5. "Fast Times at Ridgemont High" (1982)

Outside the timeless pleasure of a topless Phoebe Cates and the comedy styling of Sean Penn as Jeff Spicoli, Amy Heckerling's film of Cameron Crowe's high school undercover story handles the touchy subjects of identity crisis and unwanted pregnancy and presents most everyone, teachers included, as fumbling awkwardly through life. Even the sight of Cates untying her bikini comes with the embarrassment of Judge Reinhold getting caught in the bathroom with his pants down.

Angst-ometer rating: 6

Sample quote: "When it comes down to making out, whenever possible, put on side one of Led Zeppelin IV."

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