CftC: Disney’s Legend of Sleepy Hollow

Let’s round off:



with a true Halloween classic, in every sense of the word!




From Washington Irving’s page to Disney’s screen, we have the (hilariously) most faithful adaptation of The Legend of Sleepy Hollow. 

A man named Ichabod Crane comes to Sleepy Hollow, a small, superstitious rural town, circa 1790.


He immediately makes waves with his strange mannerisms and appearance (bookish, thin, scarecrow-y, attractive (?)), and though he is pranked and prodded repeatedly by the town Gaston, Brom Bones,

brom bones

Ichabod makes a nice little place for himself in town. He becomes the resident schoolmaster and helps out the people individually, surviving off of their charity.

Ichabod quickly becomes enamored of Katrina Van Tassel, the young, attractive heiress to the largest farm in the county.


Does anyone else think she looks like Cinderella with out-of-whack Barbie proportions?

This brings him into further conflict with Brom, who had the monopoly on Katrina’s attention prior to Ichabod’s arrival. Katrina eggs Ichabod on, up until the party her father throws on Halloween night.

After wowing the townsfolk, Katrina, and her father with his dancing, Ichabod sits down to dinner with everyone. Brom tells a story about a specter that haunts Sleepy Hollow on Halloween, the Headless Horseman, (in that fun little song showcased above) to frighten the schoolmaster.

The party ends, the guests go home; Ichabod, for some reason, being one of the last to depart. He encounters the Horseman alone in the woods, and the next morning, is found to be missing.


Brom Bones marries Katrina soon after, looking smug all the while, and the people debate whether or not the Horseman is real, and what could have become of Ichabod. Ultimately, it’s left up in the air.

In the words of the Nostalgic Critic: “It’s a classic ghost story with a classic ghost story ending.”

This has always been one of my favorite movies of the season. The animation is fun, and the colors, when not being dark and shadowy, are popping with bright, fall colors. The story is narrated by the incomparable Bing Crosby, which makes the cartoon feel old but also classy and unique, and he gets ample opportunities to croon. As much as I love Thurl Ravenscroft, I like Bing’s version of “The Headless Horseman Song” better. It just seems more subtle, but still tongue and cheek.

The plot is conveyed through narration and cartoonish miming; silly, funny, and bursting with personality. And yet, as also pointed out by the Nostalgia Critic, the story has dark, off undertones as you watch.


Ichabod seems nice enough at first, if a bit greedy and glutinous, but once Katrina enters the picture, he goes into full-on douchebag mode. He wants to marry her for her home, looks, and money, and explicitly imagines taking her father’s place when he dies. He then sucks up to the man at the party, grinning all the while. It is made painfully, unmistakably clear to us that he is trying to woo both old Van Tassel and his daughter for his own selfish ends.

Kind of funny, given how often Disney is heckled for presenting us with unrealistic romantic relationships.


Believe it or not, those kinds of “for gain” relationships do happen, and not just once upon a time. But I think what really redeems Ichabod, in the end, is that he isn’t the worst person to walk the face of the earth. He has some damn near villainous tendencies, but the other characters aren’t good either, so it’s hard to argue that he’s misusing innocent people.


Katrina flirts like it’s her only hobby, pitting two men against each other because she’s bored and wants even more attention. She has no intention of going with Ichabod, but she gives him so much false hope.

Brom, meanwhile, is the town darling and rowdy all in one. He bullies Ichabod and many others who draw Katrina’s attention away from him. It’s also implied that he might have dressed up like the Headless Horseman in the end, either killing the schoolmaster or convincing him to skip town.

Who knows? He told the story, then looked smug after the incident. Hell, he even owns a black horse.


You can ultimately feel for Ichabod in the end, despite all that he’s “said” and done, because if he really did die and it was a real Headless Horseman, neither of which we know for sure, he didn’t deserve it. No matter how you slice it, the horrible little man made us laugh and smile.


But what is the cautionary tale here? Don’t shoot for the stars? Don’t try to steal other guys’ girlfriends, even if the girls openly invite you?

My theory is it’s: don’t be the last person to leave the party. In the original story, Ichabod proposed at the party and Katrina turned him down, so he left dejected and, possibly, too distracted.

The only impediment to kids’ enjoyment of this movie, that I can think of, is the old timey speak and SAT words, but the cartoon faces and antics will keep their focus and give them the basic gist of things. Adults can get a solid laugh out of said cartoonishness; the absurdity of the animation, with Bing Crosby talking over the whole things. And I think they will enjoy following along with the story.

Disney’s The Legend of Sleepy Hollow does have scary and disturbing moments towards the second half (the Horseman himself can take this up to eleven for kids), but those are the most memorable.

You have not heard crazy, fun, over-the-top evil laughter until you have watched this.

Buy it on it’s own, or get a copy paired with The Wind in the Willows, called Ichabod and Mr. Toad. Although, hilariously enough, even the opening song emphasizes the Ichabod part more than the Mr. Toad part. The stories fit well together, but the selling of said combo feels a bit phoned in.



8/10. The chase and the song alone are worth it.

*As per usual, most of the pics don’t belong to me. The title card does, though. Twas done by the gracious and talented Zero, who can be found here. Check her out! 🙂


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