Wonder Boys (2000)

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Celebrated novelist and university lecturer Grady Tripp is suffering from a nasty case of writer's block. Unable to finish his second novel, he searches for answers in his private life: a mess ever since his wife left him and he began an affair with the university's chancellor, Sara Gaskell, behind the back of her husband. Tripp's life is changed forever when he agrees to help gifted yet socially inept student James Leer out of a difficult situation, setting in motion a spiral of comical events.