Most Popular Headless Horseman Movies and TV Shows
- Movies or TV
- IMDb Rating
- Instant Watch Options
- In Theaters
- On TV
- Release Year
1. Gladiator (2000)
R | 155 min | Action, Adventure, Drama
A former Roman General sets out to exact vengeance against the corrupt emperor who murdered his family and sent him into slavery.
Votes: 1,259,152 | Gross: $187.71M
2. 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.
Votes: 314,032 | Gross: $101.07M
3. 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.
4. The Adventures of Ichabod and Mr. Toad (1949)
Approved | 68 min | Animation, Comedy, Family
An animated adaptation of "The Wind in the Willows" followed by an adaptation of "The Legend of Sleepy Hollow".
7. Scooby-Doo Meets the Boo Brothers (1987 TV Movie)
Not Rated | 93 min | Animation, Comedy, Family
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 »
8. Headless Horseman (2007)
R | 87 min | Horror
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.
9. The Curse of the Cat People (1944)
Approved | 70 min | Drama, Horror, Mystery
The young, friendless daughter of Oliver and Alice Reed befriends her father's dead first wife and an aging, reclusive actress.
10. Scooby-Doo and the Goblin King (2008 Video)
Not Rated | 75 min | Animation, Adventure, Comedy
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.
11. 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 can marry her, ultimately, ... See full summary »
13. The Hollow (2004 TV Movie)
R | 83 min | Fantasy, Horror, Thriller
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 »
14. 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.
15. Lego Scooby-Doo!: Haunted Hollywood (2016 Video)
Not Rated | 75 min | Animation, Comedy, Family
The Scooby gang try to rescue an old movie studio, which is not only threatened by developers, but a series of movie monsters too.
16. 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 »
17. The Smurfs: The Legend of Smurfy Hollow (2013 TV Short)
G | 22 min | Animation, Short, Comedy
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 »
18. Disney's Halloween Treat (1982 Video)
Unrated | 47 min | Animation, Family
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."
19. 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?
20. The Night of the Headless Horseman (1999 TV Movie)
63 min | Animation, Horror
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 »
21. Curse of the Headless Horseman (1972)
PG | 75 min | Horror
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.
22. The Headless Horseman (1922)
Not Rated | 68 min | Comedy, Drama, Horror
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 »
26. The New Misadventures of Ichabod Crane (1979 TV Movie)
30 min | Animation, Family
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.
27. The Haunted Pumpkin of Sleepy Hollow (2003 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.
28. Ichabod! (2004)
70 min | Family, Musical
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 »
32. Andrew Sawyer's Ichabod (2007)
45 min | Romance
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 »
34. 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 »
Game of Thrones (2011–2019)
Battle of the Bastards
TV-MA | 60 min | Action, Adventure, Drama
Jon and Sansa face Ramsay Bolton on the fields of Winterfell. Daenerys strikes back at her enemies. Theon and Yara arrive in Meereen.
The Chronicle (2001–2002)
Bring Me the Head of Tucker Burns
Comedy, Horror, Sci-Fi
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.
Kolchak: The Night Stalker (1974–1975)
TV-PG | 51 min | Horror, Mystery, Thriller
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.
Sleepy Hollow (2013–2017)
TV-14 | 44 min | Action, Adventure, Crime
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.
Halloween Hound: The Legend of Creepy Collars: Part 1
TV-Y7 | Adventure, Comedy, Family
"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.
Halloween Hound: The Legend of Creepy Collars: Part 2
TV-Y7 | Adventure, Comedy, Family
Wishbone and the gang participate in Oakdale's first annual Halloween scavenger hunt, complete with a haunted house.
Ghost Whisperer (2005–2010)
Head Over Heels
TV-PG | 44 min | Drama, Fantasy
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.
Bat Pat (2015–2016)
TV-Y | 12 min | Animation
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
Sleepy Hollow (2013–2017)
Heads of State
TV-14 | 43 min | Action, Adventure, Crime
One of Ichabod's greatest foes arrives in Washington to threaten the safety of the highest officials.
South Park (1997– )
Imaginationland: Episode II
TV-MA | 22 min | Animation, Comedy
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.