We've all known someone like Miles (Paul Giamatti), a failed novelist who's sliding into middle age with little to show for himself other than the expertise he's acquired in a rarefied realm, expertise that allows him to feel less like a slob and more like a snob. For Miles, who's still reeling from a divorce that most of us would have gotten over by now, the rarefied realm is wine, el vino. Women and song can wait till later. Right now, all Miles wants to do is swish, sniff and sip glass after glass of fermented grape juice in all its wondrous variety and complexity.
But a road trip to California's Santa Yuez Valley, where the wineries line up like rides at a theme park, could change all that. Miles has asked along his old college roommate, Jack (Thomas Haden Church), a former soap-opera actor reduced to making a comfortable living doing commercial voice-overs. For Jack, who's scheduled to get married as soon as he gets back to Los Angeles, wine, like life, is something to be swigged, not sipped. And the week-long traipse through the vineyards that Jack has planned for him is a last chance to sow some wild oats.
Sideways, which Alexander Payne has directed from a novel by Rex Pickett, is an oenophile's Tin Cup, a comic ode to the male ego as it swells to the size of a beach ball and shrinks to the size of a pea. Despite Miles' desire to spend the whole week identifying the various flavor notes as they land softly on his palate - "a soupÃon of asparagus," he says with an air of pristine self-satisfaction - Jack is determined to get both of them laid. And he doesn't mind telling a few white lies, perhaps even some darker ones, in order to get the job done.
Enter Stephanie (Sandra Oh), a wine pourer who falls for Jack's faded-glory routine, and Maya (Virginia Madsen), a waitress who knows almost as much about wine as Miles does. Payne handles the relationship between Miles and Maya so delicately that we never stop to ask ourselves why a woman like Maya, so soulfully beautiful, might be interested in a guy like Miles. Credit also goes to the actors. Madsen, in her 40s, is as lovely as ever, and Giamatti, who doesn't exactly look like leading-man material, puts us in touch with Miles' own soulful beauty, his heightened sensitivity.
Church used to routinely knock the one-liners out of the park on "Wings," and he supplies a lot of the laughs here. But when he and Giamatti get their Oscar-and-Felix number going, it's like a whole new kind of odd couple, one that's firmly grounded in reality. Miles and Jack probably shouldn't be friends anymore, and maybe they won't be after this bachelor-party-from-hell is finally over. In the meantime, they're stuck with each other, a couple of guys who should be moving forward with their lives but instead keep moving sideways. Rarely has failure been limned so successfully.