Figura Obscura: Headless Horsman figure from Four Horsemen Studios

Headless Horseman

There are places where the walls between this world and the next grow thin, allowing spirts from beyond to roam unbidden between the two worlds. One such place is a small village on the East bank of the Hudson River in New York. Originally named North Tarrytown, this haunted glen is more commonly known as Sleepy Hollow.

Rumored to have been bewitched long ago, stories of strange happenings and distant voices on the air have long been told in Sleepy Hollow. The most dominant spirt that haunts this enchanted region is that of a headless, cloaked rider atop a great black steed – the Headless Horseman. Said to be the restless ghost of a Hessian Trooper who lost his head to a cannonball during some long-forgotten battle of the Revolutionary War, the Headless Horseman rides forth on the blackest of nights, desperately searching for his lost head. Any who are unfortunate enough to meet the Galloping Hessian on his ride are never to be seen again, the only proof of their encounter with the dread apparition being the shattered remains of the jack-o-lantern he often uses in place of his lost head.

The Legend of Sleepy Hollow

Ichabod Crane pursued by the Headless Horseman, by F.O.C. Darley, 1849

One of the most enduring and instantly recognizable symbols of the Halloween season is that of “an apparition of a figure on horseback without a head.” We are, of course, referring to none other than the Headless Horseman, who is the subject of Four Horsemen Studios’ latest Figura Obscura release.

The character of the Headless Horseman was first found in a collection of essays and short stories titled The Sketch Book of Geoffrey Crayon, Gent. Written by American author, Washington Irving, the story was first published in 1819 and it remains an early example of American literature that is still with us, and still quite popular, today.  This popularity is in no doubt thanks to the iconic character of the Headless Horseman, a character who actually only appears in a few pages of the short tale. Still, despite this brief appearance, or maybe because of it, the image of a cloaked rider atop a “black horse” has been one that has captured the imagination of fans for over two centuries.

In the story titled The Legend of Sleepy Hollow, we visit a settlement called Greensburg, which is more commonly known as Tarry Town. In this area there can be found a “sequestered glen” known as Sleepy Hollow. A haunted place said to have been “bewitched by a High German Doctor during the early days of the settlement”, rumors still swirl of this strange glen. Visitors are said to have visions and to fall into trances as they hear music and voices on the air. There are also many local tales of haunts and strange happenings that the residents of Tarry Town are only too happy to relate.

This tale goes on to tell that the “dominant spirit that haunts this enchanted region” is, indeed, this aforementioned Headless Horseman. Said to be a Hessian trooper whose head was separated from his body thanks to a cannonball during a battle of the Revolutionary War, the Horseman now rides forth each night looking for his lost head. Unlucky travelers who find themselves on the road late at night may encounter this dread apparition and his mighty steed, and woe to anyone who dares to stand in the way of the Headless Horseman’s nightly ride.

The bulk of this story is actually focused on a lanky schoolmaster named Ichabod Crane and his quest to woo the lovely Katrina Van Tassel. His chief competition in this pursuit is Abraham Brunt, the rowdy local hero more commonly called Brom Bones. The doings of these three characters are truly the focus of this short story, yet if you ask anyone to name a character from The Legend of Sleepy Hollow, they almost certainly reply with The Headless Horseman.

Figura Obscura - Headless Horseman

In truth, there is logical debate as to whether or not the one scene where the “Galloping Hessian” appears is actually even the restless specter in question. The end of the story finds Ichabod rebuked by Katrina and sullenly riding away on his horse, Gunpowder, only to meet “a horseman of large dimensions and mounted on a black horse of powerful frame.” Dashing away from this rider, who immediately gives chase, Ichabod is horrified to eventually discover that the pursuer is headless, and that his “head” is resting on the saddle before him.

Ichabod tries to escape from the headless rider, but as he looks back, he discovers that the Horseman is now hurling his head at the terrified schoolmaster! This is the last we hear from Ichabod Crane.

The commonly held theory of this ending is that the “Horseman” was actually Brom Bones playing a trick on the man who was his chief rival for the hand of young Ms. Tassel. The “head” that was thrown was likely a pumpkin, a theory reinforced by the fact that Ichabod’s hat and a smashed pumpkin were all the evidence of the lanky schoomaster that was found on the morning after this fateful ride.

