Having emerged as one of the foremost directors of American dark comedies during the late 1990s, director Alexander Payne traded in a few pats of humor for a few pounds of depression with 2002's sprawling, leisurely paced About Schmidt. Sideways continues the trend: While peppered with humor, the film produces countless moments of sadness, irritation and discomfort. Payne has not lost his ability to penetrate our neurotic quirks and interpersonal failings; on the contrary, he does so with more subtlety than ever, and seems less interested in sugarcoating his efforts with comic relief. The results are admirable yet often quite dreary.
Paul Giamatti stars as unpublished novelist Miles Raymond, whose divorce of two years ago still dogs him daily. Miles' college roommate, fading soap-opera actor Jack (Thomas Haden Church), joins him on a California road trip to celebrate the latter's impending matrimony. But Miles soon finds that the wine-tasting tour he's meticulously planned bores his friend. Instead, Jack declares his true objective: to get both men laid. Miles objects partly on moral grounds and partly out of fear, but mostly because he'd rather stay in and drink.
But while stopping at a sleepy restaurant known for its choice wine selection, Miles admits a crush on vino-centric waitress Maya (Virginia Madsen). After Jack chats up spunky server Stephanie (Sandra Oh) at a local winery and discovers the two women are friends, Jack sets up double dates for the foursome. The first evening goes awkwardly for Miles, who describes his latest unwieldy manuscript to Maya while Jack and Stephanie vigorously get it on in the background. An unsparing week of lies, obsessions and infidelities follows.
Unlike Jack Nicholson's Warren Schmidt, Miles isn't headed for old age lacking any self-knowledge or interests. Instead, he's constantly punishing himself with self-knowledge and boring others with his hobby. After he self-importantly sniffs and swishes his wine, Miles employs ludicrously flowery terminology to deliver rapturous assessments of each bottle he tastes annoying Jack, for whom all wines pretty much taste "good." Nervous, temperamental and dipsomaniacal, Miles faces chances for romantic happiness that depend on finding a very patient woman who shares his niche interest. Perhaps because this über-underdog wants deep down to be a good guy, we eventually root for this unlikely outcome.
Not so with Jack. A cultural blank and an unmitigated bastard, he's the lunkhead who always gets the girl but never should. His initial enthusiasm for this vacation has little to do with his friendship with Miles and everything to do with his own penis. Even as he earnestly advocates for romance between Miles and Maya, he unconsciously sabotages Miles' chances by telling misguided lies to both women. Jack has stubbornly passed the point in life where he might change, and there's no charm whatsoever to his incorrigibility.
It takes convincing performances to extract such extreme reactions. On paper, Miles might resemble Giamatti's turn as Harvey Pekar in American Splendor, but on the screen, he's an altogether different bundle of hyperactive neuroses. If Miles approached us at a party, we'd all probably duck, yet when his heartbreak comes, we're willing to share his pain. Church, on the other hand, has the thankless task of bringing to life a cowardly, drab womanizer who'd be at home in In the Company of Men or even Carnal Knowledge. He did his job; expect to despise him.
Yet this depressing believability makes Sideways Payne's most difficult film to assess thus far. His earlier films fired satirical darts in all directions, and with more verve. Here, the women are saints while the men misbehave; that Payne draws these lines with more realism than ever only accentuates the fatalistic emotional landscape of Sideways, and makes the few notes of optimism Payne eventually strikes feel somewhat forced. Still, the movie says more than a little about self-centered American assholes and their prospects for rehabilitation, which makes it, if not an easy film to love, at least an easy one to respect.