The Headless Horseman

Join Kelli as she goes over the mythology of the Headless Horseman. Most of us associate the headless horseman with Washington Irving's book, the Legend of Sleepy Hollow. But the idea of a ghostly rider looking for his head, or perhaps a decapitated ghost haunting local villages, goes all the way back to medieval Europe, perhaps even deeper into ancient Celtic mythology.

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The Headless Horseman
Intro
Welcome to A Popular History of Unpopular Things, a mostly scripted podcast that makes history more fun and accessible. My kind of history is the unpopular stuff - disease, death, and destruction. I like learning about all things bloody, gross, mysterious, and weird. 

We’re continuing on with our 2024 spooky APHOUT season where the episodes are about all things Halloween - ghouls, vampires, demons, witches, and ghosts. 

And for those of you watching these episodes on YouTube, you’ll be treated to a new APHOUT episode every Sunday for the whole spooky season! 

Now one of the spectres that many associate with Halloween is the Headless Horseman, which for many is the one who rides around the graveyard and village of Sleepy Hollow. In 1820, Washington Irving wrote “The Legend of Sleepy Hollow,” a short story that inspired the now-famous story of a decapitated ghostly rider haunting the small New York town. The story has been turned into a whole bunch of movies; the two that come to mind first for me are the 1949 Disney animated short and the Tim Burton-directed film that came out in 1999, “Sleepy Hollow.” But there have been a bunch more. 

And don’t even get me started on other forms of media, like video games… my brain instantly goes to the fourth chapter of King’s Quest VII, which was a great Sierra game from my childhood. But the character has been in Skyrim, some Assassin’s Creed games, and even WoW, among many others.

But what fascinates me even more is that the myth of a headless horseman doesn’t just belong to Sleepy Hollow and Washington Irving’s imagination; it goes back to Medieval European folklore. There’s Dullahan, the Irish Headless Horseman; Ewen the Scottish Headless Horseman; there are some in Wales, including - and please forgive my Welsh - “Fenyw heb un pen [fen-new],” or “the headless woman;” German ones from the Rhineland; the Green Knight that Gawain decapitated from Arthurian folklore; and even “El Muerto” from Southern Texas. Some of these stories predate Washington Irving’s Sleepy Hollow version, and some came later. Like El Muerto.

So today, I want to go over the history of the Headless Horseman mythology. We’ll start with a brief historical context to get a good sense of the mythology of these legends. Then we’ll go over the most popularized version - the Legend of Sleepy Hollow himself - because this feels like an excellent way to celebrate Halloween this year; chasing down one of the spooky, ghostly staples of the holiday.

So let’s get started!
Historical Context
Now normally on the APHOUT podcast, we take a look at the historical context - the things happening in history around an event or person that explain why. So for example, when we learned about the Pendle Witches not too long ago, we had to talk about witch trials and laws and such in early 17th century England, that’s the 1600s, around the time the event took place. That gave us an idea of why the witch trials happened in 1612 and not, say, 20-30 years earlier. But for today’s episode, since we’re primarily talking about mythology, I want to try and trace where the headless horseman comes from and why it’s stuck around for so long.

Despite most Americans associating the Sleepy Hollow legend with Washington Irving’s book, the myth of a headless horseman goes way back to the Medieval Period in Europe. 

One of the earliest myths is that of the Dullahan. And I apologize in advance for any pronunciation errors.

The Dullahan of Ireland is a mythological headless horseman. Because he’s part of mythology, there are several stories that explain how he became headless and what his deal is, so let’s explore some of them.

One story suggests that he was a soldier who lost his head in battle, and as a ghost he is doomed to roam around searching for that lost head for eternity. Other stories suggest that he has his decapitated head, but he’s so angry about his death that he hunts down others to be dead alongside him.

The Dullahan is usually depicted as a rider on a black horse, or sometimes in a carriage with six black horses. Fire comes out the horses’ nostrils as they rush around Irish country lanes looking for victims. In some stories, he rides around in a carriage made with various human bones, which is very thematic. He wears a long black cloak, and in the stories where he already has his head, he holds it up high for everyone to see, and so that he can see everyone, and choose a victim to hunt down. The head itself is gross and rotten, which is a pretty gnarly image.

