The Darkest Teen Movies of All Time

There are two kinds of teenagers: those who get all choked up with happiness at the end of movies like Dirty Dancing or Can’t Hardly Wait and those who prefer ice-cold comedies like Heathers. As your Flavorwire editors have always fallen into the latter camp, we were intrigued (and cautiously optimistic) to learn, last week, that Heathers is getting a small-screen reboot. In fact, the news inspired us to compile a list of the dark teen movies we love the most, all of which we’ll probably re-watch in anticipation of the TV series. The selections after the jump range from black humor to true tragedy (but we’ve left out teen horror flicks because that’s a whole other post). What ties them together is the rare acknowledgment that high school isn’t all dances, football games, and makeovers.

Heathers (1989)

The movie that brought us some of the best one-liners in film history (“What’s your damage, Heather?”; “I love my dead, gay son!”) also changed teen movies forever. Instead of representing the popular clique as something to make yourself over and date your way into, it gave us three vicious, croquet-playing girls all named Heather (Shannen Doherty, Kim Walker, and Lisanne Frank) and their friend Veronica (Winona Ryder), who was too smart to uphold their regime for long. Big changes come to the excellently named Westerburg High when Ryder’s character meets Christian Slater’s JD, an iconoclastic new kid with a violent streak. Sure, he turns out to be just as bad for Veronica as the Heathers, but his acts of vengeance are so much more entertaining.