Line #38 Literature/TheLegendOfSleepyHollow


1	[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/the_headless_horseman_pursuing_ichabod_crane.jpg]]
2
3	->''"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!"''
4
5	"The Legend of Sleepy Hollow" – also known informally as "The Headless Horseman" – is a short story by the American author Creator/WashingtonIrving, originally published in February 1820 as one 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 folk legend (particularly in the re-told versions of Karl Musäus), transplanted to a Hudson Valley, New York setting and mingled with Irving's genial satire of human, and particularly American, foibles.
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7	The story has been given [[DerivativeWorks/TheLegendOfSleepyHollow a great many adaptations]] since Irving's time, with the "quilting frolick" of the original tale frequently getting transferred to [[UsefulNotes/AllHallowsEve Halloween]].[[note]]In actuality, Halloween was not widely celebrated in the United States at the time the story was written, let alone when it takes place. The holiday only started to catch on in the U.S. when Irish and Scottish immigrants brought it over in the mid-19th century.[[/note]] In more than one adaptation it is strongly implied that the Horseman is a genuine supernatural apparition, although Irving's original story leaves things more ambiguous.
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9	The story is in the PublicDomain and can be read [[http://www.eastoftheweb.com/short-stories/UBooks/LegSle.shtml here]].
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11	''The Sketch-book of Geoffrey Crayon, Gent.'' also included another Irving short story destined to become famous: "Literature/RipVanWinkle".
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13	----
14	!!Tropes associated with "The Legend of Sleepy Hollow" include:
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16	* AlasPoorVillain: Since later stories have taken to interpreting the Horseman as a genuine supernatural entity, Ichabod's unknown fate with it becomes a whole lot darker.
17	* TheAllegedSteed: Gunpowder, Ichabod's horse, is clearly past his prime.
18	* 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 readers to decide, and what answer they decide on completely changes the story.
19	* AntiHero: Ichabod himself. Despite displaying a number of positive traits, Irving focuses largely on his flaws: envy, avarice, gluttony, and sloth.
20	* 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 author never loses sympathy with him.
21	* BigEater: Ichabod, and yet, he's beanpole thin.
22	* BoisterousBruiser: Brom Bones, a musclebound giant who loves to pull pranks and have fun.
23	* BookBurning: After Ichabod's disappearance, his books on the occult are burned by Hans Van Ripper, who decides that literacy in general is a bad thing and stops sending his children to school.
24	* {{Bowdlerise}}: In the original text, the invitation to the "quilting frolick" is delivered by "a negro," whose behavior is described patronizingly. Later on, at the party, there is a rather condescending description of the black household servants being much impressed with Ichabod's dancing. Modern reprints are apt to either cut these descriptions or else remove references to race, turning the characters into merely clownish servants.
25	* 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 and gullible man, in contrast to the rational and hard-headed Bones, so in a sense, Brom is actually the smarter of the two.
26	* 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.
27	* CallAPegasusAHippogriff: The narrator, when referring to the Horseman and his steed, uses the terms "ghost" and "goblin" interchangeably. Today, in the age of fantasy lore, we would see the two concepts as sharply delineated, but in Irving's day, most supernatural concepts were seen as basically the same thing.
28	* 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.
29	* 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.
30	* CoolHorse: Both played straight, with Brom's black horse, Daredevil, and inverted, with Gunpowder, the broken-down MoodyMount that Ichabod borrows from an irascible farmer, although we're told that Gunpowder probably ''used to be'' this trope.
31	* CorporalPunishment: Ichabod is a firm believer in the golden maxim, "Spare the rod and spoil the child." Still, he is careful to administer justice with discrimination.
32	* DeadHatShot: [[NeverFoundTheBody The only thing ever conclusively found of Ichabod is his hat]] with a shattered pumpkin close beside it, leaving it ambiguous as to whether he survived his encounter with the Horseman.
33	* 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.
34	* EthnicMenialLabor: There are some rather dated descriptions of the black servants at Van Tassel's home. See {{Bowdlerise}}, above.
35	* 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.
36	* FoodPorn: One of the aspects of the story that makes it such good autumn reading: Ichabod loves to eat, and much of the story focuses on his quasi-erotic imaginings regarding lovingly prepared seasonal food. At one point the narrator even apologizes that he can't describe the food in ''even more'' detail, because he needs to get on with the story.
