Getting A-head of The Season

The story of the cultural significance of the Headless Horseman myth is enough to make your head fall off.

By David Buck

Today in Tedium: Most of us probably don’t remember too many of our middle school reading assignments. Among that pile of forgotten homework and pristine storybooks probably resides an old short story called The Legend of Sleepy Hollow (sometimes erroneously referred to as The Headless Horseman). Whether you read it or not, you may have at least seen the old cartoon version or otherwise discovered it another way—even if it was via that bizarre Tim Burton film. One way or another, the Headless Horseman myth has perpetuated itself into the pop culture of the twenty-first century. The hideous supernatural creature that so terrified poor Ichabod Crane is rooted in reality. The Headless Horseman story continues to live in our collective memories even today. But Washington Irving’s macabre tale—or at least the creature playing the titular role—has its origins in folklore. In today’s Tedium, we’re dissecting an ancient legend, and some of the pop culture it helped to create. So hang on to your hats (if you’ve got ‘em) because today we’re exploring the real story of The Headless Horseman — David @ Tedium

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The year Washington Irving’s The Legend of Sleepy Hollow was published. Written while he lived in England, the tale caught on and eventually inspired not only a wealth of other stories and media, but also plenty of fun social activities centered around geographical locations on the east coast. Irving’s story drew heavy inspiration from existing stories and ghost stories he probably heard as a child. In Irving’s story, the origins of the headless rider are fairly simple. He was a Hessian soldier who lost his head to a wayward cannonball while fighting on America’s behalf in the American Revolution.

Sleepy Hollow

An illustration from a printing of Washington Irving’s The Legend of Sleepy Hollow, circa 1893. In monochrome, because Google Books’ scanner butchered the original image. (Google Books)

Feeling a little sleepy and hollow

As someone with Irish ancestry—even if my name is as generic as they come—I’ve always found the stories, myths, and legends of the Irish to be captivating. In my youth, one of my favorite stories was always The Legend of Sleepy Hollow (The Headless Horseman). Washington Irving’s tale isn’t really an Irish folktale, but it’s rooted in those grand traditions and seems largely based on the mythological creature known as the dullahan.

From his birthplace of New York City, he built the makings of a writing career (in the process coining two famed terms in relation to the city, “Gotham” and “Knickerbocker,” the latter being an early pen name). Then, after enlisting to fight in the War of 1812, he moved to Europe, where he would reside for 17 years. While in England, he wrote a series of short stories that he delivered to his brother Ebenezer, who then published them under the title The Sketch Book of Geoffrey Crayon, Gent. Among the stories he wrote during this fruitful period included “Rip Van Winkle,” along with the beloved tale that would essentially become one of America’s very first horror stories.

Part of what makes The Legend of Sleepy Hollow work is Ichabod Crane’s characterization. Throughout the story, one can feel his abject terror as he comes to grips with the cold reality of his situation. The story at once weaves a surreal tale while also providing a truly scary antagonist. Over time, the fear derived from the Headless horseman and its accompanying myth has dulled, but that doesn’t make Irving’s story any less important as one of the first truly Gothic American horror stories.

The story was likely inspired by Sir Walter Scott’s The Chase and other 19th century writings about the mythical dullahan. Scott’s story is about a hunter who’s doomed to hunt the same creatures forever. It’s in a similar vein to Irving’s story and fits right alongside it on the literary shelf.

Part of it might also have been inspired by some of the Hessian mercenaries fighting alongside American revolutionaries during the war. And one such story, a Hessian mercenary has his head blown off during one of the first cannonball volleys in a small battle. The story goes that the soldier was buried in a shallow grave in Sleepy Hollow. That’s where things take a turn for the spooky. Apparently, the soldier can’t rest until it finds its original head or absconds with the head of another. Thus, the Legend of Sleepy Hollow was born. Maybe.

Whether this is an accurate inspiration for the story or not, it’s definitely a good story and speaks to the legacy of dullahan as a menacing creature of the night.


The death toll from yellow fever that gripped New York in 1798, where a young Washington Irving grew up. The Irving family fled the area and moved to Tarrytown, where Irving drew inspiration for his later writing and characters. The fact that he grew up in an area gripped by a deadly disease, heard ghost stories throughout the area, and likely heard about the Hessian soldier’s grisly death all undoubtedly helped inspire his magnificent tale of terror.


A portrayal of the dullahan concept in the 1828 book Fairy Legends and Traditions of the South of Ireland. (Google Books)

The legend of the Dullahan is rooted in Irish folklore

In The Legend of Sleepy Hollow, the Headless horseman chases Ichabod Crane through the night, only to disappear in the morning leaving nothing but a smashed pumpkin behind. The abject terror of a fearful figure pursuing someone on horseback through the night is certainly a nightmare come to life.

The real dullahan—sometimes called Gan Ceann—is a totally different beast.

The terrifying visage of a dullahan was a bad omen; a portent of doom. It often meant something bad was about to happen to whoever is being visited by the spectral creature.

