Headless Horseman is a film that aired on the Sci Fi Channel in October 27, 2007, based on the legend of the Headless Horseman. The movie takes the tack that the Washington Irving story was the "white-washed" version and the events in this horror film is the real story. It stars Richard Moll and Billy Aaron Brown and is directed by Anthony C. Ferrante.
After going through the woods on the way to a party, seven teenagers stumble upon a town called Wormwood Ridge. The townspeople are celebrating a Headless Horseman ceremony, which unbeknownst to the teenagers requires human heads from young people. The teens, with the help of a young tow-truck driver named Candy (who is initially on the town's side, but later feels guilty and decides to help the teens), attempt to escape the town before they are killed.
Tropes used in Headless Horseman include:
- Adaptational Villainy: The Headless Horseman from the original tale was portrayed as an enigmatic figure with very little hints on his background and was only used for scare effect. Here he was a Satan worshiper and child murderer and his evil personality is still intact as the Horseman.
- Badass Preacher: Calvin Montgomery (the man who would later be resurrected as the Headless Horseman) was a child murdering Satan worshiper. He was finally taken down by a priest who took Calvin's sword, doused it in holy water, and used it to kill him.
- Bear Trap: A bear trap buried in the road shreds the tires of the teens' van. They later discover the woods are lined with bear traps to stop the sacrifices from escaping. Tiffany falls on one and is decapitated.
- A Bloody Mess: When the van crashes, Tiffany thinks she has a head wound and worries that she is going to have a scar. When Doc examines the 'wound', he discovers the 'blood' is actually red nail polish from when she was painting her toenails.
- Camera Fiend: Lizzie. Through the opening scenes, she is shown taking photos of anything and everything. She only stops when the inhabitants of Wormwood steal her camera.
- Cannot Cross Running Water: Headless cannot cross running water. As the town of Wormwood Ridge is surrounded by a deep gorge—accessible only by two bridges—this means he cannot leave the town, and the townsfolk have to lure in victims for him.
- Car Fu: Candy runs over Pa Rusk with the tow truck when he tries to stop him from leaving town.
- Nash tries to run Headless down with a convertible, resulting in Headless leaping over the car and decapitating him in mid-air in his most badass kill.
- Cavalry Betrayal: While trying to escape Wormwood Ridge, the teens flag down the sheriff's cruiser. Sheriff Otis invites them in and promises to get them to safety. However, he is part of the conspiracy and goes to deliver them back to town.
- Cobweb Jungle: The inside of the Headless's cellar is shrouded in cobwebs.
- Combat Tentacles: When the Headless Horseman's head is starting to reform, it initially manifests as a writhing mass of tendril which Headless uses to grab hold of Ava.
- Cut Himself Shaving: The explanation Pa Rusk gives when Sheriff Buck asks him his head his covered in blood.
- Deadly Disc: In the prologue, Headless decapitates a Confederate soldier with a razor edged disc.
- Defector from Decadence: Candy, who decides that she has had enough of Wormwood's murdering ways and helps the teens escape on the proviso that they take her with them. It is also revealed that she is the only person in town who is not a descendant of Calvin Montgomery.
- Depraved Dwarf: The clan of murderous inbred rednecks in Wormwood Ridge includes several dwarfs. One of them, known as 'the Rag Doll Man', makes rag dolls and then chops their heads off to represent the travellers who have lost their heads to the Horseman.
- Distant Prologue: The film opens during The American Civil War when two Confederate soldiers guarding a bridge are attacked by Headless. The film then jumps ahead about 150 years to a group of teens on a road trip to attend a Halloween party.
- The Ditz: Tiffany. After Doc discovers that the 'blood' on her forehead is really red nail polish, her reaction is an astounded "Oh! So that's why it didn't hurt!"
- Epic Flail: When the teens are attempting to escape through the woods, Headless attacks them from horseback wielding a morning star. He knocks down Tiffany who falls on a Bear Trap and is decapitated.
- Extremely Short Time Span: Barring the prologue (which plays out in Real Time on one night during The American Civil War), the film occurs over one Halloween.
- Fingore: Seth raises his hand in an attempt to ward of the Horseman's axe. Instead, it cuts off his fingers.
