The Legend of Sleepy Hollow: The Horror of the Pedagog

Jacob Crawford
4 min readOct 25, 2022

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The Legend of Sleepy Hollow (Clyde Geronimi & Jack Kinney, 1949)

The Legend of Sleepy Hollow gets paired with The Wind in the Willows as The Adventures of Ichabod and Mr. Toad. Mr. Toad and all his exhaust-huffing antics are great, but they’re not fitting for the Spooktacular, so we’ll have to discuss those another time.

As a grade-schooler, we were shown The Legend of Sleepy Hollow every year. I’m not sure why, but I always looked forward to it. I feel like Bing Crosby is synonymous with the Christmas season, but he always reminds me of Halloween. He plays narrator here and carries most of the dialogue. Bing kicks things off by telling us about the new schoolmaster, Ichabod Crane, in unflattering descriptions that can be summed up as: my goodness, get a load of this freak! Isn’t he weird? Well, let me tell you something else…this guy fucks! The word pedagog (which I guess means teacher) is also thrown around a lot.

Odds Bodkins! Gadzooks! Look at this spook of spooks!

Local cool guy Brom Bones is immediately put off by Ichabod, so much so that it distracts him from a drinking session with the Sleepy Hollow Boys and a bunch of fun-loving animals. To make matters worse, Ichabod immediately starts cleaning up with the ladies. The cartoon makes it seem like his canoodling is primarily food-motivated. He’s shown housing pies and whole chickens, but I think that’s just a way at hinting at his other insatiable appetites. When Ichabod’s attentions turn to Katrina Van Tassel, daughter of the richest man in town, Brom resolves to do something about the carpetbagger.

At the Van Tassel Halloween Party, Brom tells the story of the Headless Horseman in the form of a song, and, let me tell you, it’s a banger:

When he goes a-joggin
‘Cross the land,
Holdin’ a noggin’,
In his hand,
Demons take one look and groan,
And hit the road for parts unknown

The (notoriously superstitious?) Ichabod falls for it hook, line, and sinker. He’s sweatin’, shakin’, pouring coffee everywhere, and putting way too much pepper on his hard-boiled eggs (which you should definitely have at your next Halloween bash). When he sets off for home, the forest is a veritable house of horrors, complete with a chorus of sinister-sounding frogs and menacing owls. So, when the actual Horseman shows up, Ichabod is already pretty keyed up. The animation here is just top notch as the gawky Crane flips and contorts himself to elude the Headless one. He eventually makes it across the bridge to safety — one of the rules spelled out in Brom’s little ditty — but the Horsemen still lobs a fiery pumpkin that hits its mark. The people of Sleepy Hollow never see Ichabod again, but hear rumors that he might have gone off to another town and sired a bunch of equally-goony children. Sounds like a good bet to me.

I’ve seen someone describe The Legend of Sleepy Hollow as being the spirit of autumn distilled to its very essence. I’d have to agree. It captures so much of what I love about the season — the colors, good food, spooky stories, long shadows, the chill in the air, dogs drinking beer, and birds that scream “BEWARE”. I’ve never read Washington Irving’s original story. I have no idea if Ichabod is so lusty (or “food-obsessed”) or if Brom is such a talented showman in that version and I don’t care. At just a little over a half-hour, Disney’s adaptation is such an easily ingestible little gem to get you in the holiday spirit.

My love for this classic was part of what lead me and my wife to take a little trip up to the real Sleepy Hollow, which lies just a little ways north of Newww York Citayyy on the Hudson River. From Baltimore, it’s just a three hour drive. As we approached, there was a fog-filled pond and some winding roads that seemed to fit the bill, but once we drove a little further, we could see it was really just your average blue-collar town. I guess I was foolish to expect a rustic little village whose character fully embraced this spooky story all year round. People gotta live their lives, ya know? There was a single street sign with a horseman on it though, so the legend still lives on a little.

Is it scary? Depends on how much of a pedagog you are.

Streaming: The Legend of Sleepy Hollow is available as the 2nd part of The Adventures of Ichabod and Mr. Toad on Disney+.

Part of my 2022 Halloween Spooktacular

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Jacob Crawford

Went to school for film once upon a time, eventually wound up working for a couple arts organizations focused on film. Currently: DC Environmental Film Festival