[[quoteright:325:[[Literature/TheLegendOfSleepyHollow http://static.tvtropes.org/pmwiki/pub/images/The_Headless_Horseman_5.jpg]]]]
[[caption-width-right:325: He's looking for a replacement, [[LosingYourHead 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!''
-->-- ''Disney/TheAdventuresOfIchabodAndMrToad''

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 [[OffWithHisHead he will try to take others' heads]]. Sometimes, the Horseman will carry a [[StingyJack 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 TropeCodifier is Washington Irving's ''Literature/TheLegendOfSleepyHollow'', although that is arguably an UnbuiltTrope, as it is strongly implied that the Headless Hessian that pursues Ichabod Crane is actually local blade Brom Bones playing a prank to scare the shit out of the schoolmaster.

A common modern variation [[MyHorseIsAMotorbike replaces the live horse]] [[CoolBike with one of steel]].

The probable SisterTrope to LosingYourHead.


* 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.

[[folder:Anime and Manga]]
* ''LightNovel/{{Durarara}}'' has a more modernized version of the Dullahan... the horse takes the form of a CoolBike (landing it into MyHorseIsAMotorbike territory). The mount's spirit [[TheShadowKnows 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 "horseman" is actually a BikerBabe. Bonus points for it's name being a multi-referencial 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.
* ''Manga/PrincessResurrection'' 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.
* A headless biker features in episode 19 of ''Anime/GhostStories''.
* Episode 3 of ''Anime/DreamHunterRem'' features one of these from feudal Japan.
* Okayado has female Dullahans show up in ''Manga/DeadlineSummonner'', ''Manga/TwelveBeast'' and ''Manga/DailyLifeWithMonsterGirl'', in two instances without a steed, in the other riding a centaur.
* ''Manga/InterviewsWithMonsterGirls'' features a Dullahan schoolgirl known as Machi who carries her head separately from her body.
* Lala is a Dullahan that joins the cast of ''Manga/DailyLifeWithMonsterGirl''.

[[folder:Comic Books]]
* In Creator/MarvelComics 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.
* Creator/MarvelComics 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.
* ComicBook/{{Vampirella}} once travelled to Sleepy Hollow where she confronted the Headless Horseman.
* In a ''WesternAnimation/CasperTheFriendlyGhost'' comic, Casper encounters the Horseman, who finally does meet up with his long-lost noggin, which has been going around as the "Horseless Headman".
* In ''DC Universe Halloween Special 2008'', ''The Ballad of Jonathan Crane'' is a retelling of the Horseman's legend with the characters from ''Franchise/{{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. [[spoiler: The whole thing is a nightmare due to over exposure from Crane's fear toxin.]]
* The comic book series ''ComicBook/{{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.
* King Vold, master of the wild hunt in ''ComicBook/{{Hellboy}}''. Inspired by the Norwegian tale of the "Green Giant."

[[folder:Fairy Tales]]
* The German Legends of Creator/TheBrothersGrimm (''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/SleepyHollow'' by Creator/TimBurton, only very loosely based on the Washington Irving story.
* The Disney animated ''[[Disney/TheAdventuresOfIchabodAndMrToad 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 ''Literature/TheLegendOfSleepyHollow''.
* ''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 ''Film/{{Gladiator}}''.

* ''Literature/TheLegendOfSleepyHollow'', the TropeCodifier.
* 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 ''Literature/HarryPotter''. Every year, they [[DreamCrushingHandicap consistently deny]] Nearly Headless Nick's application to join on the grounds that many of their SeveredHeadSports require one's head to be [[LosingYourHead completely detachable]].
* ''Literature/{{Discworld}}'':
** Tiffany Aching briefly encounters a headless horseman in ''Discworld/TheWeeFreeMen'':
---> '''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 [[ThePurplePeopleEaterEffect 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 PeekABogeyman in the ''Literature/GraveyardSchool'' series. [[spoiler:She's one of the students at the school. Not that she's not undead . . . as in ''Film/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl'', she can pose as living during the daytime. Fortunately, she's completely harmless.]]
* ''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." [[spoiler: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.]]
* Nikolai Drakov creates a headless horseman as part of his plot to derail the course of the American Revolution in the Literature/TimeWars novel ''The Hellfire Rebellion''.
* ''Literature/SkulduggeryPleasant: 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 [[OnlyMostlyDead reversible]], if you weren't ''supposed'' to.) [[spoiler: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 [[KilledOffForReal really kill her]] if she was alive at the time.]]
* One of the ''Literature/FreddyThePig'' 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.
* In the ''Literature/BenSnow'' story "The Headless Horseman of Buffalo Creek", Ben investigates a local legend of a headless horseman and uncovers a brutal murder.
* In a 2010 erotic retelling of ''Literature/TheLegendOfSleepyHollow'', by Deanna Wadsworth, Brom Bones does more than masquerade as the Headless Horseman.
* In the MonsterMash noir ''Literature/CityOfDevils'', 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.
* A number of Headless Apparitions appear in ''Literature/NoMansLandTalesFromTheWeirdWars'', ranging from an Indian, to a G-man, to a Soldier. The two present day versions are expies of Comicbook/ThePunisher and Comicbook/GhostRider.
* Children's author and poet Jack Prelutsky has a 1980 book called ''The Headless Horseman Rides Tonight'', which naturally includes a poem about this character.


