Home » Sleepy Hollow High Gave Me Nightmares (And Not the Good Kind)

Sleepy Hollow High Gave Me Nightmares (And Not the Good Kind)

Sleepy Hollow High

With the recent announcement of 2022’s Scream, the fifth in the series, and the upcoming arrival of Halloween, I could only think of one thing. A film once praised by Femme Fatales Magazine as “Scream meets Dawson’s Creek.” A film which is more like if someone on Dawson’s Creek had a bizarre coma fantasy based on Scream after watching it once.  I’m talking about Sleepy Hollow High.

My knowledge of this film dates back to my middle school career in the early 2000s. One day, my dad and sibling informed me of this movie’s existence at National Wholesale Liquidators but they did not pick up a copy for me. The title remained in my head for years. But it wasn’t until my college graduation back in 2014 that I picked up a copy of the film. 

Sleepy Hollow High Poster

This was an experience I wasn’t prepared for in any way, shape, or form.

The process of watching Sleepy Hollow High is, to me, eerily similar to an actual fever dream I had in high school. And it’s disturbing how the film feels more like something a high school student imagined while delirious with a 101 temperature.

Directed by Chris Arth and Kevin Summerfield, Sleepy Hollow High was distributed directly to video by Scorpio Pictures in 2000. It was a story of five delinquents forced to do community service in lieu of jailtime. While picking up garbage at Sleepy Hollow Park Grounds under the supervision of school counselor Mr. E (played by director Summerfield), the five teens are stalked and hunted down by a pumpkin-masked killer implied to be the Headless Horseman.

Sleepy Hollow High ranks up there for me with other cinematic “masterpieces” like Trick or Treats, Fever Lake, Campfire Stories, and Spookely the Square Pumpkin. Movies which must be seen to be believed… for better or worse. Everything about Sleepy Hollow High screams “amateur hour,” from the quality of the video, to the lighting, the use of music, and the the “acting”. Everything.

I don’t normally like to spend time trying to bash films. And I don’t mean to bash Sleepy Hollow High, so much as connect with other people that have experienced it and compare notes. I wouldn’t describe Sleepy Hollow High as  “So bad, it’s good”. It’s more “So bad, they haven’t yet invented the word to describe what it is.” It defies expectations and belief. It’s the sort of movie you sit through, then wonder how you’d be able to properly describe it to someone else because they wouldn’t believe you.

Our opening credits begin with eerie, mournful music playing while someone collects newspaper articles about disappearances and unsolved murders in the town of Sleepy Hollow. The orange-tinted scenery transitions to dark blue, as an unnamed jogger runs through the woods listening to generic rock music when she’s suddenly frightened by a black horse and attacked by a sword-wielding stranger. Her screams cut to what is clearly an image of the moon found on the late ’90s Internet. Clearly, we have entered another world.

Out of our cast of “teenage” delinquents, the only one who tries to carry any real presence to affect the story is our “protagonist” Shannon (Meagan Lopez). A quintessential late ’90s bad girl entering the new millennium, Shannon’s edgy claim to infamy is hacking into the school’s computers and accessing everyone’s files. While being stuck with her cohorts on trash duty, Shannon tries to execute a form of power on her terms by revealing secrets to get a rise out of those around her.

In Diana’s (Wendy Donigian) case, Shannon talks about how she needed to transfer schools for acting sexually aggressive against a teacher. In Mr. E’s case, Shannon responds to his patronizing attitude by discussing how he lost his previous job for attacking a kid. When these both blow up in Shannon’s face, she later tries to talk Bobbi (Maria Cooper) out of cutting her wrist and gets Bobbi to admit she’s pregnant by her boyfriend Z (Rueben Brown).

The unreality of the movie is enhanced by some of the dialog, like Shannon discussing her own suicide attempt with Bobbi. In her words:

Shannon: Cutting open your arm isn’t the answer. It’s all glamour. No real pay off?

Um. Okay.

As well as much earlier, where Z and Bobbi get their revenge on a kid named Justin (Darryl Lozupone) who snitched on them for dealing drugs. They strung him up in the park at night and write words like “snitch” on his chest with chocolate syrup. While Bobbi spreads syrup on his armpits:

Z: God damn, look at them goosepimples. Play with his nipples he seems to like that.


Beyond Shannon, the only other character to really bring something to this movie is our Pumpkin Man (Antonio Benedict).

Shannon: What Pumpkin Man?! You didn’t say anything about a Pumpkin Man!

Pumpkin Man

Pumpkin Man

No, they couldn’t just call him the Headless Horseman despite that he literally rides a black horse, cuts off heads with a sword that looks like it came from a 99 cent store, and is in a movie set at Sleepy Hollow High School. 

With an ensemble not even Christopher Walken could pull off (or maybe he could), and a horse whose neighs are digitally inserted through the marvels of computer magic, the Pumpkin Man cuts through the cast without speaking a single line.

So much of this movie is a disjointed fog, it’s a wonder anyone is able to follow to the end. An ending which, for all intents and purposes, will have you screaming in frustration when it suddenly brings us back to the very beginning with the person saving those newspaper articles.

This Halloween season, if you’re brave enough to experience a movie that’ll have you question reality and ask yourself the age old quandary “What the HELL did I just watch?!,” I suggest you try Sleepy Hollow High. And if you’re truly brave, maybe even braver than I am, give the music video a try.

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Written by Jude Deluca
Jude Deluca is a Capricorn who identifies somewhere under the ‘asexual' banner. Their gender identity is up in the air at the moment. As a horror lover, Jude's specialty is the discussion of young adult horror fiction like Goosebumps and Fear Street. Jude proudly owns the complete Graveyard School series by Nola Thacker. Jude's favorite horror sequel is A Nightmare on Elm Street 5: The Dream Child. Their favorite final girl is Alice Johnson. As a child, Jude was the only nine-year-old at their school who knew everything about 1959's The Bat. Jude's dislikes include remakes that take themselves too seriously and torture porn.
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