30. Bring It On 2000
They're sexy, they're cute, they're popular to boot! Kirsten Dunst plays Torrance, the bright-eyed cheerleading captain who must save her high school's squad from a major cheeragedy: going down as the team who stole routines. In the end, we learn there's more to cheerleading than loads of hairspray, teeny halter tops, and back-stabbing: These are athletes who know how to really bring it. We give this comedy five spirit fingers up! — Lindsay Soll

29. Gregory's Girl 1982
Gregory's Girl is short on stars, long on soccer, and it sounds like a Weird Al Yankovic parody of Rick Springfield. But it is also sweetly hilarious as gangly Scottish teen Gregory (Gordon John Sinclair) falls for an out-of-his-league girl. The result is guaranteed to make viewers feel much better about their own post-pubescent awkwardness — unless they, too, ever tried to romance someone with the information that ''When you sneeze, it comes out your nose 180 miles an hour.'' — Clark Collis

28. Back to the Future 1985
A.K.A. the coolest movie ever to feature a Huey Lewis and the News song. The film ingeniously literalizes high school's sexual frustration and disdain for one's parents by having Michael J. Fox's Marty McFly getting hit on over and over again by Lea Thompson as his young, future mother (thanks to that time-traveling DeLorean). It just goes to prove that the parental units were just as horny back in the day as we were. — Gilbert Cruz

27. To Sir, With Love 1967
Way before Mr. Holland began teaching his opus and Michelle Pfeiffer was molding dangerous minds, Sidney Poitier was taming a room of unruly British teens with his real-life lessons and tough-love tactics (a boxing glove to the stomach, anyone?). Having himself played an insubordinate kid in 1955's Blackboard Jungle, the student masterfully becomes the teacher in this sappy but never maudlin tale of inspiration and tolerance. — Michelle Kung

26. Pretty in Pink 1986
Perhaps the most controversial ending to a teen romance ever. (Behind Romeo and Juliet? Fine.) Should Andie (Molly Ringwald) have chased after rich, repentant Blane (Andrew McCarthy), or stayed at the prom with poor, devoted Duckie (Jon Cryer)? That we, women now in our 30s, still care is a testament to John Hughes' script about love across class lines (point for Blane); the meaning of friendship and individuality (point for Duckie); and the evil nature of wealthy high schoolers in crisp, white clothing (point for James Spader). — Mandi Bierly