Headless Horseman

A specific type of undead (sometimes a ghost, sometimes a physical revenant), the Headless Horseman is a headless rider who haunts woods and roadways, often the one where he lost his head, in search of victims. Sometimes a Headless Horseman just seeks to scare, other times he will try to take others' heads. Sometimes, the Horseman will carry a jack-o'-lantern in place of his lost head.

Tales of headless riders have existed in folklore for centuries, most notably the Irish legend of the Dullahan (see examples below), but the Trope Codifier is Washington Irving's The Legend of Sleepy Hollow, although that is also a slight subversion, as it is strongly implied that the Headless Hessian that pursues Ichabod Crane is actually.

The probable Sister Trope to Losing Your Head.

Advertising

 * The Headless Horseman has appeared in some commercials for Netflix representing the horror movies.

Anime and Manga

 * Durarara with a more modernized version of the Dullahan... the horse takes the form of a Cool Bike. Although interestingly it used to be a horse--it's just disguised. It's shadow is still of a horse, and it can be heard whinnying.
 * Princess Resurrection has a headless horseman in both the manga and the anime. Both were a result of an empty suit of armor/ghostly horseman getting it's head stolen and running amuck looking for it.
 * A headless biker features in episode 19 of Ghost Stories.

Comic Books

 * In Marvel Comics teen humor comic Misty, Misty's hometown of Shady Hollow had its own headless horseman legend. Misty's rival tries disguising herself as the headless horseman to scare Misty in one issue.
 * Marvel Comics has done at least two horror comic stories featuring the ghost of the Headless Horseman in Uncanny Tales #2 and Supernatural Thrillers # 6. Both were set in a contemporary Sleepy Hollow and featured someone pretending to be the ghost, only for the real ghost to take offence.
 * Vampirella once travelled to Sleepy Hollow where she confronted the Headless Horseman.
 * In a Casper the Friendly Ghost comic, Casper encounters the Horseman, who finally does meet up with his long-lost noggin, which been going around as the "Horseless Headman".

Fairy Tales

 * The German Legends of The Brothers Grimm (Deutsche Sagen) recount two German folk tales of a headless horseman:
 * One is set near Dresden in eastern Germany. In this tale, a woman from Dresden goes out early one Sunday morning to gather acorns in a forest. At a place called "Lost Waters", she hears a hunting horn. When she hears it again, she turns around she sees a headless man in a long grey coat sitting on a grey horse.
 * In another German tale, set in Brunswick, a headless horseman called "the wild huntsman" blows a horn which warns hunters not to ride the next day, because they will meet with an accident.

Film

 * Sleepy Hollow by Tim Burton, only very loosely based on the Washington Irving story.
 * Don't forget the Disney animated The Legend of Sleepy Hollow, which is, of course, an adaptation of Irving's story.
 * The Headless Horseman (1922) was the first film version of The Legend of Sleepy Hollow.
 * The Hollow is a 2004 teen horror movie. It tells the story of Ian Cranston, a high school student who just found out he's the descendant of Ichabod Crane. With the help of his girlfriend, Karen; a local bully named Brody, and the old cemetery caretaker, Claus Van Ripper, Ian now must stop the newly resurrected Headless Horseman.
 * In the 1974 movie Curse of the Headless Horseman, a phantom horseman who appears every night with a human head tucked under his arm lets it be known that he is searching for eight gunfighters.
 * The Syfy original movie Headless Horseman plays with this trope. The location is changed (the deep South) and the horseman's backstory and motivation for head chopping is changed. About the only real similarity is that heads get cut off.
 * A non-supernatural but still creepy example would be the negotiator sent by the Romans to the Germanic chief just before the battle at the beginning of Gladiator.

Literature
"Tiffany: He had no head!
 * The Legend of Sleepy Hollow, the Trope Codifier.
 * 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, an 1865 novel by Mayne Reid.
 * The Headless Hunt from Harry Potter. They denied Nearly Headless Nick's application to join because many of their games require one's head to be truly detachable, or so they claim.
 * Tiffany Aching briefly encounters a headless horseman in The Wee Free Men:

Toad: Well that is the major job qualification."


 * The Tourist's Guide to Lancre claims that Magrat's home village, Slippery Hollow, is home to the legendary headless horse rider. Why he rides a headless horse, and what the reins are attached to, legend does not relate.
 * A more modern version, a headless bicyclist, shows up as a Peek a Bogey Man in the Graveyard School series.
 * The Fifth Horseman: A Sleepy Hollow Legend (by Gregg Gonzalez) is a novel about a terrifying battle with the supernatural in the town of Sleepy Hollow, set over the course of September and October, one year in the late 1980s. The Headless Horseman itself is inhabited by Chaos, the Fifth Horseman of the Apocalypse, who "brings anarchy, conspiracy, suspicion, paranoia, confusion, mistrust and doubt - all of which destroy man from the inside out."
 * Nikolai Drakov creates a headless horseman as part of his plot to derail the course of the American Revolution in the Time Wars novel The Hellfire Rebellion.
 * Skulduggery Pleasant: Mortal Coil features the Dullahan as the servant of a banshee: twenty-four hours after hearing the banshee's wail, the Dullahan drives up in his Coach-a-Bowers to get you. Anyone who enters the Coach-a-Bowers dies (though it is reversible, if you weren't supposed to.)
 * Ben Snow investigates a local legend of a headless horseman and uncovers a brutal murder in "The Headless Horseman of Buffalo Creek".
 * In a 2010 erotic retelling of The Legend of Sleepy Hollow, by Deanna Wadsworth, Brom Bones does more than masquerade as the Headless Horseman.