Let’s put it this way: you did not want to be visited by a dullahan.

In other stories, the dullahan is a king who ruled Ireland called Crom Dubh who offered decapitated sacrifices to the Old Gods. Dullahans and banshees often appear in stories together as portents of doom. It isn’t unlikely to read a story about a doulon appearing with a banshee. In some ways, the dullahan is the male equivalent of the banshee as it once people something bad is about to happen. The main difference is a dullahan can choose who is going to die, unlike the banshee.

Dr. Emily Zarka—a PhD in British Romantic Literature (with an emphasis on Gothic literature) — is a true authority on folklore and everything to do with monsters. She also knows a lot about this terrifying creature.

Per Zarka, the instance of seeing a dullahan doesn’t mean it’s going to kill you. Instead, he might be there to warn you of someone close to you passing or he might cause you to go blind.

Black carriages, drawn by headless horses, and the cracking of a whip. Sometimes, the whip is a disembodied human spine. In some cases, the dullahan is driving a carriage, covered in skulls, with human thigh bones as spokes for wheels.

Most of the time, a dullahan’s head is fairly close by: under its arm, on its horse or carriage, or even floating around the rider. Further differentiating it from Irving’s headless horseman, the dullahan also rides a headless horse. That’s right; the steed on which the dullahan rides is itself a headless abomination.

Decapitation and taking the heads of one’s enemy are common themes in art and stories from medieval times. In Ireland, it spoke to the grim realities of what life was like at the time. Per Zarka, one of the main reasons the dullahan is depicted as headless is because it was considered

Some say gold can stop a dullahan in its tracks, but if you saw one of these creatures on your way home, that would probably be the last thing on your mind.

“The story of the headless horseman in popular culture usually has horses, nighttime journeys, carriages, and graveyards—all things that we find in dullahan legends.”

— Dr. Emily Zarka, in the PBS Monstrum episode on the Dullahan. Zarka speaks at length about his the dullahan is more of a forewarning that suffering or death will impact you or a loved one soon. (Tedium reached out to Zarka—who is amazing and someone who’s work you should definitely follow—earlier this year, who gave us permission to provide a quote or two from the video. Thanks, Dr. Z!)

Billy Butcherson, one of the most famous head-losing zombies in modern Halloween-themed films, got a nice showcase in Hocus Pocus 2.

The faerie spirit also makes numerous appearances in pop culture

Headless ghosts/ghouls aren’t exactly the same thing, but they share a unique similarity to the dullahan (see if you can guess what it is).

This similarity essentially puts them in the same category as something to be feared or something that wreaks havoc in a narrative sense. That’s probably why we see instances of headless ghosts in so much media.

Scooby-Doo, The Headless Horseman (1922), The Adventures of Ichabod and Mr. Toad, Sleepy Hollow, The Headless Ghost, Hocus Pocus (and its sequel)—all of them feature versions of either the Headless horseman or a headless ghost in some capacity. The latter features a zombie—the ex-lover of one of the Sanderson sisters who also happens to be kind of a good guy—that loses his head for a while in the film. Even The Real Ghostbusters (more on that in a moment) took a turn at spinning the tale into something that worked for the 1980s.

So what is it about the headless ghost—and the dullahan in particular—that seems to ignite the flames of Hollywood’s imagination? It probably has something to do with the enduring nature of ghost stories and Gothic horror.

Ghost stories have been passed down for centuries as a means of teaching people, helping them come to terms with fear, and understanding the world around them. Some of the best ghost stories also offer hope. These ideas transcend mere entertainment and can often lead to helping people lead better lives.

There are so many iterations of The Legend of Sleepy Hollow in film,it can be difficult to keep up with all the adaptations. Some of the more notable adaptations follow the story well. Tim Burton’s take is a little underwhelming. Then there’s the 1959 film Darby O’Gill and the Little People, which features a more true-to-folklore depiction of the dullahan.

Outside of film, the headless horseman and headless ghosts also like to make appearances in songs.

“With Her Head Tucked Underneath Her Arms” tells the story of Anne Boleyn’s ghost harassing King Henry VII (we covered this one in-depth in our Halloween Special a few years ago.

The Headless Ghost” by Jimmie Maddin is a fun tune, filled with puns, making it a perennial Halloween favorite.

Headless Horseman” by Thurl Ravenscroft tells the story of a Google and banshee jamboree where the worst ghost there is the Headless horseman. Kay Starr did a wonderful rendition of the same tune for a classic Betty Boop cartoon.

There are many, many more movies and songs that talk about the headless horseman in particular and the more abstract concept of the Headless ghost. But that, of course, is a story for another time.

“I seen the Dullahan myself, stopping on the brow of the hill between Bryansford and Moneyscalp late one evening, just as the sun was setting. It was completely headless but it held up its own head in its hand and I heard it call out a name. I put my hand across my ears in case the name was my own, so I couldn’t hear what it said. When I looked again, it was gone. But shortly afterwards, there was a bad car accident on that very hill and a young man was killed. It had been his name that the Dullahan was calling.”

