Director Alexander Payne’s Sideways is such a giddy pleasure that it’s hard to talk about without wanting to share every little secret you discover along the way. You sit through it with an expansive grin of pleasure that leaves your face only when it dissolves into guffaws of deep laughter.
Paul Giamatti and Thomas Haden Church play Miles and Jack, friends since college, now well past 30. Miles (Giamatti) is an eighth-grade English teacher with a 1,000-page novel he can’t get published. He’s been divorced for two years but is still depressed about it, popping Xanax and harboring dreams of getting back together with his ex-wife.
Jack is the handsome one, a semi-successful actor. Years ago, he played a doctor on a popular soap opera; now he does occasional voiceovers, hoping for his next big break. In the days before Jack’s wedding, he and Miles, his best man, jump in Miles’ battered old convertible and head northwest from Los Angeles for a weeklong tour of the wineries in the Santa Ynez Valley, north of Santa Barbara, to taste a little wine and play a little golf.
And, as far as Jack’s concerned, get a little laid. He intends to hook up with some available woman before he settles down, and as far as he’s concerned, the mopey, anal-retentive Miles is long overdue for similar action himself.
Miles, however, is serious about his wine. At their first stop, he patiently walks Jack through the paces, showing him how to judge the color, the bouquet and the flavor of the liquid as it sloshes around the gums, the tongue, the teeth. Halfway through his lecture, though, with Jack gamely (if uncomprehendingly) following along, Miles stops suddenly and stares at him with distaste: “Are you chewing gum?”
That’s how the week seems to be shaping up—in fact, it seems to be the story of Miles’ and Jack’s lives: They don’t have much in common, but they’re pals in some sort of unexplainable “guy thing” that they don’t have to explain to each other and couldn’t explain to anyone else.
The story gets going in earnest when the boys meet Stephanie (Sandra Oh), a pourer at one of the tasting rooms, and Maya (Virginia Madsen), a waitress at a restaurant near their motel in Buellton. Jack and Stephanie hit it off at once. She doesn’t know that she’s Jack’s last fling. For that matter, Jack himself isn’t so sure; in his shallow, love-the-one-you’re-with way, he begins to wonder if he’s really ready for marriage.
The courtship between Maya and Miles is altogether more tentative and guarded—oddly so, considering they’ve had a nodding acquaintance from his earlier trips to town. But it’s always been just small talk over dinner while she worked. Now they find themselves unexpectedly in a real conversation, supposedly talking about their shared interest in wine but—in a delicate, uncertain way—actually telling each other hidden things about themselves.
Sideways is adapted from Rex Pickett’s novel by Payne and his writing partner Jim Taylor, with whom he also wrote his earlier films About Schmidt, Election and Citizen Ruth. Payne seems to get better and more incisive from one movie to the next, and this is probably his best one yet. It’s a movie without villains: Miles may be something of a bore and a schmuck, and Jack something of a horse’s ass, but neither of them is really a bad guy. That’s what makes the dumb mistakes they make on this trip all the more comically exasperating: We can see, even if they can’t, the folly of where they’re headed.
One of the pleasures of an Alexander Payne film is seeing how his actors bring out the best in his and Taylor’s script, and vice versa. Of Giamatti, of course, we’ve come to expect it. And Oh has one hell-hath-no-fury scene that would raise gooseflesh on a statue. But Madsen and Church surprise us. After years of steady, unexceptional work, they seem suddenly to flourish, and it’s as if we’ve never seen them before. Who knew they had this in them?
But then, that sums up the pleasure of Sideways: seeing not only what the actors have in them, but also Jack and Miles themselves. They come through the week better friends and better men, and we’re glad we met them.