Title Matching "Sleepy Hollow" (Sorted by Popularity Ascending)



1. Sleepy Hollow (1999)

R | 105 min | Fantasy, Horror, Mystery

7.3
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65 Metascore

Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people, with the culprit being the legendary apparition, The Headless Horseman.

Director: Tim Burton | Stars: Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon

Votes: 367,689 | Gross: $101.07M

2. Sleepy Hollow (2013–2017)

TV-14 | 45 min | Action, Adventure, Crime

7.3
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Ichabod Crane is resurrected and pulled two and a half centuries through time to unravel a mystery that dates all the way back to the founding fathers.

Stars: Tom Mison, Lyndie Greenwood, Nicole Beharie, Orlando Jones

Votes: 62,154

3. The Legend of Sleepy Hollow (1949)

Approved | 34 min | Animation, Short, Comedy

7.8
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In a small town, a brewing romantic rivalry with a local tough and a school-teacher culminates in a terrifying ride in the night.

Directors: Clyde Geronimi, Jack Kinney | Stars: Bing Crosby, Billy Bletcher, Pinto Colvig, Jud Conlon's Rhythmaires

Votes: 5,423

4. Headless: A Sleepy Hollow Story (2022– )

Comedy

9.2
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Ichabod Crane arrives in Sleepy Hollow for a fresh start, but his roommate, The Headless Horseman, has different plans for him.

Stars: Sean Persaud, Sinead Persaud, Gabe Greenspan, Mary Kate Wiles

Votes: 107

5. The Legend of Sleepy Hollow (1999 TV Movie)

105 min | Adventure, Horror, Mystery

5.0
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Ichabod Crane, a Yankee wanderer, arrives in Sleepy Hollow and becomes the new schoolmaster. He meets Katrina Van Tassel, and blissfully fantasizes about how he can marry her, ultimately ... See full summary »

Director: Pierre Gang | Stars: Brent Carver, Rachelle Lefevre, Vlasta Vrana, Kathleen Fee

Votes: 1,070

6. The Legend of Sleepy Hollow (1980 TV Movie)

PG | 104 min | Comedy, Fantasy, Horror

6.1
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Angered that Katrina has grown fond of schoolmaster Crane, Brom Bones determines to scare off the interloper by filling his head with spooky tales of a Headless Horseman. Crane disparages ... See full summary »

Director: Henning Schellerup | Stars: Jeff Goldblum, Paul Sand, Meg Foster, Laura Campbell

Votes: 767

7. Sleepy Hollow High (2000)

81 min | Horror, Mystery

2.7
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5 teenagers are forced to clean up the woods of Sleepy Hollow, but one by one they are decapitated by a man with a jack-o-lantern mask and a sword, but who could it be?

Directors: Chris Arth, Kevin Summerfield | Stars: Meagan Adele Lopez, Ruben Brown, Antonio Benedict, Wendy Donigian

Votes: 504

8. The Haunted Pumpkin of Sleepy Hollow (2002 Video)

Not Rated | 47 min | Animation, Comedy, Family

6.4
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It's Halloween and friends Nick and Kate are on a mission to find the biggest pumpkin in the patch. Unfortunately, the pumpkin they choose is haunted by the ghost of the Headless Horseman, and he wants his head back.

Stars: Joanna Ruiz, Jules de Jongh, Eric Meyers, Tom Clarke Hill

Votes: 120

9. The Legend of Sleepy Hollow (1972)

G | 13 min | Animation, Short

6.4
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John Carradine narrates the Washington Irving story of Ichabod Crane and the Headless Horseman.

Director: Sam Weiss | Star: John Carradine

Votes: 137

10. Sleepy Hollow

Horror | Announced

Plot kept under wraps at this time.

Director: Lindsey Beer

11. Sleepy Hollow Virtual Reality Experience (2015 Video Game)

Fantasy

6.7
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Star: Tom Mison

Votes: 7

12. Legends of Sleepy Hollow (2021– )

Horror

3.3
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New Amazon Prime series that features tales of (sub)urban legends.

Stars: Marilyn Oran, Steven Wishman, Amanda Sonnenschein, Zora Iman Crews

Votes: 34

13. Sleepy Hollow (2019 Video)

Comedy

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Director: Molly Deans Paradis | Stars: Jacob Glazer, Cylie Cabrera, Derek Langley, Judah Epps

14. Sleepy Hollow: Behind the Legend (2001 Video)

29 min | Documentary, Short, Horror

6.9
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Director: Toby Reisz | Stars: Peter Cullen, Tim Burton, Christina Ricci, Johnny Depp

Votes: 270

15. Sleepy Hollow High

Adventure, Horror | Announced

A modern twist on Washington Irving's classic tale

16. A Trip to Sleepy Hollow (2009)

Short

6.8
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James Rolfe documents his visit to the village in which Washington Irving based his famous tale "The Legend of Sleepy Hollow" off of.

