This Walt Disney produced short has a bang-up ending to an otherwise saccharine story. Based on the tale by Washington Irving, this is only thirty three minutes long, and plays shorter. Bing Crosby is both the offscreen narrator and sings the lacking songs by Don Raye and Gene de Paul. Itinerant schoolmaster Ichabod Crane arrives in a small New York community. He is noticed about town, not only for his strange appearance but his penchant for constantly eating. He falls in love with Katrina Van Tassle, and her father's money-rich farmland. His rival for her affection is Bram, the local hunky bully. Ichabod attends a dance, where he and Bram vie for Katrina's hand. After a very funny slapstick sequence, Bram scares Ichabod with the story of the Headless Horseman. Ichabod rides out into the night, and sure enough the climax involves him and his slow plow horse trying to outrun the Horseman and his black steed.
Up until the dance, the film does not really gel. The songs are immediately forgettable, even with Crosby's voice behind them. The film works when it crosses into Warner Brothers' Loonie Tunes territory, as the physical comedy is very funny and makes up for the rest of the film. An example of weakness is the afterthought plot point that Crane is very superstitious. The pacing is very hurried, as if producer Disney did not want the kids to get bored before the final hilarious set-piece. A funny, but not perfect short animated piece, "The Legend of Sleepy Hollow" is goofy silliness in at least the last half.
