The best (of feeling the worst) of teen heartbreak

This newly minted Academy Award-winner for Best Adapted Screenplay captures with piercing honesty the dizzying highs and despairing lows of first love. Seventeen-year-old Elio (Timothée Chalamet) falls hard for his father’s graduate assistant, Oliver (Armie Hammer), and the two share a magical summer in Italy together. Alas, Oliver must eventually return to the U.S., at which point this tale of first turns love into a crushing account of first heartbreak.

Baz Luhrmann did every high-schooler on the planet a favor when he contemporized William Shakespeare’s tragedy as a tale of gun-happy gang warfare. Freed of its costume drama constraints, the work becomes a deeply felt depiction of young love, which makes it all the harder to bear as it nears its double-suicide climax. It was the first time teen heartthrob Leonardo DiCaprio’s scarred a generation of moviegoers as a doomed romantic lead. The iceberg was two years away.  

Boaz Davidson’s remake of his Israeli coming-of-age hit “Lemon Popsicle” boasts some horrendously outdated sexual politics, but if you can look past the rampant misogyny (and it’s hardly your problem if you can’t), the film has a broken, battered heart at its core. In short, just when it looks like the nice guy protagonist has wooed the girl of his dreams away from his jerk friend, she goes right back to him. Roll credits over our hero crying his eyes out as James Ingram’s “Just Once” plays on the soundtrack.

Josh Boone’s adaptation of John Green’s popular YA weepie brings the pain and then some with its story of two teenaged cancer patients (played by Ansel Elgort and Shailene Woodley) who fall hopelessly in love with one another. The film is not timid in its quest to make you bawl out loud in a crowded theater, but there’s no shame when everyone in the theater around you is doing likewise.

Its central dramatic dilemma feels fairly quaint today, but many contemporary moviegoers were horrified by Elia Kazan’s treatment of teenage sexual awakening in 1961’s “Splendor in the Grass.” The film tackles issues of class with its proximity to the 1929 stock market crash, but it still resonates today primarily due to the performances of its unreasonably attractive leads, Natalie Wood and Warren Beatty. Wood is sensational in the film as Deanie, a confused young Kansan who is counseled by her mother to repress her libidinal urges.

Peter Bogdanovich’s 1971 masterpiece is based on Larry McMurtry’s semiautobiographical novel about three teenage friends (Jeff Bridges, Cybill Shepherd and Timothy Bottoms) growing up in a dying Texas town. The adults are disillusioned, and the kids are well on their way; in the absence of hope or purpose, everyone sleeps around and/or maintains a permanent state of inebriation. It’s bleak as hell, capturing with zero sentimentality the go-nowhere desperation of small town American life.

Best keep the hankies handy when you watch this ruthlessly effective tearjerker based on Nicholas Sparks’s 1999 bestseller about a small-town bad boy (Shane West) who falls for the minister’s daughter (Mandy Moore) when he’s forced to participate in the school play as punishment for his rank hooliganism. Their romance is just beginning to blossom when he learns she has leukemia. This brings them closer together over a brief period of time. A surprise box office hit in 2002, the film has become the “Love Story” of high school romances.

“You’re tearing me apart!” Teenage angst has never been treated with greater sensitivity and compassion than in Nicholas Ray’s 1955 classic. James Dean became a sensation (albeit posthumously) for his portrayal of Jim, a kid driven to delinquency by his parents’ combative relationship. His friends, Judy (Natalie Wood) and Plato (Sal Mineo), are equally messed up, but in different ways. For a film this influential, it’s surprising how fresh it feels sixty-plus years later.

James Cameron’s instant classic about the doomed passenger ship shattered box office records thanks to repeat business from teenage girls, all of whom swooned over the romance between Kate Winslet’s 17-year-old heiress and Leonardo DiCaprio’s scrappily handsome artist. It’s broad Hollywood melodrama, but there was clearly something relatable in Rose’s frustration at being married off to a selfish cad (Billy Zane), and empowering in her ability to turn heartbreak into a positive force in her life.

“The Spectacular Now” is that rare teenage drama that doesn’t fall back on sex-crazed hijinks or disease-of-the-week tragedy to get across its coming-of-age story. Miles Teller plays a high school senior who is committed to living in the “now,” which entails being soused most of the time. His impulsiveness leads him into a promising romance with bookish classmate Shailene Woodley. There’s not a clichéd moment in this high school romance, which makes the inevitable heartbreak hit that much harder.

