History Main / HeadlessHorseman

[[folder:Card Games]]
* ''TabletopGame/MagicTheGathering'': The basic [[https://scryfall.com/card/leg/102 Headless Horseman]] appears as a Zombie Knight creature in the old Legends expansion set. There's also the [[https://scryfall.com/card/eve/95 Stillmoon Cavalier,]] likewise a Zombie Knight, from the more recent Eventide set.
* ''TabletopGame/YuGiOh'' has the [[http://yugioh.wikia.com/wiki/Headless_Knight Headless Knight]] and [[http://yugioh.wikia.com/wiki/Ghostrick_Dullahan Ghostrick Dullahan.]]
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* 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.
* 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.
* "The Legend of Sleepy Halliwell" was an episode of ''Series/{{Charmed|1998}}''. 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.
* 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]].

* It once served as a major plot point on ''Series/GhostWhisperer.''
* The ''Series/KolchakTheNightStalker'' episode "Chopper" features a headless biker bent on revenge.

* An episode of ''Series/MurderSheWrote'', of all things, which relocated it to a prep school, and tied it in with the required murder.

* "[[Recap/WishboneS2E01And02TheLegendOfCreepyCollarsParts1And2 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.

* 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.

* ''WesternAnimation/CostumeQuest'': Wren's costume in "Baking is Best with Friends" is [[PunnyName Headless Horse-Wren]], actually.

* 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 [[https://en.wikipedia.org/wiki/Battle_of_Wörth battle of Wörth]] (UsefulNotes/FrancoPrussianWar, 1870), who was beheaded by a Prussian shell. The horse continued to charge with the headless body standing on it.

* 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 [[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.

* In ''VideoGame/DragonQuestXI'', 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. Various weaker variants of this monster appear as low level {{Mook}}s throughout the rest of the game, not all of which have horses.

* 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.

Tales of headless riders have existed in folklore for centuries, most notably the Irish legend of the Dullahan (see below for examples), but the TropeCodifier is Creator/WashingtonIrving[='s=] story ''Literature/TheLegendOfSleepyHollow'' (although it's arguably an UnbuiltTrope there, as it is strongly implied that the Headless Hessian that pursues Ichabod Crane in the climax is actually local rowdy Brom Bones [[ScoobyDooHoax playing a prank]] to scare the shit out of the schoolmaster, his would-be romantic rival).

Tales of headless riders have existed in folklore for centuries, most notably the Irish legend of the Dullahan (see below for examples), but the TropeCodifier is Creator/WashingtonIrving[='s=] story "Literature/TheLegendOfSleepyHollow" (although it's arguably an UnbuiltTrope there, as it is strongly implied that the Headless Hessian that pursues Ichabod Crane in the climax is actually local rowdy Brom Bones [[ScoobyDooHoax playing a prank]] to scare the shit out of the schoolmaster, his would-be romantic rival).

* "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.

he's out looking for a head to swap\\

->''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.\\