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John Cusack played a great lead in the  2000 film adaptation of High Fidelity - a top 10 music movies in our book.  But his most famous scene in a movie remains the one from his 1989 debut feature film, Say Anything, when, as hopelessly love struck Lloyd Dobler, Cusack appeared below the window of the object of his affection holding a boom box over his head blaring Peter Gabriel's In Your Eyes.  That brief scene accounted for a major sales resurgence of an album that had already achieved a number of milestones in the three years since its release.
During the Hollywood Bowl concert (10/7) marking the 25th anniversary of the So album, Cusack emerged from the wings of the stage, boom box in hands, presented it to Gabriel and made his exit, appropriately, without a word.  Say Anything director Cameron Crowe was in the audience and tweeted about it.  Cusack responded by urging his fans to follow Crowe on Twitter and 'occasionally suggest' that he and Crowe should do another movie together.