3. Peter Gabriel, 'In Your Eyes' in 'Say Anything' (1989)
Who else but Cameron Crowe could create a moment like this: John Cusack stands outside Ione Skye's house, holding up a boombox. He's playing their song, "In Your Eyes," to remind her of their shared memories, but also to express everything he wishes he knew how to tell her himself. Crowe turned this into a Romeo & Juliet balcony scene for the ages. (And turning a prog-rocker like Peter Gabriel into prom fodder was a mighty strange achievement in itself.) When they filmed it, Cusack's boombox was actually playing Fishbone, but it doesn't really matter what the music is. The whole point of the scene is making you think of the song you would play on that boombox, if you had to do it right now.