The Headless Horseman is a fictional character who appears in a short story called “The Legend of Sleepy Hollow” which is in a collection of The Sketch Book of Geoffrey Crayon written by Washington Irving. It was made legendary through literature and films, with the result that a variety of stories about “The Headless Horseman” are still told today. Some people have even reported seeing the Headlesss Horseman over the centuries. However, whether these sightings are fact or fiction is not known.

Background Information

The legend of the Headless Horseman begins in a town near North Tarrytown, New York named Sleepy Hollow. The Horseman was supposedly a Hessian soldier of unknown rank; one of many such hired to suppress the American Revolutionary War. During the war, the Horseman was one of 548 Hessians killed in a battle for Chatterton Hill, wherein his head was severed by a cannonball. He was buried in a graveyard outside an Old Dutch Church of Sleepy Hollow. Thereafter he appears as a ghost, who presents to nightly travelers an actual danger (rather than the largely harmless fright produced by the majority of ghosts), presumably of decapitation. He carries his own head on his person or that of his horse and uses it as a weapon, though he also carries a sword. In Sleepy Hollow, a Tim Burton film, the Horseman is seen to also be skilled with an axe.

Variations

The headless horseman from The Legend of Sleepy Hollow is similar to figures of other stories. German folklore compiled by the Brothers Grimm states that the headless horseman seeks criminals in which the punishment of the crime was beheading. He is described as a “a headless man in a long gray coat sitting on a gray horse”.
In Texas, the headless horseman is a criminal who was beheaded, tied upright on a gray horse, and left to wander Texas. This story was originally told in The Headless Horseman, an 1865 novel by Mayne Reid.
Today, an online variation of the headless horseman appears in the MMORPG World of Warcraft, in which the headless horseman is a summoned spirit who attacks the person that summoned him and then turns to attack the strongest of the surviving characters.

Literature

The headless horseman has appeared in many forms of literature throughout history and throughout the world. Many different countries have their own unique version of the legend in which some form of the headless horseman appears. In the United States, various states have their own version of a headless horseman tale; Texas' version of the legend, written by Thomas Mayne Reid in 1865 or 1866, tells of ghosts of beheaded horse thieves, who roam the countryside.

The more noted and recognizable headless horseman of today imitates the one that appears in Washington Irving's short story, which was published in 1820. The story is set in America, within a 1790's Dutch settlement that residents nicknamed “Sleepy Hollow”. Its protagonist is a schoolteacher named Ichabod Crane, whose apparent demise results from a meeting with the horseman. The horseman himself is allegedly a Hessian soldier from the Revolutionary War who was decapitated by a cannonball and now roams Sleepy Hollow on the back of his horse, with his severed head resting upon the pommel of his saddle. He is therefore covalently called the 'Galloping Hessian'. The Horseman is said to be incapable of crossing the bridge (a possible reference to the belief that ghosts cannot cross water), although he is shown throwing his head across a river to strike down Ichabod Crane. Ichabod's fate is left ambiguous; some of the background characters allege that he has been "carried off" by the Horseman, while others suggest that he has been frightened out of the county by the ghost and by the prospect of facing his landlord, later to become a lawyer in Philadelphia. It is implied later that the Horseman was in fact Brom Bones, Ichabod's rival for the hand in marriage of the local beauty Katrina van Tassel, who imitated the legend of the Galloping Hessian on purpose to kill or frighten away his competitor. The fact that a shattered pumpkin is found beside Ichabod's abandoned hat supports this, in that the pumpkin may easily have been used to simulate the Horseman's severed head. Intriguingly, there is no mention of a severed head in the story heard by Ichabod, though it is prominent in his own encounter with the Horseman.

Other adaptations include collections of short horror stories such as The Headless Horseman: And Other Goulish Tales, poems such as The Headless Horseman Rides Tonight: More Poems to Trouble Your Sleep, and even plays such as The Mystery of the Headless Horseman.

Other Media

The horseman appeared in the film Sleepy Hollow, which premiered in 1911.
Since then, the Headless Horseman has been a staple of the horror community, appearing in films beginning in the early 1900s to current times, such as Sleepy Hollow (1999).
The horseman has been a recurring character within a vast range of the cinematic community but has also appeared in children's cartoons such as Scooby Doo: Headless Horseman of Halloween (1996).

The Headless Horseman appears in Disney's The Adventures of Ichabod and Mr. Toad (1949), which retells the Irving story almost verbatim. On a related note, this Headless Horseman is seen as a regular guest in Disney's House of Mouse amongst the villainous guests.
A version of the Headless Horseman appears in the Ravenloft campaign setting for the Dungeons & Dragons roleplaying game. This version is a "darklord" of a mobile domain which overlays itself on random stretches of barren road and hunts for lone travelers with the assistance of several of the heads of previous victims.

In A Hollow Sleep by Chris Ebert, the Horseman is given an identity of "Heinrich Luneberg" and his origins explored. The story is told from his perspective.
The Headless Horseman was featured in the Are You Afraid of the Dark? episode, "The Tale of the Midnight Ride".
In the Beetleborgs Metallix episode "Headless Over Heels", the Headless Horseman accused Wolfgang of stealing his head. When he arrives in Charterville looking for his head, he attempts to find it or take one of the other monsters' heads in exchange. It is revealed that Little Ghoul had his head, which she used as a bowling ball and later returned to him. Bolts were then attached to the head to keep it from falling off again.
The Headless Horseman was seen amongst the evil creatures in the South Park episode "Imaginationland Episode II".
The Headless Horseman has appeared in some commercials for Netflix, representing the horror movies.
Renditions of him have also appeared in television shows such as Dark Shadows (1966), Faerie Tale Theater (1982) and The Young Ones (1982).
The Headless Horseman is also a powerful boss monster in the MMORPG MapleStory.
A version of the Horseman appears in the MMORPG World of Warcraft, as a seasonal powerful boss monster on Halloween. He gives powerful loot, and many players encounter him.
In the webcomic series The Adventures of Dr. McNinja, a revived Benjamin Franklin is turned into a Headless Horseman based on a serum Dracula (under the alias "Alucard") had given him. While still with his head, Franklin had intense cravings for hair, and was pursued by various ghosts until his head exploded, returning him to true "headless" state.