->''"On mounting a rising ground, which brought the figure of his fellow-traveller in relief against the sky, gigantic in height, and muffled in a cloak, Ichabod was horror-struck on perceiving that he was headless!"''

"The Legend of Sleepy Hollow" (also known informally and somewhat incorrectly as "The Headless Horseman") is a short story by American author Washington Irving, first published in February 1820 as part of a series of stories later collected as ''The Sketch-book of Geoffrey Crayon, Gent.'' As with a number of Irving's stories, the plot is based on German legend (particularly in the re-told versions of Karl Musäus), transplanted to a New York state setting, and mingled with Irving's genial satire of human, and particularly American, foibles.

The story has been subject to a great deal of adaptations since Irving's time. The "quilting frolick" of the original is often transferred to Halloween. In more than one adaptation it is strongly hinted that the Horseman is a genuine supernatural apparition.

The story is PublicDomain and can be read [[http://www.eastoftheweb.com/short-stories/UBooks/LegSle.shtml here.]]

''The Sketch-book of Geoffrey Crayon, Gent.'' also included another Irving short story destined to become famous: "Literature/RipVanWinkle".

!!Tropes associated with "The Legend of Sleepy Hollow" include:

* [[AlasPoorVillain Alas, Poor Anti-Hero]]: Since later stories have been interpreting the Horseman as a genuine supernatural entity, Ichabod's unknown fate with it becomes a whole lot darker.
* TheAllegedSteed: Gunpowder, Ichabod's horse, is clearly past his prime.
* AntiHero: Ichabod himself. Despite displaying a number of positive traits, Irving focuses largely on his flaws; envy, avarice, gluttony, and sloth.
* AntiVillain: Brom Bones is depicted as displaying all the qualities of a Great American Hero: bravery, recklessness, and square-jawed, good ol' boy charm. As such, even though the entire story (in one interpretation) hinges on the consequences of a prank he pulls, the reader never loses sympathy with him.
* AmbiguousEnding: Was Ichabod killed by the Horseman or did he just flee from Sleepy Hollow and move somewhere else? Was the Horseman actually supernatural or was it just Brom trying to scare Ichabod off? It's up to the reader to decide, and what answer they decide on completely changes the story.
* BigEater: Ichabod, and yet, he's beanpole thin.
* BrainsEvilBrawnGood: Ichabod, the intellectual schoolmaster, is portrayed as weak-willed, venal and effeminate; while Brom Bones, the barrel-chested stallion-breaker, is portrayed as honorable, or at least more honorable than Ichabod. On the other hand, Ichabod is a deeply superstitious man, in contrast to the rational Bones, so in a sense, Brom is actually the smarter of the two.
* BreakoutVillain: The Horseman only had a very brief scene in the already short story just near the end, and it's implied that it might not even be a real ghost. In spite of this, the sheer mystique and inherent scariness behind the character ended up making it a horror icon on par with Literature/{{Dracula}} and Literature/{{Frankenstein}}, with numerous movie adaptations and modern day takes on the character coming out in the years since Washington Irving's story was published.
* CannotCrossRunningWater: The ghost, it's said, always vanishes while crossing the bridge adjacent to the Old Dutch Burying Ground. This turns out to be false in the end, as the Horseman is described as having passed by Ichabod after throwing the pumpkin head at him, meaning he probably did cross the bridge unharmed.
* ChekhovsGun: The Church Bridge. Ichabod crosses it, hoping that it would allow him to evade the horseman like in Brom's story. It doesn't work.
* CoolHorse: Both played straight, with Brom's black horse, Daredevil, and inverted, with Gunpowder, the broken-down hack that Ichabod borrows from an irascible farmer.
* EarnYourHappyEnding: If Ichabod did survive, he went on to a successful career as a judge; it appears he's stopped trying to scrounge money off others and earned his fortune all by himself.
* FlatCharacter: The Headless Horseman is frightening, but it isn't really given any characterization beyond "Scary Headless ghost who chases Ichabod on horseback". Justified, as its appearance may or may not have been a ruse cooked up by Brom Bones to scare off Ichabod. The closest personality trait assigned to it is as being an "arrant jockey" when Brom tells his story of racing the horseman, but this encounter may or may not just be a story he made up. Ironically, this ends up adding to the mystique and terror behind the character.
* FoodPorn: Ichabod loves to eat, and much of the story focuses on his quasi-erotic imaginings regarding lovingly prepared food.
* GhostlyGoals: The Headless Horseman can't move on to the afterlife until he's found a head to replace his own.
* GreenEyedMonster: Ichabod is described as having "large green glassy eyes", and as being envious of Baltus van Tassel's wealth.
* HeadlessHorseman: The TropeCodifier.
* HellishHorse: The Hessians horse is described as having a powerful frame which, combined with the silhouette of the horseman atop, looks like a "gigantic monster ready to spring upon the traveler", even before Ichabod realizes its rider is headless.
* HolyBurnsEvil: Subverted. Brom's story claims the Horseman can't cross the Church bridge, and that he bolted and vanished in a flash of fire. Ichabod exploits this by running across the bridge. It doesn't work--the horseman throws his pumpkin head at Ichabod and gallops off past him unharmed.
* HorrorStruck: Averted, in that Ichabod fervently believes in all supernatural phenomena -- even when (as it is strongly implied) the phenomena ''aren't'' supernatural. Later adaptations sometimes play the trope straight.
* HotForStudent: Ichabod gives Katrina psalmody lessons. She's eighteen, though, and also this was considered a much more mature age, one far more ready for marriage at the time the story is set.
