Sleepy Hollow (1999) Sleepy Hollow is a film surrounding the 1799 tale of the headless horseman. Icabod Crane, of the New York police, goes to the town to investigate several violent and unsolved murders. The public and town council reports to Crane that they fear that the horseman is responsible. Believing this explanation to be absurd, Crane searches for a more realistic answer. When he witnesses the horseman beheading one of the town counsel members, Crane immediately begins to buy into the tale and intends to discover how to put a stop to the murders.