Most Popular Headless Horseman Movies and TV Shows

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1. Gladiator (2000)

R | 155 min | Action, Adventure, Drama

8.5
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    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
67 Metascore

A former Roman General sets out to exact vengeance against the corrupt emperor who murdered his family and sent him into slavery.

Director: Ridley Scott | Stars: Russell Crowe, Joaquin Phoenix, Connie Nielsen, Oliver Reed

Votes: 1,259,152 | Gross: $187.71M

2. Sleepy Hollow (1999)

R | 105 min | Fantasy, Horror, Mystery

7.3
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    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
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: 314,032 | Gross: $101.07M

3. Sleepy Hollow (2013–2017)

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

7.4
Rate this
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  

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: 56,183

4. The Adventures of Ichabod and Mr. Toad (1949)

Approved | 68 min | Animation, Comedy, Family

7.0
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    1 2 3 4 5 6 7 8 9 10 7/10 X  
74 Metascore

An animated adaptation of "The Wind in the Willows" followed by an adaptation of "The Legend of Sleepy Hollow".

Directors: James Algar, Clyde Geronimi, Jack Kinney | Stars: Bing Crosby, Basil Rathbone, Eric Blore, John McLeish

Votes: 11,461

5. Tees Maar Khan (2010)

Not Rated | 135 min | Comedy, Crime

2.5
Rate this
    1 2 3 4 5 6 7 8 9 10 2.5/10 X  

Posing as a movie producer, a conman attempts to trick an entire village into helping him rob a treasure-laden train.

Director: Farah Khan | Stars: Akshay Kumar, Katrina Kaif, Akshaye Khanna, Rajiv Laxman

Votes: 10,545 | Gross: $1.08M

6. The 82nd Annual Academy Awards (2010 TV Special)

TV-14 | 217 min | News

6.8
Rate this
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  

Steve Martin and Alec Baldwin host the Oscars.

Directors: Hamish Hamilton, Anne Fletcher, Richard A. Preuss, Pete Docter, Henry Selick | Stars: Macaulay Culkin, Ryan Reynolds, Charlize Theron, Quentin Tarantino

Votes: 1,687

7. Scooby-Doo Meets the Boo Brothers (1987 TV Movie)

Not Rated | 93 min | Animation, Comedy, Family

7.1
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    1 2 3 4 5 6 7 8 9 10 7.1/10 X  

After the death of Shaggy's Uncle Beaureguard, he, Scooby, and Scrappy arrive at his uncle's plantation to collect the inheritance. But as soon as they arrive, they find it is haunted by ... See full summary »

Directors: Paul Sommer, Carl Urbano, Ray Patterson | Stars: Don Messick, Casey Kasem, Sorrell Booke, William Callaway

Votes: 3,227

8. Headless Horseman (2007)

R | 87 min | Horror

3.8
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    1 2 3 4 5 6 7 8 9 10 3.8/10 X  

Seven college kids take a shortcut on their way to a party and unfortunately end up in Wormwood, where the spirit of the Headless Horseman hunts them one by one.

Director: Anthony C. Ferrante | Stars: Billy Aaron Brown, Rebecca Mozo, Richard Moll, Arianne Fraser

Votes: 934

9. The Curse of the Cat People (1944)

Approved | 70 min | Drama, Horror, Mystery

6.9
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    1 2 3 4 5 6 7 8 9 10 6.9/10 X  

The young, friendless daughter of Oliver and Alice Reed befriends her father's dead first wife and an aging, reclusive actress.

Directors: Gunther von Fritsch, Robert Wise | Stars: Simone Simon, Kent Smith, Jane Randolph, Ann Carter

Votes: 5,417

10. Scooby-Doo and the Goblin King (2008 Video)

Not Rated | 75 min | Animation, Adventure, Comedy

6.4
Rate this
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  

Scooby-Doo and Shaggy must go into the underworld ruled by the Goblin King in order to stop a mortal named The Amazing Krudsky who wants power and is a threat to their pals, Fred, Velma and Daphne.

