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9 Teen Movies That Are Sad and Cool at the Same Time

Let's call them "tragically hip."

9 Teen Movies That Are Sad and Cool at the Same Time
Fox | Miramax

The movie adaptation of John Green's Paper Towns hits theaters this weekend, and while it's not Green's saddest story (that title belongs to The Fault in Our Stars) it's still marked by a tragic, if more mundane, tone. Green's books, and likewise both the recent adaptations of them, aren't just tragic though, they're deeply plugged into youth culture, making the sad-yet-cool stories irresistible to readers and moviegoers alike. With that in mind, we set out to find some of the best tragically hip movies of all time.

1. Romeo + Juliet (1996)

What It's About: Two lovers whose families are embroiled in a generations-long blood feud. It's Shakespeare's final word on young love and it's been copied ad nauseum for about 400 years. Baz Luhrmann was an up-and-coming Australian indie filmmaker with only one title to his name when he broke out big with a reimagining of Romeo & Juliet that happily embraced strange anachronisms while strictly adhering to the Bard's original script.

What Makes It Tragic: [SPOILERS?] Romeo and Juliet come so close to successfully running away together, but, of course, they both end up dead.

What Makes It Hip: Baz Luhrmann's take on the classic story boasted star-making performances from Leonardo DiCaprio and Claire Danes, cinematography that looked like the ideal version of an MTV video, and one of the best movie soundtracks of the '90s.

2. The Virgin Suicides (1999)

What It's About: Five sisters who all commit suicide. The story is set in the 1970s during the Vietnam war and told from the perspectives of the now adult boys who were mystified at their deaths. The reasons for their suicides are never explained, but the movie finds both horror and hilarity in the mundane. It provided a new kind of sexy role for Kirsten Dunst, and it was director Sofia Coppola's first feature film. 

What Makes It Tragic: The movie is filmed more like a comedy than a tragedy, but for all the laughs and airiness, it's still a movie about five girls committing suicide, so it's pretty dark.

What Makes It Hip: Sofia Coppola has been criticized for being more style than substance, but her movies really are unimpeachably cool, and this might be the coolest. It wrings cynical laughs from watchers who would, most of the time, never even smirk at such dark material. It's got Kirsten Dunst at her smuggest and Josh Hartnett in a hilarious '70s wig and Kathleen Turner hamming it up as the girls' mom. It also boasts an amazing soundtrack that mixes the hits of the '70s with a score by French indie duo Air.

3. Paper Towns (2015)

What It's About: Cara Delevingne plays an 18-year-old who disappears one night shortly before her high school graduation. Before she runs away, she invites a childhood friend along for a night of revenge-inspired mischief that makes him feel, for the first time, like he's truly alive. Never mind the fact that before that night the two had barely spoken for years. When she disappears, he decides he's in love and with the help of a few friends he sets off on a mission to find her.

What Makes It Tragic: Encroaching adulthood makes kids act out in unpredictable ways. Paper Towns shows how those actions can alternately hurt the people around us and make us feel ridiculously foolish.

What Makes It Hip: For one thing, Cara Delevingne is the coolest supermodel since Kate Moss. Add in a soundtrack curated in part by screenwriter/producer and indie music fetishist Scott Neustadter, and for a minute you really do believe we should live every day with our hearts pounding against our chest cavities.

4. The Perks of Being a Wallflower (2012)

What It's About: Directed by Stephen Chbosky, and based on his novel of the same name, the film stars Logan Lerman as Charlie, a troubled high school kid who befriends siblings Sam (Emma Watson) and Patrick (Ezra Miller). They're sort of the cool freaks in their high school, and it's not long before Charlie starts to fall in love with Sam. While that's happening, her brother is trying to navigate the choppy waters of being a gay 17-year-old and Charlie is troubled by some dark repressed memories. The movie, like the book, deals candidly with the not-so-flowery side of growing up.

