Headless Horseman

He's looking for a replacement, and he's not picky about where it comes from.

With a hip-hip and a clippity-clop
He's out looking for a head to swap
So don't try to figure out a plan
You can't reason with a headless man!

— The Adventures of Ichabod and Mr. Toad

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 human victims. Sometimes a Headless Horseman just seeks to scare, other times he will attempt to take others' heads. He may also be depicted carrying 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, but the Trope Codifier is Washington Irving's story The Legend of Sleepy Hollow (although it's arguably an Unbuilt Trope there, as it is strongly implied that the Headless Hessian that pursues Ichabod Crane in the climax is actually local rowdy Brom Bones playing a prank to scare the shit out of the schoolmaster, his would-be romantic rival).

A common modern variation replaces the live horse with one of steel.

The probable Sister Trope to Losing Your Head. See also Hellish Horse, Nuckelavee, and Our Centaurs Are Different for other monsters related to horses.

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Examples:

Advertising

• The Headless Horseman has appeared in some commercials for Netflix representing the horror movies, delivering films to somebody's house and getting stuck in traffic jams.
• There also exists the inversion the Horseless Headsman, currently shilling for Snickers. It's the one in which he starts out as the 'Horseless Headsman' until a snickers restores him to himself.
• Naturally, you can't take two steps in Sleepy Hollow, New York without running into a sign with the Headless Horseman on it.

Anime and Manga

• Female Dullahans show up in Deadline Summoner, 12 Beast and Monster Musume, in two instances without a steed, in the other riding a centaur.
• In chapter 57 of Delicious in Dungeon, Laios is nearly killed by a horseless dullahan, but it spares his life in exchange for the body of the conveniently decapitated bicorn the party had just killed, which becomes its steed. An omake reveals how it lost its previous horse: they ran into Mithrun, and he teleported it off a cliff.
• Episode 3 of Dream Hunter Rem features one of these from feudal Japan.
• Durarara!! has a more modernized version of the Dullahan... the horse takes the form of a Cool Bike (landing it into My Horse Is a Motorbike territory). The mount's spirit is still of a horse, but coming upon the remains of a motorcycle 20 years ago inspired the current ride. It can be heard whinnying, and it can revert to a horse on occasion. And the horsewoman is actually a Badass Biker. Bonus points for its name being a multi-referential language-based pun (popular in Japanese media) referring to the difficulty the Japanese language would have in pronouncing "Dullahan" and the revving of a bike, amongst other things.
• A headless biker features in episode 19 of Ghost Stories.
• Interviews with Monster Girls features a Dullahan schoolgirl known as Machi who carries her head separately from her body.
• Lala is a Dullahan that joins the cast of Monster Musume. She acts like she's The Grim Reaper, but it's quickly revealed that she's really just a gothy teenager who likes to pretend she's the Grim Reaper. It's eventually revealed that she's an actual psychopomp who's pretending to be a gothy teenager pretending to be the Grim Reaper.
• 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 its head stolen and running amuck looking for it.

Card Games

• Magic: The Gathering: The basic Headless Horseman appears as a Zombie Knight creature in the old Legends expansion set. There's also the Stillmoon Cavalier, likewise a Zombie Knight, from the more recent Eventide set.
• Yu-Gi-Oh! has the Headless Knight and Ghostrick Dullahan.

Comic Books

• In a Casper the Friendly Ghost comic, Casper encounters the Horseman, who finally does meet up with his long-lost noggin, which has been going around as the "Horseless Headman".
• The comic book series Chopper written by Martin Shapiro, is a modern-day reimagining of the headless horseman. It features a headless outlaw biker on a motorcycle who collects the souls of sinners. The only people who can see him are those who have consumed a strange new ecstasy-like drug that triggers their sixth sense and opens a gateway to the afterlife. During the hallucinogenic high, any characters who have committed significant sins are hunted by the headless ghost. Once the drug wears off the victim is safe and beyond his ghostly reach.
• In DC Universe Halloween Special 2008, The Ballad of Jonathan Crane is a retelling of the Horseman's legend with the characters from Batman. Naturally, the role of Ichabod Crane is taken over by Jonathan Crane, who encounters numerous versions of Gotham's heroes and villains before encountering a Batman-like version of the Headless Horseman. The whole thing is a nightmare due to over exposure from Crane's fear toxin.
• King Vold, master of the wild hunt in Hellboy. Inspired by the Norwegian tale of the "Green Giant."
• 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.
• 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.
• Vampirella once travelled to Sleepy Hollow where she confronted the Headless Horseman.
• Dark Horse Comics has put out at least one annual Halloween anthology comic titled "Headless Horseman" in which the title character plays host to the various stories, ala the Crypt Keeper. However, from the cut of the uniform worn, and from the cleavage our host displays when wearing a bathrobe whilst playing video games (long story), it is obvious that she is a headless horsewoman.

