In 1799, a New York City police constable is sent to the upstate village of Sleepy Hollow, which is suffering from a series of brutal decapitations. Dead are a wealthy father and son, Peter and Dirk Van Garrett, and the widow Emily Winship. Crane is met by the town elders, including the wealthy businessman Baltus Van Tassel (Michael Gambon), the Reverend Steenwyck (Jeffrey Jones), town notary James Hardenwyck (Michael Gough), and the magistrate Samuel Philipse (Richard Griffiths). They assure Crane that the killer is the undead apparition of a headless Hesian mercenary from the Revolutionary War.
Ichabod Crane, however, is a scientist and skeptical of all things paranormal. He boards with Baltus Van Tassel and his second wife Lady Van Tassel (Miranda Richardson) and takes a shine to Van Tassel’s daughter from a previous marriage, Katrina, (Christina Ricci). When Jonathan Masbath (Mark Spalding), a servant of the Van Garretts, is killed, Crane takes the victim’s son (Mark Pickering) under his wing. They exhume the victims and learn that the widow died pregnant. Philipse is the next to be killed.
Young Masbath, Ichabod Crane, and Katrina enter the Western Woods to search for the Horseman’s grave. They find a crone witch (also Miranda Richardson) who tells them the Horseman’s grave is at the Tree of the Dead. Crane digs it up and finds the skull missing, and he believes it is being used by someone to control the Horseman. The tree is the portal between the Beyond and the living world and the Horseman will not stop taking people’s heads until his is returned.
The Horseman (Christopher Walken) kills the midwife Beth Killian (Claire Skinner) and her family, and Katrina’s suitor Brom Van Brunt (Casper Van Dien). Crane is wounded but survives. He believes the Horseman is attacking people involved in a conspiracy. Hardenbrook reveals that the first victim, Peter Van Garrett, had secretly married the widow, and left his estate to her and her unborn child. He decides that all of the victims except Brom were beneficiaries or witnesses to the will, and the master of the Horseman is he who would otherwise have inherited--Baltus, a relative of the Van Garretts.
Katrina burns the evidence, Hardenbrook commits suicide, and Steenwyck holds a town meeting to discredit Ichabod Crane. But Baltus bursts in to announce that the Horseman has killed Lady Van Tassel. The Horseman attacks the church but cannot enter. The elders all turn on each other.
Stanwyck kills Lancaster and is then killed by Baltus, who is harpooned and beheaded by the Horseman. Ichabod discovers that the diagram Katrina drew beneath his bed and in the church was not to summon the Horseman but as a protection from him. Lady Van Tassel, alive and well, reveals herself as the master of the Horseman. She faked her death and killed the Van Tassel servant girl to pass her body off as her own.
She takes Katrina to the windmill and summons the Horseman to behead her. It seems she and her sister were members of the poor Archer wing of the family, who pledged themselves to Satan if he would raise the Horseman. She used fear, blackmail, and lust to fool and manipulate everyone, and gradually eliminated everyone in her way but Katrina. Crane and Masbath rush to the windmill as the Horseman arrives. The windmill is destroyed and they race to the Tree of the Dead. Ichabod arrives with the Horseman’s skull, which he gives to the Horseman, who spares Katrina and abducts Lady Van Tassel down to Hell with a kiss. Ichabod returns to New York with Katrina and young Masbath just as the 19th Century dawns.
The film was directed by Tim Burton, loosely based on Washington Irving’s 1830 short story The Legend of Sleepy Hollow. It began as a low-budget slasher film to be directed by Kevin Yagher from a script by Andrew Kevin Walker, but it became a more ambitious project under Tim Burton and was ultimately praised by critics for performance, direction, screenplay, and the powerful musical score by—who else?—Danny Elfman. It won the Oscar for Best Art Direction. Upstate New York and Sturbridge, Massachusetts were scouted for locations but they ended up building an entire town in the U.K. Queen Elizabeth’s hunting party rode through the set at one point, because it had been built on the Royal Hunting Grounds. Production designer Rick Heinrichs created the creepy, foreboding landscape. ILM did most of the 150 visual effects shots.
When Johnny Depp learned that Goldeneye, Ichabod Crane’s horse in the film, was to be put down, he adopted it. Christopher Walken did not know how to ride and had to learn that skill for the movie. There was in fact a real Hessian soldier buried in the real Sleepy Hollow by the real Van Tassel family. Various scenes were filmed as an homage to Disney’s animated version of the story. Michael Gough came out of retirement to play Hardenbrook. There was a short cameo by Christopher Lee, as a nod to Hammer Films. Ichabod Crane faints five times, Katrina twice. In the opening scene, Martin Landau is riding in a Landau. There are 18 decapitations in the movie, two of them children. Christopher Lee said that this film changed his career, leading him to play Saruman in Lord of the Rings and Count Dooku in the Star Wars films. Johnny Depp carries it off and Christopher Walken, though not on the screen very long, is wonderful to watch.