#14: Say Anything (1989)
Peter Gabriel’s “In Your Eyes” boom-box moment is one of cinema’s greatest romantic gestures. The soundtrack captures late-’80s emotional sincerity — big feelings, big music. Songs by Red Hot Chili Peppers, Depeche Mode, and Gabriel balance angst with wonder. It’s the sound of youthful love: messy, earnest, and beautifully over-the-top. A perfect match for John Cusack’s iconic underdog charm.

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