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.

Fan Works

• Hunters of Justice: In an Elseworld story, the Wretched Weapon is a Cyborg Fusion Dance of Ruby and Penny. After her head was destroyed by Pyrrha, a green and red flame burns from her neck in its place. When she completes her modifications, the Weapon rides on a mechanical horse and carries a replica of Ruby's head in her free hand which emotes and can be used as a weapon itself. For bonus points, the Wretched Weapon came to be in Sleepy Hollow.
• The League Of Extra Ordinary Gentlemen: The Revolutionary League battled the original Headless Horseman of Sleepy Hollow in 1778, very shortly after the horsemans "birth". Despite this version of the League consisting of warriors such as Daniel Boone and Captain Stormalong, they barely survived the encounter, as the Horseman turned out to be impossible to harm through mundane means, and the League could only fight him to a stalemate until dawn, when the Horseman disappeared.
• Nine Days Down: Dullahan, the Headless Horse, is an alicorn who keeps his severed head attached to a hook on his saddle and with mist endlessly pouring from his neck stump. He leads a procession of spirits through and between the worlds, and offers those that he meets the chance to join him and leave behind life and its sorrows forever.
• Stiofán Dubh: Steve Rogers, AKA Captain America, gets his head sliced off, but due to a deal his Irish mother cut with the Irish pagan deity Crom Dubh when he was an infant, he does not die, and instead gets transformed into a dullahan, moldy cheese-stinking head, weakness to gold, motorcycle, and all. The fic focuses a lot on the practicalities of Cap's new situation- the only thing he can say is people's names, which will kill them, making him functionally mute until he learns sign language; he "sees" by sensing where people and things like walls and thresholds are, but he can't see color or detail; he eats by cutting up his food very small, sticking a funnel into his exposed esophagus, and dumping the food in; and Tony has to make him a special metal cover for his neck stump so it doesn't leak fluids all over the place. When Cap does eventually decide that he wants to do the modern dullahan thing and ride around the country smiting evil from his motorcycle, Tony modifies his neck-cap with a socket that will hold a prosthetic head, so that at least he'll look mostly normal if he gets pulled over or has to be in populated areas as long as he keeps his motorcycle helmet on and the visor closed.

Film — Animated

• In The Haunted Pumpkin of Sleepy Hollow, the eponymous story turns out to be a legend in-universe based on the true story of an Evil Sorcerer, who returns from the afterlife as a headless horseman and seeks to retrieve his head (which was turned into a pumpkin) so he can regain his powers.
• In Hotel Transylvania, the cabby for the hotel turns out to be a monster that uses a greenish, detachable jack o'lantern instead of an actual head, driving a motorized carriage instead of a horse.
• The Adventures of Ichabod and Mr. Toad, as the title indicates, features an adaptation of Irving's story.
• A Headless Horseman makes a cameo appearance in Shrek 2 as one of the patrons at the Poisoned Apple, and appears as part of Prince Charming's army of villains in Shrek the Third.

Film — Live Action

• In the Will Hay film Ask a Policeman, the coastal village of Turnbotham Round is terrorised by a headless horseman. Unlike most examples this one more closely follows the Irish folktale (see below).
• The poster for Black Sabbath depicts a Headless Horseman riding past a group of terrified women and brandishing a severed head, although this never appears in the actual film. The severed head does, though.
• 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.
• 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.
  "They say no."
• The Headless Horseman (1922) was the first film version of The Legend of Sleepy Hollow.
• 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.
• 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.
• Sleepy Hollow (1999) by Tim Burton, only very loosely based on the Washington Irving story.
• In Sleepy Hollow High, the killer disguises himself as the Headless Horsemean.

