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.

Jawbreaker (1999)

Partially inspired by Heathers, Darren Stein’s Jawbreaker came out a decade later and took the tired makeover plot to a demented extreme. Three girls so popular they’re almost superhuman accidentally kill their friend on her birthday and are forced to reinvent geeky Fern Mayo (Judy Greer) as her replacement in their clique, the Flawless Four. From Rose McGowan’s dominatrix-like performance as the group’s leader, Courtney Shane, to the perversion of purity implied in a teenage girl’s death by jawbreaker to McGowan’s quite literally perverse sex scene with then-boyfriend Marilyn Manson, it’s a movie that suggests something rotten hidden beneath the candy-colored twin sets of even the most clean-cut, socially successful queen bees.

Better Off Dead (1985)

A teen comedy about a high-school kid who keeps trying — and failing — to kill himself after his girlfriend leaves him for a jock? We laughed out loud, and maintain that Lane Myer is still the best role of John Cusack’s career, but we can only imagine the uproar if a mainstream film aimed at teenagers with such a controversial premise came out in 2012.

Carrie (1976)

We know — we said there wouldn’t be any horror films in this roundup, but while we resisted the urge to include the likes of Scream and Slumber Party Massacre, there’s just no way to make a list of the darkest teen movies without including Carrie. Brian De Palma’s adaptation of Stephen King’s 1974 novel is the ultimate tale of a misfit (Sissy Spacek) who gets her revenge on the school full of tormentors who have made her entire life miserable. For fans of devastating prom scenes, telekinesis, and strong menstrual themes, it’s a classic.

The Craft (1996)

In keeping with the supernatural theme, here’s The Craft, a movie that may have been styled like a horror film but was most certainly a teen drama. Featuring an all-star cast of young ’90s alterna-celebs — Fairuza Balk! Robin Tunney! Neve Campbell! Rachel True! Skeet Ulrich! — it centers around a foursome of high-school girls who form an improbably powerful coven and set about using magic for all the things you’d think 16-year-olds might use magic for (beauty, love, turning the tables on bullies). Things get out of hand fast, as the baby Wiccans learn exactly what Courtney Love meant about getting what you want and never wanting it again.

Saved! (2004)

What do you do when your boyfriend tells you he’s gay? Well, if you’re Mary Cummings (Jena Malone), a rising senior at American Eagle Christian High School, you take a conk on the head as a sign from God that you need to save his soul — by having sex with him. Then, because teaching kids about contraception is sinful, you get pregnant. That’s the starting point for Brian Dannelly’s hilarious satire of born-again Christian values and the effect they have on teenagers who don’t fit in, which is also notable for excellent performances by Mandy Moore and Macaulay Culkin. Saved!, with its message of acceptance, may espouse a brighter worldview than some of the other films on this list, but the picture it paints of kids shaped by religious fundamentalism is unquestionably bleak.

Pump Up the Volume (1990)

The year after starring as a sexy teen outcast psychopath in Heathers, Christian Slater became “Happy Harry Hard-on” — a sexy teen outcast pirate radio host (real name: Mark Hunter) who plays bands like Bad Brains and The Jesus and Mary Chain and serves #realtalk years before the advent of the hashtag. Equal parts comedy, drama, and romance, Pump Up the Volume takes high-school love affairs to an unusually dark place, while also exploring the lengths the adult world will go to in silencing suicidal, self-harming, or otherwise at-risk kids.

Kids (1995)

In the grand scheme of things, the stakes of most teen movies aren’t that high. Will the girl of the protagonist’s dreams go to prom with him? Will the ugly duckling (i.e., pretty girl in glasses and ill-fitting jeans) emerge as a socially acceptable swan? But Larry Clark and Harmony Korine’s controversial Kids explored the irreparable consequences of sexual promiscuity and drug abuse in the lives of young teenagers in post-HIV New York. Telly, a 16-year-old boy who loves to have sex with junior-high virgins, is one of the most terrifying characters in film history.

The Virgin Suicides (1999)

Speaking of virgins: Nothing is sadder, at least in the world of teenage mythology, than the story of five beautiful, innocent, blonde sisters who take their own lives.

Rebel Without a Cause (1955)

One of the first teen-angst movies is still, many would argue, the best. James Dean cemented his status as youth icon in Nicholas Ray’s era-defining examination of high-school alienation and the increasingly unbridgeable gap between generations. The scene in which Dean’s Jim takes a field trip to the Griffith Observatory and learns about the end of the universe dramatizes the emotional intensity of teenage fatalism more vividly than anything else we’ve seen on the big screen. That alone would qualify Rebel Without a Cause for this list; taken together with the ending, it’s a killer.