The Legend of Sleepy Hollow

1949 Directed by Clyde Geronimi, Jack Kinney

Bing and Walt ride herd on The Headless Horseman!

Washington Irving's tale of Ichabod Crane and the headless horseman is brought to life, narrated by Bing Crosby.

Bing Crosby Pinto Colvig

Alternative Titles

La légende de la Vallée Endormie, La leggenda della valle addormentata, Las aventuras de Ichabod y el Sr Sapo

family animation

34 mins More details at IMDb TMDb Report this film

Popular reviews

Review by SilentDawn ★★★★★ 3

100
It's not officially October without a viewing of this delightful motion picture. Autumnal and spooky in all the right ways. 🎃
Review by SilentDawn ★★★★★ 10

100
Just bathe me in it. The wood. The oblivion of tree limbs and echoing screams and endless nightmares. Bing Crosby crooning away the final desperate moments of Crane's existence. The outstretched wail of the full moon beckons the light of evil, cackling and smiling along the path. All that's left was his hat.
Review by Ian West ★★★★★ 3

Whatever you call it... October. Autumn. Fall. The Harvest. Halloween. Samhain. All Hallows’ Eve—this captures it.
Review by Joe ★★★★★ 2

This is pure Halloween, distilled to its romantic, dark, gothic, and silly essence, compacted into 34 minutes and anchored by 1949 horror host Bing Crosby. I'd not seen this since childhood, but I remembered almost all of it, down to every small sight gag and bit of business. Kids are just better at watching movies than adults are.
Review by Branson Reese 6

This is possibly the most viewed movie of my entire life due to my dad showing it to us constantly growing up. I think it’s great but that’s irrelevant. Even if it sucked (it doesn’t) I would not care. It’s foundational.
Review by Allison M. 🌱 ★★★

Pretty sure I saw this as a kid, but I watched it again just in case.
The songs were dated and cheesy.
Vegan alert:
Whole roast turkey
Review by Jason the Feature Creature ★★★★½

“A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.”
Iconic Halloween imagery. A must watch fore all youngsters and oldsters alike. Bing Crosby narrates and sings of ‘The Headless Horesman.’ Based upon Washington Irving’s gothic classic.
Review by Noah Thompson ★★★★ 4

Don't try to figure out a plan. You can't reason with a headless man.
Watched this completely on a whim, and it's a quick watch, so why the hell not? The more spooky vibes I can fit in this month, the better. I love this. When I was little, I used to very often check out a VHS copy of The Adventures of Ichabod and Mr. Toad from my local library, and more often than not, I either wouldn't pay attention to the Mr. Toad part or I'd even just skip straight to The Legend of Sleepy Hollow. This is a small, charming, funny, and even for a little animated short from 40's Disney, a spooky time. Combine some still…
Review by Artpig (Brett) ★★★★½

One of the best things Disney has ever made.
Happy Hallowseve!
Review by maskull ★★★★½

My Eyes Hurt When I Go Outside, It's Too Bright!!! (or, My Halloween Horrorfest 2018) Movie #3
Bing Crosby's voice makes me feel all warm and safe and I'm laughing at the silly slapstick Romantic entanglements on the screen. Then the song about The Legend of Sleepy Hollow begins and from then on it's one of the best, scariest (with a bit of humour still) kid's animated films. And it's all rather gorgeous to look at.
Review by Matthew L. Brady ★★★★½

The screaming laughter of the Horseman is still playing in my head like a broken record player.
The Legend of Sleepy Hollow started off light hearted with it's funny scenes with are main character acting cocky and foolish. But it's not until it takes a big turn towards the end. What started off so funny and ended so unspeakable frighting, and that's why this short animated film is brilliant.
Review by Artpig (Brett) ★★★★★ 2

(Quick note: Will make a post about it soon but thanks all for over 700 followers. You all don't know how much you are helping me through a weird time in my life and I love you guys)
Anyways, here's another classic halloween essential for me.
Sorry for all the 5/5s lately, I've just been picking quality crap to watch and review.
The Legend of Sleepy Hollow is the most underrated film in the Disney company. Ultimately, this film didn't find its audience because it was put in a package film with one of the worst Disney films of all time, Mr. Toad. It's so dreadfully bad, and its the first short you have to sit through. It's mean spirited,…

Recent reviews

Review by Adam Sweeney ★★★★★

Amazing to consider the risks that Disney used to take with their films. Who knows what they're bothering with these days.
Review by SAMSAM ★★★★½

Fucken spectacular, especially those last 13 minutes or so. I adored watching this as a child and I love it more now. The set-up is short and sweet, the rivalry well built up and then everything in the woods is GLORIOUS. I love this.
Odds bodkins. Gad zooks. Take a look at that spook of spooks
Review by Brogan Luke Bouwhuis ★★★

RANKINGS: Disney Animated Specials
This terrified me as a child. My cousin really wanted to watch it so my parents kept sending me to her house with the VHS, except I didn't want to rewatch it and kept swapping out the tape with Richard Simmons' Sweatin' to the Oldies Vol. 3. After it happened a few times my mom began to double-check the case before we left, so I got good at sneakily switching out the tape right before went out the door and even once when we had already gotten in the car. My mom thought she was going insane.
And that's the story of how four-year-old Brogan gaslit his own mother to get out of being scared by…
Review by Abdulmajeed Al-Sibae ★★★★★

Just picked 4 random DVDs to watch in the car for a ride, and one of them was Fables Vol. 1, which included this and The Prince and the Pauper.
Yeah, this is basically an easy watch for me, and I'll never get bored of it.
The songs, the gags, the animation, the narration... etc, it all hits in the right spot for me.
Review by sean ★★★

katrina w the BAYANG
Review by UlchabanOiche ★★★★★

A classic, through and through.
Review by J C

I cared more about the fate of Ichabod’s dopey horse than many full length feature film protagonists
Review by tylergodwin3 ★★★

This was a cute animation and I loved Bing Crosby’s narrations and singing. There were some funny parts like the Halloween party but I felt like 85% of the movie happened before the Headless Horseman showed up. It definitely felt like the short could have been longer. I had never seen this movie before but I would like to watch it again during Halloween again.
Review by Trey Bien ★★★★½

HOLDS UP
Review by Flicks With Friends ★★★★★

Honestly, this adaptation of the Irving Berlin American folk tale is sheer perfection. Everything from the quality of the Disney animation, to the character designs, to Bing Crosby's dulcet tones as narrator... it just doesn't get any better than this.
Some films are annual rewatches because of their themes or important dates, some films demand to be annual rewatches because they are just that good.
#CountdownToHalloween
Review by FilmCritic2001 ★★★

Quite good
Review by ms_marlowe ★★★ 1

Wait, this is narrated by Bing Crosby AND it's a musical??