Game Books

• In Howl of the Werewolf, the Headless Highwayman is the specter of a former bandit known as "Lord Filthy Lucre" who infested the countryside but was executed. His mortal lover, Meg the innkeeper's daughter, dabbled into Black Magic to revive him.

Literature

• In the Ben Snow story "The Headless Horseman of Buffalo Creek", Ben investigates a local legend of a headless horseman and uncovers a brutal murder.
• In the Monster Mash noir City of Devils, headless horsemen are one of many monsters in the world. They tend to work as drivers, either taxi or limo, and spectral chargers are a relatively common sight in Los Angeles traffic.
• Discworld:
  • Tiffany Aching briefly encounters a headless horseman in The Wee Free Men:
    Tiffany: He had no head!
    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.
• 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." The Horseman is finally defeated when it is sucked from its physical body and confined in a certain crystal skull, which first has to be activated via a special ritual.
• One of the Freddy the Pig mysteries involved a short man with a frame built atop his shoulders, a very long coat, and a painted bowling ball masquerading as a headless horseman.
• Ghost Roads: Rose meets a dullahan, though she doesn't have a horse. Dullahans, like bean sidhe, are beings that were never "alive" in the first place, and they take the form of a parasitic head that manipulates a headless corpse.
• Graveyard School: A more modern version, a headless bicyclist, shows up as a Peek-a-Bogeyman in the series. She's one of the students at the school. Not that she's not undead... as in Pirates of the Caribbean: The Curse of the Black Pearl, she can pose as living during the daytime. Fortunately, she's completely harmless.
• The Headless Hunt from Harry Potter. Every year, they consistently deny Nearly Headless Nick's application to join on the grounds that many of their Severed Head Sports require one's head to be completely detachable.
• The Headless Horseman, an 1865 novel by Mayne Reid.
• The Headless Horseman Rides Tonight: More Poems to Trouble Your Sleep: In "The Headless Horseman", the black-clad Headless Horseman rides an alabaster steed upon the wind. Beneath his left arm it holds its skeletal head with its "harsh and hollow" voice while with his right arm he wields a scythe. The horseman may or may not be a psychopomp. On one hand, he rides to take a soul with him and anyone could be that soul. On the other hand, the horseman's overall look taps into that of the Grim Reaper and he's also referred to as the "minister of death".
• 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.
• KonoSuba: The first of the Demon King's generals Kazuma and his party face is Beldia, a headless knight who's explicitly identified as a Dullahan. Interestingly, his horse is also headless.
• The Legend of Sleepy Hollow, the Trope Codifier.
• In a 2010 erotic retelling of The Legend of Sleepy Hollow, by Deanna Wadsworth, Brom Bones does more than masquerade as the Headless Horseman.
• Headless bikers and bounty hunters are not-uncommon sights in the Nightside. Considering that aliens, werewolves, superheroes, demons, ninjas, and cyborgs from the future are also not-uncommon sights in the Nightside, the occasional headless dude doesn't attract any particular attention.
• A number of Headless Apparitions appear in No Man's Land: Tales from the Weird Wars, ranging from an Indian, to a G-man, to a Soldier. The two present day versions are expies of The Punisher and Ghost Rider.
• The Reluctant King: A local legend in book three has the headless ghost of a bandit lord still riding the mountain where he died. Jorian actually asks if the ghost is riding the ghost of his horse (with the innkeeper admitting that he was the first person to ask that).
• Rowley Jefferson's Awesome Friendly Spooky Stories: The Headless Horseman appears in story 5, The Human Head, and his name is Gunther. He was born without a head and befriends Anders, someone born without a body. They become best friends, but they both have a crush on the same girl, which eventually tears the apart. He becomes evil after the girl chooses Anders over him.
• 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.) Like when the Dullahan takes Valkyrie to Doctor Nye to get her true name sealed, which requires her to die first because getting the necessary symbols carved into her heart would really kill her if she was alive at the time.
• Sonic the Hedgehog in Castle Robotnik: There is one roaming around outside, what really freaks Sonic out (who has become accustomed to the weirdness by this point) is that the horses are headless too.
• The Headless Rider, the last Strange Matter novel before the series was rebranded as a sci-fi/action title, featured a headless motorcyclist who went throwing flaming skulls capable of exploding on impact. It's greatly implied, if not outright stated, that the Rider's not a ghost nor is he just a guy in a costume. He's a man who lost his head in a motorcycle crash with a tanker truck full of toxic waste, and exposure to said waste turned him into a headless mutant. The ending of the book mentions the Fairfield sheriff's department was able to arrest him, again, even though he has no head.
• 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.
• Dullahans appear in Volume 3 of We Walk the Night as the soldiers of the Morrigan.