Director: Joe Sichta | Stars: Frank Welker, Casey Kasem, Grey Griffin, Mindy Cohn

Votes: 1,867

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

105 min | Adventure, Horror, Mystery

5.0
Rate this
    1 2 3 4 5 6 7 8 9 10 5/10 X  

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

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

Votes: 867

12. Wicked Woods: A Descendants Halloween Story (2019 TV Special)

5 min | Animation

6.9
Rate this
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  

On Halloween night, Mal, Evie, Carlos, and Jay wander into some wicked woods and have a frightful time.

Director: Melissa Goodwin Shepherd | Stars: Cameron Boyce, Dove Cameron, Sofia Carson, Sarah Jeffery

Votes: 10

13. The Hollow (2004 TV Movie)

R | 83 min | Fantasy, Horror, Thriller

4.5
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    1 2 3 4 5 6 7 8 9 10 4.5/10 X  

Restless spirits stir this Hollow's Eve, beckoning Ian Cranston, the last blood relative of Ichabod Crane, back to Sleepy Hollow. Thundering hooves unleash a wave of bone-chilling screams ... See full summary »

Director: Kyle Newman | Stars: Kevin Zegers, Kaley Cuoco, Nick Carter, Ben Scott

Votes: 1,926

14. The Legend of Sleepy Hollow (1949)

Approved | 34 min | Animation, Short, Comedy

7.9
Rate this
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  

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, Pinto Colvig, Jud Conlon's Rhythmaires, Clarence Nash

Votes: 3,754

15. Lego Scooby-Doo!: Haunted Hollywood (2016 Video)

Not Rated | 75 min | Animation, Comedy, Family

5.9
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    1 2 3 4 5 6 7 8 9 10 5.9/10 X  

The Scooby gang try to rescue an old movie studio, which is not only threatened by developers, but a series of movie monsters too.

Director: Rick Morales | Stars: Frank Welker, Matthew Lillard, Grey Griffin, Kate Micucci

Votes: 995

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

PG | 104 min | Comedy, Fantasy, Horror

6.3
Rate this
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  

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: 600

17. The Smurfs: The Legend of Smurfy Hollow (2013 TV Short)

G | 22 min | Animation, Short, Comedy

6.2
Rate this
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  

When Brainy Smurf is favored to win the annual Smurfberry Hunt for the ninth year in a row, Gutsy Smurf sets out to discover how Brainy wins every year. Gutsy?s investigation takes him into... See full summary »

Director: Stephan Franck | Stars: Jack Angel, Fred Armisen, Hank Azaria, Gary Basaraba

Votes: 602

18. Disney's Halloween Treat (1982 Video)

Unrated | 47 min | Animation, Family

8.5
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    1 2 3 4 5 6 7 8 9 10 8.5/10 X  

Contains memorable scenes from "Snow White and the Seven Dwarfs," "Fantasia," "Lady and the Tramp," "Peter Pan," "One Hundred and One Dalmatians," and "The Sword in the Stone."

Stars: Bobby Driscoll, Peggy Lee, Bing Crosby, Cate Bauer

Votes: 262

19. Sleepy Hollow High (2000)

81 min | Horror, Mystery

2.8
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    1 2 3 4 5 6 7 8 9 10 2.8/10 X  

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 Lopez, Ruben Brown, Antonio Benedict, Wendy Donigian

Votes: 247

20. The Night of the Headless Horseman (1999 TV Movie)

63 min | Animation, Horror

5.3
Rate this
    1 2 3 4 5 6 7 8 9 10 5.3/10 X  

In this classic tale based on "The Legend of Sleepy Hollow," Ichabod Crane, the town's new schoolmaster, is instantly enamored with Katrina Van Tassel, but he must compete for her love with... See full summary »

Director: Shane Williams | Stars: Jeff Bennett, Clancy Brown, Tia Carrere, Debi Derryberry

Votes: 203

21. Curse of the Headless Horseman (1972)

PG | 75 min | Horror

1.9
Rate this
    1 2 3 4 5 6 7 8 9 10 1.9/10 X  

A phantom horseman who appears every night with a human head tucked under his arm lets it be known that he is searching for eight gunfighters.