[[folder:Live Action TV]]
* The ''Series/KolchakTheNightStalker'' episode "Chopper" features a headless biker bent on revenge.
* In the ''Series/AreYouAfraidOfTheDark'' 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 ''Series/{{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 FateWorseThanDeath trope as well.
* ''Series/TheAndyGriffithShow'' had Andy trying to read ''The Legend of Sleepy Hollow'' to Opie when he kept getting interrupted.
* "Halloween Hound: The Legend of Creepy Collars" is the second-season premiere of ''Series/{{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 ''Series/MurderSheWrote'', 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 ''Series/GhostWhisperer.''
* The first episode of ''Tall Tales And Legends'' features an adaptation of ''Literature/TheLegendOfSleepyHollow''.
* In the ''Series/BeetleborgsMetallix'' 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 ''Series/DarkShadows''.
* In episode two of ''Series/LostGirl'', 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 ''Series/TheChronicle'', a headless biker hunts down and beheads several [[AssholeVictim obnoxious]] [[JerkAss characters]]. [[spoiler:It's ''not'' DisproportionateRetribution; they're all escapees from hell]].
* In the ''Series/MidsomerMurders'' episode "The Dark Rider", a killer lures several victims to their deaths by masquerading as a headless horseman from local legend.
* A legend of a 'headless highwayman' features in one episode of ''Series/MetalMickey''.
* In ''Series/SleepyHollow'', Ichabod Crane dies on the battlefield in 1781, killed by a Hessian Soldier (though the show's depiction of such borders on InNameOnly, sharing only a name and nationality [[spoiler: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 HeadlessHorseman, he is also Death, one of the four horsemen of the apocalypse, and a dangerous antagonist.


* [[http://www.madcoversite.com/mad059printid.jpg This cover]] from a 1960 Halloween issue of ''Magazine/{{Mad}}''.

* Apparently a fascination for Music/TheyMightBeGiants, who namedrop the HeadlessHorseman 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 Music/WarrenZevon. Roland is a Norwegian mercenary, skilled with a Thompson submachine gun, who gets murdered by a fellow mercenary during the Congo War of TheSixties. His ghost tracks down and murders his assassin, and [[ForeverWar goes on to stalk the war zones of the world]].

[[folder:Myth and Legend]]
* The TropeMaker[=/=]UrExample is [[http://pg4anna.tripod.com/Dullahan.htm The Dullahan]], an [[http://en.wikipedia.org/wiki/Dullahan Irish faerie]] (Unseelie court) that carries its head under its arm, and rides a massive black horse. 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 -- [[{{Psychopomp}} it means you're going to die soon]]. Sometimes instead of a basin, a Dullahan [[UpToEleven wields a human spine]] [[NightmareFuel as a whip]] and flicks blood at passersby from said spine. No gates and doors can bar their passage, but gold scares them away.
** 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 it's own body''.
** One of the myths of the Dullahan says that it drove a horse-drawn carriage known as a Coiste Bodhar (Death/Silent Coach) - sometimes pulled by headless horses.
* 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 ''VideoGame/ThePinballOfTheDead'', Kuarl, half of Judgement, is an animated headless suit of armor.
* A variation appears in ''Pinball/JokerPoker'' -- 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.