Live-Action TV

• The Andy Griffith Show had Andy trying to read The Legend of Sleepy Hollow to Opie when he kept getting interrupted.
• 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.
• 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.
• "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.
• In episode 8 of The Chronicle, a headless biker hunts down and beheads several obnoxious characters. It's not Disproportionate Retribution; they're all escapees from hell.
• A headless horseman featured in an episode of Dark Shadows.
• It once served as a major plot point on Ghost Whisperer.
• The Kolchak: The Night Stalker episode "Chopper" features a headless biker bent on revenge.
• 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.
• A legend of a 'headless highwayman' features in one episode of Metal Mickey.
• In the Midsomer Murders episode "The Dark Rider", a killer lures several victims to their deaths by masquerading as a headless horseman from local legend.
• An episode of Murder, She Wrote, of all things, which relocated it to a prep school, and tied it in with the required murder.
• In Sleepy Hollow, Ichabod Crane dies on the battlefield in 1781, killed by a Hessian Soldier (though the show's depiction of such borders on In Name Only, sharing only a name and nationality And in this case not even that as the solider was Crane's own, British friend who was raised from the dead). Before collapsing, he decapitates the Hessian and the two die side by side. When he awakens some 230 years later in the modern day United States, the Hessian has also risen, still minus his head, riding a white horse with red eyes. As well as the Headless horseman, he is also Death, one of the four Horsemen of the Apocalypse, and a dangerous antagonist.
• The first episode of Tall Tales And Legends features an adaptation of The Legend of Sleepy Hollow.
• "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.

Magazines

• This cover◊ from a 1960 Halloween issue of MAD.

Music

• Apparently a fascination for They Might Be Giants, who namedrop the Headless Horseman in their songs "You Probably Get That A Lot" and "Headless". "Authenticity Trip" contains references to Sleepy Hollow and to Ichabod Crane, but not to the Horseman himself.
• "Headless Horseman", a song by Pigmy Love Circus on the album The Power of Beef (2003).
• "Roland the Headless Thompson Gunner" by Warren Zevon. Roland is a Norwegian mercenary, skilled with a Thompson submachine gun, who gets murdered by a fellow mercenary during the Congo War of The '60s. His ghost tracks down and murders his assassin, and goes on to stalk the war zones of the world.

