Sideways (2004)

USA, 126 minutes 
Director: Alexander Payne
Writers: Alexander Payne, Jim Taylor
Photography: Phedon Papamichael
Music: Rolfe Kent
Cast: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh

Everything in this dire romantic comedy, from the preoccupations of the two losers who occupy center stage to the myriad perfectly observed details of California life to the insipid jazzy soundtrack, is just right. Paul Giamatti with his wonderfully swallowed guttural growl is proficient as ever as Miles, a junior high English teacher, wannabe novelist, and wine-snob drunkard watching his life fall apart from his own self-pity. He is usually annoying, and often wrenching. His buddy Jack, played by Thomas Haden Church, is even more annoying and equally affecting as a commitment-phobic sex addict and two-bit actor. Old college friends, the two have little to connect them any longer beyond low-level golf skills, compulsive lying, and a shared sense of profound disappointment with themselves and their lots. But their affection for one another is genuine, not desperate, as becomes evident over the course of the week-long trip through California's wine tourist country prior to Jack's doomed wedding that makes up the bulk of the movie. In form it's thus a species of road movie, but for me in many ways it updates the Woody Allen I appreciated from the late '70s and Hannah and Her Sisters, the Chekhovian impulse for mild, occasionally discomfiting set pieces of grown-ups (who are also children, which is all of us) grappling with the pains and complexities of romance and life and meaning. Virginia Madsen as Maya, a sensitive and intelligent recently divorced woman who works as a waitress in the wine country while she pursues a degree in horticulture, somehow lifts the whole thing a notch higher even as her character raises the stakes. With her own interest in wine, Maya is drawn to something in Miles—more likely that's a fantasy of director/writer Alexander Payne, but set that aside for the moment. The conversations between Miles and Maya as they find themselves falling into each other's orbits, the discussions of interests and motivations and dreams, are impossible. Do people really talk like that? Well, they do here, and the conversations are exquisite and endearing, the movie's unbearably attractive heart, the point where my guard dropped all on its own and left me vulnerable to the shenanigans. Call it the tenor of Madsen's voice. The resolution that's offered would have to be categorized as fantasy, but it's a relief from the surprising degree of pain of the closing scenes—Giamatti always has the face to carry off such anguish, it's basically his bread and butter—and ultimately leaves a beautiful note to end on: Madsen's lovely voice again, and the way she addresses Miles, speaking to an answering machine.