37	-->Happily, Ichabod Crane was not in so great a hurry as his historian, but did ample justice to every dainty.
38	* GhostlyGoals: The Headless Horseman can't move on to the afterlife until he's found a head to replace his own, or so the legend would have you believe.
39	* GoldDigger: Ichabod is much impressed by Katrina's beauty and charms, but what seems to really get his attention is her dad's money.
40	* GreenEyedMonster: Ichabod is described as having "large green glassy eyes", and as being envious of Baltus van Tassel's wealth.
41	* HaveAGayOldTime: "The gallant Ichabod now spent at least an extra half hour at his toilet" doesn't mean ''quite'' what it would mean nowadays. When this was written, "toilet" meant "dressing table."
42	* HeadlessHorseman: The TropeCodifier.
43	* HellishHorse: The Hessian's 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. Of course, it's implied that this is really just Daredevil.
44	* 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.
45	* 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.
46	* HorseReturnsWithoutRider: The day after Ichabod Crane's encounter with the Headless Horseman, Gunpowder the horse is found near his master's home while Ichabod has mysteriously disappeared. [[AmbiguousEnding Whether he fled Sleepy Hollow out of fear or was spirited away by the Horseman is left up to interpretation.]]
47	* 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.
48	* {{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.
49	* KavorkaMan: Ichabod's a pretty odd-looking man (though some illustrators successfully translate his description into more ''distinctive'' than ugly), but he's extremely popular with the young single women of Sleepy Hollow thanks to being educated and an excellent conversationalist. He exploits this by scrounging dinners off of them and their families when he comes calling on them, all while dreaming of how he loves Katrina...[[WesternAnimation/TheDoverBoys 's father's money]].
50	* LostInImitation: Pretty much every interpretation after the original either has the HeadlessHorseman be truly supernatural (when the original leaves it up in the air but offers the possibility Brom did it), 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". The other option being that Ichabod is actually the Horsemen with Ichabod's head), or both. The Disney version is actually relatively close to the original, preserving the ambiguity.
51	** 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?
52	** Film and stage, being visual media, can't hide their ambiguities behind text, as literature can. In the short story, the Horseman is narrated as being completely real, ''until'' the ending when it is hinted it was actually Brom in disguise. The horrific scene is then revealed to have possibly taken place entirely in Ichabod's mind. It would be incredibly hard to stage such a scene in reality without giving the game away one way or the other, so it's not surprising most adaptations choose not to try.
53	** 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 horseman 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.[[note]]Though the Disney cartoon gives this a HandWave in its VillainSong, stating the horseman is "tired of his flaming top - he's got a yen to make a swap!"[[/note]] Likewise if the Horseman was real, he damn sure wouldn't have thrown a perfectly good head at an annoying schoolmaster either.
54	** 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.[[note]]There are generally two orders to read the Sketchbook in. One is by the serialized order and then by the all in one edition. Regardless though the order of these three stories is the same in both editions.[[/note]] 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.
55	** In many adaptations, Ichabod's encounter with the Headless Horseman takes place on Halloween night because of course it does. The original story doesn't specify Halloween, as it wouldn't, since Halloween was not widely celebrated in the U.S. back then, and even when it began to be a better-known festival, it was mostly a Scottish and Irish holiday, and would have little meaning for the Dutch-Americans of Sleepy Hollow. It is mentioned to have taken place in the autumn, so technically, it ''could'' be on Halloween. However, any version that portrays the "quilting frolic" as a Halloween party is committing an anachronism. This trend is believed to have began with the Disney version.
56	* LoveTriangle: Ichabod and Brom vie for Katrina. It's mentioned that she has other suitors, but they are not named, and it would seem both Ichabod and Brom regard each other as the only serious contenders for her love. See OperationJealousy below, though.
57	* MaybeMagicMaybeMundane: The story hints at both a natural and a supernatural explanation for Crane's disappearance.
58	* MeaningfulName: "Ichabod" is traditionally translated as "Inglorious," while "Crane" hints at the schoolmaster's tall, thin frame and beaky nose.
59	--> "The cognomen of Crane was [[LampshadeHanging not inapplicable to his person]]. 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."
60	* MeatOVision: A rare literary example, when Ichabod sees Van Tassel's farm.
