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!