Director: James Rolfe | Star: James Rolfe

Votes: 38

17. The Legend of Sleepy Hollow (1912)

Short, Comedy, Drama

6.0
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Here is the heart-rending narrative of Ichabod Crane, the schoolmaster of Sleepy Hollow, and his strenuous courtship, the quilting bee, the village dance, the bragging of Ichabod and the ... See full summary »

Director: Étienne Arnaud | Stars: Alec B. Francis, John G. Adolfi, Dorothy Gibson, Louis R. Grisel

Votes: 19

18. Rip Leaving Sleepy Hollow (1896)

Not Rated | 1 min | Drama, Short

4.3
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A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.

Director: William K.L. Dickson | Star: Joseph Jefferson

Votes: 542

19. Welcome to Sleepy Hollow (2020)

63 min | Documentary

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"Welcome to Sleepy Hollow" is a feature length documentary chronicling the 2019 Sleepy Hollow Theatre and Arts Park season in Bismarck, ND. This film showcases their three productions with ... See full summary »

Director: Samuel Sprynczynatyk | Stars: Nelson Abrego, Dylan Beck, Michelle Bohlen, Job Christenson

20. Glenn Danzig Presents: The Legend of Sleepy Hollow (2005 Video)

12 min | Short, Comedy, Musical

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Stars: Todd, Daniel N. Butler

21. Sleepy Hollow (1911)

Short, Drama

6.5
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It's said "There's no true love without jealousy," yet Henry Taber overstepped the mark in this direction, and, although Tess was the most devoted of wives. Henry saw in every man upon ... See full summary »

Director: Milton J. Fahrney | Star: Albert Brighton

Votes: 18

22. Ichabod - Sketches from Sleepy Hollow (2014)

8 min | Short, Horror

6.3
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Director: Hobey Ford | Star: Hobey Ford

Votes: 8

23. The Legend of Sleepy Hollow (2014)

32 min | Short, Drama

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Stars: Frankie Piccione, Elhum Saljooki

24. Sleepy Hollow Fire (2016)

4 min | Documentary, Short | Completed

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In June of 2015, the Sleepy Hollow a wildfire spread under extreme heat and wind conditions into the Broadview Subdivision of Wenatchee, Washington. More than 30 homes and businesses were lost in a two hour period.

Director: Jeff Ostenson

25. Sleepy Hollow (2016)

Comedy, Drama, Family

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Director: Ashley Nasiadka | Stars: Jamie Barr, Chloe Bean, Lincoln Bennett, Laela Carswell

26. Sleepy Hollow (1921)

Documentary, Short

4.4
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Votes: 6

27. The Legend of Sleepy Hollow (1908)

Short, Drama

5.9
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Votes: 27

28. Rabbit Ears: The Legend of Sleepy Hollow (1988 Video)

Animation, Short

9.4
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Votes: 9

29. A Journey to Sleepy Hollow (2016)

Documentary, Short

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this Documentary explores the history of the town of Sleepy Hollow and the story by Washington Irving including the legend of the Headless Horseman

Director: Anthony Raus | Star: Hunter Froelich

30. Sleepy Hollow Theater (2008–2015)

Horror

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A hosted horror movie show with Bryan Hogue as Jack Shadow and Ava Hogue as Aura.

Stars: Bryan Hogue, Ava Hogue, Richard Braden

31. Who's the Ghost in Sleepy Hollow (1977)

90 min | Comedy, Horror, Romance

5.7
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Director: Wen-Hsien Hsu | Stars: Chi-Wing Lau, Bao-Yu Wang, Chi-Yu Chang, Yung-Hsiang Chin

Votes: 9

32. Blockception - Minigames of Sleepy Hollow (2019 Video Game)

Adventure

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Director: William Mackenzie | Star: Jordan Paul Haro

33. Roebus One: Sleepy Hollow (2018 Music Video)

Music

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Director: Bill Nobes | Stars: Roebus One, Britteny Berlin, Victorya Mosley, Izir Lewis

34. The Magical World of Disney (1954–1997)
Episode: The Legend of Sleepy Hollow (1955)

TV-G | 60 min | Adventure, Drama, Family

8.7
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Features The Legend of Sleepy Hollow (1949), originally from The Adventures of Ichabod and Mr. Toad (1949).

