Miles (Paul Giamatti) is the most self-aware lead character yet in an Alexander Payne film, so of course he’s despondent. Payne’s previous films specialize in characters grappling with self-delusion, like retiree Warren Schmidt of About Schmidt and self-important Tracy Flick of Election. But Miles is different — he walks with the slumping posture of, well, a Paul Giamatti character, and he has no choice but to live by his insecurities.
Jack (Thomas Haden Church), on the other hand, covers his with several layers of restless horniness. Jack is a washed-up actor about to marry Christine (Alysia Reiner), and he’s Miles’ best friend from college, who doesn’t understand why Miles can’t just get over his divorce. Or his oft-rejected novel. Or his increasing dependence on wine, or the accompanying feeling that, as a middle-aged man, he has long ago peaked. Jack and Miles embark on a trip through California wine country, as a last hurrah for Jack’s bachelorhood. Miles want to drink fine wine and play golf; Jack wants to drink anything and pick up women.
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