68. Lloyd Dobler
Say Anything...
Heartbreak. One of the worst feelings a person can have. Loving somebody who won't love you back and the pain that comes with the realization that you can't have this person. It sucks, it hurts, and it's awful. Lloyd Dobler knows.
An underachiever and aspiring kickboxer, Dobler begins a relationship with intelligent but socially awkward valedictorian Diane Court (who looks like Ione Skye so there is no god damn way she is socially awkward). Lloyd seeks advice from both his sister and several close female friends who are seriously looking out for Lloyd's best interests in his first serious relationship.
But as Diane's father (Frasier's father) goes under investigation by the IRS for tax violations committed at his nursing home, she worries that she should be spending more time with him. Add on top of that the fact that Diane's dad doesn't approve of his daughter dating someone like Lloyd, and soon it's Splitville for the two of them.
Lloyd's crushing heartbreak as his first serious love goes kaput is a real downer and John Cusack is such a fine actor to make us all recall our own moments of love and loss.
Defining moment: Waiting outside Diane's window, blasting Peter Gabriel from a boombox above his head.
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