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Making a Monster: The Headless Horseman

Sleepy Hollow

As with most places on Earth, ghost stories are a deeply ingrained part of American culture and history. Every town, even every city have their haunted houses and their local legends. It has always been a common fascination, one both carried over from Europe and mixed with the beliefs and local folklore of the Indigenous People. As America established itself as a country, both before and after the Revolutionary War, those legends and stories found common themes that transformed them into something more distinctive to the region, making them more fundamentally American, though those European influences always remained concretely clear. After the Revolutionary War, more and more ghost stories—both on the fictional page and in reported encounters or local folklore—became about the ghosts of dead soldiers. The Civil War only strengthened that. And it has held, somewhat, ever since. Gettysburg is still believed to be one of the most haunted places in America to this day.

When Washington Irving wrote his short story The Legend of Sleepy Hollow (1820), the story naturally had no shortage of American and European folklore to draw from. There had been a long line of ghost stories predating it, even some that shared extreme similarities, situations, and faces—or, in this case, the lack thereof. After all, even Headless ghosts have long been a part of American and European legend. But Irving’s influences were, in most cases, more specific, probably to an unexpected degree for even a casual fan of the story or the author.

Irving was born in New York City and even though he lived in Europe for nearly twenty years, he frequently wrote of his home state and was deeply inspired by local history and legends. Irving stands out among so many authors of classic horror tales as The Legend of Sleepy Hollow was really the only ghost story he ever actually wrote. His stories were much more considered classically literary, and he always blended his fiction with real life elements, especially locations and people that either made an impression on him or that he had personally come to know. Both fiction and non-fiction were major interests of his as a writer. For every Rip Van Winkle there was a biography of George Washington.  So it’s no surprise that those fictional, folkloric and real world elements all blended together in The Legend of Sleepy Hollow.

The first major inspirations came from Irving’s lengthy research into actual legends and ghost stories from around the world. Headless ghosts featured prominently in European folklore dating back centuries. In Ireland, the dullahan was said to be a demonic fairy that rode a horse, carrying his own head under his arm. According to legends, he even carried a whip made from human spines. The dullahan, like most headless horsemen in folklore, was said to be an omen of death. When the demon stopped riding, a death would always occur. In some versions of the story, he would say a name and the person with said name would die on the spot, and in others he would be seen as the driver of a black carriage. Scottish folklore had its own Headless Horseman as well, a soldier named Ewan decapitated at the Isle of Mull. In this story, though, both the horseman and the horse were said to be headless.

In English folklore, a Headless Horseman is the titular knight of the classic 14th century poem, Sir Gawain and the Green Knight. One of the most highly praised Arthurian stories, Sir Gawain and the Green Knight is also one of the most prominent chivalric romances in the classical tradition. It’s an archetypal tale of a hero’s quest and a search to prove one’s skill against insurmountable odds. In this case, those odds are personified by a horseman. In the poem, Sir Gawain is a Knight of the Round Table who receives a challenge from the Green Knight to strike him with an axe on the condition that he will take a return blow one year and one day from the day of the challenge. Confident in his abilities, Gawain takes the challenge and decapitates the knight, only for the knight to pick up his head and leave, reminding Gawain of their next meeting. It is, ultimately, a tale of proving oneself, proving one’s courage against a faceless threat that is seemingly beyond death and there’s clearly some DNA in that concept that would make its way into Irving’s classic story.

During the Revolutionary War, the area surrounding New York’s Tarrytown was—according to Irving’s own writing—a home of great and chivalrous men from all over, as well as some horrific battles on account of the fact that it was in close range of the British and American line. One particular location is of note to the eventual development of The Legend of Sleepy Hollow. After the Continental Army abandoned the Bronx River, giving way to British Occupation, Westchester County became something of a no man’s land. It was home to a great many skirmishes, more than are believed to have even been recorded. Many of the battles were between Loyalists and the British soldiers, but there were also Hessian sharpshooters who frequently battled with the American soldiers in that area. According to Jonathan Kruth’s Legends and Lore of Sleepy Hollow & The Hudson Valley, a fallen Hessian who lost his head in battle was not only buried in Sleepy Hollow, but was even buried in the Old Dutch Burial Ground by the Van Tassel family. All of those names, of course, are of extreme importance to the classic story.

