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Literature / The Legend of Sleepy Hollow

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"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, 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.

The story has been subject to a great many adaptations since Irving's time, with the "quilting frolick" of the original frequently getting transferred to Halloween.note  In more than one adaptation it is strongly hinted that the Horseman is a genuine supernatural apparition, although the original story leaves things more ambiguous.


The story is in the Public Domain and can be read here.

The Sketch-book of Geoffrey Crayon, Gent. also included another Irving short story destined to become famous: "Rip Van Winkle".

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

  • Alas, Poor Villain: 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.
  • The Alleged Steed: Gunpowder, Ichabod's horse, is clearly past his prime.
  • Anti-Hero: Ichabod himself. Despite displaying a number of positive traits, Irving focuses largely on his flaws; envy, avarice, gluttony, and sloth.
  • Anti-Villain: 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.
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  • Ambiguous Ending: 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.
  • Big Eater: Ichabod, and yet, he's beanpole thin.
  • Book Burning: 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.
  • Bowdlerise: In the original text, the invitation to the "quilting frolick" is delivered by "a negro," whose behavior is described patronizingly. Modern reprints are apt to either cut the description of his behavior or replace the word "negro" with "messenger."
  • Brains Evil, Brawn Good: 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.
  • Breakout Villain: 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 Dracula and Frankenstein, with numerous movie adaptations and modern day takes on the character coming out in the years since Washington Irving's story was published.
  • Cannot Cross Running Water: 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.
  • Chekhov's Gun: 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.
  • Cool Horse: Both played straight, with Brom's black horse, Daredevil, and inverted, with Gunpowder, the broken-down hack that Ichabod borrows from an irascible farmer.
  • Dead Hat Shot: The only thing ever conclusively found of Ichabod is his hat, leaving it ambiguous as to whether he survived his encounter with the Horseman.
  • Earn Your Happy Ending: 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.
  • Flat Character: 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.
  • Food Porn: Ichabod loves to eat, and much of the story focuses on his quasi-erotic imaginings regarding lovingly prepared food.
  • Ghostly Goals: 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.
  • Green-Eyed Monster: Ichabod is described as having "large green glassy eyes", and as being envious of Baltus van Tassel's wealth.
  • Have a Gay Old Time: "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."
  • Headless Horseman: The Trope Codifier.
  • Hellish Horse: 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.
  • Holy Burns Evil: 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.
  • Horror Struck: 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.
  • Hot for Student: 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.
  • Lost in Imitation: Pretty much every interpretation after the original either has the Headless Horseman 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.
    • It doesn't help that for most readers the Headless Horseman is 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?
    • 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.
    • 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  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.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 Scarecrow Solution. 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.
    • 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. 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.
  • Love Triangle: 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.
  • Maybe Magic, Maybe Mundane: The story hints at both a natural and a supernatural explanation for Crane's disappearance.
  • Meaningful Name: "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."
  • Moody Mount: Ichabod's borrowed horse Gunpowder: "The animal he bestrode was a broken-down plow-horse, that had outlived almost everything but its viciousness."
  • Never Found the Body: 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.
  • New England Puritan: Ichabod Crane seems to be this trope, being portrayed as extremely superstitious and easily willing to believe folk legends. Given Washington Irving was a native of New York, this may have been a Take That! towards New Englanders.
  • Offscreen Moment of Awesome: 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.
  • Off with His Head!: The Headless Horseman is given some backstory; he's believed to be the ghost of a Hessian troopernote  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".
  • One-Gender School: 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  Adaptations tend to ignore this and portray Ichabod teaching a coed class.
  • Operation: Jealousy: Katrina uses Ichabod to pull this on Brom.
  • Our Ghosts Are Different: Besides the Horseman himself, references are made to ghostly funeral processions, a wailing woman in white, and the ghost of British spy Major John André.
  • Pumpkin Person: The Headless Horseman is sometimes depicted with a jack-o'-lantern in place of his head.
  • Purple Prose: 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.
  • Rounded Character: 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 positive traits thrown in for good measure.
  • Satellite Love Interest: Katrina isn't given much characterization other than being the love interest of both Ichabod and Brom.
  • Scarecrow Solution: Why Brom laughed whenever the pumpkin was mentioned.
  • "Scooby-Doo" Hoax: Likely the Trope Maker, depending on whether you interpret the Horseman as real or not.
  • Sexily Modest: 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, to display the prettiest foot and ankle in the country round."
  • Shout-Out: Not only the usual literary allusions of the period, but especially to Irving's own fanciful Knickerbocker History of New York.
  • Short Story: The story's entire text takes up less than 30 pages when printed in a small novel.
  • Take It to the Bridge: 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":

