10. "Brick" (2005)
Rian Johnson achieved an almost impossible feat with "Brick" -- he created a neo-noir and set in a contemporary California high school with characters gabbing dialogue straight from 1940s crime fiction, and it wasn't ridiculous. A sensational Joseph Gordon-Levitt stars as Brendan, an outsider high schooler who channels Sam Spade while investigating the mysterious death of his ex-girlfriend (Emilie de Ravin, from "Lost") while his trusty friend The Brain (Matt O'Leary) shares clues and quips. Brendan contends with all sorts of characters, including teenage femmes fatales; bossy, Moose Malloy-ish dumbbell athletes; useless stoners (one he slaps around with Bogart panache spitting out: "Throw one at me if you want, hash head. I've got all five senses and I slept last night, that puts me six up on the lot of you"). The greatest creation, however, is Lukas Haas' brilliant sociopathic drug dealer named The Pin, a bug-eyed and quietly menacing cross between Peter Lorre and Sydney Greenstreet. The drama, tension and fantasy of high school is astutely observed via the picture's shadowy style and clever one-liners (who wouldn't want to be that quick-witted when a bully puts up his dukes?) and though adults hang in the periphery of the film, you'll never forget a scene involving The Pin, his mom, milk and cookies.
9. "My Bodyguard" (1980)
Tony Bill's "My Bodyguard" is better than it has any right to be. Its David and Goliath story is a cookie cutter set for yucks, easy inspiration and a big payoff that, as a critic looking to get quoted might write, leaves the audience cheering. But then it becomes a lot more than the nerdy new kid Clifford (Chris Makepeace) enduring the high school bully (Matt Dillon) who steals his lunch money when the 98-pound weakling hires himself a real Goliath, a moody, brooding hulk named Linderman (Adam Baldwin). In spite of the scary rumors surrounding Linderman (that he raped a teacher and murdered his brother), Clifford seeks out the bad boy, at first to simply make his hellish high school existence endurable. But as the two hang out, he learns more about the so-called school "psycho" -- that the poor kid is gripped with guilt about the accidental death of his brother, his family life is tragic and he's reverted to a shell because his life contains little joy. Both performances are astoundingly touching (especially Baldwin, who manages to be incredibly real, poignant and then actually kind of scary) and the movie works as a darkly sweet ode to all of the freaks and geeks slouching through the hallways, hoping for a real friend.
8. "Heathers" (1989)
A startling, darkly funny teen picture, "Heathers" -- starring Winona Ryder and a Jack Nicholson-impersonating Christian Slater -- remains a nice antidote to all those life-positive '80s John Hughes films. Here, the jocks and the snobs, particularly a Nazi-like clique of girls all named Heather, get theirs in creative, incredibly mean style. Heather-ette Ryder (her name is Veronica but she manages to get in with the cool chicks), longs for something more than the "diet coke heads." When new boy Slater swaggers into the lunchroom, she's smitten. The two become a homicidal duo, engaging in a murder spree that looks like a rash of suicides (one involves a cup of Drano). The humor's positively black and the dialogue is priceless: "Heather why do you have to be such a mega bitch?" Answer? "Because I can be."
7. "Election" (1999)
This movie isn't just a dead-on satire about the tumultuous, dog-eat-doggedness of high school overachievers (and popular underachievers), it's also a savvy satire about U.S. politics in general. Written and directed by Alexander Payne (before he skewered oldsters in "About Schmidt" and dumpy oenophiles in "Sideways") the brilliant "Election" stars Reese Witherspoon as the hysterically and insanely ambitious Tracy Flick, an A student who is running for class president. She's so earnest and single-minded that the movie could simply revolve around what an unlikable, secretly contemptuous brown-nose she is. But instead it reveals that her archenemy is none other than a likable teacher, Mr. McAllister (Mathew Broderick), who is still upset with her getting his creepy colleague fired for having an affair with the teenager. So, yes, he's not exactly one-note sympathetic either. When he convinces the dim bulb but nice school jock (Chris Klein) to run against Tracy, her world spins out of control when she realizes her hard work means nothing in the face of massive popularity. When the jock's lesbian, anarchistic sister enters the race, the movie becomes an accidental examination of the Bush, Gore and Nader campaign (I'm not saying which character represents any of these candidates). The acerbic, witty and wickedly funny movie only goes to show that life is always like high school.
6. "Carrie" (1976)
High school can really suck. Especially if you're a quiet little red-haired wallflower with a psychotic overly religious mother and a violent dose of telekinetic powers that are unleashed when angry. And if you're Carrie White (the fabulous Sissy Spacek), you've got plenty to make you angry. Brian De Palma adapted Stephen King's novel perfectly, making high school a playground for the cruel and unusual, reflecting the real-life horrors of later, adult life and the surging, hormonal complications of becoming a teen. When Carrie is invited to the prom as a trick, we watch with deep compassion as she dresses herself into the truly beautiful young woman she is, only to be doused with pig's blood when crowned prom queen. Spacek made history with this role speaking for all the teenage disenfranchised with her final act of retribution (destroy ALL!). The finale is strangely liberating but also terribly sad. This remains an absolutely touching classic that transcends its genre.