Thomas Crofton Croker had a fun description in his 1828 book of folklore, titled “Fairy Legends and Traditions of the South of Ireland.” A man named Charley comes across the horseman, and here’s how he describes the head. Quote:
“It looked like a large cream cheese hung round with black puddings: no speck of color enlivened the ashy paleness of the depressed features; the skin lay stretched over the unearthly surface, almost like the parchment head of a drum.

Two fiery eyes of prodigious circumference, with a strange and irregular motion, flashed like meteors upon Charley, and a mouth that reached from either extremity of two ears, which peeped forth from under a protrusion of matted locks of lustreless blackness. This head… burst upon his view in all its hideousness.”
End quote.

It’s also interesting to note that there are several stories of dullahans in that book, suggesting the Dullahan isn’t just one being, but any headless, evil creature. There’s even a story of a dullahan posing as a beautiful woman to lure a man named Larry into her clutches.

But anyways. Let’s just stick to the typical Irish Dullahan descriptions.

After the Dullahan finds a victim, he will systematically hunt them down. If anyone happens to be looking out at him as he passes by, they will be instantly blinded; the Dullahan will take their eyes out with a whip made from a skeletal spine, or perhaps blind them by throwing blood into their eyes. Some dullahans have whole conversations with their targets, while others can only speak once on a particular hunt, and the word he speaks is the name of his victim. And once the Dullahan says the victim’s name, they are doomed to die, and nothing they can do will save them. Which is pretty metal.

Can the Dullahan be stopped? Well, he apparently appears at night during certain festivals… you’d imagine important Celtic holidays like Beltane or Samhain. Go check out last year’s Halloween episode for more information on those holidays! But apparently he doesn’t like precious metals like gold, so if you throw gold on the ground in front of him, he’ll turn back and run. 

So where did the myth of the Dullahan come from?

Some believe that he is supposed to be the embodiment of Crom Dubh [crom duhve], a Celtic deity that represents fertility. The story goes that King Tighermas [Tiarnas], back was Ireland was still firmly Celtic, worshipped Crom Dubh [Duhve], who demanded yearly human sacrifices in the form of decapitation. So when Christianity swept over Ireland and human sacrifices stopped, Crom Dubh took the form of the Dullahan to collect the heads and souls he wanted. Which helps explain why the legend survived beyond the days of the Celtic world pre-Catholicism.  And in fact, the headless horseman as a supernatural entity was used as an explainer for otherwise unexplainable deaths.

Croker notes in his book that, quote,
“Places where any fatal accident has occurred, or any murder has been committed, are seldom without a supernatural tale of terror, in which the headless coach and horses perform their part.” End quote.

And this helps explain why the headless horseman has stuck around for a while, evidenced by the dozens of iterations we’ve had. The most famous, at least in my opinion, being the Headless Horseman of Sleepy Hollow.

So where did Washington Irving likely get his idea? According to Hudson Valley Historian Elizabeth Bradley, Irving may have gotten the idea for his horseman from Sir Walter Scott, who wrote The Chase in 1796, which was a translation of a German poem called The Wild Huntsman which was based on Norse mythology! So this myth is allll over the place. Bradley notes that, quote, 
“Irving had just met and become friends with Scott in 1817 so it's very likely he was influenced by his new mentor's work… The poem is about a wicked hunter who is doomed to be hunted forever by the devil and the ‘dogs of hell’ as punishment for his crimes.”
End quote.

But according to the New York Historical Society, Irving may have just been inspired by a Hessian soldier who had his head blown off by a cannonball during the Battle of White Plains in October 1776 during the American Revolutionary War. The Hessians were German soldiers who supported and fought for the British troops in the American Revolutionary War. In fact they fought in a bunch of wars for European powers in the 18th century, so they had lots of experience. And if you’re wondering, they were called Hessians because most of the Germans who fought in this band of troops came from either Hesse-Kassel or Hesse-Hanau. So, you know. Hessians.

But anyways, regardless of where Irving got his inspiration, he wrote the short story The Legend of Sleepy Hollow in 1820, largely considered to be America’s first fictional ghost story. And because the Hessian it’s probably based on died around Halloween, the larger myth of the Headless Horseman of Sleepy Hollow has become a Halloween specter. 