[[folder:Tabletop Games]]
* A Headless Horseman acts as a minor domain lord in the ''TabletopGame/{{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 ''TabletopGame/{{Deadlands}}''.
* The "wildermasque" in ''TabletopGame/{{GURPS}} Creatures of the Night'', which steals a new conveyance on every rampage.
* ''TabletopGame/MagicTheGathering'' has this [[http://gatherer.wizards.com/Pages/Card/Details.aspx?multiverseid=1442 as a Black creature]] from the old Legends expansion set.
** Also, there's the [[http://gatherer.wizards.com/Pages/Card/Details.aspx?multiverseid=153037 Stillmoon Cavalier]] from the more recent Eventide set. It's a white/black hybrid creature.
* The Dullahan appeared in the second ''TabletopGame/{{Pathfinder}} Bestiary''.
** In addition, 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 TheWildHunt.
** A squad of Headless Horsemen made from Cossacks are important underlings for UsefulNotes/GrigoriRasputin in the penultimate part of the ''Reign of Winter'' Adventure Path.
* ''TabletopGame/YuGiOh'' has the [[http://yugioh.wikia.com/wiki/Headless_Knight Headless Knight]] and [[http://yugioh.wikia.com/wiki/Ghostrick_Dullahan Ghostrick Dullahan]].

* ''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.


[[folder:Video Games]]
* A Dullahan is a [[ThatOneBoss notoriously difficult]] BonusBoss in ''VideoGame/GoldenSunTheLostAge''. Either he or a new Dullahan also shows up in ''[[VideoGame/GoldenSunDarkDawn Dark Dawn]]''. In neither instance does he have his horse.
* Dullahan also shows up as a boss, and has a normal Skeletal enemy variety (Sometimes even in the same game) in some of the ''Franchise/{{Castlevania}}'' games. Interestingly, he's rarely mounted.
* A Dullahan also shows up in a few of the ''Franchise/FinalFantasy'' games, including ''VideoGame/FinalFantasyMysticQuest''.
* ''VideoGame/GhostMaster'', 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 ''VideoGame/WorldOfWarcraft'' (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 [[RhymesOnADime 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 "[[DecapitationPresentation Bring me the head of]]... [[FridgeLogic 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.
* [[HellishHorse Hecarim]] in ''VideoGame/LeagueOfLegends'' has a skin that is literally this as he's a centaur,[[note]]A literal Horseman[[/note]] Headless Hecarim, although he does wear a pumpkin on his shoulders.
* There is a Dullahan boss early on in ''VideoGame/VagrantStory'' 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 ''VideoGame/ShiningForce'' 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 ''VideoGame/{{AdventureQuest}}''; the Horseman monster is indeed headless, but is actually a combination between a horse and a man, rather than a horse-rider.
* ''VideoGame/ShadowMan - 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 [[CrowningMomentOfAwesome Shadow Man calls him an asshole]].
* Headless Harn/Heart Heat Harn from ''VideoGame/BattleMonsters'', who actually ''fights'' with his own disembodied head, complete with spitting out fireballs and swinging it around like a weapon.
* During the 2010 ''VideoGame/TeamFortress2'' 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 [[AxCrazy 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 [[NiceHat 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 ''VideoGame/BreathOfFireIV'', 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 BonusBoss in his own right.
* The Headless Horseman is a powerful boss monster in the MMORPG ''VideoGame/MapleStory''.
* ''VideoGame/TheBindingOfIsaac'' as had a Halloween update that can cause one of the Horsemen Bosses to become replaced by the Headless Horseman.
* In ''VideoGame/TheElderScrollsVSkyrim'', you may encounter a headless horseman riding along the roads at night.
** [[GoodBadBugs Or running after]] [[CrowningMomentOfFunny his horse on foot.]]
* In ''VideoGame/HouseOfTheDead 2'', the first boss, Judgement, is a headless suit of armor (Kuarl) controlled by a flying goblin (Zeal) that you have to hit.
* Decapitated Rasetsumaru in ''VideoGame/SamuraiShodown'' remains alive and well, and still can talk.
* In ''VideoGame/{{Puppeteer}}'', he serves as the mayor of [[HalloweenTown Hallowee-Ville]].
* Sekibanki from ''VideoGame/{{Touhou}}'' may count. She is supposed to be a [[https://en.wikipedia.org/wiki/Rokurokubi 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.
* ''Franchise/AssassinsCreed'':
** The Horseman appears in ''VideoGame/AssassinsCreedIII'' as a side quest for Connor to disprove his existence. [[spoiler: He finds out the Horseman is indeed real, and actually beheading people.]]
** In ''Videogame/AssassinsCreedRogue'', he also appears in Sleepy Hollow where Shay can only kill him by [[spoiler:shooting at the pumpkin over his tombstone]]. He is so iconic Abstergo Entertainment would obviously include him as an easter egg in their game.
* Appears on a level of ''VideoGame/DragonsLair''. Dirk has to dodge him and is unable to use his sword due to the Horseman casting a spell on it.
* In ''VideoGame/FateGrandOrder'' has ''the'' Headless Horseman show up as [[spoiler: one half of Hessian Lobo, the Shinjuku Avenger. Because the Horseman is more akin to an UrbanLegend 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. ]]

