Villains Wiki

Hi. This is Thesecret1070. I am an admin of this site. Edit as much as you wish, but one little thing... If you are going to edit a lot, then make yourself a user and login. Other than that, enjoy Villains Wiki!!!


Villains Wiki
Villains Wiki

This Villain was proposed and approved by Villains Wiki's Pure Evil Proposals Thread. Any act of removing this villain from the category without a Removal Proposal shall be considered vandalism (or a futile "heroic" attempt of redemption) and the user will have high chances of being terminated blocked. You cannot make said Removal Proposal without permission from an admin first.
Additional Notice: This template is meant for admin maintenance only. Users who misuse the template will be blocked for a week minimum.

This article's content is marked as Mature
The page Mature contains mature content that may include coarse language, sexual references, and/or graphic violent images which may be disturbing to some. Mature pages are recommended for those who are 18 years of age and older.

If you are 18 years or older or are comfortable with graphic material, you are free to view this page. Otherwise, you should close this page and view another page.

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


This version of the headless horseman is unlike most other versions in that he was a child serial killer named Calvin Montgomery even before becoming the horseman. He was also a Satan worshipper and would sacrifice multiple children to him to become stronger. Eventually, a priest defeats him and he ends up hanging in the town until his head comes off. He would make a deal with Satan that he would take the heads of seven to get his own back.

For nearly a century he has been doing 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 to prevent Satan and Headless from stealing the town.

During the events of the film, the group of teens would shows up. He first murders Seth and beheads him. He then murder Tiffany and Doc and picks of nearly all the teens until only Candy, Liam, and Ava are alive. He's defeated when the bridge is burned, engulfing the entire town and making him dissapear.


This version of the Headless Horseman much like most versions is unable to speak and shows very little emotion. Unlike most versions though he was already evil before becoming the horseman and does show some hints of sadism.


  • This version of the Headless Horseman is different from most with the fact he was already evil before losing his head and becoming the horseman.


           Sleepy Hollow logo.png|Villains

Headless Horseman

The Adventures of Ichabod and Mr. Toad: Headless Horseman
Sleepy Hollow (1999): Lady Van Tassel | Headless Horseman | Reverend Steenwyck
Headless Horseman (2007): Headless Horseman | Satan

Moloch | Henry Parrish | Hidden One | Malcolm Dreyfuss

Moloch's Servants & Horsemen
Ancitif | Andy Brooks | Demons | Four Horsemen of the Apocalypse | Conquest | Headless Horseman | Famine | Hessians (Gunthur) | War | 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

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