- Headless Horseman: Every seven years, Calvin Montgomery rises from the grave on Halloween as a Headless Horseman.
- Hellgate: There is a bubbling spring in Calvin Montgomery's cellar. This was where he used to place the bodies of his victims when he was human murderer. After being transformed into the Headless Horseman, he delivers the heads of his victims here to keep his pact with Hell.
- Hillbilly Horrors: A van full of teenagers stumbles into Wormwood Ridge: a Town with a Dark Secret south of the Mason-Dixon line that is not marked on the maps. The town is populated entirely by the descendants of a child-murdering Satan worshiper and has suffered from considerable inbreeding. Every seven years they lure in sacrifices for the Headless Horseman to keep the bargain with Hell intact.
- Horror Doesn't Settle for Simple Tuesday: Calvin Montgomery rises as a Headless Horseman every seven years on Halloween.
- Identical Grandson: Sgt. Mosby Rusk is identical to his descendant Pa Rusk. Possibly justified as the Rusk family is drawing from a very limited gene pool.
- It Works Better with Bullets: Nash grabs Sheriff Otis's gun out of his holster and points out the sheriff. When the sheriff draws his backup piece, Nash pulls the trigger several times only for nothing to happen. Otis then points out that the revolver is a single-action and that it has to be cocked before it will fire.
- Jack Bauer Interrogation Technique: Lizzie extracts the information the group needs from Kolchak by hitting him in the knee with a hammer till he tells them what they want to know.
- My Horse Is a Motorbike: Liam and Lizzie lock the Headless Horseman inside the garage and set fire to it. After the garage explodes in a fireball, Headless comes crashing out through the doors on a motorbike.
- Off with His Head!: Headless makes all of his kills by decapitation.
- Ow, My Body Part!: Kolchak Jefferson Stillwall at one point when he gets hit in the kneecap by a metal hammer.
- Punk in the Trunk: Seth attempts to hide from the Horseman in the trunk of a junked car. Unfortunately, he keeps his head out, so the Horseman jumps on the trunk, causing it to close and decapitate him.
- Reusable Lighter Toss: Liam spreads gasoline around Rusk's garage and then lights it by tossing Doc's lighter inside.
- Scary Scarecrows: In the prologue, the confederate private walks past a scarecrow only to stop and realize it is the headless body of the scout. Later, Headless poses as a scarecrow to terrify the teens. Doc questions why there is a scarecrow in the middle of a forest. When he turns around, the scarecrow pole is empty.
- Shoot the Fuel Tank: The sheriff shoots the gas tank of his own truck to stop the teens escaping: blowing up the truck and killing himself in the process.
- Shortcuts Make Long Delays: Seth, at Tiffany's urging, decides to take a shortcut to the Halloween party along a road that is not on the GPS, claiming it will knock two hours of their journey. Instead, it gets them stranded in Wormwood Ridge, a Town with a Dark Secret.
- Sinister Scythe: When Liam attacks Headless with the holy sword, Headless defends himself by wielding a pair of sickles.
- Stingy Jack: More than once, Headless appears with a jack-o-lantern in place of his head. Destroying the gourd does nothing to slow him down.
- Suggestive Collision: When the van blows a tire and runs off the road, Liam and Ava are thrown off the seat and end up lying on top of each other. They both comment, awkwardly, on this situation.
- Town with a Dark Secret: Wormwood Ridge is populated entirely by the descendants of a child-murdering Satan worshiper. Every seven years they lure in sacrifices for the Headless Horseman to keep the bargain with Hell intact.
- *Twang* Hello: Headless announces his presence at one point by throwing a knife through the radio Liam is holding in his hand and pinning it to a tree.
- When the Clock Strikes Twelve: Headless has until midnight on All Hallows Eve to deliver the seven heads of his victims. If he fails, Hell will claim him and the entire town.
- When the Planets Align: The Horseman rises once every seven years on All Hallows Eve when the entirety of the constellation Hydra is visible in the sky.
- Would Hurt a Child: Calvin Montgomery was a child-murdering Satan worshiper before being killed and resurrected as the Headless Horseman.
