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It all started with this man, a long, long time ago, Calvin Montgomery. He tortured the young people of Wormwood Ridge, he would take them to his cellar, and when he was done with them, it was off with their head. The ritual, so he collected the young ones in his jail, they became his family, until they reached a certain age, then they were sent to the pit.
~ Candy about Calvin when he was still human.

Calvin Montgomery, better known as the Headless Horseman, was the titular main antagonist of the 2007 horror film, Headless Horseman that was based on the novel, The Legend of Sleepy Hollow. As a human, Calvin was a serial killer who preyed on children before he was killed and transformed into the Headless Horseman where, every seven years, he would then rise in order to collect seven heads to regrow his own.

History[]

That version of the Headless Horseman was a child serial killer who was named Calvin Montgomery even before he became the Horseman. He was also a Satanist and sacrificed multiple children to him in order to become stronger. Eventually, a priest defeated him and Calvin ended up hanging in the town until his head came off. He then made a deal with Satan that he would take the heads of seven people in order to get his own back.

For nearly a century, he did exactly that. Most of the good townsfolk left so all that was left was Calvin's Children and they would assist him in his quest for seven heads in order to prevent Satan and the Headless Horseman from stealing the town.

During the events of the film, a group of teens showed up. The Horseman first murdered Seth and beheaded him. He then murdered Tiffany and Doc and picked off nearly all of the teens until only Candy, Liam, and Ava were left standing. He's then defeated when the bridge was burned, which engulfed the entire town and made him disappear.

Personality[]

That version of the Headless Horseman was much like most versions: He was unable to speak and showed very little emotion. Unlike most versions though, that Horseman showed some hints of sadism.

External Links[]

Navigation[]

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Book
Headless Horseman

Movies
The Adventures of Ichabod and Mr. Toad: Headless Horseman | Brom Bones
Sleepy Hollow (1999): Lady Van Tassel | Headless Horseman | Reverend Steenwyck | Lord Crane
The Haunted Pumpkin of Sleepy Hollow (2003): Headless Horseman
Headless Horseman (2007): Headless Horseman | Satan

Television
Main
Moloch | Henry Parrish | Hidden One | Malcolm Dreyfuss

Moloch's Servants & Horsemen
Ancitif | Andy Brooks | Demons | Four Horsemen of the Apocalypse (Conquest | Headless Horseman | Famine | War) | Hessians (Gunthur) | Headless Horseman's Head | Gina Lambert | Lilith the Succubus | Order of the Blood Moon | Pied Piper | Serilda of Abaddon | Tree Monster

British Army
Abraham von Brunt | Banastre Tarleton | Benedict Arnold | William Howe

Hidden One's Servants
Pandora | Kindred

Dreyfuss Enterprises
Abraham von Brunt | Logan MacDonald | Helen Donovan | Jobe

Others
Atticus Nevins | Carmilla Pines | The Devil | Evil Frank Irving | Golem | James Colby | Katrina Crane | Leena Reyes | Mary Wells | Orion | Ro'kenhronteys | Solomon Kent | The Four Who Speak As One

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