HomeMovies31 Days of Horror 2014: The Legend of Sleepy Hollow

31 Days of Horror 2014: The Legend of Sleepy Hollow


Ichabod Crane arrives in Sleepy Hollow to be the new schoolmaster. All of the women in town want to be with him, but he has his sights set on Katrina Van Tassel, the wealthiest girl in town. This new interest finds him trouble from the town bully and the Headless Horseman.


The Legend of Sleepy Hollow is a Disney film from 1949. Bing Crosby is the narrator and provides the voices for every character, which is incredibly fun considering his voice is very deep and sing-songy. The songs themselves are horribly infectious and I find myself singing them randomly throughout the year. In fact, I can’t even hear Bing Crosby’s name without bursting out into “Bum bubby bum bum boo boo boo.” To clear that up, Ichabod sings that when he is teaching some women in town how to sing and it ends in a dog howl that confuses Ichabod and makes the women melt. It is one of the funniest parts of the whole film.

Ichabod, compared to a scarecrow, is tall and thin with giant feet. He has no chin and a long point nose. From appearances, he is nothing special but the women cannot get enough of his charm. The one woman he wants, Katrina Van Tassel, is obviously in love with Brom Bones and tries to get his attention by flirting with Ichabod to make him jealous.

Now, Ichabod is a superstitious man and Brom Bones knows it, so he tells him the story of The Headless Horseman, who rides around on Halloween night in search of a head to replace his own missing one. The only way to secure your safety from The Headless Horseman is to ride as fast as you can to the other side of the bridge, where the Horseman cannot follow. When Ichabod faces the Horseman and disappears, it is unknown whether Brom played a trick to keep him away from Katrina or if the Horseman succeeded in his task.

As a kid, my father would check the newspaper TV guide for when the movie would be coming on TV so I could be home from Trick or Treating early enough to watch it when it came on The Disney Channel. My parents would have the fire going and hot chocolate ready for us, because Octobers in New York were freezing, and we would all snuggle up on the couch and watch together.

To this day, I still watch The Legend of Sleepy Hollow every October with a mug of hot chocolate and, weather permitting, the fire going.

I have so many warm memories attached to this film. Maybe this year, you can use it to make your own with your kids or, if you don’t have any, just enjoy it on your own.


Ann Hale
Ann Hale
Just a giant nerd in love with horror, 80's action flicks, Star Wars and Harry Potter. Hit me up on Twitter or Instagram @scarletjupiter to talk horror or just to browse the horror collection.

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