|“||The horseman was a Hessian mercenary, sent to these shores by German princes to keep Americans under the yoke of England, but unlike his compatriots who came for money, the Horseman came for the love of carnage. When battle was joined, there you'd find him. He rode a giant black steed named Daredevil. He was infamous for riding his horse hard into battle, chopping off heads at full gallop. He had filed his teeth down to sharp points to add to the ferocity of his appearance. This butcher didn't finally reach his end...until the year of '79, not far from here in our Western Woods. They chopped off his head with his own sword, even today the Western Woods is a haunted place, where brave men will not venture. For what was planted in the ground that day...was a seed of evil.||„|
|~ Baltus van Tassel describing the horseman and his past brutality.|
He starts out as a Hessian mercenary, sent to fight in the American Revolutionary War. However, unlike his companions who came in for money, the Hessian came for his love of carnage and has spent his years riding into battle with his horse Daredevil, chopping off the heads of American soldiers. It wasn't until the winter of 1779, as he is hiding from his enemies in the Western Woods after they shot down Daredevil (much to the Hessian's distraught), he encounters two little girls gathering up firewood. The Hessian calmly tells the girls to be quiet, but one of them (Mary Archer) gives him away by snapping a stick, alerting the American soldiers to his location and causing the other girl to flee away in fear. This resulted the Hessian to meet his death as the soldiers chopped off his head with his own sword. After witnessing the Hessian' death and burial by the soldiers, the young Mary sells her soul to the Devil so that she would raise the headless Hessian from the dead and use him to get revenge on the Van Garrett and Van Tassel families for driving her family out from their rightful home in Sleepy Hollow.
During the start of the film, he is seen being risen from the grave, but now headless, as he goes around chopping off heads of people in Sleepy Hollow. Upon his arrival, New York police constable Ichabod Crane (the protagonist of the film) soon learns that the skull from the Horseman's grave was dug out and stolen to to control him. He also learned that all of the victims (except for Brom Van Brunt, who was only killed by the Horseman in self-defense, since he wasn't chosen to be a victim) had special ties to the Van Tassel family and that the argument was over the land rights and fortune that the Van Tassel family have inherited. It wasn't until Baltus Van Tassel was killed, that the next morning, Ichabod suddenly realizes that Baltus' second wife Lady Van Tassel (who was actually a grown Mary Archer) was the one who was controlling the horseman into committing the murders.
Near the climax, Lady Van Tassel summons the Horseman again to murder her stepdaughter Katrina so that she can secure the entire fortune to herself, but Ichabod defeats her (with the help from young Masbath, whose father was a victim of the Horseman) and returns the skull back to the Horseman. After the head is restored back to its original form, the Horseman is now free from Lady Van Tassel's control, and he decides to spare Ichabod, Katrina, and Masbath. After reuniting with Daredevil, the Horseman spots the unconscious Lady Van Tassel, recognizing her as the little girl who betrayed him to his death years ago. Without hesitation, the Horseman angrily grabs Lady Van Tassel and gives her a bloody kiss, and he and Daredevil gallop themselves back to Hell, taking a screaming Lady Van Tassel in hopes to make her pay for her crimes.