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The Night of the Headless Horseman - Watch Legally and Safely

The Night of the Headless Horseman

Countries: United States,
Release Date: October 28, 1999
Year: 1999
Runtime:63 min
IMDb Rating:

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 Brom Bones, who will stop at nothing to win her. Ichabod thinks that Brom is his biggest obstacle, but to his surprise, there is someone — or something — else out there who will change his life forever.

How to Watch The Night of the Headless Horseman Legally and Safely

If you want to stream The Night of the Headless Horseman through reputable and legal services, there are a few good options depending on where you are. Subscription platforms like HBO Max, Disney+, Netflix, Amazon Prime Video, and Apple TV+ sometimes carry The Night of the Headless Horseman films or related DC titles—though availability depends on your country.

If you’d rather not commit to a subscription, there are ad‑supported, free (but legal) platforms such as Tubi, Pluto TV, Peacock or Crackle (where available in your region) that occasionally host superhero films.

Lastly, don’t forget about library‑linked streaming options like Kanopy or Hoopla (if your library or university is registered), and official uploads by film distributors on YouTube—these can also give you legal access to classic movies.

Clancy Brown     , Tia Carrere     , Jeff Bennett