Director: John Kirkland | Stars: Ultra Violet, Marland Proctor, Claudia Reame, Don Carrara

Votes: 330

22. The Headless Horseman (1922)

Not Rated | 68 min | Comedy, Drama, Horror

4.9
Rate this
    1 2 3 4 5 6 7 8 9 10 4.9/10 X  

The village of Sleepy Hollow is getting ready to greet the new schoolteacher, Ichabod Crane, who is coming from New York. Crane has already heard of the village's legendary ghost, a ... See full summary »

Director: Edward D. Venturini | Stars: Will Rogers, Lois Meredith, Ben Hendricks Jr., Charles E. Graham

Votes: 210

23. El Charro de las Calaveras (1965)

79 min | Horror, Western

5.5
Rate this
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  

Episodic film in which a masked hero combats a trio of classic monsters.

Director: Alfredo Salazar | Stars: Dagoberto Rodríguez, David Silva, Alicia Caro, Pascual García Peña

Votes: 141

24. The Legend of Sleepy Hollow (1972)

G | 13 min | Animation, Short

6.5
Rate this
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  

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

Director: Sam Weiss | Star: John Carradine

Votes: 49

25. El jinete sin cabeza (1957)

91 min | Horror, Western, Mystery

5.7
Rate this
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  

The Headless Horseman is a horror film from Mexico, directed by Chano Urueta.

Director: Chano Urueta | Stars: Luis Aguilar, Flor Silvestre, Jaime Fernández, Pascual García Peña

Votes: 29

26. The New Misadventures of Ichabod Crane (1979 TV Movie)

30 min | Animation, Family

7.6
Rate this
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  

Sleepy Hollow, a town plagued by the Headless Horseman, hires the most educated person they can find to fight him - Ichabod Crane. He, talking horse and dog, and Rip van Winkle go on the quest. But the Horseman has a secret.

Director: Vic Atkinson | Stars: Kreskin, Pat Buttram, George Lindsey, Larry D. Mann

Votes: 19

27. The Haunted Pumpkin of Sleepy Hollow (2003 Video)

Not Rated | 47 min | Animation, Comedy, Family

6.6
Rate this
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  

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.

Director: Vong Zeven | Stars: Joanna Ruiz, Jules de Jongh, Eric Meyers, Tom Clarke Hill

Votes: 75

28. Ichabod! (2004)

70 min | Family, Musical

7.8
Rate this
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  

Katrina Van Tassel must come to a heart-wrenching decision: should she marry the schoolmaster Ichabod Crane (whom her parents have deemed worthy of her hand), or should she remain truthful ... See full summary »

Director: Rick Ramage | Stars: Peter O'Meara, Nathan Anderson, Bob Gunton, Charisse Stewart

Votes: 45

29. Sleepy Hollow: Behind the Legend (2000 Video)

29 min | Documentary, Short, Horror

7.3
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    1 2 3 4 5 6 7 8 9 10 7.3/10 X  

Add a Plot

Director: Toby Reisz | Stars: Joel Aron, Tim Burton, Peter Cullen, Steve Dent

Votes: 235

30. The Headless Horseman (1934)

9 min | Animation, Short

5.5
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    1 2 3 4 5 6 7 8 9 10 5.5/10 X  

Add a Plot

Directors: Ub Iwerks, Shamus Culhane, Al Eugster

Votes: 90

31. Unhallowed (II)

Thriller | Announced

In a town enamored with its own "Unhallowed Horseman" legend, a distraught teenage boy must come to terms with his own demons and perhaps the Horseman himself.