What Makes It Tragic: Lots of things. Charlie is still recovering from his best friend committing suicide. Patrick is beaten up and called a "faggot." Sam has terrible taste in guys. The most tragic reveal is saved for the end, though.

What Makes It Hip: Sam and Patrick and Charlie are like cool-yet-geeky high school friends you wish you'd had. They listen to David Bowie and the Smiths. They're into art and poetry. And they put on screenings of The Rocky Horror Picture Show.

5. Rebel Without a Cause (1955)

What It's About: James Dean plays Jim, a troubled teen in the 1950s who throws a sleepy high school into chaos when he shows up and changes everything. The hot girl (Natalie Wood) wants to love him. The local toughs (including Dennis Hopper) want to kill him. And the legitimately troubled (probably closeted gay) kid (Sal Mineo) wants to literally be him. Nearly every tragic teen movie made since has seemingly borrowed some element from this fast-paced archetypal drama.

What Makes It Tragic: The probably-closeted definitely-troubled kid who gravitates to Jim is Plato, played by Sal Mineo. Nobody gives this kid a break and he's driven to act out in a way that ultimately gets him killed by police. Seeing this devastates Jim, who's revealed to be thoughtful, sensitive and wise. The end of the movie leaves us wondering if Plato's death at the hands of the local police will harden Jim into the hood everyone assumed he was to begin with. Natalie Wood plays Judy, a girl whose father calls her a "tramp" and is arrested for curfew violation under suspicion of being a prostitute.

It's all extra tragic when you consider that all three of the film's stars met with untimely deaths. Dean died in a car crash about a month before the movie's release, and Mineo was stabbed to death in 1976 near his West Hollywood apartment. Wood died in 1981 in a mysterious late-night boating accident. Also, Mineo actually lived the indignities of being a closeted gay man in the 1950s until he came out in the '60s. He was virtually blacklisted in Hollywood for coming out, ruining his career. When he was murdered at 37, Mineo was thought to be on the cusp of a career comeback.

What Makes It Hip: James Dean's performance and look in Rebel pretty much defined cool for the next 10 or 15 years, and still resonates with hipsters today. Add in Mineo's heart-breaking performance and his place in gay cinema history, and you've got something that's an enduring artifact of coolness.

6. The Fault in Our Stars (2014)

What It's About: Cancer. Everyone's got cancer, so you know this isn't going to end well. Shailene Woodley plays Hazel, a 16-year-old girl who's been battling lung cancer for years. At a support group, Hazel meets Gus, a charming, good-looking guy who lost the lower half of one leg to cancer. They promptly fall in love but she's worried that with cancer she's like a grenade that will destroy the lives of the people she loves when she dies.

What Makes It Tragic: [SPOILERS!] Because our two main characters are surrounded by other cancer patients, there's a lot of room for tragedy. Gus' best friend loses his eyes to cancer. HIS EYES! Hazel carries around a secret memory of her parents talking about being parents in the past tense. The author with whom Hazel and Gus become obsessed turns out to be a total prick, but it's only because his daughter died of cancer and Hazel looks just like her. The final nail in the tragic coffin is that Gus, not Hazel, is hit hard with a relapse of his cancer that ultimately kills him.

What Makes It Hip: Probably more than any other author, John Green has a special gift for connecting with teens. He understands why grown-ups are soul-sucking horror shows of the boring lives their kids will soon lead. He understands how kids talk, connect, inflate, overreact, and experience both pain and joy with an intensity that doesn't exist for most people over 30. It comes through in his writing, making his work sort of innately cool, which is some kind of magic trick for someone writing YA cancer fiction. Combine that with spot-on pop culture references and a great soundtrack, and you've got something that really resonates with its target audience.

7. Less Than Zero (1987)

What It's About: Clay (Andrew McCarthy) is a well-to-do kid from LA who comes back from his freshman year at college on the East Coast to discover his high school girlfriend Blair (Jami Gertz) and best friend Julian (Robert Downey Jr.) have been sleeping with each other and they're both addicted to drugs. It's far worse for Julian, who owes money to a local dealer named Rip (a deliciously evil James Spader), and starts hooking to pay back the money. It's remembered mostly for being the movie where a young Robert Downey, Jr. is a gay prostitute/drug addict. And despite all the movie's heavy-handed moralizing, he still kind of comes away as the movie's tragic hero.

