It’s early September, and those of us who are grateful that we don’t have to pack up our bookbags and head back to high school are still probably having stress dreams about forgetting our locker combinations and having to dress-out for P.E. Luckily, those days are far behind us, but it’s still the season to remember with fondness (or regret, depending on where you stood on the social ladder) those four long years of high school. Why not do so by watching a few of the best movies made about being in a teenager trapped in those claustrophobic halls of learning?
It’s the quintessential teenage sex comedy of the late ’90s, which ushered in a whole slew of gross-out teen comedies in the new millennium.
The first film in the classic time-travel trilogy is, at its heart, a hilarious high school comedy based entirely on a potential case of incest.
This adaptation of Jim Carroll’s memoir stars Leonardo DiCaprio as a young man whose drug addiction spirals out of control.
John Cusack stars in this dark comedy about a young man who attempts suicide (over and over again) after his girlfriend dumps him.
John Hughes’ classic teen drama might be the first film to take teen angst seriously.
Rian Johnson’s stylish teenage noir takes inspiration from the hardboiled detective stories of Dashiell Hammett.
It’s the quintessential cheerleader movie, and one that spawned a handful of ridiculous straight-to-video sequels.
I might be the only person who prefers the movie to the later TV series, but Kristy Swanson’s cheerleading vampire killer always knocked my socks off.
Amy Heckerling’s ’90s masterpiece was so good that neither she nor star Alicia Silverstone ever really managed to match its success.
A classic, serious look at two high school students on the Near North Side of Chicago as their carefree lives change once they get mixed up with a pair of car thieves.
Teen angst never looked so goth.
Our national obsession with turning classic works of literature into trashy teen melodramas peaked in 1999 with this modern-day telling of Les Liaisons Dangereuses, complete with lapdances and “Bittersweet Symphony.”
Based on a memoir that was unfortunately titled My Posse Don’t Do Homework, this is the essential white-teacher-teaches-inner-city-kids movie, and it includes the vastly important Coolio track “Gangsta’s Paradise.”
This film inspired boarding-school fantasies in millions of teens who just wanted a place to go where they could appreciate poetry and be moody all the time.
This Scarlet Letter-inspired comedy starring Emma Stone is probably the finest cinematic screed against slut-shaming.
Alexander Payne’s deliciously biting dark comedy features Reese Witherspoon in her greatest role as the ambitious (and terrifying) Tracy Flick.
The trials and tribulations of students at the New York High School of Performing Arts is incredibly groovy. Who doesn’t love a hot lunch jam?
Amy Heckerling’s impressive debut launched the careers of numerous young actors and provided masturbation material for millions of young men in the ’80s.
Sure, it’s more of a get-out-of-school movie than a back-to-school movie, but John Hughes’ comedy established the titular character as a teenage hero (and likely inspired a lot of people to pick “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it” as their senior quote).
Leave it to Midwestern teens to rebel against the fascist tyranny of the anti-dancing factions.
See this movie if only to watch Sarah Jessica Parker and Helen Hunt as wee, dorky (yet fun) teen girls trying to “make it” on a Solid Gold-type show, Dance TV. Bonus points if you can spot the Doherty (Shannen, that is).
The movie musical about horndog greasers in the 1950s is a cinematic classic, even if the cast is hilariously too old to play convincing high school students.
Teenage suicide is rarely funny unless it involves Liquid-Plumr and quips like, “Fuck me gently with a chainsaw.”
A direct descendent of Heathers, Jawbreaker is a much more campy teenage murder comedy, featuring the always-hilarious Judy Greer!
Here’s a completely under-appreciated teen sex comedy about a high school journalist who dresses as a boy to combat sexism. Yes, of course she’s topless by the end of the movie.
Peter Bogdanovich’s adaptation of Larry McMurtry’s novel launched the careers of Cybil Shepard and Jeff Bridges and picked up eight Oscar nominations, proving that movies about teens can be serious, too.
