- Johnny Depp reportedly based his portrayal of Ichabod Crane on Withnail, from Withnail & I (1987), as played by Richard E. Grant.
- The scene where Ichabod Crane crosses the covered bridge and hears the frogs underneath croaking "Ichabod" and "Headless Horseman" is a tribute to Disney's 1958 animated version of The Legend of Sleepy Hollow (1958) (featured in The Adventures of Ichabod and Mr. Toad (1949)), in which Ichabod Crane, crossing a bridge, hears the frogs croaking the same words. Director Tim Burton, a former Disney animator, has cited the Disney version of the tale as his main inspiration for the look and style of his film. The scene of Ichabod Crane riding the Horseman's horse backwards is also taken from the earlier film.
- Christopher Walken, who plays the Headless Horseman, played a schoolteacher in The Dead Zone (1983), in the beginning of which he tells his class to read "The Legend of Sleepy Hollow."
- The town Sleepy Hollow was created from the ground up in three months. At the time of filming, it was the largest set built in England and was put up in record time. The last set that held this record was built for Billy Elliot (2000).
- The Western Wood was built on a sound-stage so everything, the weather, light, could be controlled.
- The Windmill was too large to be constructed on a sound-stage because it was over five stories high. The sails alone weighed over 2 tons.
- The final chase sequence on the coach in the Western Wood took three weeks to film.
- It was really Johnny Depp who was being dragged after the coach. He wore a type of protective armour under his costume.
- The Horseman's horse is named Daredevil, the same name of Brom Bones' (Brom Van Brunt's) horse in Irving's original short story; the horse was purchased in Seville, Spain.
- Christopher Walken's character has no speaking lines, aside from a couple of "HAA"s to his horse and "shhhh."
- Director Trademark: [Tim Burton] [scarecrows]
- This was originally to be a Kevin Yagher directorial project. Tim Burton later took over the project, with Kevin Yagher remaining on with co-producing credits among others.
- The dress worn by Katrina Anne Van Tassel (Christina Ricci) in the last shot of the movie has the same pattern as Michael Keaton's outfit in the climactic scene of Beetle Juice (1988) also directed by Tim Burton.
- Tim Burton and the crew of the movie built the small town Sleepy Hollow complete with rooms, floors, and stairs. The town was dismantled after filming was completed.
- Historically, Ichabod Crane was a very unattractive man. Johnny Depp wanted to add prosthetics to his face to make himself look ugly, but Tim Burton wanted to base the character on Crane's more unattractive personality traits - his reported squeamishness and eccentricity.
- According to Tim Burton, the opening shots of Peter Van Garrett were shot by Conrad L. Hall, who was a friend of the film's director of photography, Emmanuel Lubezki.
- Star Johnny Depp adopted Goldeneye, the horse that played Gunpowder, Ichabod Crane's horse in the film, when he heard it was going to be put down.
- While Tim Burton admired Andrew Kevin Walker's original script, he hired the famed playwright and Academy Award-winning screenwriter Tom Stoppard as script doctor. Stoppard did an uncredited re-write to tone down the violence of Walker's script.
- Ichabod Crane faints six times in the movie.
- At the start of filming the three-way axe battle with Ray Park, Johnny Depp and Casper Van Dien, Casper Van Dien broke the index finger of his left hand. Although extremely painful, he carried on without telling anyone as he didn't want his part cut short.
- Ichabod Crane and Katrina Van Tassel were, reportedly, real people
- Winona Ryder was offered the role of Katrina Van Tassel, but turned it down.
- A mechanical horse, an updated model of one used in earlier films, was used for studio shots.
- Johnny Depp did all of his own stunts for the final scene where he is dragged by the horse - he had bullet-proof clothing underneath his wardrobe.
- This film features three sith lords from the Star Wars prequels, Ray Park (Darth Maul), Christopher Lee (Count Dooku ) and Ian McDiarmid (Darth Sidious).
- During the last scene Ichabod, during his explanation to Katrina and Young Masbeth of how easy New York is to navigate, says, "The Bronx is up and the Battery's down." This is a line from the song "New York, New York" which is featured in the movie On the Town (1949).
- Casper Van Dien in real life is related to the Van Tassels (Christina Ricci's character's family; she is his love interest in the film).
- Casper Van Dien gained 30 pounds for his role of Brom.
- The production notes on the DVD reveal that Johnny Depp based his characterization on the late Roddy McDowall (Fright Night (1985)), Angela Lansbury (The Mirror Crack'd (1980)) and Basil Rathbone (The Adventures of Sherlock Holmes (1939) and others).
- Liam Neeson, Brad Pitt and Daniel Day-Lewis were all considered for the role of Ichabod Crane.
- Marlon Brando was sought as The Hessian Horseman.
- Although the headless horsemen in the books and fairy tales is physically not allowed to cross the bridge, as it is known as a safe haven for the characters, in this version he can cross it freely.
- Michael Gough came out of retirement to play Notary Hardenbrook.
- Although Tim Burton claims the windmill scene was a reference to Frankenstein (1931), which he lovingly quoted in Frankenweenie (1984), a stronger link can be made to Will Hay's Oh, Mr. Porter! (1937) which also featured a windmill but not a headless horseman.
- This was the very last movie produced on laserdisc anywhere in the world.
- During the promotional interviews for the film, Johnny Depp gave Sir Michael Gambon the 'task' of mentioning Claudia Schiffer's knickers in every press interview. According to Gambon, when interviewed on BBC _Top Gear (1978)_ , he succeeded easily. Mind you, Gambon admitted that he lies in all interviews, so this may not be true after all!
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: There are 18 decapitations in this film.
- SPOILER: In The 39 Steps (1935), the professor shoots Hannay in the chest, and it appears that he is dead. However, the bullet was stopped by a hymnbook in the breast pocket of the coat he was wearing. In Sleepy Hollow (1999), Ichabod is shot and saved in a similar manner; this time the bullet lodges in a book of magic spells.
- SPOILER: The scarecrow in the scene where Peter Van Garrett gets his head cut off by the headless horseman is the opening pumpkin/scarecrow from Tim Burton's The Nightmare Before Christmas (1993).
- SPOILER: Christopher Walken often talked about Sleepy Hollow as his first movie with a kissing scene. But he already had one in The Deer Hunter (1978) in which he kisses Meryl Streep and in The Dead Zone (1983). He also had a kissing scene with Grace Jones in A View to a Kill (1985).
- SPOILER: Michael Gambon wanted to keep his severed head and send it via proxy to interviews and dinner parties
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