Whatever decade a teen movie is set in, it manages to capture the same feelings: the dread of the first day, the thrill of a new crush, the Byzantine rules of the social hierarchy. (There’s also, usually, an emphasis on style; as young people flirt with new identities, they try on the clothes to match.) With school back in session, we asked W's editors to name the classics they return to year after year. The list spans four decades and every genre of adolescent chaos, from boarding-school rebellion and cheerleading espionage to Beverly Hills matchmaking and Hogwarts homework. Consider it your syllabus for the semester ahead.
Orange County (2002)
Twenty years before he was taking on the global luxury travel sector with The White Lotus, Mike White dissected the college admissions process with the script for this 2002 teen flick produced by MTV Films. Colin Hanks stars as a slacker who returns to high school his senior year with a sudden, unshakable quest to get into Stanford. Like a season of White Lotus, there’s a stellar cast of comedy legends and beloved character actors (Lily Tomlin, Jack Black, Dana Ivey, Leslie Mann, John Lithgow, and, most importantly, Catherine O’Hara as the perpetually tipsy mother). Here, though, is a warning that getting into the right college is not the ultimate test of your worth as a human, nor does acceptance present an answer to all of your problems. —Kyle Munzenrieder, Senior Editor, News and Strategy
Where to watch: Amazon Prime
Election (1999)
Election stars Reese Witherspoon as Tracy Flick, an annoyingly ambitious high schooler with a blunt bob and a burning desire to become school president. With her “Pick Flick” slogan and her severe campaign strategy, Tracy is poised to win, especially because she’s running against no one. But when football star Paul Metzler (Chris Klein) is foisted into the running, things take a turn. Directed by Alexander Payne, Election expertly satirizes American politics, classroom popularity, and good old prep. On my first viewing about five years ago, I couldn’t believe I had never seen it before. It’s been a high school comedy classic for me ever since. —Natalie Michie, News Writer
Where to watch: Paramount+
Bring It On (2000)
They just don’t make movies like this anymore. Seriously, there have been six sequels to Bring It On, and none of them even came close to the original (though the 2006 film, Bring It On: All or Nothing, starring Solange Knowles and Hayden Panettiere with a Rihanna cameo, does deserve a moment of recognition). There was an irreplicable magic at play in the original 2000 film—led by rival cheer captains Kirsten Dunst and Gabrielle Union—that holds a special place in my heart. Set in the world of competitive high school cheerleading, the story follows newly appointed captain of the Rancho Carne Toros Torrance (Dunst) as she discovers that her predecessor, Big Red, was stealing cheers from Isis (Union) and the East Compton Clovers. From its opening dream cheer sequence to the competitive toothbrushing scene between Torrance and edgy new kid Cliff (Jesse Bradford), Bring It On maintains its momentum throughout, thanks in large part to Eliza Dushku’s rebellious Missy. The film is irreverent and quotable, but it also maintains a fairly poignant take on cultural appropriation and intellectual theft. Most of all, it’s just immensely entertaining. Don’t agree? That’s irrelevant. After all, “This is not a democracy, it’s a cheerocracy.” —Carolyn Twersky Winkler, Staff Writer
Where to watch: Amazon Prime
Dead Poets Society (1989)
I love fish-out-of-water stories, and what better place for that tension to play out than a Vermont boarding school for boys, where the tenets of “tradition, honor, discipline, and excellence” are upheld by the elite, Ivy League-bound pupils? In this 1989 film by director Peter Weir, English teacher John Keating (played by the late San Francisco legend Robin Williams) lands a job at his alma mater, Welton Academy (the kids there call it “Hellton”). He turns things upside-down at the traditional institution with his energetic, offbeat teaching style, which calls for “seizing the day” and “sucking the marrow out of life.” Keating bestows upon his class lessons of poetry and love, while calling them “twerps” and encouraging them to “pursue women”; basically, carpe diem, as he instructs them on the first day of classes. Don't feel like you have to follow one particular path, and trust your own heart. Come for the inspiring message (and preppy autumnal imagery), stay for young Ethan Hawke, who is incredible in this movie. —Maxine Wally, Senior Digital Editor
Where to watch: Amazon Prime
Mean Girls (2004)
Soon, it’ll be October 3rd, and that can only mean one thing: it’s time to put on a rhinestone-encrusted tank top, plaid mini skirt, pointed pumps, and Mathletes jacket, just in time to hit eighth period. The Tina Fey project that has aged the best, Mean Girls will forever remind me of the jungle that was mid-aughts high school—the good, the bad, and the plastic. —Claire Valentine McCartney, Culture Editor
Where to watch: Peacock
Legally Blonde (2001)