Myth and Legend

• The Trope Maker/Ur-Example is an dubhlacan, or dúlachán, anglicized as "the Dullahan", an Irish fairy that carries its head under its arm, and either rides a massive black horse or drives a massive black coach. Most of the details come from tales collected by an antiquarian named Thomas Croker in 1828, who had a rather condescending attitude to the common Irish people, could not himself speak Irish and was known for embellishing the stories he was told, so it's still debated how much of the detail is actually genuine folklore.
  • In one description its head is much larger than a normal human's, with a literal ear-to-ear grin full of sharp teeth, big glowing eyes, and flesh that is often described as having the color and texture of moldy cheese. Getting a basin of blood thrown on you by one is a bad omen — it means you're going to die soon.
  • Modern versions often say the Dullahan wields a human spine as a whip and flicks blood at passersby with it. Interestingly this seems to be a combination of two things from Croker's book - an incident where the coachman lashes his whip at a witness's eyes, and a line in Croker's poem where the spine is actually the coach's axle. The "spine-whip" appears to date no earlier than the 1990s.
  • In some versions, the Dullahan's horse is not only also headless, but its head floats alongside it as it rides. Its head is just as horrific and rotten as its master's head, and is larger than the rest of its own body.
  • One of the myths of the Dullahan says that it drove a horse-drawn carriage known as a Cóiste Bodhar (literally "deaf coach" but idiomatically meaning that is completely silent) — sometimes pulled by headless horses.
  • The dullahan's motives also tend to vary: In some regions, he got separated from his head and he's looking to get it back, but in other regions where he still has his head, he's so bitter and enraged that he came back SOLELY to murder people.
• One of Costa Rica's better known spooks is the Headless Priest; a Catholic priest beheaded for his bad behavior that roams the Earth unable to rest. A lesser known spook, the Headless Pirate, roams Coco's Island guarding the alleged pirate treasure buried somewhere there.
• In the Brazilian Folklore, there's a legend from the state Maranhão about a real-life woman, Ana Jansen, whose ghost appears accross the streets of the capital in a carriage conducted by a headless slave and pulled by headless horses.

Newspaper Comics

• The Far Side: The Horseman comes home from his day at work, and is greeted by his family, who are also all headless, including the pets.
  • Another cartoon sees Ichabod Crane suing the Horseman for assault.

Pinball

• A variation appears in Joker Poker — in the electro-mechanical version of the game, a roly-poly cartoon jester fills the center of the playfield, wearing a crown and with his nose serving as a "5X Multiplier" light. The solid-state version keeps the crown and the light, but inexplicably removes his head all together.
• In The Pinball of the Dead, Kuarl, half of Judgement, is an animated headless suit of armor.

Podcasts

• In Less is Morgue it turns out that Riley summoned a dullahan to curse their middle school nemesis, and he's been hounding her ever since. When Evelyn convinces Riley to try and call him off they mess up the summoning and get an incubus, who turns out to know the horseman in question, quite intimately.

Tabletop Games

• 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.
• Pathfinder: The dullahan appears in the second Bestiary as a form of headless undead riding on a Hellish Horse (although particularly powerful dullahans can summon a full carriage pulled by six such horses), and which gains extra power over its victims if it targets them by name.
  • Part 3 of the Shattered Star Adventure Path features a powerful, unique dullahan known as the Dark Rider who seems to combine elements of the traditional headless horseman (namely the whip made from a spine and calling their victim's name) with The Wild Hunt.
  • A squad of dullahans made from Cossacks are important underlings for Grigori Rasputin in the penultimate part of the Reign of Winter Adventure Path.
• 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.

Theatre

• The Legend of Sleepy Hollow (2009), an opera, with music by William Withem and libretto by Melanie Helton.
• 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.
• Tarrytown is a contemporary musical based on the love triangle between Ichabod, Brom, and Katrina... except Ichabod is gay and attracted to married Brom while befriending his wife, Katrina. The musical ends with Ichabod's drug-induced hallucination of the Headless Horseman (implied to actually be Brom) who knocks him into the river, never to be heard from again.