This searingly passionate emotional epic centers on a same-sex romance between an introverted teenager (Adéle Exarchopoulos) and a slightly older art student (Léa Seydoux), and was notable upon release for its lengthy and graphic sex scene. Now that everyone’s done blushing, it deserves to be remembered and celebrated as one of the most brutally authentic depictions of young love – from initial attraction to world-ending heartbreak – ever put to film.

Everything works out at the end of John Hughes’s coming-of-age classic, but that doesn’t make it any easier to watch poor Ducky (Jon Cryer) set himself up for emotional devastation in his futile romantic pursuit of his longtime best friend Andie (Molly Ringwald). The wrong-side-of-the-tracks/yuppie scum coupling between Blane (Andrew McCarthy) and Andie is less resonant, but the performances (particularly Harry Dean Stanton’s as Ringwald’s father) make it at least relatable.

A 14-year-old outcast (Corey Haim) makes fast friends with the super-cute new girl in town (Kerri Green) over summer break. Then school starts, and they’re forced by social dictates into their respective cliques. Lucas, however, won’t stand for it, and watching the little guy try to upend high school norms in the name of true love is both winning and agonizing. The heartache of the story is compounded by the sight of a young Haim demonstrating such promise in his first lead role.

Stephen Chbosky adapted and directed his own coming-of-age novel in which an introverted sophomore (Logan Lerman) tries to survive high school while overcoming clinical depression and repressed trauma. It’s a tall order, and the film is a tough sit at times; Gen Xers might find that Chbosky’s vivid recreation of the early 1990s cuts close to (and sometimes straight through) the bone. Ezra Miller steals whole chunks of the film as Lerman’s brash best friend.

It’s not easy to sympathize with the obnoxious Max Fischer (Jason Schwartzman) in Wes Anderson’s quirky coming-of-age classic, but you’ve got to admire the audacious pluck of a kid who reimagines Sidney Lumet’s “Serpico” as a high school stage play. It’s also not hard to understand why he goes gaga for his private school’s new first-grade teacher (Olivia Williams). It’s doomed to be an unrequited romance, but we still feel the sting as he watches her gravitate toward the morose industrialist played by Bill Murray.

Diego Luna and Gael García Bernal play a pair of oversexed teenagers who hit the road with a beguiling and gorgeous older woman (Maribel Verdú). Alfonso Cuarón’s riotously entertaining, brilliantly shot-and-performed bacchanal starts off a sex comedy, then slowly turns into a wistful rumination on the joy of youth and the disquieting understanding that, once the fun is over, we’re all headed to the same place. 

“They’re all going to laugh at you!” Stephen King’s terrifying tale of teen telekinesis gets a stylishly gory going over by maestro Brian De Palma. Sissy Spacek gives an emotionally shattering performance as the sweet Carrie White, who’s tormented by her classmates, teachers and, most cruelly, her religious fanatic mother. Spacek painfully drives home what it’s like to be the bullied girl in school, and, when she’s had enough, how it feels to be able to dish out some extra-sensory payback.

Gina Prince-Bythewood’s hoops-centric love story is told in four quarters over the course of seventeen years. The second quarter is set in high school, where its star-athlete protagonists (Omar Epps and Sanaa Lathan) battle to prove themselves on the court, while struggling (especially in Lathan’s case) to make sense of their feelings for each other. It’s in this segment of the film that Prince-Bythewood expertly sets up her heartrending finale.

Peter Sollett’s tale of young love on the Lower East Side launched the careers of Victor Rasuk, Judy Marte and Melonie Diaz. Rasuk plays a hormone-addled teenage boy whose pride is wounded when he’s suspected of having hooked up with an undesirable girl. To prove his desirability, he pursues the pretty Marte, who initially wants nothing to do with him. Sollett's story avoids cliché at every turn as he brings these two authentically awkward kids together.

Introverted sixteen-year-old Agnes (Rebecka Liljeberg) has a crush on her pretty and far more outgoing classmate Elin (Alexandra Dahlström), and it kills her that these feelings seem destined to be unrequited. That feeling of not being able to get through to the person you’re crazy about is the source of tremendous agony (and cringe-inducing laughs) in Lukas Moodysson’s coming-of-age dramedy.