Ichabod disappeared, likely driven away from Tarry Town in his terror. While some readers have suggested that Brom may have killed the schoolmaster, it is more likely that Brom Bones was simply looking to scare him away. After all, Brom is described as having “more mischief than ill-will in his composition.”

Regardless of how you believe this story ends, restless ghost or mischievous prank, it is clear that the most enduring images of this classic tale are of the headless rider and his mighty black steed.

The Headless Horseman Rides into the Modern Age

The Legend of Sleepy Hollow has not only been reprinted countless times for new audiences to enjoy, but the story has also been used as the basis for numerous other entertainment vehicles, from cartoons to movies to television and beyond. The Headless Horseman has ridden forth many, many times over the years!

The first modern adaptation of this story is likely the 1922 silent film called “The Headless Horseman.” A more commonly known version, however, would have to be an animated one that arrived almost 25 years later from the Walt Disney Company.  “The Adventures of Ichabod and Mr. Toad” was released in 1949, and it included an extended chase scene that very much positioned the Horseman as a ghost rather than a human trickster in disguise. This story remains part of the Disney lexicon, and there is still a “Sleepy Hollow” quick service restaurant in the company’s Walt Disney World Magic Kingdom park!

While the Disney version of this story is more light-hearted, for a darker take on this tale the 1999 Tim Burton directed “Sleepy Hollow” fits the bill. This version of the story takes some significant liberties with the backstory of the Horseman and the reason for his nightly rides. It also changes the dynamic between the story’s three main characters of Ichabod, Katrina, and Brom!

Figura Obscura - Headless Horseman

These examples are, of course, just a few of the adaptations that exist of this classic story. There have also been numerous television shows that have used the characters of the Headless Horseman, Ichabod Crane, and others to tell both faithful and very much updated versions of this story. Some notable examples include a 1979 after-school special called “Once Upon a Midnight Scary” that was narrated by Vincent Price, a 1980 television film starring Jeff Goldblum as Ichabod and Dick Butkis as Brom Bones, an episode of “The Real Ghostbusters” cartoon that reimagined the headless rider as a punk-rock motorcyclist, or the 4-season run of “Sleepy Hollow” that saw Ichabod transported to the 21st century where he fights both crime and supernatural forces!

The character of the Headless Horseman is also a popular choice for Halloween costumes, and readings of “The Legend of Sleepy Hollow” are quite common during October each year. Beyond simple readings of the story, certain locations, like the actual Sleepy Hollow, are known to throw an even bigger celebration in honor of their favorite decapitated rider!

Figura Obscura - The Headless Horseman

Visiting Sleepy Hollow

Yes, there is actually a real Sleepy Hollow. In truth, there are multiple Sleepy Hollows in the United States, but the one most relevant to this story can be found in Westchester County, New York (which is only about 40 minutes away from Four Horsemen Studios). The author of The Legend of Sleepy Hollow, Washington Irving, was actually born in New York (Manhattan), and although he wrote his famous story while away on business in England, he did eventually move back to the United States and he died in Tarrytown, New York – a name you should recognize from the story of the Headless Horseman. Washington Irving is now buried in Sleepy Hollow Cemetery.

Sleepy Hollow was originally known as North Tarrytown, and they officially took their new name in 1996. As you’d expect, Halloween is pretty popular in Sleepy Hollow. According to their website “Halloween in Sleepy Hollow has something for everyone: haunted hayrides, gothic mansions, blazing pumpkins, farmers markets, live music, street fairs, Halloween parade, and of course, the Headless Horseman!” Many Halloween fans in the Northeast US have added Sleepy Hollow, NY onto their “must visit” list of locations to haunt during October each year.

Many other locations also celebrate this story during Halloween. For example, in Sturbridge, MA (which is about 135 miles North of Sleepy Hollow), the “living history museum” of Old Sturbridge Village put on an outdoor production of “The Legend of Sleepy Hollow” each October for a few years. The audience for this event would find themselves walking from location to location in the “village”, where a small acting troupe would perform the story. The event culminated in a lively “party” that recreated the event at the Van Tassel estate, and finally a moonlit encounter with none other than The Headless Horseman! While this production has ended, it is an example of how The Legend of Sleepy Hollow remains a popular story that can be enjoyed by fans in a variety of ways.

