In writer-director Cameron Crowe’s debut film, original Gen X underachiever Lloyd Dobbler (Cusack) isn’t sure about a lot of things as he graduates from high school. But he is sure that Diane Court (Skye) is the girl of his dreams. In a bold move, Lloyd invites Diane to a graduation party, and, to the surprise of everyone, she accepts. Lloyd and Diane start a friendship with potential that blossoms into love. Lloyd is the steadiness Diane needs as the rest of her world crumbles after the IRS begins investigating her father (Mahoney) for tax fraud. The stress of the investigation and her impending departure for college end their relationship. To win Diane back, Lloyd makes one of the most iconic grand gestures in film history. — Erin Ritter
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