50. Splendor in the Grass 1961
Young love — especially when it's with the star of the football team — can make a girl crazy. Literally. In pre-Depression, small-town Kansas, good-girl Natalie Wood is so tortured by her sexual urges for beau Warren Beatty and conflicting pressure to be moral that she attempts suicide after a school dance and ends up in a sanitarium. It's the ultimate depiction of overwhelming first love, and — sorry, religious right — a chilling PSA against the dangers of teen abstinence. — Josh Wolk
49. Sixteen Candles 1984
It's tough to turn 16. But when your entire family forgets your birthday, it only makes that day worse. Molly Ringwald puts on a brave face as her character endures basically the worst week of her life, whether it's having her panties taken by Anthony Michael Hall or getting groped by her grandma (''Fred, she's gotten her boobies!''). The awkwardness is all hilarious, though, especially watching a young Joan Cusack attempt to use the water fountain in orthodontic head gear. — Tim Stack
48. Just One of the Guys 1985
Every generation has its variant on the girl-dresses-as-boy, girl-as-boy-falls-for-boy, boy-freaks-out tale. And this immensely fun, if minor, romp from the '80s perfectly captures the decade's raunch-lite spirit and funky fashion sense. As the cross-dresser caught in the middle, Joyce Hyser's aspiring journalist learns the hard way that there's more to being a dude than just stuffing a tube sock down your pants. — Michelle Kung
47. Napoleon Dynamite 2004
The plot is insignificant, the lead character (Jon Heder) is a petulant spaz, and the pace creeps along just barely faster than a John Deere. Still, this sleeper hit succeeds because it manages to mock and celebrate high school geekdom with a bone-dry, unsentimental tone. The inane one-liners, absurd non sequiturs, and sheer stupidity of the characters don't just bring back memories of adolescence, they make you feel like a teenager again, giggling at something idiotic without knowing exactly why. — Michael Endelman
46. Flirting 1992
She's a Ugandan beauty in a prep school populated by blond Aussies (including young Nicole Kidman and Naomi Watts); he's a gawky stutterer obsessed with Camus. Given their shared outsider status at their respective institutions, is there any doubt that Danny (Noah Taylor) and Thandiwe (Thandie Newton) end up falling for each other? Wryly tender and respectfully told, director John Duigan's coming-of-age romance is a warm and fuzzy confection that stops short of being icky. — Michelle Kung
