The Legend of Sleepy Hollow

The Legend of Sleepy Hollow (1949) is a Disney animated short you can watch online on iFILM, directed by Clyde Geronimi and Jack Kinney. At just 37 minutes, it adapts Washington Irving's famous tale of gangly schoolteacher Ichabod Crane — a newcomer to a quiet Dutch-American town who falls for the prettiest girl around and then, on one dark autumn road, meets the Headless Horseman. Bing Crosby narrates the whole thing in a tone that sits perfectly between playful and unsettling. It's the kind of Halloween classic that works on kids and adults at the same time — spooky enough to stick in memory, light enough to revisit every autumn. Stream The Legend of Sleepy Hollow (1949) online on iFILM.