"I'll show you how valuable Elle Woods can be!" The film that launched Reese Witherspoon into superstardom is an American classic for a reason. A story of tenacity and kindness, the first Legally Blonde film (only the first!) is one of my all-time favorites because of the beautiful colors and fashion and hair and French acrylic sets and Tiffany heart tag necklaces (and the bend-and-snap montage). Moreover, I can understand Elle, a West Coast girl, misinterpreting the rigid codes of the tony Northeast. The feminist message behind the storyline is empowering and endearing. You might find Elle to be a silly valley girl at first, but you root the hardest for her in the end. —MW
Where to watch: Amazon Prime
House Party (1990)
If you loved Dario Vitale’s first and only Versace collection, then you will love House Party. Director Reginald Hudlin’s 1990 teen comedy starring Kid ‘n Play (aka Christopher ‘Kid’ Reid and his sky-grazing flat top and Christopher Martin) is packed with the kind of bold color, oversized tailoring, leather, denim, and gloriously over-the-top party dressing that suddenly feels very now. With the ’90s renaissance showing no signs of stopping across the runways, the film practically doubles as a mood board for your wardrobe. Also, the living room dance battle is the stuff of legend. —Katie Connor, Executive Digital Director
Where to watch: Amazon Prime
Clueless (1995)
Cher and Dionne plaid mini-skirt suits define back-to-school style. The Beverly Hills teenagers' quest for popularity and good grades centers around a romantic setup between teachers. Through the many trials and tribulations Beverly Hills High School presents, they learn about much more than just matchmaking. Today, the film serves as fashion inspiration for many, as well as quoting material. “As if!” —Molly Cody, Associate Entertainment Editor
Where to watch: Netflix
About a Boy (2002)
“It happens, and I wish it didn’t, but that’s life, isn’t it?” That’s pretty much the ethos of the Weitz brothers’ 2002 masterpiece, About a Boy. Be warned, Hugh Grant has arguably never looked better, though his character (Will) is wildly unlikeable. Will is an unemployed, apathetic bachelor who uses young Nicholas Hoult (Marcus) as his fake son to meet single moms. Marcus is the film's real heart. He’s a sweet and strange child who is bullied relentlessly at school: dorky clothes, horrific bowl cut, sings falsetto when he’s nervous. The bullying scenes are tough to watch, especially considering Marcus’s life at home with his only parent: a depressed and volatile Toni Collette (Fiona). Somehow, Will becomes the one adult who truly shows up for Marcus; watching a completely hopeless adult and child accidentally save each other through quick, deadpan comedy is an absolute delight. About a Boy is peak early-2000s, quintessentially English, and at times slightly problematic. What could be better? —Tess Feldman, Assistant to the Editor-in-Chief
Where to watch: Amazon Prime
Eighth Grade (2018)
With Bo Burnham back in the zeitgeist thanks to Phoebe Bridgers’s latest album (Burnham, Bridgers’s partner, co-wrote seven songs), it’s as good a time as any to revisit his feature directorial debut. Eighth Grade is a sweet, cringe-inducing ode to adolescence that follows 13-year-old Kayla (Elsie Fisher) through her last week of middle school. Her painfully awkward YouTube videos will haunt you—in a good way—and have you signing off on every conversation with “Gucci.” You’ll get it when you see it. —KC
Where to watch: Netflix
Harry Potter and the Sorcerer's Stone (2001)
Head back to Hogwarts: the one school that would put any kid’s summer vacation blues to shame. While you may never receive that life-changing owl from the school of Witchcraft and Wizardry (or Ilvermorny if you’re stateside), you can certainly live vicariously through the preteen Harry Potter as he explores the most magical school on earth. Forget back-to-school shopping at Target and watch Harry shop in Diagon Alley for mystical school supplies. Experience Potter’s fantastical class schedule filled with broomstick-flying and potion-making. And of course, dive into a tale of adventure and mischief with Potter and friends for the convenient length of the school year, break for summer, and come back as a second year for The Chamber of Secrets. —Abrigail Williams Hallaren, Associate Social Media Manager
Where to watch: HBO Max
Fast Times at Ridgemont High (1982)
Long before Clueless, there was Fast Times at Ridgemont High, which is basically the blueprint for the modern teen movie. Amy Heckerling’s 1982 classic follows a group of Southern California high schoolers as they juggle annoying jobs, bad dates, questionable decisions, and one very laid-back surfer named Jeff Spicoli, played by one very young, very blonde Sean Penn. Come for the quotable lines (“All I need are some tasty waves, a cool buzz, and I'm fine.") and peak ’80s style; stay for the surprisingly sincere look at how messy growing up can be. —KC
Where to watch: AMC+
The Princess Diaries (2001)
Revisit one of Anne Hathaway’s most iconic characters in this San Francisco prep-school fairytale. Awkward American teenager Mia Thermopolis (Hathaway) becomes heir to a European throne overnight after her late father’s regal identity is revealed. In this coming-of-age comedy, Hathaway stumbles (literally) through high school, balancing best friends, bullies, and boy troubles, all while preparing for her new role as Princess of Genovia with the help of her newfound grandmother and queen, played by Julie Andrews. —AWH
Where to watch: Disney+