61	-->In his devouring mind’s eye, he pictured to himself every roasting-pig running about with a pudding in his belly, and an apple in his mouth; the pigeons were snugly put to bed in a comfortable pie, and tucked in with a coverlet of crust; the geese were swimming in their own gravy; and the ducks pairing cosily in dishes, like snug married couples, with a decent competency of onion sauce. In the porkers he saw carved out the future sleek side of bacon, and juicy relishing ham; not a turkey but he beheld daintily trussed up, with its gizzard under its wing, and, peradventure, a necklace of savory sausages; and even bright chanticleer himself lay sprawling on his back, in a side dish, with uplifted claws, as if craving that quarter which his chivalrous spirit disdained to ask while living.
62	* MoodyMount: Ichabod's borrowed horse Gunpowder: "The animal he bestrode was a broken-down plow-horse, that had outlived almost everything but its viciousness."
63	* TheMunchausen: At the party, Van Tassel and a few of the other elderly gentlemen swap fanciful war stories.
64	-->Just sufficient time had elapsed to enable each story-teller to dress up his tale with a little becoming fiction, and, in the indistinctness of his recollection, to make himself the hero of every exploit.
65	* 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.
66	* NewEnglandPuritan: Ichabod Crane seems to be this trope, being portrayed as extremely superstitious and easily willing to believe folk legends, in contrast to the hard-headed Dutch locals of Sleepy Hollow. Given Washington Irving was a native of New York, this may have been a TakeThat towards New Englanders.
67	* 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.
68	* OffWithHisHead: The Headless Horseman is given some backstory; he's believed to be the ghost of a Hessian trooper[[note]]German auxiliary troops serving alongside the British army during the American Revolutionary War; and they were ''not'' mercenaries - they were official troops sent by the German government. The Hessians also had a reputation for being even more brutal than the British[[/note]] 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".
69	* OldTimeyAnkleTaboo: Katrina is said to favor "a provokingly short petticoat, to display the prettiest foot and ankle in the country round."
70	* OneGenderSchool: It's pretty strongly implied that Ichabod is teaching an all-boys school, since there's never any reference to female pupils and students collectively are referred to as simply "boys" a couple times. Presumably, Sleepy Hollow is provincial enough that they don't think girls need an education at all.[[note]]Or more precisely, the girls would be limited to [[https://en.wikipedia.org/wiki/Dame_school dame schools]].[[/note]] Adaptations tend to ignore this and portray Ichabod teaching a coed class.
71	* OperationJealousy: The narrator speculates that Katrina was never really interested in Ichabod, and was only using him to spur Brom into finally proposing.
72	* OurGhostsAreDifferent: Besides the Horseman himself, references are made to ghostly funeral processions, a wailing woman in white, and the ghost of British spy [[https://en.wikipedia.org/wiki/John_Andr%C3%A9 Major John André]].
73	* PumpkinPerson: The HeadlessHorseman is sometimes depicted with a jack-o'-lantern in place of his head. In the text, Ichabod sees the horseman carrying a severed head and eventually throwing it at him; in the morning, the locals find the shattered remains of a pumpkin, suggesting that this is what Ichabod actually saw. There's no reference to the pumpkin being carved into a jack-o'-lantern[[note]]Historians are uncertain whether anyone was carving jack-o'lanterns yet when this story was written. Even if the practice did exist, it would not have reached a secluded Dutch New York community yet.[[/note]], but as the story became more and more a fixture of Halloween culture, depicting the pumpkin with a carved face just started to seem right.
74	* 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 [[FoodPorn heaped-up delicacies of an old Dutch table]], or the varied apparitions that haunt the Hollow.
75	* RoundedCharacter: Although his most-obvious traits are his greed and gluttony, 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.
76	* SatelliteLoveInterest: Katrina isn't given much characterization other than being the love interest of both Ichabod and Brom. The narrator freely confesses he doesn't really know what was going on in her head.
77	* ScarecrowSolution: Why Brom laughed whenever the pumpkin was mentioned.
78	* ScoobyDooHoax: One of the earliest examples to still be remembered, depending on whether you interpret the Horseman as real or not.