Corey Haim starred as the titular nerd who braves bullies and football in this teen melodrama that also starred Charlie Sheen and Winona Ryder (in her film debut).
Tina Fey’s Mean Girls might be the last quotable teen movie, and re-watching it always forces us to think about what Lindsay Lohan could have been.
Francis Ford Coppola’s 1983 adaptation of S. E. Hinton’s classic novel about teenage gangs in Oklahoma featured then-unknown Tom Cruise, Diane Lane, Patrick Swayze, and Rob Lowe.
Matt Dillon made his film debut in this angsty drama about teenage rebellion, which achieved cult status and inspired the video for “Smells Like Teen Spirit.”
This dreamlike time-travel comedy-drama stars Kathleen Turner as a divorced woman in the ’80s who relives her senior year in the ’50s, this time with the self-awareness to know she shouldn’t end up with her doof of a high school sweetheart (played with utmost goofiness by Nicolas Cage).
Stephen Chbosky wrote and directed this adaptation of his much-beloved novel, providing a respectful and endearing look at one awkward, introverted student as he treads the heady waters of high school.
This classic pretty much started the trend of the over-the-top, raunchy teen sex comedy.
This love story about a girl from the wrong side of the tracks and the two dudes who love her is arguably John Hughes’ (and Molly Ringwald’s) best movie.
The ultimate juvenile delinquent film basically established the subject matter as a genre and immediately became a pop-culture touchstone.
P. J. Soles stars as the world’s biggest Ramones fan in this musical comedy in which rock ‘n’ roll-obsessed students take over their high school, much to the chagrin of the stodgy faculty.
Wes Anderson’s dark comedy is probably his best (sorry, Tenenbaums fans) and reinvigorated the career of Bill Murray while making audiences fall in love with the dorky charm of Jason Schwartzman.
The ugly world of New England prep schools is explored in this drama starring Brendan Fraser as a working-class Jewish student harassed by his anti-Semitic classmates.
Wes Craven’s meta-slasher flick reintroduced a maligned genre and brought a fresh, postmodern take on the teen horror film, which would be both copied and parodied for a decade afterward.
This is the ultimate Pygmalion update, in which a beautiful girl gets uglied-up with a pair of thick-framed glasses and some overalls. Let us all lament the careers of Rachel Leigh Cook and Freddie Prinze, Jr.
It’s less sexy than ’80s cross-dressing comedy Just One of the Guys, but this silly update of Shakespeare’s Twelfth Night is Amanda Bynes’ finest work, and features the hilarious David Cross and Julie Hagerty in supporting roles.
Terrible sequel. But fantastic and ridiculous teen musical, with Lauryn Hill’s attempts at acting as an added bonus.
Like an It Gets Better video, Sixteen Candles follows an awkward teen played by Molly Ringwald whose parents forget her birthday, whose underwear is stolen by the school nerd, and who eventually gets the guy of her dreams. Just like life!
Edward James Olmos got an Oscar nomination for his role in this true story of a man who basically made all of us wish we were better at math.
Amy Sedaris brings her ridiculously hilarious Jerri Blank to the big screen in this movie version of her Comedy Central show, featuring original cast members and co-creators Paul Dinello and Stephen Colbert (and plenty of A-list cameos).
Real-life best friends Seth Rogen and Evan Goldberg penned this movie that’s basically about themselves as awkward teenagers just trying to get laid.
This Michael J. Fox comedy is probably the second-best puberty allegory (next to the just-as-terrifying The Exorcist).
Probably the most accomplished teen adaptation of a Shakespeare play, it features Heath Ledger and Julia Stiles as the pitch-perfect modern-day Petruchio and Katherina.
Here’s a rare case of a black teacher saving the lives of troubled white kids, but that’s how it works in London, I guess.
Is an homage to homaging a thing? It’s like an extra-tacky (and sweaty) Brian De Palma film, featuring the oldest-looking high-school students ever depicted on film, as well as that long-awaited glimpse of Kevin Bacon’s penis.