Hughes' maiden voyage was a crowning achievement in gratuitous teen misery: Sam (Molly Ringwald) is forgotten on her sixteenth birthday, and her secret "sex quiz" falls into the hands of her crush -- who happens to be the most popular boy in school. In short, her life is a living hell. That is, until a nerdy admirer (Anthony Michael Hall) helps her nab the guy in exchange for her underwear. Oh, the horror.

Hughes' Emotional Maturity: 15, going on 16

Sixteen Candles, Anthony Michael Hall, Molly Ringwald, 1984. © Universal Pictures. Photo courtesy of the Everett Collection.