The Headless Horseman is often cited as being, along with the Firebird in Fantasia 2000 (1999), The Horned King in The Black Cauldron (1985), and Chernabog in Fantasia (1940), as one of the scariest villains in the Disney canon. Disney still receives complaints from parents about the character frightening their children.
Ichabod Crane and Brom Bones later became the inspiration for the characters of Lumiere (in human form, possibly) and Gaston in Beauty and the Beast (1991).
The song "Headless Horseman" is considered one of the darkest songs written for a Disney film. It, much like "Worthless" from The Brave Little Toaster (1987) and "Hellfire" from The Hunchback of Notre Dame (1996), was nearly cut from the film.
While the characters are fictional, the place names and landmarks depicted in "The Legend of Sleepy Hollow" (1820) are mostly factual. The "Tarry Town" of the short story is the village of Tarrytown in Westchester County, New York. It was founded by Dutch settlers in the 17th century. It is located about 25 miles (40 km) north of midtown Manhattan in New York City. Some of the other landmarks are located in the nearby village of North Tarrytown, which was long nicknamed Sleepy Hollow and was officially renamed to this name in 1996. Washington Irving himself was buried in the Sleepy Hollow Cemetery.
When shown on American television in 1977 shortly after the death of Bing Crosby, the end credits included a frame noting his passing and contribution as narrator/singer.