2. Fast Times at Ridgemont High (1982)
Based on the Cameron Crowe book in which the writer went undercover in a California high school for a year, Fast Times explores a great many critical coming-of-age themes that, well, who cares because: it has Phoebe Cates, Jennifer Jason Leigh, and SPICOLI!
It's also engaging to consider that actors Nic Cage (credited as Nicholas Coppola for the first and only time), Forest Whitaker, and Sean Penn have all since received Oscars, as has Cameron Crowe. Eric Stoltz, you're next! *bwaaaaahhhhahahaha*