* {{Jerkass}}: Ichabod gets less and less appealing as the story goes on, peaking when he thinks of how, once he's married Katrina and acquired her father's great wealth, he'll tell everyone he associated with as a schoolteacher to screw off.
* LiteraryAgentHypothesis: The story purports to have originated at some four removes from Irving himself, as 1) [[SameFaceDifferentName Geoffrey Crayon]]'s recounting of 2) the notes of American Dutch "historian" [[SameFaceDifferentName Diedrich Knickerbocker]] containing an account by 3) a poor and [[UnreliableNarrator whimsical storyteller]] of 4) the legendary lore of the old Dutch wives of the New York colony.
* LostInImitation: Pretty much every interpretation after the original either has the HeadlessHorseman be truly supernatural (when the original strongly implies it was Brom Bones in disguise), Ichabod be slain by the Headless Horseman (in the original, it's declared he ran away from the Hollow and has taken to living elsewhere, though the locals prefer to ignore that news because him being carried away makes for "a better story"), or both.
** It doesn't help that for most readers the Headless Horseman is [[RuleOfCool just too cool of a villain]] to be only a hoax. He's become one of the most famous horror icons. Come on, a cackling headless horseman who prowls the roads looking for heads? How is that not awesome?
** Many adaptations portray the Horsemen using a jack o lantern for a head even though that is a bit of a misconception. The Horsemen of the original tale is out looking for his own head or a replacement. The one that chases Ichabod is carrying a pumpkin but it is on the horse's saddle and he tosses it forward as a projectile. With the two major theories being A. It's Brom Bones tossing a pumpkin to make Ichabod think it's a severed head or B. The horsemen needs some kind of weapon to get his prey off a horse, a pumpkin will do. Either way, if the Horseman could just use a jack o lantern for a head, he'd probably have gone home already. Likewise if the Horseman was real, he damn sure wouldn't have thrown a perfectly good head at an annoying schoolmaster either.
** In some ways this suffers loss from people forgetting how it was originally published. Had you have read the entire Sketchbook you'd find this story is the third story to feature supernatural antics. Rip Van Winkle has the ghosts seem completely real and even swears to the tale. The Spectre Bridegroom is believed to be supernatural by most of the characters even though the reader knows the whole thing is a ScarecrowSolution. By the time you get to this tale, the idea that everything is not wrapped up is clearly done on purpose by Irving. Also debunking some claims the supernatural was never in Irving's attempts, but considering people have little memory of the sketchbook nor that Sleepy Hollow and Rip are connected and let alone there was a third one in there might not even be common among some English teachers lecturing on the subject,
* MaybeMagicMaybeMundane: The story hints at both a natural and a supernatural explanation for Crane's disappearance.
* MeaningfulName: "Ichabod" is traditionally translated as "Inglorious," while "Crane" hints at the schoolmaster's tall, thin frame and beaky nose.
--> "He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weather-cock perched upon his spindle neck to tell which way the wind blew. To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a cornfield."
* MoodyMount: Ichabod's borrowed horse Gunpowder: "The animal he bestrode was a broken-down plow-horse, that had outlived almost everything but its viciousness."
* NeverFoundTheBody: The story leaves it ambiguous whether the Horseman killed Crane, or simply scared him away from Sleepy Hollow. The only thing left behind at the scene of their encounter was Gunpowder the horse, a trampled saddle, a discarded hat, and a mysterious shattered pumpkin.
* OffscreenMomentOfAwesome: Brom Bones tells a story of how he raced the Headless Horseman one night for a bowl of punch and ''won''. He claims that he didn't even anticipate that he would win and that it was simply luck that the Horseman couldn't cross the covered bridge.
* OffWithHisHead: The Headless Horseman is given some backstory; he's believed to be the ghost of a Hessian trooper that had his head shot off by a stray cannonball during "some nameless battle" of the American Revolutionary War, and who "rides forth to the scene of battle in nightly quest of his head".
* OperationJealousy: Katrina uses Ichabod to pull this on Brom.
* OurGhostsAreDifferent: Besides the Horseman himself, references are made to ghostly funeral processions, a wailing woman in white, and the ghost of British spy [[HistoricalDomainCharacter Major John André]].
* PumpkinPerson: The HeadlessHorseman is sometimes depicted with a jack-o-lantern in place of his head.
* PurpleProse: Some modern readers may be put off by Irving's luxuriant descriptions, typical of the early nineteenth century, of the New York landscape, or the heaped-up delicacies of an old Dutch table, or the varied apparitions that haunt the Hollow.
* RoundedCharacter: Although his most-obvious trait is his greed, Ichabod is actually a rather multi-faceted character. Beyond his selfish ambitions, Ichabod is also superstitious, imaginative, has a (typically unhealthy) sense of curiosity, and even has some [[PetTheDog positive traits]] thrown in for good measure.
* SatelliteLoveInterest: Katrina isnt given much characterization other than being the love interest of both Ichabod and Brom.
* ScarecrowSolution: Why Brom laughed whenever the pumpkin was mentioned.
* ScoobyDooHoax: Likely the TropeMaker, depending on whether you interpret the Horseman as real or not.
* ShoutOut: Not only the usual literary allusions of the period, but especially to Irving's own fanciful ''Knickerbocker History of New York''.
* ShortStory: The story's entire text takes up less than 30 pages when printed in a small novel.
* TakeItToTheBridge: Crossing the covered bridge is seemingly the only way to escape the Headless Horseman, but it turns out to not be the case.
!!Adaptations based on "The Legend of Sleepy Hollow":


