11. 'Pretty in Pink' (1986)
Countless girls around the world have shed tears at the closing credits, humming along with O.M.D.'s "If You Leave" and sobbing "Why, Molly? Why?" Most 1980s teen flicks had soundtracks full of corporate-rock filler, but John Hughes curated this one into one of the finest new wave anthologies. It's all lavish sadness, with tunes from Echo and the Bunnymen, New Order and the Smiths – the kind of music Duckie needs to hear when he's sitting alone in his room.