No one understands the plight of the middle-aged white guy like Alexander Payne. The filmmaker who brought out the pathos of Matthew Broderick's sad-sack high-school teacher in Election and explored the hopelessness of getting older in About Schmidt delivers another pitch-perfect rumination on the futility of life in his new film, Sideways. Payne may well be the most insightful American filmmaker of the last decade, and his great talent is that even as his films plumb the depths of life's despair, they remain hilarious, poignant and strangely life-affirming.
Sideways is Payne's most gentle film to date, leaving the Midwestern drab of the director's native Nebraska, the setting of his first three films, and heading to California's wine country, where old college buddies Miles (Paul Giamatti) and Jack (Thomas Haden Church) are on a one-week vacation before Jack is to get married. Miles is a divorced middle-school English teacher and failed novelist, the kind of self-pitying but somehow lovable narcissist that Giamatti perfected in American Splendor. Jack is a has-been actor still coasting on his old soap opera appearances and occasional commercial work. Miles, a dedicated oenophile, is set on having a bonding experience with his old buddy for the week, sampling the finest wines, playing golf and sending Jack off in style to his new bride. Jack, however, could care less about his friend's wine fetish, and wants nothing more than a final fling (or two) before settling down. He's also determined to get the terminally mopey Miles a little action of his own.
This sounds like the setup for a terrible, crass buddy comedy, yet in Payne's hands it's anything but. Miles and Jack meet two locals, waitress Maya (Virginia Madsen) and winery employee Stephanie (Sandra Oh, Payne's wife), and the connections between the two men and two women serve as catalysts for both wicked humor and complex self-reflection.
Miles, still depressed over his divorce and pining for his ex, takes every chance to sabotage his potential relationship with Maya, behaving like a petulant child even as she tentatively reaches out to help him heal his wounds. His erudite love of wine is a thin cover for a raging alcoholism, fueled by the failure of his novel (pointlessly titled The Day After Yesterday), the failure of his marriage, and what he sees as the general failure of his life. It's easy to see that Maya holds the key to Miles' salvation, but Payne and his regular co-writer Jim Taylor (working from a novel by Rex Pickett) never let things go the easy route, nor do they allow for a pat ending. Everything the characters achieve must be worked for, no matter how much the audience may want to see it.
While Miles is clearly the film's focus, Jack is really no better off, despite his relative wealth, success and good looks. Scared to death of marriage, he rushes headlong into an affair with the uninhibited Stephanie, neglecting to tell her that he's got a wedding in a week. Jack is more than just a cad who's playing an emotionally vulnerable woman for a fool; he's emotionally vulnerable, too, genuinely wondering whether he wants to go through with his wedding and harboring thoughts of running away to the wine country and opening a vineyard.
Even as Miles and Jack both do some incredibly stupid things, and look forward to the rest of their lives with little optimism, Payne makes you root for their success. He manages to keep surprising us with developments in the story, as characters behave in unexpected but entirely realistic ways. He also makes excellent use of a cast of underappreciated actors, each given their chance to shine.
Giamatti has been building a head of critical steam since his spot-on evocation of comic book writer Harvey Pekar in American Splendor, and he delivers here in a big way, making Miles believable both as a hopeless loser and an appealing object of romantic attention. Church, best known for sitcom parts on Wings and Ned & Stacey, and Madsen, best known for lots of straight-to-video horror flicks, both get their juiciest roles in years and don't waste the opportunities. Oh, with the smallest role of the four, looks as luminous as you'd expect the wife of the director to look, and makes the most of the sassy, wounded Stephanie.
If Sideways isn't as biting or insightful as Election or About Schmidt, it makes up for it by being warmer and perhaps more truthful, showing the highs along with the lows. It's Payne's first film with a genuine love story, even if it's one tempered by uncertainty. In the end, it's still one of the most moving pictures of the year, a sweet but unsentimental look into life's law of diminishing returns.