Title Matching "SLEEPY HOLLOW" (Sorted by Popularity Ascending)
1. Sleepy Hollow (1999)
R | 105 min | Fantasy, Horror, Mystery
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: 367,777 | Gross: $101.07M
2. Sleepy Hollow (2013–2017)
TV-14 | 45 min | Action, Adventure, Crime
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: 62,169
3. The Legend of Sleepy Hollow (1949)
Approved | 34 min | Animation, Short, Comedy
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
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
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: 1,071
6. The Legend of Sleepy Hollow (1980 TV Movie)
PG | 104 min | Comedy, Fantasy, Horror
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: 768
7. Sleepy Hollow High (2000)
81 min | Horror, Mystery
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
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
John Carradine narrates the Washington Irving story of Ichabod Crane and the Headless Horseman.
Director: Sam Weiss | Star: John Carradine
Votes: 137
12. Legends of Sleepy Hollow (2021– )
Horror
New Amazon Prime series that features tales of (sub)urban legends.
Stars: Marilyn Oran, Steven Wishman, Amanda Sonnenschein, Zora Iman Crews
Votes: 35
13. Sleepy Hollow (2019 Video)
Comedy
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
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
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
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
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
"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
Stars: Todd, Daniel N. Butler
21. Sleepy Hollow (1911)
Short, Drama
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
Director: Hobey Ford | Star: Hobey Ford
Votes: 8
23. The Legend of Sleepy Hollow (2014)
32 min | Short, Drama
Stars: Frankie Piccione, Elhum Saljooki
24. Sleepy Hollow Fire (2016)
4 min | Documentary, Short | Completed
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
Director: Ashley Nasiadka | Stars: Jamie Barr, Chloe Bean, Lincoln Bennett, Laela Carswell
29. A Journey to Sleepy Hollow (2016)
Documentary, Short
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
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
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
Director: William Mackenzie | Star: Jordan Paul Haro
33. Roebus One: Sleepy Hollow (2018 Music Video)
Music
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
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
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
Stars: Roger Ebert, Michaela Pereira
37.
Tall Tales & Legends (1985–1988)
Episode:
The Legend of Sleepy Hollow
(1985)
Comedy, Drama, Family
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
Star: Barbie Wilde
39.
LNC (2014)
Episode:
Continuum Meets Sleepy Hollow - Out of Time with LNC
(2014)
Talk-Show
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
42.
Dark Toons (2020– )
Episode:
Sleepy Hollow
(2020)
Animation, Comedy, Horror
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
Director: Ryan Hollinger | Star: Ryan Hollinger
45.
Most Haunted (2002– )
Episode:
Sleepy Hollow
(2008)
44 min | Horror, Reality-TV
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
Director: Julien Pavageau | Star: Julien Pavageau
47.
Scare Fighter 3 (2018–2020)
Escape from Sleepy Hollow Way!
(2018 Podcast Episode)
Adventure, Comedy
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
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
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