Miles and Jack are as different as night and day, with small-time actor Jack coasting on his aging, still chiseled looks and natural, borderline-smarmy charm to get whatever and whomever he sets his eyes on. In terms of strength, physical appearance, and go-getter attitude, the more average Miles has no hope of matching Jack. Their friendship, which the viewer learns began when they shared a dorm room their freshman year in college, is an unlikely, somewhat unhealthy one, with Jack seemingly using Miles to feel better about himself and Miles going along with it because, otherwise, he'd be alone.

Based on the novel by Rex Pickett, "Sideways" has been directed by Alexander Payne, a distinguished writer-filmmaker with a gift for creating multidimensional, blindingly real lead characters who always seem to be going through some kind of existential life crisis. The film is more subdued than Payne's great last two features, 1999's "Election" and 2002's "About Schmidt," which found surprisingly funny humor in the most dark and painful of people's personal experiences, but shares thematic characteristics. Like Matthew Broderick's high school teacher in "Election" and Jack Nicholson's lonely retiree in "About Schmidt," Miles is an uncertain man who has begun to despair about the low level of meaning his life has so far held. "Sideways" is not as funny as Payne's past offerings, and occasional attempts at broad comedy are some of its most obvious, least effective moments. Better, then, is its perceptive portrait of these two wildly different friends, Miles and Jack, both searching for identity and worth in diverse ways, and finding them in unexpected places.

With Jack set to get married in just a week, Miles has set up a trip for them—one last hurrah—to the Santa Ynez and Solvang areas of California's Wine Country. Miles, a wine connoisseur, sets out to teach Jack about the techniques of smelling and tasting the alcoholic beverage, and the subtleties within recognizing the good from the bad, but Jack has another goal in mind: he wants to go wild and get laid before he steps into marriage. Soon they have paired off with two lovely women they meet, Miles with soulful waitress and past acquaintance Maya (Virginia Madsen), and Jack with feisty wine pourer Stephanie (Sandra Oh). Miles and Maya bond over their love of wine and their shared frustrations in past relationships, while Jack and Stephanie veritably hit it off, in and out of the bedroom. What neither women know, however, is that Jack is getting married, and his promises of a future with Stephanie have been but sweet-nothings that she has understandably taken seriously.

In terms of the overall cinematic package, "Sideways" is more outwardly blemished than "Election" and "About Schmidt." The comedic flourishes, although sometimes successful, come off on occasion as too over-the-top to be believed, such as Miles' reaction to learning his ex-wife has remarried. Likewise, there are a few awkward scene transitions that throw you out of the moment, and one or two dramatic moments, particularly Jack's emotional catharsis near the end, that are strained. Lest it seem that way, however, "Sideways" is far from a failure, and its often low-key study of human interactions and bonding is quietly truthful and erudite.

Director Alexander Payne and co-writer Jim Taylor (2001's "Jurassic Park III") see their flawed characters and their complex circumstances with an uncompromising honesty and fondness that few filmmakers today could hope to achieve. Payne does not sugarcoat them, nor does he view anyone as purely virtuous. Instead, they appear as real people do, growing to mean more to the viewer because they never come off as mere screenwriting formulations. Most intriguing of all, Payne and Taylor are adept here at developing characters through their discussions and knowledge of wine. Those walking into "Sideways" without knowing much about the art of wine tasting will leave two hours later feeling as if they have had an informative, fascinating rush course on the subject.

The building romance between Miles and Maya, a perfect match who wade uncertainly through the waters of beginning a new relationship, is the film's heart and soul. Paul Giamatti (2000's "Duets"), a smart character actor, has collected another exquisite notch on his belt as Miles, who worries that his life will never amount to anything and doesn't know if he is prepared to put his heart on the line again for another woman. For Virgina Madsen (1999's "The Haunting"), her Oscar-caliber work as Maya is the type of sensitive, standout performance that could revitalize a current mid-level career. Giamatti and Madsen carry a palpably steamy chemistry together with little more than sharing conversations and participating in a single kiss.

The other two central actors bring their own weight to the proceedings, with Thomas Haden Church (2001's "3000 Miles to Graceland") owning the part of Jack, who uses his known sexual magnetism to get what he wants without putting much thought into others' feelings, and the always-reliable Sandra Oh (2003's "Under the Tuscan Sun") sweetly striking as the unknown victim of Jack's lies, Stephanie. Memorable, vivid supporting work fills the movie's outer edges with no more than a scene or two apiece, including Marylouise Burke (1998's "Meet Joe Black") as Miles' mother; Jessica Hecht (TV's "Friends") as Miles' ex-wife, Victoria, whose caring appearance in the climax comes as a surprising revelation to what the viewer has already envisioned of her; and newcomer Missy Doty as a plain-Jane waitress who Jack seduces.

The novel beauty of the California coast's wine country is brought to indelible life courtesy of Phedon Papamichael's (2003's "Identity") lush cinematography, complete with gloriously rolling yellow hills, sun-dappled trees, and endless vineyards sweeping across the countryside. The original setting brings added value and depth to the picture, a refreshing respite to so many big-city pictures, capturing the laid-back feel and luminescence of its people and land. When "Sideways" tries too hard to be broad comic or overtly dramatic, the film modestly stumbles, but only for a minute or two at a time and only sparsely. Director Alexander Payne is wise to recognize more often than not that he doesn't need to try to do these things, anyway. His accurate, unrushed, and touching procurement of his characters and the lives they lead, mistakes and all that they commit and learn from, is where "Sideways" garners its freshest, most wise sensibilities.