Director: James Algar | Stars: Bing Crosby, John Dehner, Walt Disney

Votes: 58

35. Shirley Temple's Storybook (1958–1961)
Episode: The Legend of Sleepy Hollow (1958)

30 min | Drama, Family, Fantasy

7.3
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Director: Paul Bogart | Stars: James Bridges, Jimmy Carter, Russell Collins, John Ericson

Votes: 12

36. Siskel & Ebert (1986–2010)
Episode: Sleepy Hollow/42 Up/The World Is Not Enough/Mansfield Park/Rosetta (1999)

TV-PG | Talk-Show

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Stars: Roger Ebert, Michaela Pereira

37. Tall Tales & Legends (1985–1988)
Episode: The Legend of Sleepy Hollow (1985)

Comedy, Drama, Family

6.9
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A retell of Washington Irving's 1820 Halloween novel.

Director: Edd Griles | Stars: Ed Begley Jr., Beverly D'Angelo, Charles Durning, Tim Thomerson

Votes: 50

38. Hold Tight! (1982–1987)
Episode: Sleepy Hollow (1987)

Family, Game-Show, Music

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Star: Barbie Wilde

39. LNC (2014)
Episode: Continuum Meets Sleepy Hollow - Out of Time with LNC (2014)

Talk-Show

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What happens when Continuum's future cop and pulled-from-the-past Sleepy Hollow's Ichabod Crane team up? You get some temporal shenanigans.

Stars: Ariel Kasten, Jonathan Strickland

40. Picture Box (1966–1993)
Episode: The Legend of Sleepy Hollow (1980)

Family

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Star: Alan Rothwell

41. Volshebny fonar (2015–2016)
Episode: Little Sleepy Hollow (2015)

Animation, Short, Fantasy

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42. Dark Toons (2020– )
Episode: Sleepy Hollow (2020)

Animation, Comedy, Horror

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The Halloween classic rides again. Doug gives his thoughts on why this short has stayed with people for so many years. Let's take a look at "Sleepy Hollow" on a new episode of Dark Toons.

Star: Doug Walker

43. The Ryan Hollinger Show (2010– )
Episode: Revisiting The Horror of SLEEPY HOLLOW (2018)

Horror, Talk-Show

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Director: Ryan Hollinger | Star: Ryan Hollinger

44. The Dark Side of NY (2019)
Episode: Sleepy Hollow Cemetery... (2019)

Documentary

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45. Most Haunted (2002– )
Episode: Sleepy Hollow (2008)

44 min | Horror, Reality-TV

4.7
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The name "Sleepy Hollow" is engraved in popular culture and is synonymous with one of the most famous ghost stories in the world, that of the Headless Horseman. The "Most Haunted" team ... See full summary »

Director: Karl Beattie | Stars: Yvette Fielding, Brian Shepherd, Ciarán O'Keeffe, Lesley Smith

Votes: 7

46. Le Ciné-club de M.Bobine (2008– )
Episode: Sleepy Hollow de Tim Burton, l'analyse de M. Bobine (2020)

Short

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Director: Julien Pavageau | Star: Julien Pavageau

47. Scare Fighter 3 (2018–2020)
Escape from Sleepy Hollow Way! (2018 Podcast Episode)

Adventure, Comedy

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Looks like our heroes have found themselves stuck in one eerie neighborhood. Only escaping the street of Sleepy Hollow Way can break the curse. Beware the Headless Horseman.

Stars: Max Brown, Roman Brown, Brady Echols, Ginger Echols

48. Minty Comedic Arts (2015– )
Episode: 10 Things You Didn't Know About Sleepy Hollow (2020)

16 min | Talk-Show

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Stars: Mark Bishop, Johnny Depp

49. Stories Podcast: A Bedtime Show for Kids of All Ages (2014– )
The Legend of Sleepy Hollow (2016 Podcast Episode)

22 min | Family

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Halloweeen time. Here is an only-slightly-spooky take on the Legend of Sleepy Hollow with original songs. The Headless Horseman is coming...or is he? Ichabod Crane finds out.

Stars: Dan Hinds, Amanda Weldin

50. Stuff You Should Know (2008– )
Short Stuff: Jack O'Lanterns and Sleepy Hollow (2021 Podcast Episode)

Documentary

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