Washington Irving's "The Legend of Sleepy Hollow" is an American myth. Translated to film shortly after the birth of the movie industry, this short story became mythic through repeated retelling. Although two major films come immediately to mind--Disney's 1949 The Adventures of Ichabod and Mr. Toad and, fifty years later, Tim Burton's Sleepy Hollow--the tale has had a host of afterlives. We will explore these movies and many others, as well as television adaptations and even contemporary novels, in order to explore how this gothic, but comic, story became a cultural landmark. The early pairing of the legend with Halloween fueled the growth of both together. Burton's film brought the story back to the adult world of horror, opening the floodgates to new adaptations. In 2013 Fox Television aired Sleepy Hollow, a re-imagining of Ichabod Crane and Rip Van Winkle. Although lasting only four seasons, this new version spun off yet more inventive retellings that have not slowed since. This book explores unexpected connections between the many adaptations of this tale, weaving the story together anew for each generation.