Derivative Works / The Legend of Sleepy Hollow

aka: Sleepy Hollow

There are enough adaptations to lose your head over.
^{Clockwise from top left} Sleepy Hollow (1999), Sleepy Hollow, Headless: A Sleepy Hollow Story, and Mystery Legends: Sleepy Hollow

This page lists works adapting or inspired by the early 19th century short story "The Legend of Sleepy Hollow" about a man named Ichabod Crane who arrives in the town of Sleepy Hollow, Westchester County, New York, and gets confronted to a local folk tale about a Headless Horseman prowling around the town, who may or may not exist.

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Original work:

• "The Legend of Sleepy Hollow" (1820), a short story written by Washington Irving.

Adaptations and derivative works:

Films — Animation

• The Adventures of Ichabod and Mr. Toad (1949), a Disney Animated Canon Anthology Film that adapts the story in its second half.

Films — Live-Action

• The Headless Horseman (1922), a silent film
• The Legend of Sleepy Hollow (1980), a Made-for-TV Movie starring Jeff Goldblum.
• Sleepy Hollow (1999), an unabashedly supernatural and loose adaptation by Tim Burton starring Johnny Depp.
• The Legend of Sleepy Hollow (1999), a Hallmark Hall of Fame Made-for-TV Movie.
• Sleepy Hollow High (2000), a invokedDirect to Video teen slasher film.
• The Hollow (2004), a teen horror film centered around a descendant of Ichabod Crane.
• Headless Horseman (2007)

Literature

• The Fifth Horseman: A Sleepy Hollow Legend (1999), a novel by Gregg Gonzalez.

Live-Action TV

• The Tale of the Midnight Ride (1994), an episode of Are You Afraid of the Dark? serving as a sequel to the original story.
• Halloween Hound: The Legend of Creepy Collars (1997), an episode of Wishbone.
• Sleepy Hollow (2013-2017), a television series.

Video Games

• Dark Romance: Sleepy Hollow
• Mystery Legends: Sleepy Hollow (2008)

Web Videos

• Headless: A Sleepy Hollow Story (2022), a modern adaptation where Ichabod and the Horseman are roommates.

Western Animation

• The Legend of Sleepy Hollow (1985), the first episode of Shelley Duvall's Tall Tales & Legends.
• The Legend of Sleepy Hollow (1988), as part of Rabbit Ears Productions' "Storybook Classics" series.
• The Night Of The Headless Horseman (1999)
• The Haunted Pumpkin of Sleepy Hollow (2003)
• The Smurfs: The Legend of Smurfy Hollow (2013)

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