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Whether he is the boy-band victim of "Cry Me a River," the charming cad of Friends with Benefits , or the married man in crisis of Palms , Timberlake cannot separate his real romances from his fictional ones. And that, ultimately, is what makes him the most compelling romantic lead of his generation: you never know if the music or the movie is confession or fiction. But you know it’s always, irrevocably, about love and loss.

This is where Timberlake transformed from a singer into a storyteller.

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