Review: SidewaysSwingers for middle-aged divorcees

Miles (Paul Giamatti) organizes a week-long bachelor trip for his engaged college buddy Jack (Thomas Haden Church), a jaunt through Northern California wine country. We realize as the movie progresses that Miles has set the trip up as much for himself as for Jack; Miles is the oenophile, the one who loves pinots and syrahs. Jack, a former soap opera star, is an overgrown surfer who chugs wine while chewing gum.
For those who watched Swingers, Jack is Trent, and Miles is Mike. The parallels continue. Miles is divorced but not over his ex-wife Victoria. He's uneasy around women, even those attracted to him, and he over analyzes every situation. Jack is about to be married but hasn't got the inveterate womanizing out of his system. He's an easygoing charmer with the looks of a middle-aged surfer and the personality of one who never grew up. Jack sets them up on a double date with a women who serves them alcohol at a winery (in Swingers it was a cocktail waitress at some off-Strip casino). There's a painful phone call and later a voice message from Miles, though Mike's in Swingers is far more uncomfortable. There's the distribution of condoms. While Jack puts the moves on his date Stephanie (Sandra Oh), Miles has a soulful conversation with his date Maya (Virginia Madsen), a waitress he's met before and has always been attracted to. Later, the two men play a painful round of golf. The territory of male healing treads familiar ground.
The other similarity between the two movies is that they're both very funny. After seeing the trailer, I didn't think I was ready for middle-aged men on a road trip, but the trailer doesn't do the movie justice. Alexander Payne and Jim Taylor (Citizen Ruth, Election, About Schmidt) write dialogue that is always informing us about the characters at the same time that it keeps us laughing. Only a few moments into the movie, and Miles and Jack emerge as distinct personalities with depth. Giamatti, Haden Church, and Madsen are all excellent.
It's always enjoyable to poke fun at oenophiles. Miles, at one point, babbles on about a wine while Jack looks on with wide-eyed incomprehension: "...just the faintest soupçon of asparagus, and, like a nutty Edam cheese." He says all of this with a straight face but can muster none of this eloquence when describing his own emotional hurt.
Payne's comedies have dark souls, though. Unlikeable and somewhat grotesque middle-Americans inhabit his movies (Reese Witherspoon and Matthew Broderick in Election, Jack Nicholson and his daughter's fiancee's family in About Schmidt). The movies seem to elbow us in the ribs, with a pursed lips and a point of the chin: aren't these losers pathetic? Don't you pity them? We hope most of them will find a patch of unpolluted happiness or grace, but the end credits always leave us uncertain.