Cartoons from the first half of the 20th century are creepy for a lot of reasons. For one, many of the lead animators in the early days of film had dark senses of humor. In addition, while cartoons came to be associated with kids in the age of television, these early animators weren't necessarily making films that were family-friendly.

Modern filmmakers, game designers, and artists often lift imagery from the early years of animation to make a work creepier. But long before Bendy and the Ink Machine or Cuphead, animators were doing just fine creeping out their audiences on their own.

Updated by Joshua M. Patton on December 5, 2023: These cartoons are representative of a different time in animated filmmaking, from techniques to aesthetics. Many of these cartoons were designed to be scary for children; however, as animation evolved and tastes changed, "scary" became "creepy" in a way the animators likely didn't intend. Luckily, since almost all of these films survived to the present day, readers can judge the creepy factor of each cartoon for themselves, but they may leave viewers haunted.

10 Wot a Night Is Weird and Spooky

Directed by: John Foster and George Stallings

The animation team at Van Beuren Studios had a comedy duo named Tom and Jerry fifteen years before the cat and mouse appeared onscreen. Renamed "Dick and Larry" in the '40s, the original Tom and Jerry were just a tall man and a short man who ended up getting into scrapes with each new job they took.

Their first film, Wot a Night from 1931, is a straightforward story about two taxi drivers who find themselves locked in a castle and tormented by ghosts. As cartoonish as the spirits of the castle are, their eerie movement and unblinking eyes are upsetting to most modern viewers, making it not the creepiest cartoon in history but definitely worth being among them.

9 The Devil's Ball Is a Stunning Stop-Motion Nightmare

Directed by: Maurice Burkhart; Released: 1931

Stop-motion animation always threatens to dip into creepy, uncanny valley territory, and the rudimentary stop-motion films of the 1930s are especially unsettling. The 1933 cartoon The Devil's Ball is a surreal collection of images involving tall, rail-thin spirits tormenting a young boy and throwing a surreal party.

The Devil's Ball is the creation of Ladislaw Starewicz, who essentially made the entire short himself. Considering the equipment he would have been working with at the time and the immense effort that goes into creating a stop-motion cartoon even today, Starewicz's achievement is remarkable. This entry is definitely creepy by today's standards, but animation fans will get lost in how impressive it was for its time.

8 The Headless Horseman Adapts a Classic Book

Directed by: Ub Iwerks

The Legend of Sleepy Hollow is one of the most well-known American horror stories, and its tale of a snooty schoolmaster who is tormented by the Headless Horseman has been adapted many times. Most recently, there was a TV series called Sleepy Hollow, with a modern-day twist. However, the 1934 short The Headless Horseman is an early and fairly straightforward adaptation with some cartoonish antics thrown in for good measure.

The short doesn't get spooky until the Headless Horseman sequence, but the dark, fluid animation of the famous ghost is surprisingly effective. Of course, the whole thing turns out to be a prank, but that doesn't make the sequence any less impressive.

7 Bimbo's Initiation Is Like a 1930's Midsommar

The Max Fleischer character Bimbo has largely faded from the public's memory. Originally the anthropomorphized dog boyfriend of Betty Boop, Bimbo's status as the hero of his own cartoons declined as his girlfriend ascended to super-stardom. Bimbo disappeared altogether around 1934.

One Bimbo short does stick out in people's memories, however. Bimbo's Initiation is a baffling story of Bimbo being bullied into joining a cult until he finally succumbs, mainly because Betty has already joined. The surreal torment the cult puts Bimbo through is nonsensical but still evokes something out of a nightmare.

6 Balloon Land Is Not as Cute as It Sounds

Directed by: Ub Iwerks

The bizarre 1935 short Balloon Land by Ub Iwerks may or may not have been intentionally disturbing, but for a cartoon with such a childish premise, the short's phallic imagery is impossible to ignore. The denizens of Balloon Land are all made of balloons, and they live in fear of a particularly dangerous villain to them. The short is sometimes called The Pincushion Man in honor of its unique villain.

