In American folklore, how did the Headless Horseman originate? 1. In American folklore, how did the Headless Horseman originate?from the Brothers Grimmfrom the Legend of Sleepy Hollowfrom the Irish dullahanfrom the Legend of La Llorona Loading... See all quizzes. Share this:ShareFacebookTwitterPinterestLinkedIn Related Related posts: War Horse, the movie, starred a horse named what? What did the red pony in John Steinbeck’s book of the same name die of? What do you get when you cross an American Saddle Horse stallion to an Appaloosa mare? Horse Q of the Day: Racing