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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.
Moloch's Servants & Horsemen