Video Games

• Played with in AdventureQuest; the Horseman monster is indeed headless, but is actually a combination between a horse and a man, rather than a horse-rider.
• Assassin's Creed:
  • The Horseman appears in Assassin's Creed III as a side quest for Connor to disprove his existence. He finds out the Horseman is indeed real, and actually beheading people.
  • In Assassin's Creed Rogue, he also appears in Sleepy Hollow where Shay can only kill him by shooting at the pumpkin over his tombstone. He is so iconic Abstergo Entertainment would obviously include him as an easter egg in their game.
• 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.
• The Binding of Isaac Rarely, one of the Horsemen of the Apocalypse bosses has a chance to be replaced with the Headless Horseman. He's effectively a Composite Character that uses attacks from all four original Horsemen. Like the other Horsemen, he's depicted as a bloody corpse riding a hobby horse.
• 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 Superboss in his own right.
• Dullahan also shows up as a boss, and has a normal Skeletal enemy variety (Sometimes even in the same game) in some of the Castlevania games. Interestingly, he's rarely mounted.
• Appears on a level of Dragon's Lair. Dirk has to dodge him and is unable to use his sword due to the Horseman casting a spell on it.
• In Dragon Quest XI, a monster known as a "Headless Honcho" is fought near the beginning of the second act. Notably, its shield has a face on it that talks on behalf of the headless body. The Headless Horsemen, Headless Hunters, and Headless Norsemen make their debut in this game, while the Dullahans, Dark Dullahans, and Hell’s Gatekeepers from Dragon Quest VIII reappear in this game.
• In The Elder Scrolls V: Skyrim, you may encounter a ghostly headless horseman riding along the roads at night. Alternatively, you may encounter a headless ghost chasing his spectral horse along the roads at a night.
• In Fate/Grand Order has the Headless Horseman show up as one half of Hessian Lobo, the Shinjuku Avenger. Because the Horseman is more akin to an Urban Legend than an actual Heroic Spirit, he has to team up with Lobo the King of Currumpaw for the two of them to count as an actual Servant. In the game, he rides Lobo as his mount instead of his classic horse. The Hessian also acts as a Morality Chain for Lobo and tends to serve as an intermediary between them and the protagonist should they be summoned.
• 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; he is first seen running rampant and scaring everyone around, since the skull of his body was not properly buried and fell in the hands of a ill-intentioned man, who now uses the skull to control Dragoon and abuse his powers. After you resolve the conflict with Dragoon's head, he joins your forces as an extremely powerful soldier who could only be 'bound' outdoors to roads or paths.
• A Dullahan is a notoriously difficult Superboss in Golden Sun: The Lost Age. Either he or a new Dullahan also shows up in Dark Dawn. In neither instance does he have his horse.
• In House of the Dead 2, the first boss, Judgement, is a headless suit of armor (Kuarl) controlled by a flying goblin (Zeal) that you have to hit.
• Hecarim in League of Legends has a skin that is literally this as he's a centaur,^note A literal Horseman Headless Hecarim, although he does wear a pumpkin on his shoulders.
• The Headless Horseman is a powerful boss monster in the MMORPG MapleStory.
• In Omen of Sorrow, Arctorious is an spectral knight that dons an black armor, but in place of a head, he has blue flame coming out of his neck.
• Otogi: Myth of Demons has a samurai variant with the boss Masakado, based on the infamous Real Life warlord Taira-no-Masakado, who tried to overwhelm the Emperor and was defeated and beheaded.
• In Overwatch, Pharah gets a Dullahan inspired Legendary skin for the Halloween Terror 2018 event.
• 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 Puppeteer (2013), he serves as the mayor of Hallowee-Ville.
• Decapitated Rasetsumaru in Samurai Shodown remains alive and well, and still can talk.
• 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.
• 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.
• Appear irregularly in Shin Megami Tensei as a headless knight sans horse. A noteworthy example is a female Dullahan that shows up as a mid boss in Shin Megami Tensei IV during a Challenger Quest. The fact she appears in Ikebukuro makes her a reference to Durarara!! (see the Anime folder above).
• Not with his horse, but a Dullahan is summoned and, after killing his summoner, engages in a boss battle in Strider 2.
• Tales of Berseria: Dullahan appears as a boss in Titania, where the Abbey created him through Venomization.
• The Horseless Headless Horsemann [sic] in Team Fortress 2 is the game's first boss character, who first appeared in the 2010 Halloween update in the "Mann Manor" map. He's extremely powerful, and prances around the map gleefully with an axe decapitating all in his path with a single swing. If a player manages to kill 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.
• Tofu Tower (Naka): Dullahan appear on at least two cards:
  • "Dullahan at Play", which is a woman's head at a beach on a beach lounger. Flavor Text:
    A reward for working hard.
  • "Dullahan at Work", gotten in chests around Floor 67, which is a headless suit of armor, presumably the body belonging to the bodiless head from "Dullahan at Play". Flavor Text:
    Hard work is its own reward.
• Sekibanki from Touhou Project may count. She is supposed to be a rokurokubi (though she is closer to being a nukekubi, as ZUN couldn't recall if rokurokubi was the one with extendable neck or detachable head) but accepts being called a Dullahan by Reimu and her theme is called "Dullahan Under The Willows". She also has a card associated with the Dullahan. She doesn't have a horse though.
• Warframe: Dagath is a Warframe inspired by the legend of the Headless Horseman. She was once a servant, but was betrayed twice by her Orokin masters: the first betrayal killed her Kaithe (a horse-like creature) but also mortally wounded her, leading her to be turned into a Warframe as an Emergency Transformation; the second time was an attempt at outright murdering her, which turned her face into a big hole but failed to kill her. She then took revenge on her masters, before roaming the land on the ghost of her Kaithe, demanding offerings from travellers who encounter her. In gameplay, her abilities have her summon Sinister Scythes, attune to the spirit realm for buffs, and calling forth a stampede of ghostly horses to trample her foes.
• 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 Sir Thomas, a paladin of the Scarlet Crusade who went insane after he killed his family in a raid on a town. He then began speaking in rhyme, and was killed after he began to attack other Crusaders. He was 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.

