Tag Archives: Bing Crosby

The Legend of Sleepy Hollow “Headless Horseman” (1949)


In Disney’s The Legend of Sleepy Hollow (sometimes billed as The Adventures of Ichabod), the story follows lanky schoolmaster Ichabod Crane as he attempts to woo the beautiful (and very rich) Katrina van Tassel, to the increasing chagrin of Brom Bones, the town hero. In truth, Katrina is only paying attention to Ichabod to make Brom work harder to secure her affections, but neither man knows this.


Things come to a head when a Halloween party is held at the van Tassel residence. After being upstaged by Ichabod most of the evening, Brom notices that Ichabod is superstitious (he throws salt over his shoulder after spilling some) and decides to use this knowledge to his advantage. He gathers the company around and begins to sing the story of the Headless Horseman, a terrifying ghost reputed to wander Sleepy Hollow.

Just gather ’round
and I’ll elucidate
on what goes on outside when it gets late.
Long about midnight,
The ghosts and banshees,
They get together for their nightly jamboree. 
There’s things with horns and saucer eyes
some with fangs about this size.

Oh When the spooks have a midnight jamboree,
they break it up with fiendish glee.
Ghosts are bad,
but the one that’s cursed
is the Headless Horseman,
he’s the worst.


Ichabod pays rapt attention to the song, his terror growing with every verse. “Headless Horseman” is considered one of the darkest songs ever created for a Disney film (right up there with “Hellfire” from The Hunchback of Notre Dame). According to Brom (performed by Bing Crosby), the Headless Horseman rides one night each year to search for a new head. However, if you can cross the bridge at the end of the Hollow, you’ll be safe from the Horseman’s power.

Now, if you doubt this tale is so,
I met that spook just a year ago.
Now, I didn’t stop for a second look,
but made for the bridge that spans the brook.
For once you cross that bridge, my friends,

The ghost is through, his power ends.

So, when you’re riding home tonight,
make for the bridge with all your might.
He’ll be down in the Hollow there.
He needs your head.
Look out! Beware!

Of course we’re meant to find Ichabod’s terror funny because, so far as we know, Brom is making this story up. After all, there’s no such thing as ghosts…or is there? Given how Ichabod’s encounter with the Horseman plays out, it seems possible that Brom might have been telling the truth after all (but that’s a story for another time).

Personally, I don’t remember being scared by this song as a kid (though I don’t think I saw this particular film very often), but I can see how it would be scary for some. Brom can look quite menacing when he chooses and he brings all his talent to bear on scaring Ichabod before he leaves the party. If I heard a song like that, I’d be nervous about riding home in the dark too.

What do you think of the song “Headless Horseman”? Let me know your thoughts in the comments below and have a great day!

See also:

The Legend of Sleepy Hollow “Katrina” (1949)

The Adventures of Ichabod and Mr. Toad (1949)

Disney/Dreamworks/Pixar/etc. Soundtracks A-Z

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My Thoughts on: The Adventures of Ichabod and Mr. Toad (1949)

So yesterday was my birthday!! I had a wonderful day (though the visit from the family was too short) and got some great gifts. Among which, I finally got a copy of The Adventures of Ichabod and Mr. Toad (1949), one of my favorite Disney films from childhood! Although, I should say the Ichabod Crane segment was my favorite. I’d never actually seen the entire feature (with The Wind in the Willows segment) until last night. But the story of Ichabod and the Headless Horseman, that I’d seen, and when I saw it on sale yesterday, I snatched it up!

The Story of Ichabod Crane is narrated by Bing Crosby (crooner extraordinare) and tells the story of how a lanky, gluttonous (and very superstitious) schoolteacher named Ichabod Crane came to Sleepy Hollow and fell in love with the gorgeous Katrina von Tassel, daughter and heiress of the richest man in the county.


The Legend of Sleepy Hollow “Ichabod” (1949)

But Ichabod isn’t the only suitor, the burly and fun-loving Brom Bones is in love with Katrina too! Poor Brom does everything he can think of to impress Katrina, but somehow it always backfires with Ichabod around.


The Legend of Sleepy Hollow “Katrina” (1949)

Actually, Katrina does prefer Brom (you can tell by the way she looks at him), but she continues to flirt with Ichabod to make Brom jealous (because she wants to make sure that Brom really wants her, enough to fight for her that is). Then, on Halloween night, during a party at the von Tassel farm, Brom remembers that Ichabod is deeply superstitious and he decides to regale the guests with the story of the Headless Horseman, a specter said to haunt Sleepy Hollow.

The Legend of Sleepy Hollow “The Tale of the Headless Horseman” (1949)

The song “The Tale of the Headless Horseman” is regarded as one of the darkest Disney songs ever created, and nearly didn’t make the final cut of the film. According to the song, if you should encounter the Horseman, ride for the covered bridge, because the Horseman has no power past that point. By the end of the song, poor Ichabod is scared out of his mind as he rides for home. The hollow is full of crickets, frogs and owls, all seemingly whispering the name of “Ichabod.” The poor man (and his horse) become even more terrified when they think a horse is galloping towards them, but it turns out to only be cattails banging against a log. But just as they begin to laugh in relief…the REAL Headless Horseman appears!!


The Legend of Sleepy Hollow “The Horseman appears!!!” (1949)

This part scared me silly when I was little, and why not? This guy has a diabolical laugh, a big sword, and a black, red-eyed horse that’s every bit as scary as the rider! Ichabod makes a run for it, and after several scary-but-kinda-funny mishaps, he clears the bridge, so he should be safe! But the Horseman has one trick left to play: though he can’t cross the bridge, he sends a flaming Jack-o-lantern hurling at the schoolmaster! The next morning, all that remains of Ichabod is his hat (and the pumpkin). He’s never seen in Sleepy Hollow again. Shortly thereafterward, Katrina and Brom get married, and it’s common speculation that Brom was in disguise as the Headless Horseman. I’ve thought so for years, except there’s one detail that wrecks the theory: during the chase, Ichabod clearly peeks down where the Horseman’s head should be and finds nothing there. If it was Brom in disguise, shouldn’t he have seen Brom’s head?

Regardless of whether the Horseman was real or not, I enjoyed getting to see this story again after so long. It’s a little known Disney gem that I think you will enjoy.

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