10. The Headless Horseman is one of the few Disney villains to “win”.
9. It is unclear whether or not the Headless Horseman was a real ghost or was simply Brom Bones in disguise. The original short story written by Washington Irving suggests the latter more overtly than the film. The best evidence in the film to suggest that Brom pretended to be the Horseman is the similarity between the two characters horses
8. Thurl Ravenscroft was originally going to sing “The Headless Horseman”. His version of the song can be heard on the compilation CD, “Walt Disney Records Archive Collection, Vol. 1”.
7. Many fans have questioned whether or not Ichabod or Brom is the hero as Ichabod’s ultimate aim seems to be gaining Baltus Van Tassel’s fortune. Greed is a frequent villain’s motivation in Disney films.
6. The Headless Horseman is often cited as being, along with The Horned King in The Black Cauldron and Chernabog in Fantasia, as one of the scariest villains in the Disney canon. Disney still receives complaints from parents about the character frightening their children.
5. Brom Bones later became the inspiration for the character of Gaston in Beauty and the Beast.
4. 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 and “Hellfire” from The Hunchback of Notre Dame, was nearly cut from the film
3. One of Disney’s four “Package Films”. During World War II the studio lost a lot of manpower and resources, which left it with countless unfinished ideas too long for shorts and too short for features.
2. To save money on animation, Katrina was modeled closely after Grace Martin from Make Mine Music. She also greatly resembles Slue Foot Sue from the “Pecos Bill” segment of Melody Time.
1. Just before Brom spots Ichabod for the first time, as he’s drinking his beer, his socks suddenly change lengths for a few frames.