Webcomics

• 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.
  • The process of transforming into a headless horseman also gives the victim an overpowering craving for hair, of all things.
• Blip has a headless horseman who communicates by texting with his smartphone.
• Irving in Contemplating Reiko. Though he's too much of a Butt-Monkey to be a threat.
• 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.
• He's one of the main characters in Nightmarish, in which he's the pony-and-rainbow-loving Cloudcuckoolander king of Nightmaria and the owner of the castle.
• The protagonist of the Weird West furry comic The Gravedigger is a necromancer bounty hunter whose (half-rotted) head is held on with a black ribbon. Though she claims not to be undead herself.

Web Video

• Headless: A Sleepy Hollow Story stars Sleepy Hollow's Headless Horseman in a modern-day setting, who agrees to be Ichabod Crane's roommate if Ichabod helps him find his head. A witch's spell allows the Horseman to go around without a head by reanimating the skull of a deceased person placed on his neck, whose identity temporarily takes over the Horseman's. The Horseman's condition is later revealed to be a curse originally placed on the witch Henrietta Hudson in 1621.

Western Animation

• Arthur: In The Fright Stuff, Binky suggests that he and Arthur dress up as a "headless horseguy" to scare Francine and Muffy. This idea is quickly rejected after they realize that they wouldn't be able to see out of the costume and would likely crash their bicycle.
• In Bojack Horseman, there's a Stillborn Franchise Show Within a Show about the Headless Horseman. In the last episode, the viewers are fooled into thinking that BoJack is dead by showing part of a headline saying that the Headless Horseman franchise is dead.
• Ub Iwerks produced a Headless Horseman short as part of the ComiColor Cartoons series.
• Costume Quest (2019): Wren's costume in "Baking is Best with Friends" is Headless Horse-Wren, actually.
• Headless Horsemen appear in the Courage the Cowardly Dog episode "Windmill Vandals".
• A preschool-friendly variant, No-Noggin the Headless Scarecrow, appears in the Halloween special from Curious George. It's said to kick peoples' hats off out of jealousy, having lost its own pumpkin head.
• A headless horseman appears in the audience of Daffy Duck's nightclub act in The Night of the Living Duck.
• The Headless Postman in the Danger Mouse episode "The Scare Mouse Project". In the backstory he was defeated when DM's ancestor Ichabod Mouse posted his head with insufficient postage, after which it somehow ended up in Danger HQ's mailing room. As DM points out, the monster now seeking revenge is "more of a Postmanless Head".
• The 1980s Dennis the Menace animated series had an episode where Dennis scared some people by pretending to be a headless horseman.
• DuckTales (2017) has a variation in the Headless Man-Horse. He starts as a minor antagonist, then quickly becomes friendly after getting a replacement head (from a statue of Scrooge). He then becomes a recurring extra, nicknamed Manny.
• Ed, Edd n Eddy: In the Halloween Episode Ed Edd N Eddy Boo-Ha-Ha, Ed, who's been hallucinating everyone around him as different horror monsters due to accidentally brainwashing himself with horror movies while preparing for Halloween, sees Kevin as a headless horseman, who carries a flaming jack-o-lantern as a projectile weapon. In reality, Kevin is just riding around the neighborhood on his bike, throwing eggs at people. Notably, Kevin is the only "monster" Ed insists the group run from rather than try and fight.
• Filmation's 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.
• The Funky Phantom gets a Headless Horseman, but this one comes with a twist. Ichabod Crane was doing to scare a rival away. The coward ghost, Mudsy, a.k.a the Funky Phantom, played the Headless Horseman to help save Ichabod from a beating by the rival.
