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Heathers (1988)

Director: Michael Lehmann
Stars: Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, Kim Walker

On paper, Heathers isn't all that funny. Set in an everyday high school, Winona Ryder's breakout film hinges on a clique of hateful, stuck-up girls, bullies, and teenage suicide. In all, it's one of the darkest high school movies ever made, and a big part of that mystique is credited to screenwriter Daniel Waters' crackerjack of a script, which flip-flops from vicious black comedy to emotionally gruesome moments with unwavering poise.

Ryder plays the only member of an all-girl crew of social terrorists with a conscience; after watching her cohorts torment her undeserving fellow classmates, Ryder's character and her derelict boyfriend (Christian Slater) plot to dethrone the queens of mean. Soon, one of the girls dies, along with a pair of football stars, whose corpses are positioned in a homosexually suggestive manner, spawning the memorable line, "I love my dead, gay son!"

Heathers veers into some rather twisted and bleak territories, yet, somehow, it's consistently amusing. In other words, it's the quintessential dark comedy.

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