15. Fast Times at Ridgemont High (1982)
Key players: Amy Heckerling, Cameron Crowe, Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Phoebe Cates
Why it's great: Chances are when you think of "Fast Times," you think of one or two things: Sean Penn's iconic performance as surfer pothead Jeff Spicoli and/or Phoebe Cates emerging from the pool in that red bikini (and then earning the movie its R rating). But what makes "Fast Times" so much better than the average high school comedy is that it never settles for juvenile stoner or sex jokes. As directed by Amy Heckerling and written by Cameron Crowe (based on a book he wrote about going undercover in a real high school), the movie takes its teenage characters seriously and gives them real dilemmas and crises. They work crappy jobs, they struggle with relationships, Jennifer Jason Leigh's character even wrestles with getting an abortion. "Fast Times" is a very fun, funny movie but it's also far more grown up than many comedies ever dare to be.