So now that we’ve got the context squared away, let’s take a closer look at Washington Irving’s story: the Legend of Sleepy Hollow.
Washington Irving’s Legend of Sleepy Hollow
Irving’s story takes place in a small village called Sleepy Hollow, tucked away in a glen north of the larger Dutch settlement of Tarry Town. The protagonist is Ichabod Crane, a school teacher who moves to town and falls in love with Katrina von Tassel, the daughter of a wealthy farmer.
And I just have to quote how Washington Irving describes Ichabod Crane because it’s ridiculous and he spends way too long on it. Quote:
“He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame must loosely hang together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weather-cock perched upon his spindle neck to tell which way the wind blew. To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a cornfield.” End quote.

And his description of the sad-looking schoolhouse wasn’t much kinder. I just want to know why Irving hated his main character that much. What a rough description! And I’d say the Disney adaptation very much nailed it as well. 

The 1999 version of Sleepy Hollow was directed by Tim Burton and starred Johnny Depp as Ichabod Crane, Christina Ricci as his love interest Katrina, and… get this… Christopher Walken as the headless horseman. Which is amazing. I remember liking it a lot as a kid, enough to buy the DVD in fact, and upon a rewatch for this podcast… I still liked it. But it is very different from the source material; Ichabod Crane is a constable instead of a teacher, the whole plot is just different… But I don’t mind that. It’s Tim Burton doing his thing. And from a visual standpoint, it was gorgeous and gothic, the way many Tim Burton films are. But my bigger point here is that Johnny Depp wasn’t made to look like the OG Ichabod Crane, and that film doesn’t really make the book “come alive,” so to speak.

But anyways. To summarize the original story super briefly, because you don’t need to know all the relationships and characters and subpots, Ichabod attends a party one night at Katrina’s family’s homestead. His rival, Brom Bones Van Brunt, and yes, I did just say his name was Brom Bones, tries to scare Ichabod with the story of the Headless Horseman, and he recounts the story of the decapitated Hessian soldier. According to Brom, the horseman is buried in the local graveyard and rises from his grave every night looking for his missing head. For some weird supernatural reason (so, plot) he’s unable to cross the wooden covered bridge that crosses the steam nearby the graveyard, which is why people in town, safely in their homes at night, don’t see him.

At this same party, Ichabod proposes to Katrina, but she rejects him. So, heartbroken, Ichabod borrows a horse and leaves the party and of course rides through the graveyard on the way. Because plot. Ichabod runs into the horseman, who chases him down. Crane is near the bridge, but just before he can safely escape, the horseman throws his severed head at Ichabod, who is knocked off his horse.

The next day, the horse is found back at the von Tassel homestead, but there’s no sign of Ichabod Crane. The only evidence left behind is Ichabod’s hat near the bridge, and a smashed pumpkin next to it. Katrina marries the rival, Brom Bones, and Ichabod is never heard from again. So again, if you’ve only ever seen the Tim Burton one… it’s a totally different story.

Now what’s cool about the original story is that Washington Irving left the ending open to interpretation - is Ichabod alive? Is he dead? There’s even a hint that the horseman isn’t real, and it was really Brom Bones in disguise trying to get rid of Ichabod Crane so he could win Katrina’s affections. The severed head might have just been a jack o lantern that Brom chucked at Ichabod. But that’s what makes it a good story - it allows the reader to come up with their own interpretations, which means they’ll be talking about it with their friends, and it will stay relevant. And it was clearly very successful, because now the tourism industry in Sleepy Hollow just eats up the Halloween and ghost story fans who flock to the village every year. And here I am writing an episode about it. Not to mention all the movies, video games, books, etc.

And even if the legend sometimes gets retold, isn’t that just the beauty of mythology? One of the earliest headless horsemen, the Dullahan, sure is different from its subsequent iterations. But the character itself was scary enough to endure through the ages, and the headless horseman lives on to hunt down his targets, from one Halloween to the next.
Outro
Thanks for joining me for this episode of A Popular History of Unpopular Things. My name is Kelli Beard, and I hope you’ve enjoyed the story of the Headless Horseman. Thank you for supporting my podcast, and if you haven’t already checked out my other episodes, go have a listen!

You can also support me and the show on Patreon - just look up a popular history of unpopular things. Subscribe to APHOUT on YouTube and check out my editor’s music, you can find him everywhere as Nedric. Links are in the description!

Be sure to follow my podcast, available wherever you listen, so you know when new episodes are dropped. And stay tuned to get a popular history of unpopular things.