79	* SexilyModest: Katrina Van Tassel is described as "...a little of a coquette, as might be perceived even in her dress, which was a mixture of ancient and modern fashions, as most suited to set off her charms." This includes not only "the tempting stomacher of the olden time" (a rather sexy item as it probably raised the breasts and presumably showed some cleavage), but also "...a provokingly short petticoat, [[OldTimeyAnkleTaboo to display the prettiest foot and ankle]] in the country round."
80	* ShoutOut: Not only the usual literary allusions of the period, but especially to Irving's own fanciful ''Knickerbocker History of New York''.
81	* ShortStory: The story's entire text takes up less than 30 pages when printed in a small novel.
82	* TakeItToTheBridge: Crossing the covered bridge is seemingly the only way to escape the Headless Horseman, but it turns out to not be the case.
83	* UnclePennybags: Baltus Van Tassel is "satisfied with his wealth, but not proud of it". He has no interest in increasing his wealth or holdings, and would prefer to simply maintain and manage what he already has and throw the occasional party for his neighbors. From Irving's description of the quilting frolick, Van Tassel comes across as a very generous host indeed.
84	* UnreliableNarrator: The entire chase sequence with the HeadlessHorseman is written as if it is a literal encounter with a terrifying ghost. Only in the aftermath the following morning do we learn that what Ichabod saw as a severed head was actually just a pumpkin, and it begins to be implied that Ichabod's encounter was actually a ScoobyDooHoax by Brom.
85	----
86	!!Adaptations based on "The Legend of Sleepy Hollow":
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88	[[foldercontrol]]
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90	[[folder:Comic Books]]
91	* 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.
92	* An original sequel set in the then present day titled ''The Headless Horseman Rides Again'' was the featured story of Issue Six of ''Creator/MarvelComics'' series ''Supernatural Thrillers.'' The Horseman's appearance was that of a skeleton wearing a green cape and brown gloves and boots, rather than a pumpkin for a projectile he carried a flaming skull and rather than a black horse, his steed was grey. It was the last issue of the series based off of literary material, after that the series was devoted to the Living Mummy.
93	* ''Hollow'' a DistantSequel by Creator/BoomStudios which reveals that the Horseman was [[spoiler: GoodAllAlong, chasing Ichabod away so Katrina could marry Brom Bones in peace.]]
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96	[[folder:Fan Works]]
97	* ''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]].
98	[[/folder]]
99
100	[[folder:Film -- Live-Action]]
101	* A silent version of the story appeared as early as 1908 ; in 1912 Ichabod was played by Alec B. Francis.
102	* The best-known silent version appeared in 1922: ''Film/TheHeadlessHorseman'', directed by Edward Venturini, and starring Creator/WillRogers as Ichabod Crane, filmed on location in New York's Hudson River Valley.
103	* ''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.
104	[[/folder]]
105
106	[[folder:Live-Action TV]]
107	* A made-for-TV movie version, ''[[Film/TheLegendOfSleepyHollow1980 The Legend of Sleepy Hollow]]'', was filmed in Utah in 1980. In this version, which stars Creator/JeffGoldblum as Ichabod Crane and Dick Butkus as Brom Bones, Ichabod has become a [[AgentScully disbelieving rationalist]].
108	* 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.
109	* In 1992 ''Series/AreYouAfraidOfTheDark'' aired an episode entitled " [[Recap/AreYouAfraidOfTheDarkSeason3TheTaleOfTheMidnightRide 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.
110	* Series/{{Wishbone}} reenacted the role of Ichabod Crane in the episode "[[Recap/WishboneS2E01And02TheLegendOfCreepyCollarsParts1And2 Halloween Hound: The Legend of Creepy Collars]]" in 1997.
111	* In 1999 another made-for-TV film, also entitled ''[[Film/TheLegendOfSleepyHollow1999 The Legend of Sleepy Hollow]]'' (AKA ''La légende de Sleepy Hollow''), starring Brent Carver appeared; this was a Canadian effort filmed in Montreal.
112	* ''[[Film/TheHollow The Hollow]]'' (2004) was a TV movie, starring Creator/KaleyCuoco as a teenage descendant of Ichabod Crane, that premiered on the ABC Family channel.
113	* In 2004 ''Series/{{Charmed\|1998}}'' aired an episode entitled "The Legend of Sleepy Halliwell", in which a HeadlessHorseman is beheading the teachers at the Magic School.
114	* 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.
115	* 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.
