- Actor-Inspired Element: Johnny Depp chose to make Ichabod even more delicate and fragile, citing his inspiration as Angela Lansbury's performance in the 1978 adaptation of Death on the Nile. He also took inspiration from Basil Rathbone and Roddy McDowall.
- Actor-Shared Background: The Horseman was formerly a Hessian mercenary, who were German soldiers that served as auxiliaries in the British army. Christopher Walken actually is half-German on his mother's side.
- All-Star Cast: The film has a number of recognizable actors in film and television. Besides the director (Tim Burton), you have Johnny Depp, Christina Ricci, Christopher Walken, Michael Gambon, Michael Gough, Richard Griffiths, Christopher Lee, Martin Landau, Jeffrey Jones, Casper Van Dien and Ian McDiarmid among the cast.
- Awesome, Dear Boy: Tim Burton was attracted to the project because he'd never done a horror film before, and "those are the kind of movies I like probably more than any other genre".
- California Doubling: Despite the New York setting, filming was done entirely in England. While most of it was done on sound stages, location shooting was done in Hambledon, Buckinghamshire. Some re-shoots were however done in New York.
- The Cast Show Off: Casper Van Dien gets to show off how good he is on a horse.
- Creator Backlash: A variation. Johnny Depp has never seen the film because he hates the way he acts in it.
- Creator Couple: Tim Burton's then-wife Lisa Marie plays Lady Crane in Ichabod's dream sequences.
- Dueling Works: With the Hallmark Hall of Fame Made-for-TV Movie The Legend of Sleepy Hollow, which aired on TV the same year (1999). The TV movie is Truer to the Text, but critics and audiences favored the Tim Burton movie. The Burton movie also had the largest audience to begin with and predictably left the biggest cultural mark.
- Dyeing for Your Art: Casper Van Dien gained 30 pounds to play Brom.
- Enforced Method Acting: According to the director's commentary on the DVD, during the scene in the church where Doctor Lancaster is killed by a blow to the head, they accidentally hit Ian McDiarmid so hard that he ended up having to go to the hospital.
- Fake American: The British Miranda Richardson dons an American accent as Lady Van Tassell. As does British actress Jessica Oyelowo as the serving girl Sarah.
- Fake Brit:
- Johnny Depp affects a British accent as Ichabod Crane. Likewise, Christina Ricci puts on an accent for Katrina van Tassel.
- Scotsman Ian McDiarmid affects an English accent for Dr Lancaster. As does Irish actor Michael Gambon.
- Irony as She Is Cast: Christopher Walken did not reveal until after he had been cast as the Headless Horseman, that he didn't know how to ride a horse.
- Missing Trailer Scene: Additional lines between Katrina and Ichabod about the witch in the western woods appear in the trailer but not the film.
- No Stunt Double: Johnny Depp did the final sequence in the woods without a double, wearing bullet proof clothing under his costume.
- Playing Against Type: Christina Ricci, known as Eerie Pale-Skinned Brunette Wednesday Addams, plays golden-haired ingenue Katrina. Given Ricci's type, it's a bit of a mystery whether or not Katrina is a Bitch in Sheep's Clothing. She isn't.
- Playing Their Own Twin: Miranda Richardson plays both Lady Van Tassel and her twin sister, the witch in the Western Woods.
- Production Posse: Johnny Depp's third collaboration with Tim Burton. Likewise Jeffrey Jones had worked with Burton in Beetlejuice and Ed Wood. Martin Landau had starred in that as well. Michael Gough of course had worked on the Batman films. Almost the entire design team from Batman (1989) was recruited for Sleepy Hollow too.
- Saved from Development Hell: The film sat on the shelf for most of the 90s because studios "never really saw it as a commercial movie", according to producer Adam Schroeder. It wasn't until the success of Scream (1996), The Craft, I Know What You Did Last Summer and others that horror was considered commercially viable, and it was greenlit in 1998.
- Spared by the Cut: In one draft of the script, Ichabod blackmails Reverend Steenwyck into resigning due to his obstructive nature (which is dialed up in the script), and consequently, Steenwyck doesn't kill Dr. Lancaster and then get shot himself.
- Stunt Casting:
- Martin Landau is given a cameo at the start as Peter van Garrett - the Horseman's first victim.
- Christopher Lee and Michael Gough were cast as the Burgomaster and Notary Hardenbrook because Tim Burton wanted to homage Hammer Horror. The latter was coaxed out of retirement for the part.
- Throw It In!:
- Lady Van Tassell's "watch your head" was an ad-lib by Miranda Richardson.
- The comedy bit where Ichabod is scared by a spider was thrown in because "every day there was a guy there with bugs", so they decided to use them.
- Uncredited Role:
- Tom Stoppard was an uncredited script doctor on the screenplay.
- Martin Landau as Peter Van Garrett.
- What Could Have Been:
- Daniel Day-Lewis, Liam Neeson, and Brad Pitt were considered for Ichabod Crane. This was merely a formality requested by Paramount, as Johnny Depp was always the first choice for the role.
- Johnny Depp wanted to add prosthetics to his face to make Ichabod more unattractive, in line with his book counterpart. Burton decided against it, feeling Ichabod's personality quirks were what made him unattractive.
- Winona Ryder was offered the part of Katrina, which would have reunited her and Depp from Edward Scissorhands. She turned it down.
- Marlon Brando, of all people, was the first choice to play the Hessian.
- The filmmakers had hoped to shoot on location in upstate New York, but the places they looked at didn't lend themselves to the expressionism they wanted.
- The first script had to have some of its violence toned down. Even so, it's one of Burton's goriest films.
- The witch in the western woods was to have a larger role. Katrina would mention her during her midnight conversation with Ichabod, and the latter would later find the witch beheaded outside her home. He would deduce that she was murdered by a human killer, and then find Katrina wearing her missing necklace - further implicating Katrina as the culprit.
- The final sequence was to include the Horseman being on fire, but that was scrapped because of "production problems".
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