The Pincushion Man in question has a long needle sticking out of his crotch, which he tries to use on the two children who serve as the short's protagonists. By comparison, the sequence where Pincushion Man massacres loads of balloon people seems tame.

5 Spooks Terrorized Oswald the Lucky Rabbit

Oswald the Lucky Rabbit is best known today as the character Walt Disney created before Mickey Mouse. In fact, the creation of Mickey Mouse was Disney's direct response to losing the rights to Oswald. Of course, Mickey is a legend now, while Oswald is mostly an obscurity. Still, the 1930 cartoon Spooks is a solidly spooky showcase for Oswald.

Directed by Walter Lantz, the short is far weirder and more mind-bending than anything Disney would have made. Oswald goes through an adaptation of Phantom of the Opera but with more creepy owls and deaths by deflation. The combination of the familiar Disney style, if not the characters, with the creepy aesthetics puts this film squarely in the midst of the creepiest cartoons of the past.

4 The Tell-Tale Heart Brings Poe to Life

Directed by: Ted Parmalee

Edgar Allan Poe's stories are already plenty creepy, but the Ted Parmelee animated adaptation of The Tell-Tale Heart, released in 1953, manages to make the original story even creepier. With shadowy, painted frames and sinister narration from James Mason, The Tell-Tale Heart takes the unnerving story and runs with it.

The animator Paul Julian, who is best known for his work on backgrounds for Loony Tunes shorts, adjusted his painted backgrounds for horror purposes to great effect. The resulting film was so eerie that the British Board of Film Censors rated it X, meaning it was for adults only. Still, this may be the only creepy cartoon on this list that was designed to terrify.

3 The Tale of the Priest Was Lost in a Fire

Directed by: Mikhail Tsekhanovsky and Vera Tsekhanovskaya; Destroyed: 1941

The husband-and-wife team Mikhail Tsekhanovsky and Vera Tsekhanovskaya directed the animated film The Tale of the Priest and of His Workman Balda sometime in the 1930s, but the film was never finished. Mikhail cut the four finished portions into a full movie, but it was lost in a fire caused by the bombing of the studio during the 1941 Siege of Leningrad in World War II.

The only surviving portion of the film is a short Bazaar scene, which is enough to give a sense of how unsettling the full movie would have been. The film's tormented production, cancelation, and loss only add to the sense that something very creepy was going on with The Tale of the Priest. It's a common children's fairy tale in Russia and has been adapted into books and, later, a stop-motion film.

2 Swing You Sinners! Is a Creepy Masterpiece

Directed by: David Fleischer

The Fleischer Brothers directed Swing You Sinners! and released it in 1930. The cartoon appears cute and harmless at first, following a ne'er-do-well dog character who tries to steal a chicken. But then, he stumbles into a graveyard, and things get nasty.

Ghosts, monsters, and living instruments all torment the dog by telling him he must be punished for his sins. The dog pleads for his life but to no avail. The short ends with a parade of weird imagery and the dog being eaten by a skull in the last frame.

1 The Peanut Vendor Is an Experimental Terror

Directed by: David Fleischer and Seymour Kneitel

The Peanut Vendor, a 1933 stop-motion animated film about a monkey selling peanuts, probably wasn't intended to be creepy, but it absolutely is. The monkey in question looks more like a skeletal demon with his long arms and big eyes. The movements are also uncanny, though in fairness to the animators, this was all new at the time. Setting aside the abject horror of the short's lead character, this is an important film in animation history, too. Just like with The Devil's Ball, this showed the potential of stop-motion animation.

Directors Dave Fleischer and Seymour Kneitel were experimenting with animation techniques and accidentally stumbled upon a deeply frightening set of images. The age of the film has only washed out the monkey's image further and made it look more like a skeleton. The film may have been made with good intentions, but Fleischer and Kneitel unleashed a nightmare-inducing creature, singing a lovely Mexican song about buying peanuts before going to sleep. It's the fear of what this monkey will do after everyone is asleep, however, that makes The Peanut Vendor one of the creepiest classic cartoons of all time.​​​​​​​