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Film / Sleepy Hollow High

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Sleepy Hollow High is a 2000 American horror film, specifically a slasher film, directed by Chris Arth and Kevin Summerfield.

Five delinquent classmates must perform community service at Sleepy Hollow Park Grounds, a place notorious for vandalism and for many unsolved disappearances. As the afternoon unfolds, the students begin to realize that someone is taking the Legend of Sleepy Hollow too far, and that everyone is a suspect—from the teachers and counselors of Sleepy Hollow High to their classmates and each other. It is even possible that the legend itself is true.

Sleepy Hollow High contains examples of:

  • 1-Dimensional Thinking: Mr. E attempts to escape from the Horseman by running directly along the road ahead of him, instead of running into the woods on either side where the horse might have trouble following.
  • All Just a Dream: The entire film. A Dream Within a Dream, in fact. Except the beginning and the end. Maybe.
  • Badass Longcoat: The Horseman wears a long leather riding coat. Unfortunately, his badass-itude is somewhat undercut by the rest of his costume.
  • Black Dude Dies First: The first person to be murdered is a black jogger.
  • Couldn't Find a Pen: While Justin is undergoing Unwilling Suspension, Bobbi writes the word 'SNITCH' on his chest in chocolate syrup so it will attract rats.
  • Drawing Straws: The survivors draw straws to see which one is going to hike to the gas station to call for help. Mr. E draws the short straw.
  • Dream Within a Dream: Shannon has a dream where she goes on the work detail to Sleepy Hollow Park and is attacked by the Horseman. Just as she grabbed, she wakes up screaming in Mr. Breezo's class. After school, she goes to the park where the rest of the detail are murdered by the Horseman. Just as she is about to be killed, she wakes up screaming in Mr. Breezo's class.
  • Extremely Short Timespan: Starts at midnight (the radio announcer says its approaching the witching hour) and ends at the finish of the school day (the last scene is Shannon and Diana walking home after school).
  • Forgot to Mind Their Head: Justin is trying to fix his car when he hears Z and Bobbi coming up behind him. He lifts his head suddenly and bangs it on the hood of his car.
  • Headless Horseman: The film is set in Sleepy Hollow and the killer dresses as the Headless Horseman, complete with pumpkin mask.
  • Hellbent For Leather: The Horseman wears a black leather Badass Longcoat. His other sartorial decisions are more idiosyncratic.
  • Here We Go Again!: The final scene of the film implies that the events of the Dream Within a Dream might be about to kick off for real.
  • Horror Doesn't Settle for Simple Tuesday: The film takes place on Halloween.
  • Hot for Teacher: Diana was transferred from her previous school for making aggressive sexual advances on one of her teachers.
  • Immune to Bullets: Z shoots the Horseman and he falls over. He then gets back to his feet with no ill effects.
  • Off with His Head!: The Horseman kills all of his victims by decapitating them with a sword.
  • Pivotal Wake Up: The Horseman does this after being shot by Z.
  • The Place
  • Troll: Shannon messes with Diana and Mr. E by revealing she hacked into their files alongside everyone else's, reminding Diana of how she had to transfer schools because she was sexually aggressive with a teacher and how Mr. E assaulted a student at his old school. Since the movie's a dream, it's unclear if this info's true or not.
  • Unwilling Suspension: Z and Bobbi hang Justin from the rafters of an old barn for informing on their drug dealing.