Film and television
Notable film and television variations include:
- The Headless Horseman (1922), a silent film directed by Edward Venturini and starring Will Rogers as Ichabod Crane. It was filmed on location in New York's Hudson River Valley.
- The Adventures of Ichabod and Mr. Toad (1949), an animated adaptation directed by James Algar, Clyde Geronimi, and Jack Kinney, produced by Walt Disney Productions, and narrated by Bing Crosby. This version is more lighthearted and family-friendly than Irving's original story and most other adaptations, while the climactic chase is more extended than in the original story. It was rereleased individually in 1958 as The Legend of Sleepy Hollow.
- The Legend of Sleepy Hollow (1980), a television film directed by Henning Schellerup and filmed in Utah, starring Jeff Goldblum, Meg Foster, and Dick Butkus. Executive producer Charles Sellier was nominated for an Emmy Award for his work on the movie. Crane is depicted as a skeptic regarding ghosts and the supernatural.
- "The Legend of Sleepy Hollow" (1985), the premiere episode of Shelley Duvall's Tall Tales and Legends series, stars Ed Begley Jr. as Ichabod Crane, Beverly D'Angelo as Katrina, Tim Thomerson as Brom, and Charles Durning as Doffue Van Tassel, who is also the narrator.
- "The Tale of the Midnight Ride", a 1994 episode of the Nickelodeon series Are You Afraid of the Dark?, serves as a sequel to the original story. A boy named Ian Matthews moves to Sleepy Hollow, where he develops a crush on a girl named Katie. On Halloween night, they see the ghost of Ichabod Crane and send him over the bridge that the Headless Horseman cannot cross, unintentionally prompting the Horseman to pursue them instead of Crane.
- In the 1997 Wishbone episode "Halloween Hound: The Legend of Creepy Collars", Wishbone imagines himself as Ichabod Crane and reenacts the story in his imagination when his owner goes on a Halloween night scavenger hunt with two schoolmates, but is scared off by the Headless Horseman.
- The Legend of Sleepy Hollow (1999), a Canadian-American television film directed by Pierre Gang and starring Brent Carver and Rachelle Lefevre.
- Sleepy Hollow (1999), a feature film adaption directed by Tim Burton which takes many liberties with the plot and characters, changing Crane from the local schoolmaster into a police constable sent from New York City to investigate recent murders, and the Horseman is used as a weapon against the local landowners.
- The Night of the Headless Horseman (1999), an hour-long computer-animated special using motion capture.
- Sleepy Hollow High (2000), a direct-to-video horror film shot in Maryland, in which a group of misbehaving high school students are sent to the Sleepy Hollow Park Grounds to clean up vandalism and graffiti. They soon realize that someone is taking the original legend too far.
- The Hollow (2004), an ABC Family television film starring Kevin Zegers and Kaley Cuoco, and focusing on a teenage descendant of Ichabod Crane.
- "The Legend of Sleepy Halliwell" (2004), an episode of the TV show Charmed, in which a headless horseman murders the teachers at Magic School by beheading them.
- Sleepy Hollow (2013), a crime/horror series in which Ichabod Crane is reimagined as an English professor and turncoat during the Revolutionary War, who awakens in the 21st century and encounters the Headless Horseman, a felled mercenary whom Crane had decapitated 250 years prior. Crane teams up with Abbie Mills, a lieutenant in the Sleepy Hollow sheriff's department, and together they try to stop the murderous Horseman and uncover a conspiracy involving supernatural forces. The show ran for four seasons.
- In Sleepy Hollow (1913), a piano suite by Eastwood Lane
- Sleepy Hollow (1948), a Broadway musical, with music by George Lessner and book and lyrics by Russell Maloney and Miriam Battista. It lasted 12 performances.
- »The Headless Horseman » ( 2001) by Michael Jeffrey Shapiro, for baritone, itinerant string band, and orchestra
- Sleepy Hollow (2009), a musical with book and lyrics by Jim Christian and music by Tom Edward Clark. It premiered at Weber State University in Ogden, Utah on October 30, 2009. It received the 2009 Kennedy Center American College Theater Festival Musical Theatre Award.
- Undead Ahead 2: Tale of the Midnight Ride (2019), by Motionless in White
- Ronald Colman was the host and narrator for a radio adaptation on NBC's Favorite Story on July 2, 1946 (requested by Walter Huston as that actor's favorite story).
- An adaptation was broadcast on September 19, 1947 on NBC University of the Air: American Novels.
- Bing Crosby recreated his Disney narration in Walt Disney's Ichabod and the Legend of Sleepy Hollow for Decca Records (DAU-725) in 1949.
- Lionel Barrymore narrated and wrote the music for a version of the story on Full Fidelity Lion Records (L70078), a branch of MGM Records, in 1958.
- In 1988, Glenn Close narrated a version of the story for Windham Hill Records (WH-0711), later also released on audio cassette and CD (WD-0711).
- The Legend of Sleepy Hollow (1998) - An abridged version omitting the characters of Katrina and Brom, narrated by Winifred Phillips for the Radio Tales series on National Public Radio.
- In 2009 Historic Hudson Valley released an unabridged dramatic reading by Jonathan Kruk with musical effects by Matt Noble.
- BBC Radio 7 and BBC Radio 4 Extra) have broadcast a three-part reading of the story with Martin Jarvis as the narrator.