Miles is a failed writer who works as a high school English teacher and still mopes over his two-year-old divorce. Jack is a D-list actor still trading in on his decades-old fame as a soap opera surgeon. Bolstered by the kind of clueless bravado that seems to infect most actors, Jack is on the verge of getting married to an attractive and relatively wealthy woman. Miles, being best man and best friend, suggests one last “boys only” road trip to serve as a week-long bachelor party. Since he's a wine connoisseur, Miles decides the pair will forego the usual strip clubs and head up to California wine country for a few days of drinking and driving.
Eager to sow the last of his wild oats, Jack soon veers off the predetermined path and insists that he and his pal hook up with a brainy waitress named Maya (Virginia Madsen) and a spunky single mother named Stephanie (Sandra Oh). Miles, a self-loathing snob who has had his eye on Maya for months, rejects the idea. His stubborn lack of self-esteem simply won't let the possibility of happiness penetrate his calcified funk. Plus, there's the little fact that Jack is getting hitched in San Diego at week's end. Ultimately, Jack browbeats his pal into it, and the quartet begin a five-day double date that is more-or-less doomed to run into that (conveniently unmentioned) Sunday wedding deadline.
Most viewers will quickly pick up on the fact that neither Miles nor Jack is a particularly admirable fellow. Both seem to need a pretty major smack upside the head. (Which the film will eventually provide in literal and figurative terms.) Despite all the diversions (both alcoholic and female), Miles will eventually be forced to confront just how miserable his existence has become. And it's a fair bet that Jack's bravado will fail the actor as badly as Miles' intellect has failed him.
Female viewers may have a harder time understanding the moods and actions of these two underdeveloped men-children. Male viewers are slightly more likely to sympathize with the boys' baser, more self-indulgent urges. But, then, that's the point Payne is trying to make: There's a fine line between tragedy and slapstick, and many of us are more than willing to stumble over it time and time again.
Payne's wonderfully real dialogue (not to mention the threadbare camaraderie between Giamatti and Church) paints an incredibly accurate portrait of manhood grinding its gears and going nowhere. There are moments (many of them, mind you) when you'll be pretty annoyed at these characters. But, there are also moments when you'll crawl deeply into their hearts and heads. Miles' description of his favorite grape, the Pinot Noir, as “complex,” “thin-skinned” and “hard to nourish, but worth all the trouble” is a lovely, well-delivered metaphor.
In the end, it's hard not to be struck by this film's brutal honesty. Payne has taken some seemingly problematic material (adapted from a novel by Rex Pickett) and made it, somehow, imminently relatable. We've got a couple confounding characters, a claustrophobic setting and a series of would-be elitist jokes based on wine tasting. (“Oh, no. I'm not having dinner with anyone who orders Merlot!” screams Miles at one point.) And yet, Payne's instincts in scripting as well as casting are spot-on. Giamatti, playing his usual schlub of a character, is perfect. Church, perhaps poking a bit of fun at himself, is certainly believable as the hammy cad. Madsen, who hasn't had a meaty role since … um, Candyman, is a welcome addition as probably the film's sole lead with a firm grip on self.
Like many an expensive wine, Sideways is the kind of acquired taste that will still end up leaving a bitter flavor in some folks' mouths. Those who “get” it, however, will be grateful for the chance to drink deeply from such a mature and rewarding vintage.