• The Headless Horseman appears as the main antagonist of The Haunted Pumpkin of Sleepy Hollow.
• There was an episode of Hey Arnold! about this sort of urban legend, but instead of a horseman it was a headless cabbie. Gerald first tells the story at a sleepover, then on a late-night walk through the park, the boys see the story seemingly start to come true. Actually executed both humorously and creepily at the same time.
• One episode of A Miss Mallard Mystery, "Dig To Disaster", Miss Mallard, Willard, an a banker named Harold Scoter, go to an ancient city said to be haunted by a headless duck riding the back of a warthog. Said headless duck turns out to be Harold Scoter, or rather Heraldo Scotari, dressing up as said monster to scare them off so he could continue looting the city.
• Episode 7 of Moville Mysteries features Pumpkin Reaper, an urban legend that seemed to exist in Ouigee Falls when Mo's grandmother was younger. Mo comes face to face with the monster itself when he experiences a weird time travel phenomenon. However, it turns out the whole episode was a dream, until the Pumpkin Reaper pops in the last scene.
• The Headmistress of Monster High is the daughter of the Headless Horseman. Aside from her removable head she also has a fire breeding horse.
• In the My Little Pony: Friendship Is Magic episode "Look Before You Sleep", Twilight Sparkle tells Rarity and Applejack a ghost story about "the Headless Horse".
  • Rainbow Dash tells another ghost story about the Headless Horse in "Sleepless in Ponyville". This time, Applejack wonders how the Headless Horse could see anypony, and where his brain was kept. Later, Scootaloo reasons that despite Rainbow's claims, it can't eat her because it doesn't have a mouth, but notes that the idea of a headless being is still really scary.
  Rainbow Dash: It's headless, not brainless!
• The Night of the Headless Horseman (1999) was an hour-long computer animated FOX TV special utilizing motion capture. This was an incredibly dark interpretation of The Legend of Sleepy Hollow above: not only is the Headless Horseman real, but Brom Bones makes a Deal with the Devil to invoke him to chase after and kill Ichabod Crane. That's scary enough, but the ending, where the In-Universe Narrator reveals himself as Brom Bones and how he has been damned to become the new Headless Horseman, is truly the stuff of nightmares.
• 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. (Supposedly, this is the same demon that had tried to kill Crane, and a curse was put on his family line when he escaped; the creature simply updated his appearance and steed as the world changed. The Ghostbusters are able to capture it, hopefully ending the threat forever.)
• Parodied in Rocko's Modern Life with the one-legged "Hopping Hessian".
• 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.
    • And Scooby-Doo Meets the Boo Brothers.
• The opening segment of The Simpsons episode "Treehouse of Horror VI" shows Krusty the Klown in the persona of the Headless Horseman.
• There's one who appears in The Smurfs: The Legend Of Smurfy Hollow, which turns out to be a goat that Papa Smurf used his magic on.
• In the South Park episode "Imaginationland", the Horseman is one of the "evil" characters that resides in Imaginationland.

Real Life

• Sleepy Hollow High School, in the New York suburb of the same name, uses the character from the legend as its mascot.
  • Same with Sleepy Hollow Elementary School in Virginia.
• A non-supernatural but still creepy example would be the French Colonel Louis-Charles-Henry de Lafutsun de Lacarre during the French cavalry charge at battle of Wörth (Franco-Prussian War, 1870), who was beheaded by a Prussian shell. The horse continued to charge with the headless body standing on it.

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