- Creator Backlash: A variation. Johnny Depp has never seen the film because he hates the way he acts in it.
- 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 the doctor is killed by a blow to the head, they accidentally hit Ian McDiarmid so hard that he ended up having to go to hospital.
- Fake Brit: Johnny Depp affects a British accent as Ichabod Crane.
- 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.
- 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.
- Stunt Casting: Look out for Martin Landau and Christopher Lee early in the film.
- Uncredited Role:
- What Could Have Been:
- Daniel Day-Lewis, Liam Neeson and Brad Pitt were considered for Ichabod Crane.
- 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.
Trivia / Sleepy Hollow (1999)