Shocktoberfest #24: The Headless Horseman

Welcome back to Shocktoberfest where today we will look at an American folk tale that Washington Irving turned into legend that became a Halloween icon.  This monster needs no introduction, but he’s going to get one anyway: the Headless Horseman.

Before jumping into Washington Irving’s classic tale, it should be noted that the idea of a headless horseman did not originate with The Legend of Sleepy Hollow.  As a matter of fact, the legend goes back as far as the middle ages.  Both Celtic and German folklore have older stories of headless horsemen riding through the woods to murder any trespassers.  Irish lore tells of the horrible dullahan, a rider in black carrying his head on his lap while wielding a whip made from a human spine.  When the dullahan stops riding, he calls out a person’s name, and that person dies immediately–sounds like the manga series, Death Note, also took some inspiration from the legend.

In German folklore, the Brothers Grimm collected two headless horseman myths.  One story is from Dresden in which a woman goes out to pick acorns in the forest near a place called the Lost Waters.  Upon hearing the blare of a hunting horn, she turns around to find a headless man in a long grey coat sitting atop a grey horse.  Another is from Braunschweig and tells of a headless horseman known as “the wild huntsman” who blows a horn to warn other hunters to not ride the next day lest they befall a terrible accident.  Depending on which version is being told–and there has been some crossover due to word-of-mouth retellings–the horseman either seeks out perpetrators of high crimes to punish himself or sends out a pack black hounds with tongues of fire to do his bidding.

From these old stories, Irving put a new spin on the trope to elevate the horseman to an iconic status.  Published in 1820, his story begins with a little background on our main villain.  In 1790, the Dutch settlement of Tarry Town, New York near the forest known as Sleepy Hollow has become plagued by hauntings of various ghouls and spectres, but the one causing the town the most grief is the Headless Horseman.  He’s the ghost of a Hessian mercenary whose head was shot off by a cannon ball during the American Revolution, and every night he rides to the scene of the battle on a quest to reclaim his head, and if he cannot find it, he lops off the head of anyone unlucky enough to be near him out of spite.

Unaware of the legend, a superstitious schoolmaster from Connecticut named Ichabod Crane comes to town and competes with Brom Bones for the hand of Katrina Van Tassel, the daughter of the wealthiest farmer in town, Baltus Van Tassel.  Upon learning how superstitious Crane is, Bones tells the story of the Headless Horseman during the harvest party in order to rile up Crane’s imagination.

When Crane’s attempt to secure Katrina’s hand fails, he rides home through the woods with a heavy heart.  Spooked by everything around him by the ghost stories he’d heard earlier, he treads as lightly as he can in order to not disturb any would-be ghosts.  However, upon his travels, he encounters a large and silent cloaked figure upon a horse.  When he discovers that the figure’s head is not upon his shoulders but on his saddle, he briskly races for the bridge crossing the river because according to what he had heard at the party, the Headless Horseman will vanish in a blaze of fire and brimstone upon crossing the bridge.  Crane crosses the bridge successfully but to his horror, the Horseman had climbed over the bridge and then rears his horse while throwing his severed head into Crane’s face.

The next morning, Crane has disappeared from town, leaving behind his horse, his hat and the shattered remains of a pumpkin.  Since Katrina marries Brom Bones, the story implies that the Horseman was really just Brom in disguise pulling a stunt to scare away Ichabod Crane.  But the denizens of the town believe that Crane was spirited away by the ghost of the Headless Horseman.

While Irving’s story has been adapted countless times on television, postage stamps, stage productions and radio broadcasts, there have only been three films.  The first came in 1922 and was simply called The Headless Horseman, starring Will Rogers as Ichabod Crane.  This film is famous for being the first panchromatic black-and-white feature film, and thankfully, it has been preserved for today’s audiences.

The second came in Walt Disney’s 1949 animated feature, The Adventures of Ichabod and Mr. Toad.  The first half the movie of is The Wind in the Willows–which was also very good and compliments the latter story very well–but the second half is The Legend of Sleepy Hollow, and while it is mostly a faithful adaptation, there is one key difference; the Headless Horseman is real.

The third adaptation was Tim Burton’s 1999 film, Sleepy Hollow starring Johnny Depp as Ichabod Crane and the last actor you’d expect to play the Headless Horseman.

Burton’s film has received slightly more positive reviews than negative, and even though repeated viewings have highlighted some of its problems, I still really like it.  The story devolves from a love triangle into a murder mystery, but in the case of a resurrected Hessian decapitating people, it was a clever idea to treat it more like CSI and make Crane a skeptic at the beginning, giving his character an arc he never really got in the original story.

There isn’t much else to say about this monster because if you live in the United States and celebrate Halloween, the Headless Horseman is almost the holiday’s mascot and a worthy one at that.  On a night devoted to scaring people into giving you the things you seek [candy], there is no better agent to represent Halloween than the black rider himself.  So if you go trick-or-treating this Halloween, make sure you make it to the bridge before he does.

“The Headless Horseman” – Bing Crosby