Peter Gabriel's "In Your Eyes" in Say Anything...
Film Released: 1989
One of the most iconic gestures of love ever seen in any film had underachiever Lloyd Dobler (John Cusack) trying to win the heart of class valedictorian Diane Court (Ione Skye) by blasting Peter Gabriel out of his boombox by her window. The film won over audiences for its sympathetic, reasonable portrayal of young adults.
The scene won us over because it made it cool to blast a boombox by a girl's window, which meant we could finally compete with those douchebags who only scored chicks because they played an acoustic guitar and seemed so "sensitive."