Hollywood unfurled a series of supernatural stories dealing with angels, demons, and the undead in 1999. The trend signaled the continuing interest of the public in mysteries that go beyond reason and science. That fascination was also behind Tim Burton's stylish and imaginative screen adaptation of Washington Irving's classic.

In the screenplay by Andrew Kevin Walker (Seven), Ichabod Crane (Johnny Depp) is not a rural teacher but a zealous New York City constable who is sent in 1799 to a small Hudson River community to help find the murderer who has beheaded three citizens. Upon his arrival, the townsfolk tell him the legend of the Hessian Horseman (Christopher Walken), a mercenary killed during the Revolutionary War who still scours the countryside at night seeking his head that was stolen from his grave.

Ichabod clings tenaciously to his scientific crime-solving techniques and disregards the superstitions of Sleepy Hollow's leaders who include Baltus Van Tassel (Michael Gambon), Doctor Lancaster (Ian McDiarmid), Magistrate Philipse (Richard Griffiths), Notary Hardenbrook (Michael Gough), and Reverend Steenwyck (Jeffrey Jones). However, when the Horseman beheads another victim right in front of him, the constable is unnerved. After regaining his composure, the rationalistic Ichabod ventures into the forest with young Masbath (Marc Pickering), an orphan who is the only one courageous enough to accompany him. Katrina (Christina Ricci), the daughter of Van Tassel, joins them later and brings along her white magic.

Sleepy Hollow vividly reveals the shadow side of this community where things are not what they seem to be. Ichabod's intrepid investigation eventually leads him to discover that the dread horseman is actually being summoned by a greedy and vengeful person in town. While tracking down the truth, the constable is forced again and again to confront a secret in his own past.