5. "Donnie Darko" (2001)
OK, there's much more to "Donnie Darko" than simply high school, but it belongs here because the film wouldn't work in any different milieu. Young filmmaker Richard Kelly directed Jake Gyllenhaal as our titular hero in this intriguing combination of science fiction, teen drama, romance, '80s nostalgia and teen-film satire. And more. It's 1988 in affluent Middlesex, Va., where a sleepwalking Donnie Darko receives news from a horrifying 6-foot-tall, charred bunny -- in 28 days, 6 hours, 42 minutes, and 16 seconds the world's gonna end. When a jet engine smashes into the bedroom of his house while Donnie's walking the night, he realizes that creepy rabbit just saved his life. What to do? Explore the significance of the event while attending school, argue about the sexuality of the Smurfs, fall in love, out a pedophile teacher, attend hypnosis sessions with a psychiatrist, and endure the self-help mumbo jumbo of a teacher who feels love and fear are the polar extremes that guide our life. You know, normal high school stuff. The film also features some brilliant musical sequences showcasing Tears for Fears and Echo and the Bunnymen tunes. Unseen on first release but discovered on DVD, "Donnie Darko" is now a deserved, bona fide cult classic where popular revivals are filled with the rightfully obsessed.
4. "Fast Times at Ridgemont High" (1982)
You were probably wondering when we'd get to this one. Writer Cameron Crowe went undercover in an '80s Southern California high school (when you see his autobiographical "Almost Famous," you understand how he was able to achieve such a feat), coming up with a smorgasbord of inside info that is now part of our popular vernacular. As directed by Amy Heckerling, the picture follows the new sexual exploits of mall-working Valley Girl Jennifer Jason Leigh and her more experienced older friend Phoebe Cates (who gets one of cinema's -- or locker rooms' -- most talked about bikini moments). Poor Leigh takes advice from all the wrong people, resulting in some sexual moments that never play as merely titillating, but incredibly pathetic and disturbing, especially in a comedy like this. Making up for Leigh's dramatic dilemmas, however, is the comedic icon of surfer/pothead Jeff Spicoli (yes, remember that was Sean Penn all those years ago), whose stoned-out stupidity belies a clever sarcasm that's not as dumb as it looks. Genuinely touching, with terrific music and smart, funny performances, "Fast Times" still works. Must we quote? OK one: "All I need are some tasty waves, a cool buzz, and I'm fine."
3. "Dazed and Confused" (1993)
We know some of you will get angry not seeing George Lucas' "American Graffiti" gracing this list, but Richard Linklater's "Dazed and Confused," a film that's been compared to Lucas', really feels like high school. Chronicling one day in the life of a group of Texas high school students circa 1976, the picture walks us through the drama of eight seniors who wonder about their future, search for Aerosmith tickets, and haze (and we really mean haze, '70s style) incoming freshmen. The picture's filled with future stars, all who give terrific, authentic performances, like a wonderfully sleazy Matthew McConaughey (in the greatest role of his career), Ben Affleck, Parker Posey, Adam Goldberg, Joey Lauren Adams, Cole Hauser and the lovely Milla Jovovich. Linklater really captures what the last day of school feels like (then and now) but also the issues of the era, like drugs, Watergate, feminism and other topics relevant to the '70s. Like "Graffiti," we really wonder and care about what'll happen to these teens as they cruise around to some of the era's greatest music. And we also laugh a lot. A landmark in teen cinema.
2. "Rebel Without a Cause" (1955)
"You're tearing me apart!" Who can forget young James Dean struggling with his meek father and shrew of a mother while attempting to fit in as the new kid in a '50s Los Angeles high school? Directed by the great Nicholas Ray in vibrant color and gorgeously stylized eschew angles, the film's title alone has become a catch phrase for the smart loner who wants to make any kind of mark, but, living in such an existential world, only ends up lashing out. In Dean's most popular movie, the method actor begins life in town in a police station, where he's picked up for being publicly drunk. There he meets two other misfits who will later become his best friends, Sal Mineo (who's charged with killing a bunch of puppies -- harsh!) and Natalie Wood, who's got some serious daddy issues. The three form a deep but somewhat bizarre bond after a deadly chicken race, holing up in an abandoned house where the cops and other gang members can't find them. A deeply philosophical film, Ray's picture is filled with layered musings. Dean's family life involves a lot of talking but not listening (timeless) while high school means initiation by knife. The picture is also incredibly homoerotic with Mineo and Dean engaging in some intriguing subtext attraction. There's a reason this film's so famous, of course for the iconic performance, cool, sensitivity and gorgeousness of Dean, but also for its emotionally charged subject matter. "The Catcher in the Rye" of cinema, generations of young men and women have deeply related to this film.
1. "Rushmore" (1999)
Co-written and directed by then-relatively unknown Wes Anderson and co-written and co-produced by Owen Wilson, "Rushmore" is one of the most creative, touching, and hilarious pictures to come out in the past few decades. For some, "Rushmore" is more than a movie -- it's a sublime milestone. "Rushmore" is named for the posh prep-school academy that the film's main character, 15-year-old Max Fischer (Jason Schwartzman), attends with an enthusiasm that borders on pathological. Unlike the rich kids at Rushmore, Max is there on a scholarship, though he's barely passing any of his classes. But he's got tons of spirit (he heads about every extracurricular school club) and heavy doses of arrogance. He's driving the administrators at Rushmore crazy but he's also made a friend in Herman Blume (Bill Murray), a millionaire whose speech to the students of Rushmore makes a strong impression on Max. However, thanks to a bizarre love triangle, Max will learn what heartbreak is and, in one of the film's saddest moments, be kicked out of Rushmore only to attend the drabness of regular high school. Beautifully filmed, scored, acted and so genuinely sweet, "Rushmore" is the kind of movie that makes you cry from your well of bittersweet memories, many from your high school years. And it's got one of the greatest soundtracks in film history. When Blume asks Max, "What's the secret?" Max tells him: "Find what you like to do and do it for the rest of your life. For me it's going to Rushmore." Of course it doesn't really work out that easily for Max, but his sentiment is, as future Anderson character Royal Tenenbaum would say, "true blue."