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23. Heathers (1989)
Key players: Winona Ryder, Christian Slater, Michael Lehmann, Daniel Waters, Shannen Doherty, Kim Walker
Why it's great: If comedy isn't easy, then dark comedy is nearly impossible. Not many movies even attempt morbid humor, let alone pull off the feat. But 1989's savagely witty and memorably stylized cult classic "Heathers" has become a benchmark for anyone who tries. Even with the dated hair and clothes, it's still easy to see why: especially in the pitch perfect performances from Winona Ryder as a popular high school student who hates her shallow friends and a wonderfully Nicholson-esque Christian Slater as her psychotic love interest whose practical jokes on the school's elite turn deadly. "Heathers" was the debut film for director Michael Lehmann and writer Daniel Waters, and their careers peaked there. But what a peak. How many movies include the line "F--- me gently with a chainsaw"? Just "Heathers."*
- Geoff Berkshire
*If another movie does, those bastards ripped it off from "Heathers."