[[folder: Comic Books]]
* In some versions of ''Comicbook/{{Batman}}'', Scarecrow's StartOfDarkness came when a JerkJock terrorised him with a pumpkin in deliberate imitation of the book. The gangly Jonathan Crane has also played the role of Ichabod in one ''DCU Halloween Special'', where he joins the frolick to rob the guests, but is prevented from making his escape by a headless figure in a Batsuit.

[[folder: Fan Works]]
* ''Franchise/TheMuppets'' fan artist Jay Fosgitt sent some spec pages of ''The Muppet Legend of Sleepy Hollow'' to Boom Studios. (Kermit as Ichabod, Link Hogthrob as Brom, Piggy as Katrina, and [[spoiler: Beaker as the Horseman]].) When nothing came of it, [[http://jayfosgitt.deviantart.com/art/MUPPETS-SLEEPY-HOLLOW-1-183463798 he posted them on DeviantArt]].

[[folder: Live Action Film]]
* A silent version of the story appeared as early as 1908 ; in 1912 Ichabod was played by Alec B. Francis.
* The best known silent version appeared in 1922: ''The Headless Horseman'', directed by Edward Venturini, and starring Will Rogers as Ichabod Crane, filmed on location in New York's Hudson River Valley.
* ''Film/SleepyHollow1999'', perhaps the best known version in recent times, is a Creator/TimBurton adaptation which deliberately takes considerable liberties with the original Story, making it radically DarkerAndEdgier. Johnny Depp's Constable Ichabod Crane is a much more heroic figure than Irving's gawkish, pedantic, cowardly schoolmaster, and rather than be cripplingly superstitious, he's a pioneer of forensic sciences who uses reason and deduction to solve crimes and insists that a live human is behind the Horseman murders. In fact, he's basically the ''only'' non-superstitious character in the film, at least during the earlier acts. There are also subtle themes of the complexity of religion, reason, and the supernatural woven throughout the film.