116	[[/folder]]
117
118	[[folder:Theater]]
119	* ''Sleepy Hollow'', a Broadway {{musical}} with music by George Lessner and book and lyrics by Russell Maloney and Miriam Battista was staged in 1948.
120	* In 2009 appeared ''The Legend of Sleepy Hollow'', an opera, with music by William Withem and libretto by Melanie Helton.
121	* ''Tarrytown'' is loosely based on the story, but set in modern day and shifting the focus of the love triangle from Katrina to Brom, since Ichabod [[AdaptationalSexuality is gay in this version]].
122	[[/folder]]
123
124	[[folder:Video Games]]
125	* In both VideoGame/AssassinsCreedIII and VideoGame/AssassinsCreedRogue the player character encounters the Headless Horseman.
126	** In Rogue, the Templar Shay Cormac fights a headless grenadier wielding a naval axe during the French and Indian War, finding him to be effectively invincible. Only upon firing his pistol at the pumpkin resting on the grenadier's grave is he able to dispel the spirit.
127	** In Assassin's Creed III, the Assassin Ratonhnhaké:ton, hears the legend of the Headless Horseman from colonial frontiersman Daniel Boone and takes it upon himself to investigate the rumors. Searching in the Frontier, he eventually comes upon a slew of headless bodies and hears the maniacal laughter of a horseman from afar, wearing a jack-o'-lantern for a head.
128	* There's a few [[HiddenObjectGame hidden object games]] based on the short story.
129	** The first VideoGame/MysteryLegends game, ''Sleepy Hollow'', has the player find out the fates of the residents of the titular town.
130	** One of the VideoGame/DarkRomance games is based on the short story, where lovers Kane and Katrin seek to stop the Headless Horseman's rampage.
131	* Ichabod Crane appears in ''VideoGame/TheWolfAmongUs'' as a minor antagonist, being a corrupt mayor of Fabletown who employs both Bigby and Snow White.
132	[[/folder]]
133
134	[[folder:Web Video]]
135	* ''WebVideo/HeadlessASleepyHollowStory'' is a modernized expansion, with the Headless Horseman and Ichabod, now a middle school science teacher, becoming unlikely roommates as Ichabod helps the Horseman find his lost head. Most of the plot from the short story is covered in the first episode, and characters from other Washington Irving works -- including his pseudonyms -- play key roles.
136	[[/folder]]
137
138	[[folder:Western Animation]]
139	* The story was made into a 1934 theatrical cartoon by Ub Iwerks, part of his ''WesternAnimation/ComicolorCartoons'' series. In this version, the Headless Horseman successfully scares Ichabod away, then reveals himself as Brom Bones in costume. However, in the final scene, when Brom and Katrina are about to marry, the Horseman reappears and frightens off the whole wedding party - only to unmask himself as Ichabod, ending the story on a comedic note rather than an ambiguous one.
140	* In 1949 the story was paired with a pared-down version of Kenneth Grahame's ''Literature/TheWindInTheWillows'' for Creator/{{Disney}}'s "package film" ''WesternAnimation/TheAdventuresOfIchabodAndMrToad''; the ''Sleepy Hollow'' 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 ''WesternAnimation/BeautyAndTheBeast''. Believed to have been the first adaptation of the story to change Van Tassel's unnamed social gathering into a Halloween party, and is sometimes even cited as one of the key factors in bringing the holiday into the American cultural mainstream.
141	* In 1972 a short animated version appeared, [[{{Narrator}} narrated]] by Creator/JohnCarradine.
142	* In a 1976 episode of ''The WesternAnimation/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.
143	* 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.
144	** The Headless Motorcyclist may have been cribbed from the ''Series/KolchakTheNightStalker'' episode, "Chopper."
145	* ''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.
146	** 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".
147	* 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]].
148	* ''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 to Irving that in order to pay back his "debt", he has to become the Headless Horseman himself... which he does by ''pulling off his head and leaving it on the table, laughing at the viewers''.]]
149	* ''[[Franchise/TheSmurfs The Smurfs: The Legend Of Smurfy Hollow]]'' from Sony Pictures Animation.
150	* ''WesternAnimation/TheNewMisadventuresOfIchabodCrane'', a 1979 Canadian animated special animated by Titlecraft.
151	[[/folder]]

Context Literature / TheLegendOfSleepyHollow