Sideways' antihero Miles (Paul Giamatti) may be a miserable, divorced, unpublished novelist on a downward spiral, but at least he knows his wine. At a vineyard with his friend Jack (Thomas Haden Church), Miles fussily goes through the whole tasting rigamarole: He tilts the glass to check the color, he inhales the bouquet, he swishes a sample in his mouth and makes hilariously self-important pronouncements. In one glass he claims to detect hints of citrus, passion fruit, cheese and "just a soucon of asparagus."
Hollywood usually treats wine fanciers as stuffed shirts ripe for deflation, and Sideways quickly makes clear that Miles' love of the grape provides a respectable cover for his alcoholism. Director and co-writer Alexander Payne, however, shows an unexpectedly sincere belief in wine as an emblem for the enjoyment of life. Miles and Jack seldom stop to appreciate such gifts as Sideways takes them both through a weeklong midlife crisis.
Sweating over his novel's last chance at publication, Miles eagerly anticipates a road trip of golfing and quaffing with Jack in California wine country. He arranged the trip as a wedding present to Jack, his oldest friend and a former soap opera actor. But scarcely have they hit the road when Jack announces his secret agenda to get them both laid.
Payne clearly cast Church and Giamatti against the Hollywood "type" for romantic leading men. In physique and performance, craggy Church and slumpy Giamatti embody the middle-aged blues--they could be called Glum and Glummer. Church's face looks like a rocky outcropping, and although Jack's more vivacious and aggressive than Miles, his charm shows its strain. Giamatti, attuned to Miles' imminent collapse, keeps his face in a near-wince and views the warm attentions of his single friend Maya (Virginia Madsen) with open wariness.
Jack hooks up with earthy Stephanie (Sandra Oh), who pours wine samples at a vineyard. When the four go out for dinner, their casual conversation echoes both the awkward tensions and mature confidences of midlife dating. Yet the men keep significant secrets from the women.
Miles lowers his defenses with Maya in an exquisite scene that shows how a common interest can reveal opposite personalities. Miles talks about his fondness for Pinot Noir and clearly believes the "thin-skinned, temperamental, early ripening" grape represents himself. Maya admires how a fine bottle connects her to the time and place of the vintners who made it. "And it tastes so fucking good," she says. For Maya, wine gives her a chance to experience life outside herself, but for Miles, it's all about looking inward.
Madsen and Oh (Payne's offscreen spouse) portray two of the most well-rounded and sensuous female characters of the year, and for a while Sideways unfolds like a mellow, impeccably acted idyll. The glossy vineyard scenes look like travelogue footage compared to the ugly moments at mass-appeal eateries with names like the Hitching Post. Payne's disdain for middle-American consumerism frequently feels like snobbery.
Miles and Jack's lies eventually catch up with them, and their vacation disintegrates into a hilarious, cringe-inducing series of mishaps. And though Jack at first seemed merely interested in sowing some last wild oats before his wedding, he turns out to be more compulsive and emotionally immature than Miles understood.
Mercilessly insightful, Payne shines harsh light on American men who repeatedly fail to resist their piggish instincts, like Matthew Broderick's hypocritical civics teacher in Election and Jack Nicholson's raging retiree in About Schmidt. Perhaps the filmmaker identifies more with Jack and Miles as struggling artists--he torments them only because they should know better. But when the director ultimately treats them with generosity, Sideways suggests that, like a fine wine, Payne's sensibility is turning less sour with age.