[[folder:Live Action TV]]
* A made-for-TV movie version, ''The Legend of Sleepy Hollow'' was made in 1980, starring Jeff Goldblum as Ichabod Crane and Dick Butkus as Brom Bones. In this version Ichabod has become a [[AgentScully disbelieving rationalist]].
* The ''Tall Tales and Legends'' series, produced and hosted by Shelley Duvall, featured a "Legend of Sleepy Hollow" episode in 1987, starring Ed Begley, Jr. as Ichabod Crane, Beverly D'Angelo as Katrina Van Tassel, and Charles Durning as Doffue Van Tassel, the narrator.
* In 1992 ''Series/AreYouAfraidOfTheDark'' aired an episode entitled "The Tale of the Midnight Ride," in which a boy and girl save the [[OurGhostsAreDifferent ghost]] of Ichabod Crane from the Horseman. However, this caused the Horseman to chase them instead.
* Series/{{Wishbone}} reenacted the role of Ichabod Crane in the episode "Halloween Hound: The Legend of Creepy Collars" in 1996.
* In 1999 another made-for-TV film, also entitled ''The Legend of Sleepy Hollow'' (AKA ''La légende de Sleepy Hollow''), starring Brent Carver appeared; this was a Canadian effort filmed in Montreal.
* ''The Hollow'' (2004) was a TV movie, starring Kaley Cuoco as a teenage descendant of Ichabod Crane, that premiered on the ABC Family channel.
* In 2004 ''Series/{{Charmed}}'' aired an episode entitled "The Legend of Sleepy Halliwell", in which a HeadlessHorseman is beheading the teachers at the Magic School.
* Creator/{{Fox}}'s series ''Series/SleepyHollow'', in which the Headless Horseman is actually Death, one of the four HorsemenOfTheApocalypse, and Ichabod is a RipVanWinkle revived to stop him.
* The ''Series/MurderSheWrote'' episode "Night of the Headless Horseman" combines a SettingUpdate with a murder mystery at a college, casting the Wrongly Accused Person Jessica Feels Responsible For of the Week in the role of Ichabod.

* ''Sleepy Hollow'', a Broadway {{musical}} with music by George Lessner and book and lyrics by Russell Maloney and Miriam Battista was staged in 1948.
* In 2009 appeared ''The Legend of Sleepy Hollow'', an opera, with music by William Withem and libretto by Melanie Helton.

* There's a HiddenObject game based on the story, released under the Mystery Legends name.
* Ichabod Crane appears in ''VideoGame/TheWolfAmongUs'' as a minor antagonist, being a corrupt mayor of Fabletown who employs both Bigby and Snow White.

[[folder:Western Animation]]
* In 1949 the story was paired with a pared-down version of Kenneth Grahame's ''Literature/TheWindInTheWillows'' in Creator/{{Disney}}'s ''Disney/TheAdventuresOfIchabodAndMrToad''; the story is narrated (with interspersed songs) by Music/BingCrosby. It's actually surprisingly faithful to the original story (far more so than the very loose ''Wind in the Willows'' adaptation) -- Brom Bones gets his PetTheDog moments, Ichabod's fate is left still ambiguous, and the implication that the Horseman is fake is retained. The animation of the chase scene is particularly impressive, and influenced several later Disney films, notably ''Disney/BeautyAndTheBeast''.
* In 1972 a short animated version appeared, [[{{Narrator}} narrated]] by JohnCarradine.
* In a 1976 episode of ''The ScoobyDoo / [[WesternAnimation/DynomuttDogWonder Dynomutt]] Hour'' called "The Headless Horseman of Halloween," Beth Crane, a descendant of the original Ichabod, is haunted by the Headless Horseman, who wants to gain the Crane Diamond.
* Similarly, in 1986 ''WesternAnimation/TheRealGhostbusters'' featured an episode, "The Headless Motorcyclist," with a descendant of Ichabod Crane cursed by a headless apparition (on a motorcycle, naturally) who chases her.
** The Headless Motorcyclist may have been cribbed from the ''Series/KolchakTheNightStalker'' episode, "Chopper."
* In 1988, the ''[[Series/{{ALF}} ALF Tales]]'' cartoon featured an episode in which Ichabod "Gordon Shumway" Crane is a reporter assigned by his editor, Baltus Van Tassel, to cover the HeadlessHorseman story; he discovers a [[FlockOfWolves whole herd of Headless Horsemen]].
* ''The Night of the Headless Horseman'' (1999) was an hour-long computer motion capture animated Fox TV special. This film went for one of the outright darkest InUniverse {{Alternative Character Interpretation}}s by making Brom an actual villain; [[spoiler: Brom deliberately makes a DealWithTheDevil to be rid of Ichabod, though it's left unclear if the "dark spirits" send the original Headless Horseman to get Ichabod or merely encourage Brom to take the Horseman's guise and attack him. The film ends with Brom revealed as the tale-telling InUniverse narrator, as he explains that in order to pay back his "debt", he has to become the Headless Horseman himself.]]
* ''WesternAnimation/FilmationsGhostbusters'' included an episode where the Headless Horseman appeared. However, he wasn't really malicious and his heart only went into scaring people in the name of fun. He also wasn't headless.
** Not unlike a similar WesternAnimation/{{Casper}} comic, where the Horseman finally does meet up with his long-lost noggin, who's been going around as the "Horseless Headman".
* ''[[Franchise/TheSmurfs The Smurfs: The Legend Of Smurfy Hollow]]'' from Sony Pictures Animation.
* ''WesternAnimation/TheNewMisadventuresOfIchabodCrane'', a 1979 Canadian animated special animated by Titlecraft.