25 of the creepiest Disney movies ever made

From The Adventures of Ichabod and Mr. Toad (Image via Walt Disney Productions)

23. The Adventures of Ichabod and Mr. Toad

The Adventures of Ichabod and Mr. Toad is a 1949 package film. It consists of two animated segments. One is based on The Wind in the Willows, a 1908 children’s book featuring a bunch of sentient animals. I suppose that could be weird if you try hard enough, but talking animals is pretty standard Disney fare anymore.

Of course, I’m focusing in on the Ichabod portion of the film, The Legend of Sleepy Hollow. The story of this section closely follows that of Washington Irving’s 1820 story, “The Legend of Sleepy Hollow”. Ichabod Crane is the new schoolmaster to the small village of Sleepy Hollow, New York. Sleepy Hollow is also supposedly haunted by the Headless Horseman, the spirit of a Hessian soldier who was beheaded by a cannonball in the American Revolution.

Though Ichabod is a strange, lanky figure, prone to gluttony and dandyish mannerisms, he soon becomes popular with the village’s women. Brom Bones, the local town hero and previous darling of the local girls, is put out.

When Ichabod starts to put the moves on Katrina van Tassel, daughter of the richest man in town, Brom has had enough. When Ichabod is traveling home from a late night party, he is accosted by what appears to be the spirit of the Headless Horseman. He flees town, and Brom is free to marry Katrina.

The animation is appropriately family-friendly… until you get to the Headless Horseman, that is. Poor, goofy Ichabod is chased by what seriously looks like a demon from Hell. The Headless Horseman is gigantic and swings around a similarly huge sword. It doesn’t help that he wields a flaming pumpkin, either.