The headless horseman rides again.
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, inherit her father's rich estate. Her suitor Brom Bones, the blacksmith, wants to scare him away and dresses up as the legendary Headless Horseman. During the prank, the real ghost appears and drives Ichabod off
The Legend of Sleepy Hollow (1999) is a fantasy, horror and mystery film directed by Pierre Gang, released on October 23, 1999 with a runtime of 1h 45m. It stars Brent Carver, Rachelle Lefevre, Vlasta Vrana and Kathleen Fee. Viewers rate it 5.9 out of 10 across 26 ratings.
Brent Carver
as Ichabod Crane
Rachelle Lefevre
as Katrina Van Tassle
Vlasta Vrana
as Mr. Van Tassle
Kathleen Fee
as Mrs. Van Tassle
Paul Lemelin
as Brom Bones
Michel Perron
as Mr. Van Ripper
Dawn Ford
as Mrs. Van Ripper
Lisa Bronwyn Moore
as Mrs. Van Ecke
Richard Jutras
as Mr. Van Ecke
Samuel Holden
as Ernest Van Ecke
Michael Rudder
as Pastor Van Der Veen
Danette MacKay
as Mrs. Van Der Veen
Directed by Pierre Gang, written by Washington Irving and Joe Wiesenfeld, produced by Danièle Rohrbach.
Average viewer score of 5.9/10 from 26 ratings.
**_The television version is faithful to the classic tale compared to Depp’s “Sleepy Hollow”_** In 1791, a charismatic but pompous schoolmaster from Hartford, Ichabod Crane (Brent Carver), arrives in the hamlet of Tarrytown, 26 miles north of Manhattan. He wastes no time in vying for the hand of the lovely Katrina (Rachelle Lefevre), but is opposed by the blacksmith, Brom Bones (Paul Lemelin). In the background is…
Reviewed on April 17, 2025
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The Legend of Sleepy Hollow (1999) is available to stream on Amazon Prime Video, fuboTV, Cineverse, Midnight Pulp, Amazon Prime Video with Ads, Midnight Pulp Amazon Channel, Cineverse Amazon Channel and Howdy Amazon Channel, and to rent or buy from Amazon Video. Streaming availability is checked against JustWatch data and can change by region.
The main cast of The Legend of Sleepy Hollow (1999) includes Brent Carver, Rachelle Lefevre, Vlasta Vrana, Kathleen Fee and Paul Lemelin. The film was directed by Pierre Gang. You can see the full cast and crew list, with character names, further up this page.
The Legend of Sleepy Hollow was released on October 23, 1999 and runs for 1h 45m.
The Legend of Sleepy Hollow (1999) holds an average rating of 5.9 out of 10 from 26 viewer votes, and is a good pick if you enjoy fantasy, horror and mystery films. Read the viewer reviews on this page to decide for yourself.
