Watch Sleepy Hollow (1999): stream Sleepy Hollow (1999) on Hoopla, Kanopy, or rent on JustWatch TV. Compare all streaming options for this movie on WhereCanIWatch.tv.
Sleepy Hollow
Heads will roll.
Top Pick
Free on Hoopla
HD · Included
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You can watch Sleepy Hollow (1999) for free on Hoopla, or rent on JustWatch TV.
Skeptical young detective Ichabod Crane gets transferred to the hamlet of Sleepy Hollow, New York, where he is tasked with investigating the decapitations of three people – murders the townsfolk attribute to a legendary specter, The Headless Horseman.
Sleepy Hollow is a film that explores themes of small town, steampunk, police detective. It also touches on new york state and skeptic and autumn.
Trailer
Director
Tim Burton
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3 options ranked by value · 🇺🇸 United States
Last verified 12 hours ago
Sleepy Hollow
Heads will roll.
You can watch Sleepy Hollow (1999) for free on Hoopla, or rent on JustWatch TV.
IMDb
7.2/10
RT Critics
71%
RT Audience
80%
Metacritic
Director
Tim Burton
3 options ranked by value · 🇺🇸 United States
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small town · steampunk · police detective · new york state · skeptic · autumn · 19th century · headless horseman
Watch Sleepy Hollow for free on Hoopla. Watch Sleepy Hollow for free on Kanopy. Rent Sleepy Hollow on JustWatch TV. Availability last verified May 31, 2026.