en don't really get middle-aged, real-life-style, touchy-feely movies made about them in the way women do. Cinematic portrayals of male friendship tend to be of the Swingers school—male bonding through scoring babes, rather than the more feminine motif of bonding by suffering through one's girlfriends' too-human shortcomings. Director and screenwriter Alexander Payne (Election, About Schmidt) manages to combine both the male and female traditions in Sideways, a middle-aged male buddy bonding movie about human weakness, forgiveness, and scoring babes.

A subtly written and executed treatment of Rex Pickett's "Sideways: A Novel", Sideways, the film, attempts to unravel itself slowly and gently, spending more time on character development than most films—almost too much, in fact, clocking in at 123 minutes of slow, steady unfulfillingness.

The premise is engaging enough: sensitive, nebbish protagonist and wine snob Miles (Paul Giamatti) and has-been actor and all-around LA dude Jack (Thomas Haden Church) set off for a week in southern California wine country a week before Jack's wedding. What Miles hopes will be a week of bourgeois testosteronity—golf, wine-tasting—is in Jack's mind a perfect opportunity to get laid as much as possible before his wedding.


The next step is a ribald game of Truth or Dare...

Though the film is seen through the vaguely more sympathetic lens of Miles, it's hard to tell which of the two friends is, really, more fucked up. Whereas Jack is quintessentially shallow, deceitful to himself and others, fairly amoral and obsessed with poontang, Miles has sublimated a lifetime of self-prophesied disappointments into unhealthy obsessions with wine and his own failure. As the friends encounter a pair of enthusiastic, eligible California wine-loving ladies, each becomes more disappointed with the other as the week wears on. Jack, unable to exercise self-control or respect for his friendship with Miles, is frustrated and pushy with his gun-shy friend’s inability to “close the deal” with waitress Maya (played here blandly by Virginia Madsen). Miles, on the other hand, finds it harder and harder to stand by philandering Jack, who seems to have everything Miles wants (while Jack is at least a has-been, Miles is simply a never-was) and is yet willing to squander it all for a chick who pours wine (Sandra Oh).

While the film strains for depth, dwelling on a pithy allegory of the fragility and fleetingness of special wine with the precarious charms of life (we are at one point subjected to a vaguely insipid soliloquy in which Miles describes himself under the thin guise of Pinot Noir), it often fails to reach it meaningfully. Though Giamatti and Church’s portrayals are gentle and finely wrought, the nature of their friendship is questionable. Are they really learning lessons about life and love, vulnerability and risk, as the film might seem to suggest? Or is Miles really just a huge doormat hanging out with a caring, but ultimately opportunistic, jerk?


"Dude, that was the most careless plastic surgeon I've ever seen..."

Dew-eyed Giamatti is compelling here as Miles, but it’s a little hard to feel compassionate towards the character after Jack walks all over him for the nth time. Some of it’s in the name of comedy, sure—but this is buddyism beyond the call of duty, and eventually it reflects more poorly on Miles than Jack. The film’s unfinishedness—which is to say, it’s unclear raison d’etre rather than its intentionally open-ended conclusion—is really its crippling flaw. It seems reasonable that Jack would care for Miles, especially since his esteemless friend serves willingly as a glorified lackey, but why would supposedly intellectual, sensitive Miles continue to abide Jack? For all its evenly paced detail, the film seems to leave this essential bit of irrational soul out: it never provides a convincing argument for why these two losers still love and tolerate each other so deeply, other than perhaps that they are both just that shallow and desperate, which isn’t really a satisfying answer at all.

That said, Sideways is in many senses better grounded in the real world than many of its contemporaries. For a film that seeks to both entertain and be realistic, it does both adequately well, weaving a couple of truly poignant moments (almost entirely courtesy Giamatti’s rich expressiveness) through its languid tapestry. Perhaps only middle-aged men will find this actually hits home, but at least it hits near.