Live Action TV

 * The Kolchak the Night Stalker episode "Chopper" features a headless biker bent on revenge.
 * In the Are You Afraid of the Dark episode "The Tale of the Midnight Ride" serves as a sequel to the classic story. In this episode a boy moves to Sleepy Hollow where he develops a crush on a girl. One night after the Halloween dance, they see the ghost of Ichabod Crane and send him over the bridge that the Headless Horseman cannot cross, prompting the Headless Horseman to then come after them.
 * "The Legend of Sleepy Halliwell" was an episode of Charmed. A headless horseman tries to murder the teachers and students at Magic School by beheading them. Didn't work as well as planned because a person will not die if part of their body is on Magic School grounds. This brings in the Fate Worse Than Death trope as well.
 * The Andy Griffith Show had Andy trying to read The Legend of Sleepy Hollow to Opie when he kept getting interrupted. (By the way, "Sleepy Hollow" as a bedtime story? Talk about Nightmare Fuel...)
 * "Halloween Hound: The Legend of Creepy Collars" is the second-season premiere of Wishbone. In this episode Wishbone imagines himself as Ichabod Crane and reenacts the Headless Horseman story in his imagination as his owner, a boy named Joe Talbot, goes on a Halloween night scavenger hunt.
 * An episode of Murder She Wrote, of all things, which relocated it to a prep school, and tied it in with the required murder.
 * It once served as a major plot point on Ghost Whisperer.
 * The first episode of Tall Tales And Legends features an adaptation of The Legend of Sleepy Hollow.
 * In the Beetleborgs Metallix episode "Headless Over Heels", the Headless Horseman had an encounter with Wolfgang in the old country and allergies to him is what made him lose his head. When he arrives in Charterville looking for his head, he thought Wolfgang had it and tried to claim it back (or take the head of the other Hillhurst monsters). It turns out that Little Ghoul had his head which she used for bowling and ended up giving it back. Bolts were attached to the head to keep it from falling off again.
 * A headless horseman featured in an episode of Dark Shadows.
 * In episode two of Lost Girl, Bo and Kenzi are attacked by two dullahan. Bo kills one by impaling it in the chest. Kenzi kills the second by finding its head and dropping it in a bonfire.
 * In episode 8 of The Chronicle, a headless biker hunts down and beheads several obnoxious characters..

Myth and Legend

 * The Dullahan is an Irish faerie (Unseelie court) that carries his head under his arm, and rides a black horse. Getting a basin of blood thrown on you by one is apparently a bad omen -- it means you're going to die soon. No gates and doors can bar their passage, but gold scares them away.

Tabletop Games

 * A Headless Horseman acts as a minor domain lord in the Ravenloft campaign setting.
 * In the revisited version in 4e, the horseman isn't the domain lord at all (though it's a common mistake visitors make). He's the punishment inflicted upon the actual domain lord.
 * Headless Horsemen are a type of monster in Deadlands.
 * The "wildermasque" in GURPS Creatures of the Night, which steals a new conveyance on every rampage.
 * Magic the Gathering has this as a Black creature from the old Legends expansion set.
 * Also, there's the Stillmoon Cavalier from the more recent Eventide set. It's a white/black hybrid creature.
 * The dullahan appeared in the second Pathfinder Bestiary.

Theatre

 * Sleepy Hollow (1948), a Broadway musical, with music by George Lessner and book and lyrics by Russell Maloney and Miriam Battista. It lasted 12 performances.
 * The Legend of Sleepy Hollow (2009), an opera, with music by William Withem and libretto by Melanie Helton.