On that note, it’s worth getting into some of the real names and places behind Irving’s Legend of Sleepy Hollow. The town of Sleepy Hollow itself is, of course, real. And though every story takes huge liberties with its inspirations, many of the sights, citizens and local folklore of the town made it into The Legend of Sleepy Hollow in some fairly direct ways. While the specific bridge where Ichabod Crane meets his fate at the hands of the Horseman does not exist, most of the other locations do, particularly the Old Dutch Church and surrounding burial ground. In fact, Irving himself is buried in Sleepy Hollow, though his remains lie in the Sleepy Hollow Cemetery, rather than the Church’s own burial ground.

When Irving was living in Sleepy Hollow, he became acquainted with the Van Tassel family, who became the prominent well-to-do family at the core of his famous story. In particular, he came to know Cataerina Van Tassel, who clearly became the inspiration for the story’s Katrina Van Tassel. Irving lived with her family for a brief time, and in that time he asked her permission to use her name for the story and based the character on her, at least loosely.

In 1814, Irving met a man named Ichabod Crane while he was working as an aide to New York Governor Daniel D. Tompkins. Unlike other inspirations drawn for the story thus far, the real-life Ichabod could not have been further from the character depicted in the story and clearly provided inspiration for the name alone. This Crane was an army captain. However, there was another man named Jesse Irwin who is much more widely believed to be the true inspiration for Irving’s protagonist. Merwin was a teacher who taught at a local schoolhouse in Kinderhook, a place located further north of Sleepy Hollow, where Irving lived for a few months in 1809. While his large frame clearly didn’t inspire that overwhelmingly lanky and awkward Ichabod of the story, most of the other elements of the character are clearly there. There is another member of the Van Tassel family, however, by the name of Samuel Young who was also long credited for inspiration for Irving’s famous schoolteacher. It’s entirely possible that Irving drew from all three men for inspiration, but as it stands, Merwin is the one who simply had the most clearly defined similarities.

All of these elements from so many different sources and backgrounds came together to create The Legend of Sleepy Hollow. The story itself is, simply put, one of the best fictional ghost stories ever told because it perfectly embodies the local folklore and open-endedness that come attached to real-life local legends and superstitions. It feels not like a tale being pieced together by an author, but like an actual piece of supposed history you could hear passing through any empty town on a dark night. That, I think, will always be its greatest strength. At the same time, though, it does not simply read like an account of the facts, even though that’s technically what it sets out to do. It is a story that is dripping with atmosphere, with long, stretched shadows and low-hanging fog.

Old Dutch Church of Sleepy Hollow

One of the greatest strengths of The Legend of Sleepy Hollow is its sheer simplicity. Like all great ghost stories, it’s just an archetypal tale about a man who encountered a spirit on a bridge and was never seen or heard from again, even containing all the speculation that usually accompanies those local tales as to what really happened. The story allows the reader to come to their own conclusions. In fact, it kind of forces us to do that. Did Ichabod Crane really die, or did he leave town and start a new life after Katrina’s rejection of him? Was he murdered or scared off by Brom, disguising himself as the spirit? Or are the old spinsters right when they believe, wholeheartedly, that Ichabod truly did encounter the Headless Horseman on the bridge that night?

It’s the mystery of the story that makes it so endearing. At the same time, though, there are traces of each those stories that influenced it present in the text of The Legend of Sleepy Hollow. In those old Irish and Scottish tales, the Headless Horseman was depicted as an omen of death. That’s no different here. Ichabod encounters the Horseman and tries to outrun him—making the Horseman a simplistically perfect metaphor for death itself—but he cannot. While the ending allows us to speculate on the possibility of his happy new life, he is presumed dead. Sir Gawain and the Green Knight can also be seen in The Legend of Sleepy Hollow, to some degree. In that poem, the Knight represents a test of one’s strength and bravery. Sir Gawain prevailed because of his nobility. Ichabod was brave enough to go down that path to begin with, despite truly believing the stories, but that’s the extent of it. He is terrified and his terror builds and finally explodes when he sees the Horseman. If anything, it’s a test of bravery that he does not pass. And it’s even better, on some levels, to read that with the possibility that Brom was the one dressed as the Horseman that night, as he is a much more classical hero than Ichabod and bears no small similarity to the Sir Gawain of the poem.

