettling funeral procession ever put to film and the evil queen, now in her wicked witch guise follows. She turns Koko into an even more terrifying ghost and I start crying.

The most upsetting part of the Calloway sequences are the gags. The Fleischers are cartoonists and can’t let a guy just stand on screen singing for two minutes. This is a cartoon! There has to be buckwild shit happening all over the screen. So Calloway/Koko/Ghost morphs and transforms into many cartoon-y shapes and objects while screaming old timey jazz at you.

Our three heroes… uh, die? I think? And then the queen, confident that she’s now the fairest, asks the mirror the ultimate question again and is met with the same old answer. Then she turns into a dragon? And everyone turns back to normal and runs away? They win and dance together in the snow and the short ends. Old cartoons are weird.

The Skeleton Dance (1929) – dir. Ub Iwerks

This Silly Symphony has to be the most oft-referenced and influential cartoon in the history of the medium. When someone mentions rubber hose animation or even thinks of classic cartoons, this is the short they’re thinking about.

This is before cartoons needed story or even identifiable characters. Iwerks and Disney could spend five minutes showing wacky, spooky crap happening and that was captivating enough because we were still shocked that DRAWINGS were MOVING! And even almost a century removed from that mindset, this is still an incredible short film. If there’s one thing The Skeleton Dance does better than anything else, it’s setting a mood. An owl hoots, the wind blows, a dog howls, and this creepy old cemetery complete alive. Then we’re ready for the main event.

The dead live! And they can boogie!

At least they can until a rooster crows, signifying a new day, and the skeletons need to scramble to return to their graves. Because I guess this cemetery operates on Toy Story rules? If you haven’t watched this short, you probably already feel like you have because of how often its referenced even all these years later. Either way, you should check it out.

Bimbo’s Initiation (1931) – dir. Dave Fleischer

Another Fleischer joint, Bimbo’s Initiation is a classic example of old cartoons just being plain bonkers.

Bimbo is just minding his own business when he falls into an open manhole — a calamity that, much like quicksand, I expected to experience a lot more than I have thanks to cartoons. He’s locked into the hole by a very familiar looking mouse.

At the bottom of the chute Bimbo is met by a congregation of bearded, candle headed, thicc-assed men in cloaks. Bimbo declines their invite to become a member of whatever Eyes Wide Shut shit is happening here, but is forced to suffer their initiation anyway.

The trials include being stabbed in the butt by a sword/shark, escaping a falling spiked weight, and a spanking machine that he could just, like, get off of?

Bimbo is tricked further into the labyrinth by Betty Boop where he escapes more traps, dangers, and spankings until it’s revealed that all of the members were Betty Boop! Which I guess means that this was a big, elaborate sex game to treat Bimbo to some kind of clone orgy? What’s the deal with secret societies in old cartoons anyway? This, the Loyal Order of the Water Buffalo, various references to hanging out at “the lodge”. Is this just what old white guys did before Facebook?

More cartoon cinematic spookiness awaits you on the next page!

One thought on “The Top 7 Spookiest Cartoons From The Era That Inspired Cuphead!

  1. I tend to like to bunch up Halloween cartoons for Halloween season so while it’s “too late” to show them these this year, I’ll make a mental note to show them next year because my kids really enjoyed the Disney list you guys made earlier.

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