Sixteen Candles/Pretty in Pink (1984/1986)
Please don't make us choose between Hughes' most brilliant romantic comedies. They have so much in common—Molly Ringwald pining for the high school hunk, a lovable nerd (Anthony Michael Hall's panty-stealing Farmer Ted and a pre-Two and a Half Men Jon Cryer at his very best) pining for Molly Ringwald, a happily-ever-high-school ending—yet they each seem wholly original. Though obviously '80s, their perfect embodiment of teen angst stands the test of time. The next time we catch ourselves uttering "Why don't you take The Donger to the dance?" or lip-syncing "Try a Little Tenderness," we'll tip our hat to Hughes.