|Signature villain||Headless Horseman|
|Setting:||Sleepy Hollow, New York|
Sleepy Hollow is a 1999 American period horror film directed by Tim Burton. It is a film adaptation loosely inspired by the 1820 short story "The Legend of Sleepy Hollow" by Washington Irving and stars Johnny Depp, Christina Ricci, Miranda Richardson, Marc Pickering, Michael Gambon, Jeffrey Jones, Casper Van Dien, Ian McDiarmid, Michael Gough, and Christopher Walken. The plot follows police constable Ichabod Crane (Depp) sent from New York City to investigate a series of murders in the village Sleepy Hollow by a mysterious Headless Horseman. It is also the first film by Mandalay Pictures.
Development for Sleepy Hollow began in 1993 at Paramount Pictures with Kevin Yagher originally set to direct Andrew Kevin Walker's script as a low-budget slasher film. Disagreements with Paramount resulted in Yagher being demoted to prosthetic makeup designer, and Burton was hired to direct in June 1998. Filming took place from November 1998 to May 1999, and Sleepy Hollow was released to generally favorable reviews from critics, and grossed approximately $207 million worldwide. Production designer Rick Heinrichs and set decorator Peter Young won the Academy Award for Best Art Direction.
In 1799, New York City police constable Ichabod Crane is dispatched by his superiors to the Westchester County hamlet of Sleepy Hollow, New York, to investigate a series of brutal slayings in which the victims have been found decapitated. A pioneer of new, unproven investigative techniques such as finger-printing and autopsies, Crane arrives in Sleepy Hollow armed with his bag of scientific tools only to be informed by the town's elders that the murderer is not of flesh and blood, rather a headless supernatural warrior from beyond the grave who rides at night on a massive black steed.
Crane begins his own investigation, remaining highly skeptical about the supernatural elements in the case until he encounters the Headless Horseman himself. Boarding a room at the home of the town's richest family, the Van Tassels, Crane develops an attraction to their daughter Katrina, while he is plagued by nightmares of his mother's horrific torture when he was a child. Delving further into the mystery with the aid of the orphaned Young Masbath, whose father was a victim of the Horseman, Crane discovers within the Western Woods the Horseman's grave, as well as his entry point into the natural world from the supernatural — the gnarled Tree of the Dead.
Crane finds the Horseman's skull is missing, though the murders continue until Crane uncovers a murky plot revolving around revenge and land rights with the Horseman controlled by Katrina's stepmother Lady Van Tassel, who sends the killer after Katrina now to solidify her hold on what she considers her property, a piece of land unjustly claimed by Katrina's father. Following a fight in the local windmill and a stagecoach chase through the woods, Crane eventually thwarts Lady Van Tassel by returning the skull to the Horseman, who regains his head and heads back to Hell along with his enslaver. With his job in Sleepy Hollow over, Crane, with Katrina and Young Masbath, returns to New York (where he describes as where "the Bronx is up and the Battery is down..."—Tim Burton's nod to the song "New York, New York (On the Town)" by Leonard Bernstein), in time for the new century.
- Johnny Depp as Ichabod Crane: His belief in improved methods of justice, new investigative techniques and scientific procedures is resented by his superiors, who dispatch him north to the Hudson Valley and the small town of Sleepy Hollow.
- Christina Ricci as Katrina Van Tassel: Ichabod's love interest and only heir to one of the neighborhood's richest farmers.
- Miranda Richardson as Lady Van Tassel/Crone Sister: Wife of Baltus and stepmother of Katrina. She serves as the main antagonist who has enlisted the Headless Horseman to help kill her stepdaughter and anyone who gets in the way.
- Marc Pickering as Young Masbath: An orphan who looks towards Ichabod as a father figure after his own father is murdered by the Horseman.
- Sir Michael Gambon as Baltus Van Tassel: Katrina's father. After Peter Van Garret is murdered, he is placed as the leader of the city.
- Jeffrey Jones as Reverend Steenwyck: The town preacher.
- Casper Van Dien as Brom Van Brunt: A strong and arrogant aristocratic man who is somewhat romantically involved with Katrina.
- Ian McDiarmid as Doctor Lancaster: The town doctor and surgeon in the village.
- Michael Gough as Notary Hardenbrook: The town banker and possibly the oldest citizen in the town.
- Christopher Walken as The Headless Horseman: A brutal and sadistic Hessian mercenary sent to America during the American Revolutionary War who loses his head during battle.
- Claire Skinner as the Midwife Beth Killian: The town's Midwife.
- Steven Waddington as Killian: Beth's husband.
- Richard Griffiths as Magistrate Philipse: The town's magistrate.
- Sir Christopher Lee as the Burgomaster: Sends Ichabod to investigate the murders at Sleepy Hollow.
- Alun Armstrong as the High Constable
- Martin Landau as Peter Van Garrett: Has no dialogue; and is murdered by the Headless Horseman in the opening scene.
- Lisa Marie as Lady Crane: Ichabod's mother (in flashbacks) who was involved in witchcraft and later painfully murdered by his strict religious father.
- Peter Guinness as Lord Crane: Ichabod's father (in flashbacks) who was a devoutly religious man who tortured and killed his wife after he found her practicing witchcraft.