Wonder Boys (2000)

Middle-aged literature professor Grady Tripp (Michael Douglas) is having a bad day: his wife has just left him, he’s having an affair with his boss’s wife (she also happens to be the chancellor of the university), and his editor is coming to town expecting a finished manuscript—of which he’s written very little, although he’s already used up a full ream of paper in the attempt. His own “wonder boy” years as star author far behind him, he embarks on a snowy Pittsburgh weekend odyssey that ends up involving a stoned literary prodigy (Tobey Maguire), a transvestite, a dead dog hidden in a trunk, a manuscript more promising than his own, and the stolen jacket of Marilyn Monroe. Michael Chabon’s novel of midlife crisis is wisely centered in the academic milieu: is there any more constant reminder that you’re past your prime than being surrounded by the flush of youth 24/7? We could feel our own age lines expand as we watched, but that doesn’t mean the movie isn’t smart, quick, witty, and lovable—it is. With Frances McDormand.

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