Sideways (2004)

           Miles Raymond and his friend Jack are both losers in their own, very different ways. But they were roommates as college freshmen, and so Miles takes Jack on a tour of California's wine country a week before his wedding in a sort of two-person, weeklong bachelor party of wine-tasting and golf. Miles is a clinically depressed, misanthropic, divorced, alcoholic middle school teacher whose novel has been rejected. He oozes self-hatred and is utterly endearing. Jack is a back-slapping, good looking hunk of a bit-actor who wants to bed a few women before he settles down to marriage. The plot revolves around the two women they meet on their trip, Stephanie and Maya, and the consequences for all involved. Side-splitting humor and deeply human poignancy combine in this travel narrative. I loved Paul Giamatti (Miles) in American Splendor, and he is every bit as good in this film. His character is developed more than Jack's, but perhaps Jack has little character to develop? This movie has received uniformly great reviews (a notable exception being one in the New York Times).