Alexander Payne makes Comedies. Not the eager-to-please, quick-read kind with wall-to-wall mugging, pud-tugging, and fear-of-buggering; but gently told personal crisis tales of ambiguous whimsy. Comedy by the traditional theatrical definition, where the biggest jokes are subtle sociological ones that implicate the viewer, and humor steadily gives way to scenes of human desperation. The male protagonists in Alexander Payne’s last three films—Election, About Schmidt, and his latest, Sideways—are American counterparts to Chekhov’s Vanya: invirile melancholics desperate to slow a quickening slide. And like Chekhov, Payne eases his audience into the dark corners, summoning laughter that later gets caught in the throat.

Sideways, adapted from a novel by Rex Pickett, has a familiar, perfectly banal conceit—recently divorced man joins soon-to-be-wed college buddy for a week of debauchery and disintegration—that quietly, gradually takes on weight as it goes. Paul Giamatti plays Miles Raymond, the sad sack divorcee, a novelist who may or may not be on the verge of publishing his first book, and Thomas Haden Church is Jack, his gregarious C-list actor friend. They are opposites, of course, and their interactions often result in Abbott and Costello-like exasperation, but there’s comfort between them, the ease of unlikely friendship grown intimate over time. Similarly, Sideways is patiently ingratiating—zooming in slowly so that our intimacy with the characters feels natural, if unexpected. The film earns our sympathy by taking the time to grow familiar.

Payne’s initial approach is so unhurried, and the early mise-en-scène is so unremarkable, that it’s not immediately apparent what distinguishes the film from made-for-network-television proceedurals. Miles wakes and lumbers about his bachelor pad, gets into his car, runs some errands, and picks up Jack at his future in-laws’ opulent home. Most are wide shots, from a neutral distance, marking the progress of our protagonist through the suburban landscape. Rolfe Kent’s score is particularly jaunty here, and the steady California sun is evenly distributed, no signs of shade.

Their destination is wine country, and the camera notes every exit ramp and roadside distraction along the way. Far from Miles’s characterless apartment, he seems at home in the family-owned motel and restaurant that they frequent throughout the week. It turns out that he’s been to all these places before—on wine-tasting excursions with his ex-wife—and he’s alternately proud and embarrassed by the fact that everybody knows his name. He’s a bourgeois Norm, while Jack, the erstwhile Sam Malone, just wants to party. Which makes Miles even more squirmy as he’s cajoled into fraternizing with the waitresses and wine-pourers that he’d previously kept at a class-determined distance. Jack gleefully, guiltlessly pursues an affair with a game wine pourer (and single mother) played by Sandra Oh, while unattached Miles can’t get over the news of his ex-wife’s remarriage—which only sharpens his condescending disinterest in a beautiful waitress (Virginia Madsen). The camera has gotten closer and closer, taking its first real close-ups from across the table of a double date, and holding close to Miles’s face as he crosses into intoxication and makes a unwise call to the ex. “You didn’t drink and dial, did you?” Jack asks. The music has gotten warmer, bluesier, and then vanishes altogether to make room for conversation. The waitress asks about his novel. Miles squirms. He tells her it’s called “The Day After Yesterday.” “You mean, today,” she says.

No other contemporary American filmmaker handles issues of class with more sensitivity than Alexander Payne, from the campaign for student council president that pitted a ruthless social climber against a blissfully clueless son of new money in Election, to the obvious disdain that Warren Schmidt—iconically middle class and miserable—has for the family of vaguely white-trash “pigs” that his daughter marries into in About Schmidt. We don’t admit to having a class system in America, but Payne shows us—without digressing from the points of view of his characters—how much we depend on classist presumptions to define our places in society. In Election, we hate Tracey Flick’s galling ambition so much that we’re willing to go along with Mr. McAllister’s subversion of democracy, just to put her in her place. And Warren Schmidt, searching for meaning in cloying children’s charities and garish porcelain hummels, ought to see that one person’s winnebago is another person’s hot tub, but he can’t. It’s a matter of taste, and we usually don’t have the stomach to admit that it’s money we’re trying to taste. In Sideways, class is demarcated not only by a discerning palette for fine wine but by the social advantages that possessing such a palette implies. Though Virginia Madsen’s waitress exhibits knowledge of wine, Miles doesn’t really listen to her opinions until she demonstrates an astute passion for it. Since Miles can’t really match her passion (not only is she studying horticulture but she bypasses jargon for a lovely, literate, and erotic description of pinot), it’s apparent that his own taste is as practiced as Jack’s crude pickup lines: he responds to her sophisticated seduction with a clumsy kiss and is rebuffed.

Without his WASPy ex around to impress, and with the woman he thought below him now much higher, his taste for wine becomes an embarrassing excuse for common drunkenness. Which, of course, is the common denominator. Stripped of his pretentions, Miles confronts the vast depths of his sadness. It’s no coincidence that when Payne’s protagonists reach bottom they’re not as discerning as they once were—they’ll grab whatever lifeline they find. They’re desperate, and they’re no longer hiding it. And almost instantly, they’re likeable. After playing nebbishy art-slobs for the past few years in films like Storytellingand American Splendor, Giamatti isn’t exactly stretching here, but his performance is deeply affecting. On his awkwardly bearded, wantonly blushing face, he registers at least eleven kinds of loneliness.

After stringing her along for a week, Jack gets his comeuppance from the wine pourer, only to pick up another waitress and this also ends badly. Despite his own disintegration, Miles keeps bailing him out. Never far removed from the collegiate genesis of their unlikely friendship, they obviously care for each other but they’re also going through the motions. Does it end like this, circling back to where it began, roommates more at home in other places? Payne figures that we’ve spent enough time with them to figure it out for ourselves.

The penultimate scene is a knockout. Ditching Jack’s wedding after a humiliating conversation with his ex, Miles fetches a prized pinot that he’d been privately aging and saving for a watershed occasion. Still in his tuxedo, under the harsh fluorescent lights of a fast-food restaurant, he swigs from the bottle and eats a burger wrapped in paper. High and low, swirling around on the same palette. From the look on his face, Miles doesn’t seem bothered by the taste. It’s a watershed occasion after all.
—ERIC HYNES