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    Comic Books 
  • In some versions of Batman, Scarecrow's Start of Darkness came when a Jerk Jock 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.
  • An original sequel set in the then present day titled The Headless Horseman Rides Again was the featured story of Issue Six of Marvel Comics 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.

    Fan Works 
  • The Muppets 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 Beaker as the Horseman.) When nothing came of it, he posted them on DeviantArt.

    Film — Live-Action 
  • 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.
  • Sleepy Hollow (1999), perhaps the best known version in recent times, is a Tim Burton adaptation which deliberately takes considerable liberties with the original Story, making it radically Darker and Edgier. 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.

    Live-Action TV 
  • A made-for-TV movie version, The Legend of Sleepy Hollow, was filmed in Utah in 1980. In this version, which stars Jeff Goldblum as Ichabod Crane and Dick Butkus as Brom Bones, Ichabod has become a 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 Are You Afraid of the Dark? aired an episode entitled " The Tale of the Midnight Ride", in which a boy and girl save the ghost of Ichabod Crane from the Horseman. However, this caused the Horseman to chase them instead.
  • 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 Charmed aired an episode entitled "The Legend of Sleepy Halliwell", in which a Headless Horseman is beheading the teachers at the Magic School.
  • Fox's series Sleepy Hollow, in which the Headless Horseman is actually Death, one of the four Horsemen of the Apocalypse, and Ichabod is a Rip Van Winkle revived to stop him.
  • The Murder, She Wrote episode "Night of the Headless Horseman" combines a Setting Update 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.

    Video Games 
  • In both Assassin's Creed III and Assassin's Creed: Rogue the player character encounters the Headless Horseman.
    • 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.
    • 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.
  • There's a few hidden object games based on the short story.
    • The first Mystery Legends game, Sleepy Hollow, has the player find out the fates of the residents of the titular town.
    • One of the Dark Romance games is based on the short story, where lovers Kane and Katrin seek to stop the Headless Horseman's rampage.
  • Ichabod Crane appears in The Wolf Among Us as a minor antagonist, being a corrupt mayor of Fabletown who employs both Bigby and Snow White.

    Western Animation 
  • The story was made into a 1934 theatrical cartoon by Ub Iwerks, part of his Comicolor Cartoons 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.
  • In 1949 the story was paired with a pared-down version of Kenneth Grahame's The Wind in the Willows for Disney's "package film" The Adventures of Ichabod and Mr. Toad; the Sleepy Hollow story is narrated (with interspersed songs) by Bing Crosby. 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 Pet the Dog 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 Beauty and the Beast.
  • In 1972 a short animated version appeared, narrated by John Carradine.
  • In a 1976 episode of The Scooby-Doo / 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 The Real Ghostbusters featured an episode, "The Headless Motorcyclist," with a descendant of Ichabod Crane cursed by a headless apparition (on a motorcycle, naturally) who chases her.
  • Filmation's Ghostbusters 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 Casper comic, where the Horseman finally does meet up with his long-lost noggin, who's been going around as the "Horseless Headman".
  • In 1988, the 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 Headless Horseman story; he discovers a 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 In-Universe Alternative Character Interpretations by making Brom an actual villain; Brom deliberately makes a Deal with the Devil 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 In-Universe 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.
  • The Smurfs: The Legend Of Smurfy Hollow from Sony Pictures Animation.
  • The New Misadventures of Ichabod Crane, a 1979 Canadian animated special animated by Titlecraft.