Director: Jude S. Walko

32. Andrew Sawyer's Ichabod (2007)

45 min | Romance

Rate this
    1 2 3 4 5 6 7 8 9 10 -/10 X  

In this classic retelling of Washington Irving's, "The Legend of Sleepy Hollow" director, Andrew Sawyer and writer Allison Lahikainen bring a stage feel to the screen. When Ichabod Crane, ... See full summary »

Director: Andrew Sawyer | Stars: Sal Lizard, Christina Rondano, V Nigel Taylor

33. Halloween's Most Extreme (2007 TV Movie)

TV-PG | 60 min | Documentary

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    1 2 3 4 5 6 7 8 9 10 -/10 X  

Add a Plot

Stars: Mason Pettit, Nicole Apelian, Ben Armstrong, Jim Beauchemin

34. The Legend of Sleepy Hollow (1912)

Short, Comedy, Drama

6.2
Rate this
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  

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: 8

35. DPTV Networks Visits Horseman's Hollow (2012 TV Movie)

45 min

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DPTV Networks presents..

Director: Lance Hallowell | Stars: Katie Donovan, Amanda Kay Howell, Stephanie Lalor, Jason Liles

36. Cheyenne (1984 Video Game)

Action, Horror, Western

6.2
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    1 2 3 4 5 6 7 8 9 10 6.2/10 X  

Add a Plot

Votes: 6

37. Sleepy Hollow (2013–2017)
Episode: Bad Blood (2014)

TV-14 | 43 min | Action, Adventure, Crime

8.8
Rate this
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  

The battle between good and evil comes to an explosive head.

Director: Ken Olin | Stars: Tom Mison, Nicole Beharie, Orlando Jones, Katia Winter

Votes: 993

38. Game of Thrones (2011–2019)
Episode: Battle of the Bastards (2016)

TV-MA | 60 min | Action, Adventure, Drama

9.9
Rate this
    1 2 3 4 5 6 7 8 9 10 9.9/10 X  

Jon and Sansa face Ramsay Bolton on the fields of Winterfell. Daenerys strikes back at her enemies. Theon and Yara arrive in Meereen.

Director: Miguel Sapochnik | Stars: Peter Dinklage, Kit Harington, Emilia Clarke, Liam Cunningham

Votes: 183,639

39. Sleepy Hollow (2013–2017)
Episode: Blood Moon (2013)

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

7.5
Rate this
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  

Ichabod and Abbie hunt a resurrected witch who is leaving a trail of charred corpses in her wake.

Director: Ken Olin | Stars: Tom Mison, Nicole Beharie, Orlando Jones, Katia Winter

Votes: 1,192

40. The Chronicle (2001–2002)
Episode: Bring Me the Head of Tucker Burns (2001)

Comedy, Horror, Sci-Fi

6.6
Rate this
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  

Wes and Grace investigate the serial killings committed by a headless biker wearing a jack-o'-lantern helmet, who decapitates seemingly random people with his sword. Tucker and Kristen go on a date.

Director: Sanford Bookstaver | Stars: Chad Willett, Casey Biggs, Len Cordova, Elaine Hendrix

Votes: 7

41. Kolchak: The Night Stalker (1974–1975)
Episode: Chopper (1975)

TV-PG | 51 min | Horror, Mystery, Thriller

7.7
Rate this
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  

Land development disturbs the final resting place of a headless, sword-wielding cyclist who hunts down and beheads the rival gang bikers who killed him.

Director: Bruce Kessler | Stars: Darren McGavin, Simon Oakland, Larry Linville, Art Metrano

Votes: 254

42. Sleepy Hollow (2013–2017)
Episode: Deliverance (2014)

TV-14 | 44 min | Action, Adventure, Crime

7.4
Rate this
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  

Abbie and Ichabod learn that Katrina is in imminent danger and race against the clock to help her.