Video Games

 * A Dullahan is a notoriously difficult Bonus Boss (and spell) in Golden Sun: The Lost Age.
 * And either he or a new Dullahan shows up in Dark Dawn. In neither instance does he have his horse.
 * Dullahan also shows up as a boss, and occasionally a normal enemy in some of the Castlevania games. Interestingly, he's rarely mounted.
 * A Dullahan also shows up in a few of the Final Fantasy games, including Final Fantasy Mystic Quest.
 * Ghost Master, a PC game where you control a cadre of ghostly apparitions, with a goal of scarring the wits out of all the NPCs. One of the most powerful ghosts you could recruit was a Headless Horseman called the Dragoon. Extremely powerful, but could only be 'bound' outdoors to roads or paths.
 * The Headless Horseman appears in a seasonal event in World of Warcraft (during Halloween). He flies around setting starting towns on fire and can be fought as a boss. According to the background material, he used to be a paladin of the Scarlet Crusade who went insane after his family was killed, died and got risen as an undead by the dreadlord Balnazzar. The quest to kill him is titled "Bring me the head of... Oh wait." Out of the items you can get for defeating him there's his helmet and his horse, which increases your speed on both land and air.
 * There is a Dullahan boss early on in Vagrant Story that is an empty suit of armour with no head and a large sword. Its weakness? The leather strap that holds the bottom half and top half together.
 * In the first Shining Force game, Dullahans are headless centaur knights that you start to encounter from the march to Dragonia onwards. Slightly averted in that they seem to have a face in their chestplates.
 * Played with in Adventure Quest; the Horseman monster is indeed headless, but is actually a combination between a horse and a man, rather than a horse-rider.
 * Shadow Man - 2econd Coming features the Dullahan as one of the Grigori Sephiroth, and his head detaches and flies about the arena while his invulnerable body chases the player. Oh, and Shadow Man calls him an asshole.
 * Headless Harn/Heart Heat Harn from Battle Monsters, who actually fights with his own disembodied head, complete with spitting out fireballs and swinging it around like a weapon.
 * During the 2010 Team Fortress 2 Halloween update and for Halloween events since then, the Horseless Headless Horsemann [sic] appeared in regular intervals in the new "Mann Manor" map. He's extremely powerful, and prances around the map gleefully with an axe decapitating all in his path. If a player actually manages to defeat him, they'll score an achievement and a free hat - the jack o' lantern the Horsemann was wearing in place of a head. If they go the extra mile and land a hit with a melee weapon near his dying moments, the player gets an extra rare crafting item as well.
 * In Breath of Fire IV, a number of the random encounter enemies share the same floating headless horseman. One of them is the strongest enemy in the whole game and a Bonus Boss in his own right.
 * The Headless Horseman is a powerful boss monster in the MMORPG Maple Story.
 * The Binding of Isaac as had a Halloween update that can cause one of the Horsemen Bosses to become replaced by the Headless Horseman.
 * In The Elder Scrolls V Skyrim, you may encounter a headless horseman riding along the roads at night.

Web Comics

 * The Adventures of Dr. McNinja has a storyline in which Dracula, from his moon base, hatches a plot to turn the clone of Benjamin Franklin into a headless horseman in order to find out more about the afterlife. Seriously. The headless horseman was chosen because it retains its physical form. Turns out they can also travel through space.
 * A recurring character in the horror/comedy webcomic, The Deadlys.
 * Living With Monster Girl installment "Living with Dullahan" includes a (female) Dullahan, albeit without a horse. Amusingly, she inverts the original legend by driving Death away from her boyfriend -- sometimes physically.
 * Blip has a headless horseman who communicates by texting with his smartphone.

Western Animation

 * The 1976 series of Scooby Doo had one of these characters as a villain, as did the original series. It was all a hoax, of course.
 * What's New Scooby Doo also had such a ghoul in the opening title.
 * And there was a headless skateboarder in A Pup Named Scooby Doo.
 * The Headless Horseman appears in Scooby Doo And The Goblin King.
 * The Real Ghostbusters featured "The Headless Motorcyclist", an episode with a descendant of Ichabod Crane cursed by a headless apparition on a motorcycle who chases her.
 * Filmations Ghostbusters also got one, though the account of his headlessness is interesting: "Ja, the whole headless thing was Prime Evil's attempt to make me scarier. It didn't work...I only like scary things that are fun, like Halloween." The Horseman was, for once, on the side of the heroes--he'd wrecked the life of Jake's great-grandfather and wanted to make amends.
 * There was an episode of Hey Arnold about this sort of rumor. Actually executed both humorously and creepily at the same time.
 * The 1980s Dennis the Menace animated series had an episode where Dennis scared some people by pretending to be a headless horseman.
 * Ub Iwerks produced a Headless Horseman short as part of the ComiColor Cartoons series.
 * The Night of the Headless Horseman (1999) was an hour long computer animated FOX TV special utilizing motion capture.
 * A Headless Horseman makes a cameo appearance in the second Shrek film as one of the patrons at the Poisoned Apple, and appears as part of Prince Charming's army of villains in the third.
 * The Funky Phantom gets a Headless Horseman, but this one comes with a twist.
 * The opening segment of The Simpsons episode "Treehouse of Horror VI" shows Krusty the Klown in the persona of the Headless Horseman.
 * In the South Park episode "Imaginationland", the Horseman is one of the "evil" characters that resides in Imaginationland.
 * In the My Little Pony Friendship Is Magic episode "Look Before You Sleep", Twilight Sparkle tells a ghost story about "the Headless Horse".
 * The Headless Horseman appears as the main antagonist of The Haunted Pumpkin Of Sleepy Hollow.
 * Headless Horsemen appear in the Courage the Cowardly Dog episode "Windmill Vandals".

Real Life

 * Sleepy Hallow High School, in the New York suburb of the same name, uses the character from the legend as its mascot.