The Villains Throne: The Headless Horseman

Ah October, that magical time of year when everything starts to change. It’s gets darker sooner, colder faster and everything tastes like pumpkin. The best thing about this wonderful month is of course Halloween, a time when we get to shed our own skin for a night and become someone else for a few hours while stuffing our faces with candy. Magical. So in honor of this most precious time of year I chose to discuss a villain who’s legend is as famous as the jack-o-lantern he uses as his head. That’s right, we’re talking the headless horseman

I decided to turn to our friend the headless horsemen mainly because he embodies all that makes Halloween great; spooky nights, a ghost story and pumpkins for heads. The legend of the headless horseman can be traced back to my own home state of New York in the small town of Tarrytown. The story goes that a Dutchman leaves a tavern, after having a few, and is forced to go through the famous Sleepy Hallow cemetery on his way home and begins to recall all of the ghost stories surrounding a headless Hessian soldier who was buried in an unmarked grave somewhere in the cemetery. There were legends that there was a ghost on horseback that many speculated was the ghost of the Hessian soldier. While venturing through the graves the Dutchman sees a white light rising from somewhere in the cemetery and behold there is a saddled phantom, he appears to be in a Hessian uniform…and headless! The Dutchman eventually loses the horseman and makes his way home to his wife and the legend was born.

Years later Washington Irving would famously use the legend of the Hessian solider to create his The Legend of Sleepy Hollow. The story is about the gawky school master Ichabod Crane who falls in love with the daughter of a rich farmer, Katrina Van Tassel, and is determined to win her love and her fortune. However Katrina is a famous flirt and has caught the attention of every young man in Sleepy Hollow, including Brom Van Brunt, the town bully. One night while attending a party at the Van Tassel house the story of the headless horseman is told much in the way that the folktale goes, Hessian solider buried in an unmarked grave, depending on the version you hear or see of Sleepy Hallow it says the horseman uses a Jack-o-lantern as a head while he searches for a new one. After the festivities Katrina eventually tells Ichabod it isn’t going to work, shocker, and Ichabod is sent home sad and alone. While passing through the cemetery Ichabod comes upon the Headless Horseman and is chased through Sleepy Hollow. Ichabod attempts to reach the bridge (or church depending on the rendition you see) that is said to be the end of the horseman’s territory. However it is unclear if Ichabod is successful because it cuts to the next morning where nothing is discovered but hoof prints, Ichabod’s hat and a smashed pumpkin. Some say Ichabod simply left to become a judge in another town, some claimed Brom had impersonated the horseman and followed Ichabod to get rid of his competition, but most believed the Headless Horseman had found his new head…

The legend of Sleepy Hollow and the Headless Horseman have been retold time and again both in books and on the screen. Everyone from Disney to Christopher Walken have left their mark on the story. The story continues to fascinate those who hear it and it isn’t hard to see why. The horseman is a villain in the most basic sense. He is a ghost, spooky and nameless. Although there are stories about the actual Hessian soldier buried in Sleepy Hollow, not many were aware of it and it made the horseman inhuman on a supernatural level. If his name was Fred the Guy Without a Head, it wouldn’t scare anyone. When the good people of Tarrytown heard the headless horseman, it sent chills down their spines. The horseman represented death itself, rising from an unmarked grave and looking for a new head, so not only did he represent death, but a gruesome one. Something back in 18th century New York was probably a big fear for most people. When you look back people died of the silliest things, death in their minds were lurking around every corner. Using a phantom figure that represents everything they fear and can also inflict harm and bring about that fear? Holy cow scary.

The thing that makes the headless horseman so scary to me is his language, or lack thereof. The horseman never speaks, due to lack of mouth, and that personally freaks me out. Imagine being on a horse riding through a dark graveyard and seeing a dark figure on a horse in front of you. You yell out to greet the stranger and nothing. No words, no grunt of recognition, silence. That would make me instantly on edge and suspicious. The whole appearance of the guy headless factor put aside is creepy. He is often depicted in all black and is on a black horse, he just a shadow before you. It makes him forbidding and dangerous looking. The jack-o-lantern on his shoulders are the only light coming from him. Back in the day jack-o-lanterns were meant to be pretty scary to ward off evil spirits, so imagine seeing one of those being flung at your head. Nope, I’ll pass.

If we were to stack the headless horseman against my characteristics that make a villain, he would fit the mold pretty well. Ichabod, our hero, is pretty awkward and not exactly depicted as a genius, so the fact that the headless horseman is smart enough to understand someone is trespassing over his grave and he wants their head is a pretty good match. The headless horseman has no morality, he just wants a head. I’m not sure how sexy a headless guy is to some but I’ve seen some freaky fanfiction about the Christopher Walken version, I don’t know if I would recommend it. The headless horseman is wounded because….well he has no head. So naturally his obsession would become finding a new head to replace the jack-o-lantern he uses to throw at people. His relatability I think can be seen from both ends, I think if we all lost our heads we would probably be pretty upset and want a new one. However I don’t know how many of us believe in modern day the possible reality of a headless spectrum riding around throwing pumpkins at people.
The Headless Horsemen is a ghostly figure that has haunted the town he was originated for well over a century and continues even now to fascinate and attract visitors. There are tours you can take in Sleepy Hollow today that claim to have sightings of the guy. That in my book is what makes him so great in the end. His ability to scare generations of passer byes is just a testament to his power as a villain. Here’s to the Headless Horseman, may he find a head, just not mine.

















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