* ''Webcomic/TheAdventuresOfDrMcNinja'' 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.
* A recurring character in the horror/comedy webcomic, ''Webcomic/TheDeadlys''.
* ''Living With Monster Girl'' installment "Living with Dullahan" includes a (female) [[ExactlyWhatItSaysOnTheTin Dullahan]], albeit without a horse. Amusingly, she inverts the original legend by driving [[GrimReaper Death]] away from her boyfriend -- sometimes physically.
* ''Webcomic/{{Blip}}'' has a headless horseman who communicates by texting with his smartphone.
* Irving in ''Webcomic/ContemplatingReiko''. Though he's too much of a ButtMonkey to be a threat.


[[folder:Western Animation]]
* The 1976 series of ''Franchise/ScoobyDoo'' had one of these characters as a villain, as did [[WesternAnimation/ScoobyDooWhereAreYou the original series]]. It was all a hoax, of course.
** ''WesternAnimation/WhatsNewScoobyDoo'' also had such a ghoul in the opening title.
** And there was a headless skateboarder in ''WesternAnimation/APupNamedScoobyDoo''.
** The Headless Horseman appears in ''WesternAnimation/ScoobyDooAndTheGoblinKing''.
*** And ''WesternAnimation/ScoobyDooMeetsTheBooBrothers''.
* ''WesternAnimation/TheRealGhostbusters'' featured "The Headless Motorcyclist", an episode with a descendant of Ichabod Crane cursed by a headless apparition on a motorcycle who chases her. [[spoiler: (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.)]]
* ''WesternAnimation/FilmationsGhostbusters'' 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 ''WesternAnimation/HeyArnold'' about this sort of rumor. Actually executed both humorously and creepily at the same time.
* The 1980s ''WesternAnimation/DennisTheMenace'' animated series had an episode where Dennis scared some people by pretending to be a headless horseman.
* Creator/UbIwerks produced a Headless Horseman short as part of the [=ComiColor=] Cartoons series.
* ''WesternAnimation/{{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 ''Literature/TheLegendOfSleepyHollow'' above: [[spoiler: not only is the Headless Horseman real, but Brom Bones makes a ''DealWithTheDevil'' to invoke him to chase after and ''kill'' Ichabod Crane. That's scary enough, but the ending, where the InUniverse Narrator reveals himself as Brom Bones and how he has been damned to become the new Headless Horseman, is truly the stuff of nightmares.]]
* A Headless Horseman makes a cameo appearance in the second ''WesternAnimation/{{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.
* ''WesternAnimation/TheFunkyPhantom'' gets a Headless Horseman, but this one comes with a twist. [[spoiler: 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 opening segment of ''WesternAnimation/TheSimpsons'' episode "Treehouse of Horror VI" shows Krusty the Klown in the persona of the Headless Horseman.
* In the ''WesternAnimation/SouthPark'' episode "Imaginationland", the Horseman is one of the "evil" characters that resides in Imaginationland.
* In the ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' 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 [[FridgeLogic 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:''' [[VoodooShark It's headless, not brainless!]]
* The Headless Horseman appears as the main antagonist of ''The Haunted Pumpkin of Sleepy Hollow''.
* Headless Horsemen appear in the ''WesternAnimation/CourageTheCowardlyDog'' episode "Windmill Vandals".
* A headless horseman appears in the audience of WesternAnimation/DaffyDuck's nightclub act in ''The Night of the Living Duck''.
* Episode 7 of ''WesternAnimation/MovilleMysteries'' 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. [[spoiler:However, it turns out the whole episode was a dream, until the Pumpkin Reaper pops in the last scene]].
* There's one who appears in ''[[WesternAnimation/TheSmurfsTheLegendOfSmurfyHollow The Smurfs: The Legend Of Smurfy Hollow]]'', [[spoiler:which turns out to be a goat that Papa Smurf used his magic on]].
* Parodied in ''WesternAnimation/RockosModernLife'' with the one-legged "Hopping Hessian".
* [[PunnyName The Headmistress]] of ''WesternAnimation/MonsterHigh'' is the daughter of the Headless Horseman. Aside from her removable head she also has a fire breeding horse.

[[folder: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 Henri Lafutsun de Lacarre during the French cavalry charge at [[https://en.wikipedia.org/wiki/Battle_of_Wörth battle of Wörth]] (UsefulNotes/FrancoPrussianWar), who was beheaded by a Prussian shell. The horse continued to charge with the headless body standing on it.