Brom is even, surprisingly, depicted as chivalrous. One of the most interesting things about him, especially given the story’s short length, is that Brom is clearly not made out to simply be a braggart. He’s a romantic rival who has the advantage and never loses it, he’s clearly the guy that Katrina’s going to pick from the beginning. For all his skills and charm, Irving twists the knife in a little deeper by making sure to point out that, in addition to all of this, Brom is actually a pretty good guy. That’s maybe the biggest thing to indicate the possibility that he might not be pretending to be the Horseman at the end, and that Ichabod does indeed actually encounter the spirit itself.

Of course, the biggest thing about the Horseman in the story is the backstory that he was, or is at least believed by the locals to have been a Hessian mercenary who was decapitated by a stray cannonball, something that bears a miraculous similarity to the actual Hessians of local history and the headless Hessian corpse long said to be buried in Sleepy Hollow’s own Old Dutch Burial Ground. It would certainly be unlikely for that to be any kind of coincidence.

The inspirations for The Legend of Sleepy Hollow are, obviously, numerous. Each one is an individual and diverse ingredient that comes together to create a singular flavor. The story is so perfectly pure and effective that it’s no surprise that it lent itself to so many adaptations over time. The first film adaptation of the story came in the form of 1922’s The Headless Horseman. It starred Will Rogers as Ichabod Crane. Rogers was a Cherokee citizen who appeared in over seventy films and even ran a humorous campaign for president in 1928. After that first silent adaptation, the next screen treatment was 1949’s The Adventures of Ichabod and Mr. Toad, the famed Disney cartoon narrated by Bing Crosby. Even after the blockbuster Tim Burton adaptation, this might be the most famed and beloved version of the tale.

In 1980, Jeff Goldblum played Ichabod in the under seen television film, The Legend of Sleepy Hollow, alongside Meg Foster, Dick Butkus and Charles Sellier. The story was also adapted as the premiere episode of Shelley Duvall’s Tall Tales and Legends, starring Ed Begley Jr. as Ichabod and Tim Thomerson as Brom. In 1994, one of the best episodes of Are You Afraid of the Dark? titled “The Tale of the Midnight Ride” operated as a sort of sequel to the story and even had the benefit of being the first adaptation to actually shoot in the town of Sleepy Hollow.

In 1999, Tim Burton delivered one of his best and, surprisingly, his first and only outright horror film with Sleepy Hollow. The film takes drastic liberties with the story, turning it into more of a mystery with Ichabod as a facts-obsessed, critical thinking detective and pathologist rather than a mousey school teacher. To be fair, though, those interests of the character were mentioned in the original story, even if they were not by any means at the forefront. A gory love-letter to the days of Hammer Films, Burton’s Sleepy Hollow might not best represent the story as a whole, but does beautifully portray its overwhelming sense of atmosphere, dread and the power of local superstition.

Still, nothing could ever top Irving’s original tale as one of the premiere American ghost stories ever written. While the Headless Horseman might not be a legend on the same level as Dracula or Frankenstein, he was one of the first—if not the first—true icons of American horror. The story is told and retold to this day, with more adaptations and homages than one could even possibly count. That, if anything, is a true testament to its lasting power as not only a story of archetypal, elemental horror, but one of the most important pieces of rural American fiction overall.

About Nat Brehmer

In addition to Diabolique, Nat Brehmer has written for Wicked Horror, Dread Central, We Got This Covered, That's Not Current, Dark Knight News and Tom Holland's Terror Time. As an author, he has had fiction published in several lit mags and anthologies including Sanitarium Magazine and Hello Horror, as well as novels and novellas... at least three of which are still in print. He currently lives in Orlando, Florida.

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