Much as he tries to move forward, junior high school English teacher and unpublished novelist Miles (Paul Giamatti) is going nowhere. Still muttering over the abandonment of his ex-wife, he’s angry at himself, his students’ repetitively error-ridden papers, his college roommate’s apparent happiness. In an effort to celebrate the upcoming nuptials of his old friend, sometime tv actor Jack (Thomas Haden Church), Miles arranges for a weeklong tour through the vineyards of Southern California’s Santa Ynez Valley. Imagine his dismay when Jack sees their trip as a last chance for rollicking through the bed of every girl he meets.
Adapted from Rex Pickett’s novel by Jim Taylor and director Alexander Payne, Sideways takes something of a skewed view of its road-buddy protagonists, allowing them to judge and beat up on each other emotionally, even as they profess their enduring friendship and wonder at the strangeness of women. Miles is far too uptight and imperious for Jack, who functions here as his convenient opposite, crass, self-indulgent and narcissistic. The film begins as Miles wakes late for their appointed departure, then putters through his morning routine—showering, flossing, buying his triple espresso from a local shop where the sweet clerk knows his name and usual drink—before getting on the road to pick up his friend. At last arriving at Jack’s place (“Mr. Prompt!”), Miles takes brief note of the fiancée hovering, relegated to narrative background, as he apologizes for his tardiness and the two guys hit the road.
They’re not too far along before Miles learns Jack’s ambition, to “get laid” during his last week as a single man, and worse, to find a girl for him as well: “You’ve been depressed for two years,” Jack says, “You need to get your joint worked on.” Harrumphing and sputtering (Giamatti makes such spasms watchable, despite their predictability), Miles is part horrified, part intrigued, and mostly depressed. Unable to conceive of any woman who would want him, Miles fixes on Jack’s carousing as a flagrant moral flaw, a confirmation that the world is irredeemable, that he stands apart, alone and miserable because of everyone else’s lack of appreciation for those finer aspects of living he so studiously cultivates.
Just so, Miles’ choice of the wine tour is not incidental. A self-instructed and arrogant connoisseur, he envisions an excursion into civility and snooty-class, an escape from his daily disappointments and a chance to show off his own precise knowledge. Miles prefers and identifies with the sensitive, “temperamental” pinot noir, thinking cabernet too vulgar. He also anticipates a chance to educate Jack, to bring him up into his own rarified air. Though he talks a good game, though, it soon becomes clear that Miles is using his interest in wine as a means to self-medicate; that is, he’s an alcoholic, and not a pretty one either. As Jack notes during the first moments of their drive, Miles is late because he’s “fucking hung over,” following a tasting the night before.
Jack is equally self-deceptive, and appears to have no understanding of social boundaries or rules of engagement. “I get chicks looking at me all the time, all eyes,” he asserts, “Men too.” (As Church embodies Jack, this self-love seems about right, his appeal an uncomfortable mix of tense, effortless, and smarmy.) He blithely lies up and down to Miles (oh sure, he’s read the latest draft of Miles’ novel, then doesn’t know anything about the non-revised ending) or more frequently, about himself. This even as he imagines he doesn’t need to fabricate a background for himself, as his tv stardom typically precedes him (and so what if he has to jog women’s memories of where they’ve seen him before, or not mention that he’ll be married in a week?) Worse, from Miles’ point of view, Jack has no compunctions when it comes to telling tales for his friend, asserting repeatedly that he has a novel about to be published (though Miles’ agent is having a hard time even getting publishers to read it; it perhaps goes without saying that it is an autobiographically based piece concerning the death of his father).
Irritated he might be, but Miles finds the patience to cope with Jack’s adolescent shenanigans until they come to a favorite Valley hangout, the Danish-faking Solvang Inn (as absorbing and class-defining as the vineyards appear to be, Sideways is quite aware of the pretentiousness and sheer corniness as well). Crushing on the waitress, Maya (Virginia Madsen), who brings her own knowledge of wine, Miles is mortified when Jack starts flirting with her for him. It’s not long before Jack has set up a double date, including pourer Stephanie (Sandra Oh), and the guys are launched into a web of lies and performances that simultaneously scandalize and titillate Miles.
While Jack seduces Stephanie with startling ease (even in her few moments on screen, Stephanie appears leagues beyond both Miles and Jack in terms of self-understanding and generosity of spirit), Miles takes baby steps toward impressing Maya. At her home late at night (Jack and Stephanie making comically loud sex noises in the bedroom), Miles to thrilled to learn that Maya shares his affection for complexity. Thinking briefly that he’s found a worthy woman, someone who might even return his interest, Miles opens up about his book, even hauls out a copy from his car for Maya to read.
She’s more that up to this imposition, and you even believe she forgives Miles’ previous bad, sad, drunken behaviors, because Madsen allows you to believe. Always a resourceful, thoughtful performer, Madsen almost offsets Sideways’ overriding, occasionally prosaic interest in the boys’ journey. While this journey ranges from melancholy to eruptive, broadly slapsticky to ho-hum quirky (much as Payne’s previous films, About Schmidt  and the sublime Election , also did), Madsen—low-voiced, watchful—holds your attention. As much as Payne tends to make the same movie repeatedly, Maya is a surprise, granted more nuance than Jeannie Schmidt (Hope Davis) and less comedy than the redoubtable Tracy Flick (Reese Witherspoon), and fully embodied by the superb Madsen.
Most reductively, Maya serves here to show Miles the way, to encourage him, in spite of himself, to be humble and open to feeling good for someone other than himself, to forgive Jack and also to move on from their competition. But she also extends beyond this “girlfriend” role in two particular, seemingly contradictory ways. For one, she exists mostly offscreen, an ideal Miles describes before you see her, and an object of longing once he mucks up their budding relationship, essentially by his selfish passivity. At the same time, however, Maya’s appearances are refreshing, grounded and compassionate, intimating the other world that Miles seeks so desperately.