"The Legend of Sleepy Hollow" is an 1820 short story by Washington Irving from his collection The Sketch Book of Geoffrey Crayon. It tells the story of schoolteacher Ichabod Crane who competes for the hand of wealthy Katrina Van Tassel. After leaving a party, he is pursued by the Headless Horseman and goes missing from town thereafter.
- The Fall 1983 issue of Muppet Magazine features a picture game in which the reader finds seventeen scary characters. The Headless Horseman can be seen outside the window of the haunted house.
- Ernie and Bert dress up as the Headless Horseman in the 1997 Sesame Street book Pumpkin Patch Party.
- Summer Penguin's spooky story in the 2018 Muppet Babies episode "The Teeth Chattering Tale of the Haunted Pancakes" takes place in Halloween Hollow, and features Baby Kermit as Kermabod Crane.
- Alun Armstrong played the high constable in the 1999 film
- Johnny Depp played Ichabod Crane in the 1999 film
- Charles Durning played Uncle Doffue in the 1985 Shelley Duvall's Tall Tales & Legends episode
- Jeff Goldblum played Ichabod Crane in the 1980 TV movie
- Nick Gillard was stunt coordinator for the 1999 film
- Richard Griffiths played Magistrate Philipse in the 1999 film
- Mark Hamill played Van Ripper in The Night of the Headless Horseman (1999 TV special)
- Martin Landau played Peter Van Garrett in the 1999 film
- William H. Macy played Ichabod Crane in in The Night of the Headless Horseman (1999 TV special)
- Katie Purvis was a stunt double in the 1999 film
- Miranda Richardson played Lady Van Tassel in the 1999 film
- Christopher Walken played the Hessian horseman in the 1999 film