Miles Raymond (Paul Giamatti), the sad-sack oenophile who forms one-half of Sideways, is the sort of intellectual loser often found in the work of Woody Allen and Wallace Shawn. Miles doesn’t know much — about himself, about why his marriage failed two years ago, about where his amorphous novel-in-progress is going — but he does know one thing: wine. He sniffs, sips, swishes, and analyzes the stuff like a born expert — not that anyone in his immediate sphere cares. Miles toils as an eight-grade English teacher, hoping, like many other English teachers, that a publisher will warm to his work and finance a cozy life spent at book parties and wine tastings.

Sideways, directed by the incisive Alexander Payne (Election, Citizen Ruth), follows Miles and his old college buddy Jack (Thomas Haden Church), a has-been soap actor, on a week’s vacation through the well-lit banality of California. Jack is getting married the next week, and Miles wants to take him out for a final bachelor roar — which, for the schlumpily ascetic Miles, means wine tastings and golf. Jack has fleshier goals in mind: he’s out to get as much pre-marital sex on the road as he can before entering a life of fidelity. These two nowhere men are a kind of indie-film odd couple: Miles scourges himself with self-doubt, while Jack — the sort of genially oblivious, action-oriented guy who isn’t, to paraphrase Shakespeare, sicklied o’er with the pale cast of thought — just wants to drink and get laid. Miles is nothing but a pale cast of thought.

The men arrive at various vineyards, where Miles is greeted as a regular — accepted among others who share his passion for the grape. Payne doesn’t score easy points off the wine-sniffers; they’re not presented as snobs or dorks. In fact, two of the movie’s more dynamic characters — Maya (Virginia Madsen), a grad student who waitresses at one of Miles’ favorite restaurants, and Stephanie (Sandra Oh, the director’s wife, who made a bold impression as Diane Lane’s acerbic, very pregnant friend in Under the Tuscan Sun), a wine pourer, are both also smitten with wine. The movie respects the funkiness of specialized interests; Maya and Stephanie lend oenophilia a patina of cool.

Most of the movie is a two-character play, and the rising anti-star Paul Giamatti is ideally cast as the depressive, mercurial Miles. Giamatti’s specialty is schmucks we can identify with, not because he sentimentalizes them, but because he has a rock-solid instinct for regular-guy mannerisms. Miles, in Giamatti’s hands, is pathetic but never off-putting. Sitcom actor Thomas Haden Church, of Wings and Ned & Stacey, may have the harder role as a slick womanizer with easy charisma and a streak of callousness. He gives Jack a sort of rough-hewn humility — Jack may be washed up, but by God, he was on television for a few years, and women still recognize him from the soap opera and take him to bed. He questions neither his past good fortune nor his current obscurity (he does voice-overs for commercials). He’s also a boy who never grew up, and in a key scene Church shows us the despair under the mask of the eternal frat boy.

Alexander Payne may be warming up a bit. I wasn’t a fan of his previous film, About Schmidt, which seemed too consciously tailored as a Jack Nicholson bid for indie cred. (If Nicholson wants that, he should continue to work under Sean Penn’s direction, and leave the ugly toupees at home.) That movie left me cold, but maybe only because Payne’s first two films, especially Election but also the equal-opportunity offender Citizen Ruth, were such vital satires. Sideways squirts no venom in particular; the flawed people onscreen aren’t ridiculed for who they are or what they want. Payne is a compassionate observer here, letting the dialogue scenes breathe, unafraid to throw in some slapstick (a sequence with Miles trying to retrieve a wallet is laugh-out-loud funny) but keeping the comedy rooted in the characters’ flaws and strengths. When Jack scores with women, the movie doesn’t disapprove — we see that the women are grown-ups and are choosing one-night stands with him. And when Miles lifts a glass of wine to his nose, transported by the hint of avocado or berries or whatever, the movie doesn’t nudge you to giggle. Sideways, in brief, is about happiness and where you find it, and Payne has found it in himself to allow for the comedy and tragedy of ambition. Moving forward or upward, we see here, may be overrated: If Miles never sells his book, and if Jack never finds quality acting work again, at least they can always go sideways.

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