Director: Nick Copus | Stars: Tom Mison, Nicole Beharie, Orlando Jones, Katia Winter

Votes: 527

43. Sleepy Hollow (2013–2017)
Episode: Freedom (2017)

TV-14 | 44 min | Action, Adventure, Crime

7.8
Rate this
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  

Dreyfuss finally garners enough power to infiltrate the White House, and his group of minions grow strong enough to take action. Can Team Witness stop Dreyfuss in time.

Director: Russell Lee Fine | Stars: Tom Mison, Janina Gavankar, Lyndie Greenwood, Jerry MacKinnon

Votes: 252

44. Wishbone (1995–1998)
Episode: Halloween Hound: The Legend of Creepy Collars: Part 1 (1997)

TV-Y7 | Adventure, Comedy, Family

9.1
Rate this
    1 2 3 4 5 6 7 8 9 10 9.1/10 X  

"The Legend of Sleepy Hollow' dominates as Halloween comes to Oakdale. Wishbone imagines himself as Ichabod Crane while Joe and his two schoolmates participate in Oakdale's scavenger hunt.

Stars: Soccer the Dog, Larry Brantley, Jordan Wall, Christie Abbott

Votes: 15

45. Wishbone (1995–1998)
Episode: Halloween Hound: The Legend of Creepy Collars: Part 2 (1997)

TV-Y7 | Adventure, Comedy, Family

9.0
Rate this
    1 2 3 4 5 6 7 8 9 10 9/10 X  

Wishbone and the gang participate in Oakdale's first annual Halloween scavenger hunt, complete with a haunted house.

Director: Rick Duffield | Stars: Soccer the Dog, Larry Brantley, Jordan Wall, Christie Abbott

Votes: 26

46. Ghost Whisperer (2005–2010)
Episode: Head Over Heels (2009)

TV-PG | 44 min | Drama, Fantasy

7.4
Rate this
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  

The Headless Horseman from the Legend of Sleepy Hollow is haunting Melinda and when the legendary book mysteriously shows up at Aiden's school Melinda becomes worried for Aiden's safety.

Director: Steven Robman | Stars: Jennifer Love Hewitt, David Conrad, Christoph Sanders, Jamie Kennedy

Votes: 117

47. Bat Pat (2015–2016)
Episode: Headless Houseguest (2015)

TV-Y | 12 min | Animation

Rate this
    1 2 3 4 5 6 7 8 9 10 -/10 X  

Everyone's peaceful Halloween is disturbed by a galloping horseman riding through Fogville terrorizing trick-or-treaters. Rebecca's determined to solve the mystery and discovers that the ... See full summary »

Star: Giles New

48. Sleepy Hollow (2013–2017)
Episode: Heads of State (2017)

TV-14 | 43 min | Action, Adventure, Crime

8.0
Rate this
    1 2 3 4 5 6 7 8 9 10 8/10 X  

One of Ichabod's greatest foes arrives in Washington to threaten the safety of the highest officials.

Director: Kellie Cyrus | Stars: Tom Mison, Janina Gavankar, Lyndie Greenwood, Jerry MacKinnon

Votes: 258

49. Sleepy Hollow (2013–2017)
Episode: Homecoming (2017)

TV-14 | 44 min | Action, Adventure, Crime

7.8
Rate this
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  

Ichabod and Jenny return to Sleepy Hollow to find the talisman before Dreyfuss does.

Director: Jim O'Hanlon | Stars: Tom Mison, Janina Gavankar, Lyndie Greenwood, Jerry MacKinnon

Votes: 238

50. South Park (1997– )
Episode: Imaginationland: Episode II (2007)

TV-MA | 22 min | Animation, Comedy

9.0
Rate this
    1 2 3 4 5 6 7 8 9 10 9/10 X  

With the help of Stan and Kyle, the military is able to access the portal to Imaginationland; Cartman goes to great lengths to get Kyle to suck his balls after the leprechaun bet.

Director: Trey Parker | Stars: Trey Parker, Matt Stone, Jonathan Kimmel, Mona Marshall

Votes: 2,730



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