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Disney’s THE LEGEND OF SLEEPY HOLLOW is the Perfect Movie for Fall

Disney’s The Legend of Sleepy Hollow (1949) is my go-to movie to inaugurate both fall and the Halloween season in general. It’s been that way for several years, likely born out of a desire to ease myself into all the terror and bloodshed that will follow (like all of you, I almost exclusively watch horror films from September through October). The Legend of Sleepy Hollow truly encapsulates what the season is about– it’s a playful and unobjectionable tale of terror adapted from an American classic. It is stunningly animated, perfectly paced, and succeeds in sowing the seeds of that general, nostalgic, crisp, warm, and delightful sense of fall.

Synopsis:
In a small town, a brewing romantic rivalry with a local tough and a school-teacher culminates in a terrifying ride in the night.

The Adventures of Ichabod and Mr. Toad was a package film released by Disney back in 1949. The movie featured two short (comparatively speaking) films based on both Kenneth Grahame’s The Wind in the Willows (1908) and Washington Irving’s The Legend of Sleepy Hollow (1820). The Wind in the Willows is fine, but The Legend of Sleepy Hollow is where the real magic is. Indeed, it is about as faithful an adaptation of Irving’s original short story as you’re likely to find, and it’s the perfect G-rated companion to your conventional seasonal viewing.

Special mention must go to the fantastic musical number that precedes Ichabod Crane’s trek through the woods between the Van Tassel’s farmstead and his quarters in Sleepy Hollow. Sensing that Crane is frightfully superstitious, Brom launches into a song and dance routine to spook Crane into fleeing Sleepy Hollow. Brom, voiced by none other than Bing Crosby, details how the Headless Horseman prowls the woods every Halloween in search of a head to replace the one he had lost years ago. A perennial ghost in a village renowned for its hauntings as is, the only way to escape from the Horseman is to cross the bridge over the brook before it’s too late. Katrina, Brom, and the other villagers find this hilarious– Ichabod is nearly scared to death.

The horror is most potent in Ichabod’s trek through the woods, his slow, purposeful gallop atop his horse. The first leg of the ride is replete with paranoia– courtesy of stellar sound design and animation– where every noise frightens him into submission. The wind in the trees and cattails thumping rhythmically on a log mimicking a horse’s gallop– Ichabod is convinced that every sound is the Horseman en route to steal his head.

For a kid’s movie, this sequence is genuinely unsettling, a short vignette in how to expertly craft tension and terror, even in an old Disney cartoon. The sequence lasts for several minutes until Ichabod nearly snaps. Still, there is no Headless Horseman in sight, so he and his steed begin to laugh, presumably at how silly Ichabod’s been behaving, how silly it was for him to believe Brom’s tale. Naturally, the laughter is broken up by the appearance of the actual (maybe) Horseman.

Ichabod races through the woods to flee– and again, the animation is stellar– until he reaches the bridge. He crosses safely but makes the fatal mistake of stopping to look behind himself, at which point a flaming jack-o’-lantern smashes in his face, knocking him unconscious. Fans of the story know what happens next. The following morning, Ichabod is nowhere to be found, and Katrina– on account of Ichabod’s disappearance– marries Brom in his absence. Rumors spread that Ichabod has fled and married elsewhere, and Brom looks suspiciously cognizant any time Ichabod’s disappearance is mentioned, but his actual whereabouts remain unknown. Maybe he did flee, or maybe– as those most superstitious of residents believe– he really was “spirited away” by the Headless Horseman. 

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The movie itself is buoyed by some interesting subtext culled directly from Irving’s original short story– namely the effeminate nature of Ichabod and Brom’s more conventional masculinity– and a genuine desire to frighten as well as entertain. Bing Crosby’s narration and singing are sublime, and as mentioned earlier, it’s appropriate for all ages, the kind of innocent, non-confrontational Halloween tale that’s fun without being upsetting.

Indeed, The Legend of Sleepy Hollow is perfect for late fall evenings. Picture the chilled air outside and the crunching of leaves under your feet. Think of the sun that sets just a little bit earlier and the soft rap, tap, hmpht of the branches outside. The crackle of the fire and the subtle scent of cinnamon. Cozy knit blankets and cocoa or cider. Picture family and friends gathered around the television, ready for a spooky screening. For several minutes, you can feel just like Ichabod Crane. Frightened but eager in the warm autumnal embrace of a place just like Sleepy Hollow. What better way is there to begin the fall than that?

Legend of Sleepy Hollow Poster - Disney’s THE LEGEND OF SLEEPY HOLLOW is the Perfect Movie for Fall

The Adventures of Ichabod and Mr. Toad is available to rent on Amazon or stream for subscribers of Disney Plus.

Written by Chad Collins

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