Horrorfest 2023: The Legend of Sleepy Hollow

The Legend of Sleepy Hollow

Screenplay by Erdman Penner, Joe Rinaldi and Winston Hibler

Based on the story by Washington Irving

Directed by Clyde Geronimi and Jack Kinney

Starring Bing Crosby

USA, 1949

Now, you'd think I would have seen this famous cartoon short before now, and truth be told, maybe I have. It's one of those things where the images and key scenes are so recognizable and stretch back longer than I can remember that I don't know if I actually watched this movie, read a storybook with images from it, saw clips on TV, listened to a record about it, or what. Point is, if I ever sat down and watched it from beginning to end, I don't remember doing it, so this year, I did it.

I actually watched the entirety of THE ADVENTURES OF ICHABOD AND MR. TOAD, the feature length anthology film this short comes from, but only THE LEGEND OF SLEEPY HOLLOW lends itself to spooky season in general and Horrorfest specifically, so that's the one we're talking about today.

First off, I had no idea Bing Crosby did most of the vocals, singing or not, in the film. That was a welcome surprise. He's already the voice of Christmas, now he can be the voice of Halloween, too. Just kidding. That's Vincent Price or Orson Welles or someone. But Bing does do a bang up job, here.

Secondly, while I'm familiar with the broad strokes of the tale I'd forgotten the Disney cartoon version focuses so much on Ichabod Crane's appetite, so much so that I got out Washington Irving's original story and checked it to see if that was part of the lore. It's not, really, though there is a brief section where Crane sees the bountiful farm the woman of his dreams lives on, one that he'd inherit if he married her, and dreams about all the food that would come out of it. Which brings me to another thing -- I had forgotten, or maybe never knew, Crane was motivated by greed to a certain extent.

I always remembered it as the tale of a nerdy guy who gets bullied over his crush and ran out of town by the local Chad. As told by the guys at Disney, Crane's kind of an a-hole himself, in his own way, though he doesn't deserve what he gets.

Which brings us to the moment we've all been waiting for. The entire short is basically a long wind up to the show-stopping scene where the Headless Horseman himself shows up, a demonic figure clad all in black, missing a head, and carrying an evil-looking, flaming Jack-o-lantern. Even his horse looks like it's straight out of the depths of hell. The autumnal settings (by turns bright and colorful and dark and foreboding) and the animation in general has all been up to the usual great Disney standards right up until the Horseman's grand entrance, and here it goes into overdrive in what must be one of the most stunning and memorable sequences the studio has ever produced.

Is this horror? Naw. But it is kinda scary. And even if it wasn't, it's still the perfect tale to watch unfold on a blustery fall evening. When Christmas rolls around you can watch THE WIND IN THE WILLOWS, starring Mr. Toad, who is awesome.