(Welcome to Out of the Disney Vault, where we explore the unsung gems and forgotten disasters currently streaming on Disney+.)

Now that we’re entering spooky season, it’s time to scout the Internet for hidden and not-so-hidden horror gems to add to your Halloween watch list. Of course, because of Disney’s decades-long reputation as a provider of family-friendly entertainment, a column about Disney movies is not the first place you’d look for horror recommendations. However, this series has already explored some films from the one period in the studio’s history where dark and creepy was not only allowed, but encouraged. 

However, decades before Return to Oz or The Black Cauldron traumatized kids everywhere, we got arguably Disney’s best gateway animated horror film: their animated adaptation of The Legend of Sleepy Hollow. Part of Disney’s 1949 package film, The Adventures of Ichabod and Mr. Toad, The Legend of Sleepy Hollow manages to be both family-friendly and a cool little musical to boot, but also a fantastic gateway horror film that is the perfect way to start the Halloween season.

The Pitch

For Disney, the 1940s was largely defined by a series of “package films” for a variety of reasons — a shortage of animators due to WWII, the animators’ strike, and even Bank of America ordering the studio to only produce animated shorts and finishing features already in production. The result was a series of six films consisting of multiple short films barely strung together by theme, location, or nothing at all in the case of the studio’s last package film: The Adventures of Ichabod and Mr. Toad.

Production for the film started all the way back in 1938 when Walt Disney’s animators first pitched an animated adaptation of the Kenneth Grahame children’s novel The Wind in the Willows. Though Disney was lukewarm on the potential for the film, he bought the rights to the book anyway, and production continued on and off for a few years, until Walt instructed the film be shortened down to a short feature in 1946.

Around the same time, production began on a feature adaptation of Washington Irving’s The Legend of Sleepy Hollow, but when the animators working on Sleepy Hollow realized they didn’t have enough material for a feature-length film, the short was paired with The Wind in the Willows to become Disney’s last package film — despite there being no connective tissue whatsoever between the two vastly different stories.

The Movie

Unsurprisingly, the biggest problem with The Adventures Of Ichabod And Mr. Toad is that the two stories are incredibly dissimilar in both plot and tone. If you’re here to watch the adaptation of Sleepy Hollow, you first have to sit through more than half an hour of a frog being sent to prison and escaping. If you’re a fan of The Wind in the Willows, you have little reason to continue watching after that first short concludes. The two stories are literally in the wrong order too, as the title implies Sleepy Hollow goes first, instead of second. Meanwhile, The Wind in the Willows ends after New Years before Sleepy Hollow takes us back to Halloween. 

If you can get behind the disjointed nature of the film, however, there is a lot to love here. The Wind in the Willows is a phenomenally animated short full of memorable characters. But the real star of the show is the adaptation of The Legend of Sleepy Hollow, which is not only one of the most faithful adaptations of Irving’s classic short story, but a fantastic short film.

The one major departure from the source material is the removal of the historical effect, changing Ichabod’s fear from being caused by experience in the Revolutionary War to simple paranoia and superstition in order to appeal to younger audiences. The result is a film that knows when to have the shadows in the dark woods actually be harmless squirrels, and when to make them horrifying ghouls. 

The final 10 minutes go full-throttle into horror territory, as Ichabod leaves a Halloween party having listened to the spooky tale of the Headless Horseman. All nine of Disney’s legendary “Nine Old Men” were involved in the film, and it shows. As Ichabod heads back home atop his slow and tired horse, every noise in the dark woods becomes a mini jump-scare, with plants shuffled by the wind or cattails rhythmically thumping on a log to mimic a horse’s gallop. The tension is thick even before the Horseman starts chasing Ichabod around the woods.

The Horseman itself is an incredible accomplishment of horror animation. Wearing a purple cape on top of black clothes, wielding a sword on one hand and his fiery pumpkin head in his hand while galloping atop its hellish horse, the Horseman’s laughter is both menacing and playful. Every time the Horseman is on the verge of cutting off Ichabod’s head, the film cuts away to a visual joke to deflate the tension, mixing horror and comedy for a few minutes until the Horseman throws its fiery pumpkin at Ichabod in an undeniably terrifying moment, filling the screen with hellish fire as the Horseman laughs…and Ichabod disappears.

The Legacy

After The Adventures Of Ichabod And Mr. Toad, Disney stopped making package films, and most of them were largely forgotten (a notable exception was already covered in this column). As for Ichabod And Mr. Toad, the two segments would screen separately for decades, both in theaters, home video, and as part of the Disneyland anthology series. The Legend of Sleepy Hollow even got a 14-minute animated prologue added when it was broadcasted on Disneyland, but that prologue has never been released on home media (or on Disney+ for some reason).

One weird bit of legacy for The Legend of Sleepy is that animator Andreas Deja has said that the character of Brom in the short influenced the macho villain Gaston from Beauty and the Beast!

Though this was one of the rare Disney movies that never got a theatrical re-release in its original package format, you can now experience the full The Adventures Of Ichabod And Mr. Toad experience on Disney+.

Cool Posts From Around the Web: