The Era: It's 1970s California, the era of hot rods, surfer dudes, and checkered Vans.
Cringe-Worthy Moment: Judge Reinhold having an intimate moment as he thinks of Phoebe Cates.
Classic Line: "What Jefferson was saying was, 'Hey! You know, we left this England place 'cause it was bogus, so if we don't get some cool rules ourselves -- pronto -- we'll just be bogus, too!' Get it?" Sean Penn
Why It's Classic: Sean Penn is, of course, unforgettable as Jeff Spicoli, but the movie also features other '80s and '90s stars-to-be: Forest Whitaker, Judge Reinhold, Phoebe Cates, Jennifer Jason Leigh, and others.

Fast Times at Ridgemont High, Sean Penn and Ray Walston, 1982. © Universal. Photo courtesy of the Everett Collection.