— The account of a storyteller from County Down, W.J. Fitzpatrick—not to be confused with the writer and Irish historian William John Fitzpatrick—who claimed to see a dullahan one night in County Down. It was likely between August and September, when the festival of Crom Dubh would have occurred.

Five places you might see a dullahan in other media

The headless horseman and dullahan are certainly a popular choice for film, but there are plenty of other types of media where the monster has made appearances. Here are a few places you might spot the looming specter of a dullahan outside of cinema and the small screen.

Dullahan Headless Knight

All these knights gotta be struttin’ around without a dang head.

Modern Horror Novels. Modern horror novels aren’t just kooky supernatural detectives, irreverent sibling teams taking on the unknown, or romantically liaisons between sparkly vampires, humans, and werewolves. There are plenty of them that draw inspiration or pay homage to terrifying creatures of folklore. The dullahan is no exception. Books like Dullahan: the Headless Knight offer a new take on the old tale. Even children’s books like R.L. Stine’s popular Goosebumps series had its own headless ghost in one of the books (and TV episodes) as well.

The Real Ghostbusters Cartoon. I know, I know. In the intro to this section, we specifically mentioned it wouldn’t cover Cinema or the small screen. Consider yourself tricked! But we digress. The headless horseman made numerous appearances in cartoons throughout the, but one of the more notable appearances of an updated version of Irving’s Headless Horseman came in an episode entitled “The Headless Motorcyclist,” the Ghostbusters take on a modern version of Irving’s Headless horseman, who drives a motorcycle. For a kid’s show based on an adult supernatural comedy, the show managed to dive into folklore and marry it to the concept of busting ghosts quite well. And it wouldn’t be the first time they drew inspiration into Celtic folklore, but offered a unique take on this traditional take.

Celtic Folk Music. Although popular music is a goldmine of fun songs about headless ghosts, apparitions, and all manner of scary things, sometimes you just can’t beat traditional folk music. Irish and Celtic folk music is a gold mine for understanding Irish life and some of the folk tales of this rich culture. For a more modern take, you can’t go wrong with something like Sam Kelly’s “Dullahan,” above.

Dungeons and Dragons. The famous RPG is practically a cultural juggernaut at this point. So it makes sense fans would see more monsters derived from folklore. Although I haven’t played in a long time—and have no desire to at all—I did take notice when Wizards of the Coast incorporated the dullahan into their Ravenloft setting. It takes a, shall we say, unique approach to the creature. While it tries to make it more like the Celtic fairy, it still takes some creative liberties. Instead of human bones and such adorning the carriage, it just has funeral objects. That makes sense for a game that’s aimed at a broad audience. It does feature the use of a spine as a whip, though. It’s an interesting take on the creature and almost makes me want to play the game again. Almost.

Konami’s Castlevania Series. If you’re a fan of the NES era and the Castlevania series in general, you’ve undoubtedly noticed a headless horse enemy at some point. In one entry, Castlevania: Portrait of Ruin, a traditional dullahan —complete with its head floating around it in the room—offers a truly unique boss fight in the game. Headless ghosts make appearances in several other Castlevania titles as well, notably as a knight carrying its head and later games as a horse-riding headless creature that races toward the protagonist. Outside of Castlevania, the dullahan has a rich presence and will likely continue to appear in new games in the future.

“We see a lot of these stories start to emerge in ancient Roman writings. In the first century, they wrote letters recounting ghost stories they claimed to have witnessed—chains rattling, haunted house type stories, The ghosts are never really harming anyone, but they’re always showing up. A lot of the time, the hauntings are because the person was never properly buried. It’s tied to respecting the dead.”

Paul Patterson, PhD, a professor of English at Saint Joseph’s University. According to Patterson, ancient cultures all had versions of different spine tingling tales we read or hear every year. Scary stories have been told for centuries and gothic fiction became more popular in the 18th century, leading to much of the horror literature / Cinema we have today. The stories continue to evolve today and will probably do so for years to come.

Headless ghosts and the dullahan are an enduring legacy when it comes to understanding our world through folklore. Whether they are warning us about something terrible, trying to correct bad behavior, or acting as a cautionary tale, these monsters are an integral part of our literary history.

Cultures around the world have their own version of the Headless monster. The Japanese have Nukekubi, the prowling head. Brazil has headless miles and the Hindu goddess Chinnmasta is a true force of nature.

All of these are part of a collective storytelling we all engage with at one time or another. And as time goes on, newer tales with completely different monsters will likely pop up to teach new lessons and go well beyond entertainment for future generations.


Find this one an interesting read? Share it with a pal! And thanks to David for getting ahead of things.

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Correction: An earlier version of this piece misstated where Irving wrote The Legend of Sleepy Hollow; this has now been corrected with additional details.

David Buck

Your time was just wasted by David Buck

David Buck is a former radio guy/musician who researches and writes about all manner of strange and interesting music, legacy technology, Nintendo and data analysis.

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