The Horseman Rides into Figura Obscura

As we detailed last December when we launched Figura Obscura with the release of Krampus, the idea of this line is to allow us to create cool action figures that may not easily fit into our existing Legions properties. While not meant to be strictly a “holiday line”, there are certainly a number of very cool character ideas that tie into various holidays, and those are characters we are excited to consider for this line (amongst the many other ideas and sources of inspiration we will draw from). In truth, we developed the Headless Horseman figure at the same time we developed Krampus! We had initially planned to release the Horseman as our first Figura Obscura item, but the timing was too tight to have him out for Halloween 2021, so he was pushed back a year and Krampus became our inaugural release instead.

  • Figure Obscura - Headless Horseman
  • Figure Obscura - Headless Horseman
  • Figure Obscura - Headless Horseman
  • Figure Obscura - Headless Horseman
  • Figure Obscura - Headless Horseman
  • Figure Obscura - Headless Horseman

Like that Krampus figure before him, the Headless Horseman makes uses of a number of existing Legions parts, with select new items added to fully realize the character. The Horseman himself uses body parts first introduced in our Illythia wave, but with a brand-new neck attachment to show his severed head and collar, plus two jack-o-lantern heads (one of which is overcome with flames!). We also designed a brand-new hand sculpture that includes a “peg” in the palm, allowing the Horseman to hold those pumpkins in his hand without having to worry about balancing that item perfectly in the open palm. It plugs into that new hand the same way it would plug onto a neck peg – and yes, the figure does also include a neck peg so you can use either of the pumpkins in place of the dark rider’s head!

One of the most striking new items in this set is the incredible soft goods cape that was prototyped for us by CJSIEM. That cape is fully wired, allowing fans to pose it in very dynamic ways for their displays and photography!

Similar to our Krampus release, the new Headless Horseman Figura Obscura figure comes in deluxe packaging featuring brand new artwork from Nate Baertsch (shown both earlier in this article and directly below). Every inch of this large package is covered in wonderful new illustrations made especially for this release. You can see some of it here on this page. That artwork can also be found on some of the additional items being offered, including pins, t-shirts, and mugs!

Figura Obscura - Headless Horseman box featuring art from Nate Baertsch

Another item to note on the package for our second Figura Obscura release is the addition of the new logo for this line! Our original Krampus release did not include this logo because the name “Figura Obscura” actually came after that figure was fully produced and ready to go! The version of this logo you see on the new Headless Horseman package is specific to this release, and you will notice this logo change over time based on each new Figura Obscura figure. You can read more about the creation of the “Figura Obscura keys” right here.

Figura Obscura - Headless Horseman logo

The initial version of the Figura Obscura: Headless Horseman is a limited edition, exclusive. It is available to fans just in time for Halloween 2022! The release was teased with a cryptic image reveal sent out the day before the figure would be available. Then, on the morning of October 1st, 2022, the headless rider was fully revealed as the second Figura Obscura release! An initial run of the figures went on sale at 9am EST, with a second offering planned for later that evening at 8pm EST.

Spectral Green Headless Horseman

Similar to what was done for the first Figura Obscura figure by offering a second version to the studio's retailers, in early 2023 it was announced that a new version of this popular set would be made available in our "2023 Retailer Appreciation Wave." This new version was dubbed the "Spectral Green" edtion due to the new green flames and accents it included - all of which would glow in the dark! The body on this new version was also repainted with more purples, and his soft goods cape swapped the red lining for a deep orange color! You can see the updated version of this character below.

Figura Obscura - Headless Horseman

The Figura Obscura: Headless Horseman figure rides into the collections of figure fans worldwide, leaving many wondering what is next for this exciting line of new figures from Four Horsemen Studios. Only time can answer that question, for few know what characters the Figura Obscura keys will unlock next.

All figure photos on this page come courtesy of Trevor Williams, aka One-Six Shooter, who continues to make our products look absolutely amazing.

Figura Obscura - Headless Horseman