What Makes It Tragic: [SPOILERS] First off, it's a terrible adaptation of Bret Easton Ellis's original book. All the moral ambiguity, like Clay's bisexuality and casual drug use, has been stripped, leaving a sanitized public-service-announcement of a movie that tells us, in no uncertain terms, that drugs and gay sex are BAD. So that's tragic in itself, but let's move on. Julian ends up dying of a drug overdose after being stripped of all dignity and humanity. If it weren't for RDJ's bravura performance the movie would be unwatchable.

What Makes It Hip: Young Robert Downey, Jr. and young James Spader are not to be missed. Their performances here embody that sort of '80s Robert Palmer coolness everyone seemed to aspire to in a world that flowered into existence in between when hippies existed and Nirvana released Nevermind. Just picture Ronald Reagan looking on with approving eyes stamped with money signs.

It's also cool for a soundtrack produced by the great Rick Rubin, which included LL Cool J's "Going Back to Cali" and Public Enemy's "Bring the Noise" alongside a Slayer cover of "In-A-Gadda-Da-Vida" and a title song written by Glenn Danzig. That soundtrack also includes Roy Orbison's haunting "Life Fades Away." The iconic singer died just a year later, and "Life Fades Away," which was cowritten by Danzig and produced by Rubin, would become his swan song.

8. West Side Story (1961)

What It's About: A classic in its own right, West Side Story is basically Romeo & Juliet turned into a musical and reimagined as two lovers (Tony and Maria) with allegiances to rival street gangs. Instead of Montagues and Capulets we have the Jets and the Sharks. Instead of "fair Verona" we have the Upper West Side of 1960s New York. The two gangs have turned the neighborhood into a powder keg, and the young lovers' ardor is the spark that sets it all off.

What Makes It Tragic: [SPOILERS] The Jets and Sharks may seem pretty harmless when they're doing choreographed dance numbers, but things get deadly serious when they start to rumble. Tony's best friend gets killed by Maria's brother, Bernardo, so Tony kills Maria's brother. Despite this turn of events, she's still willing to run away with him, but their plans are dashed when one of Bernardo's friends kills Tony. On the bright side, everyone involved realizes violence is bad and walks away with something to think about.

What Makes It Cool: The colors, styles, music, and beautiful cinematography combined to make this an enduring pop culture artifact of the '60s. Its appeal can't totally be understood until you've actually sat down and watched it (preferably in its original 70 mm format) and seen it for yourself. It's beautiful.

9. Kids (1995)

What It's About: A group of lower-class teens in New York whose primary concerns include finding drugs, partying, and getting laid. That kind of sounds fun (and almost normal) except that pretty much every male character in the movie is a violent, disgusting sexual predator. The film is notable for being Harmony Korine's first. (He wrote it, but didn't direct it.) It also brought us the debut of future stars Chloe Sevigny and Rosario Dawson.

What Makes It Tragic: One of the lead characters, 16-year-old Telly, starts off the movie seducing a 12-year-old girl and then explaining to his friend why he likes virgins. We soon cut to two female friends, Jennie (Sevigny) and Ruby (Dawson), getting HIV tests. Jennie's only sexual partner has been Telly, and it turns out she's HIV-positive, so she goes on a mission to stop him from having sex with anyone else. It really doesn't go well. The end of this movie is famously hard to watch.

What Makes It Cool: Despite being unrepentantly bleak and brutal, Harmony Korine's screenplay felt like it was genuinely in touch with the lives of a whole generation of unsupervised teens left to their own devices. It was one of the only movies that ever felt like it genuinely understood '90s youth culture, even if it looked only at its darkest side. The soundtrack, packed with both hip-hop and indie rock, was the cherry on top.

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