5 Film Appearances of the Legendary Headless Horseman

October 31, 2022Eric Miller
The headless horseman has been in quite a few movies and television shows. Here are five his best on-screen appearances. Composite by Coffee or Die Magazine.

The headless horseman has been in quite a few movies and television shows. Here are five his best on-screen appearances. Composite by Coffee or Die Magazine.

In the pantheon of classic horror characters, one boogeyman stands head and shoulders — well, shoulders — above the rest: the headless horseman.

From Scotland’s Ewan the Headless to Ireland’s Dullahan, the myth of a headless specter roaming the countryside on horseback exists in a number of folklore traditions. The most famous version of the myth originated in the United States. The headless horseman, as we know him here, came to life 200 years ago on the pages of Washington Irving’s “The Legend of Sleepy Hollow.” Published in 1820, Irving’s famous short story is about the restless ghost of a Hessian soldier who was decapitated by a cannonball during the American Revolution and now roams the battlefield each night in search of his severed head.

A side note: If he’s able to get along fine without his head, why keep looking for it? It’s gone, man. Move on with your life.

As previously mentioned, the headless horseman most of us are familiar with is not the only version out there, but it is arguably the best known and definitely the most monetized. In the years since Irving published his story, the tale has been told and retold in various mediums, while the headless horseman himself has become a ubiquitous character in the wider horror genre. Like we said, he seems to be doing pretty well for a guy without a head.

Since this is the 21st century, and nobody reads books anymore, here are five notable films featuring the headless horseman for you to consider adding to your Halloween scary movie watchlist. We recommend wedging one in between Friday the 13th and The Evil Dead … it just flows nicely.

Spooky coffee! Check out The Headless Horseman's Roast before it rides away ...

Silent Horseman

For a silent film, this version of the headless horseman is pretty damn creepy. Screenshot from The Headless Horseman.

‘The Headless Horseman,’ 1922

There’s just something inherently eerie about silent films. Starring Will Rogers and Lois Meredith, this black-and-white oldie is one of the earliest film adaptations of “The Legend of Sleepy Hollow.” For the sake of authenticity, the film was shot in New York’s Hudson River Valley, near the actual town of Sleepy Hollow. Ironically, the film's eponymous character only appears twice in the entire movie. Fun fact: Double exposure was used to give the headless horseman a phantom-like appearance. Take that, James Cameron.

Disney Headless Horseman

The headless horseman as seen in Disney's The Adventures of Ichabod and Mr. Toad. Screenshot from YouTube.

‘The Adventures of Ichabod and Mr. Toad,’ 1949

Produced by Disney, The Adventures of Ichabod and Mr. Toad is an animated anthology split into two segments. The first is based on the 1908 children's novel The Wind in the Willows; the second on “The Legend of Sleepy Hollow.” Yes, that pairing seems kind of strange to us, too, but hey, that’s Walt Disney for you.

Set in 1790, the second segment stays true to Irving’s original version, centering on the story of superstitious schoolmaster Ichabod Crane as he vies for the love and affection of the beautiful Katrina van Tassel against the eerie, supernatural backdrop that is Sleepy Hollow, New York. The film won the Golden Globe award for best cinematography and grossed $1.2 million in domestic rentals, which we assume was a lot of money back in those good ol’ days.

Pumpkin spice and everything ... nice? Get The Headless Horseman’s Roast to smack the sleepy right outta your hollow.

Headless Horseman Sleepy Hollow

Tim Burton and Christopher Walken created one of the more memorable versions of the headless horseman. Screenshot from Sleepy Hollow.

‘Sleepy Hollow,’ 1999

This 1999 film adaptation is loosely based on Irving’s work but stands out mostly for its heavy-hitter cast. Johnny Depp, Christina Ricci, Christopher Lee, Ian McDiarmid, and Michael Gambon are all well cast in this modern retelling of the horseman myth. Look, if you’ve got Edward Scissorhands, Wednesday Adams, two Sith Lords, and Dumbledore to star in your movie, it's gonna be spooky no matter what you do.

Let's not forget that they got Christopher Walken himself to play the headless horseman. That’s right, Christopher fucking Walken as the headless horseman. The film is worth watching based on that casting alone. Although depriving the world of a cool accent like that is an atrocity. They should have let the horseman keep Walken's trademark voice. It would have been way scarier. *Attempts terrible Christopher Walken impression* Boo.

Headless Horseman Sleepy Hollow High

Certainly the goofiest entry on our list, but hey, we dig the pumpkin head prop. Screenshot from Sleepy Hollow High.

‘Sleepy Hollow High,’ 2000

A group of delinquent teens and their principal are forced to clean up the woods of Sleepy Hollow as community service and are subsequently murdered by a sword-wielding man in a jack-o’-lantern mask. Is it a man, or is it the horseman himself? No idea, I haven’t seen the flick, but my money is on the principal. He doesn’t want to be out there any more than they do and probably resents them a little for dragging him out there. Can’t blame him. Fair warning, the IMDb reviews on this one are pretty brutal.

Spooky gear — get your BRCC skeleton shirts for Halloween or any day!

Headless Horseman

A not-so-headless headless horseman. Screenshot from Headless Horseman.

‘Headless Horseman,’ 2007

Who doesn’t love those low-budget, direct-to-TV-but-still-awesome flicks on the SyFy channel? Sharknado is a cinematic masterpiece, and I won't be convinced otherwise. I digress.

Headless Horseman is a 2007 retelling of the horseman legend that aired on the SyFy channel. Very loosely based on the source material, the film features seven college kids traveling through rural Kansas who inexplicably get themselves hopelessly lost and subsequently stranded in the middle of nowhere on the way to a party. It’s ridiculous, but what else would you expect from college kids in a horror movie? Arriving in the fictional town of Wormwood, the kids are subsequently hunted down by a supernatural headless killer plaguing the town because again, what else would you expect from college kids in a horror movie? The film is worth a watch based on the SyFy tag alone. Just temper your expectations; it's no Sharknado.

Read Next: The Real Mercenary Behind Sleepy Hollow’s Headless Horseman

Eric Miller
Eric Miller

Eric Miller is a former Army Combat Medic from Parkersburg, West Virginia. He holds a bachelor’s degree in history and has worked with homeless populations and veteran services throughout the state. He is an avid outdoorsman and has recently become interested in woodworking.

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