Do or Do Not.

Miles Raymond, the wine connossuier at the heart of Alexander Payne‘s Sideways, would surely have looked down on, if not openly mocked, the bottle of wine the wife and I opened up as we cozied down on the couch to watch this fascinating movie. The wine was an ’02 Firesteed pinot noir, and though Miles may be a fan of fine pinots, this $9.99 bottle would surely not have met his definition of “fine.” (It barely met my definition of fine, and I’m far from the wine expert Miles is–I prefer a good cold English stout with lots of suds, preferably served up with something that was once part of a cow.) Wine–the tasting of it, the savoring, the buying, the talking about it–is Miles’ passion, possibly the only passion left in his life as the movie opens.

Sideways has a very simple story driven by very complex characters: Paul Giamatti plays the emotionally crippled and neurotic Miles, who takes best pal Jack (Thomas Haden Church), an out-of-work actor who specializes in voice overs, on a week-long pre-wedding trip through California’s wine country, ostensibly to teach Jack something about wine…though Jack’s motivations for the trip reside somewhat south of his wine palate (in Jack’s words, he wants to “get his nut on,” a phrase we don’t hear nearly enough in non-pornographic movies). And that’s exactly what he does, as Miles tries to keep the fragments of his plans for their trip–and his sanity–together along the way.

Thanks to Jack’s boyish charms (and here I’m really using “boyish” as a synonym for “obnoxious”), Miles and Jack end up pairing off with two locals: Miles with the stunning Maya (Virigina Madsen), a waitress studying to be a horticulturist, and Jack with Stephanie (Sandra Oh), who works at a winery and really isn’t studying to be much of anything–she lives completely in the moment, which makes her perfect for Jack, who’s trying desperately to fit a lot of living into the moments before his wedding. The complex flavors of this foursome blend deliciously. Much like in Closer, the entire movie centers around the dynamics between and among four people, though the characters in Sideways are far less vitrolic and far more likable those in Closer.

Giamatti’s performance as Miles was easily one of the best acting jobs of the year–how he didn’t receive an Oscar nomination for his performance is completely beyond me. All I can think of is that Giamatti, normally known as a classic example of “That Guy” from any number of films, doesn’t fit the standard Hollywood concept of a “lead actor” as much as guys like Johnny Depp and Leonardo DiCaprio and Jamie Foxx. The Academy already had a “character guy” in Don Cheadle, so the short, balding, pudgy, nerdy Giamatti gets left out, and that’s really a shame. Giamatti absolutely nails the insecurity, anxiety, hurt and disappointment of Miles. It’s a tough job Giamatti has for himself in this movie: he has to take a dishonest, weak mess of a man and make the audience care for him–and root for him. And Giamatti more than meets the challenge.

Madsen’s reponsibility in this movie is almost as tough as Giamatti’s: she has to make the audience fall in love with her right alongside Miles. She accomplishes most of that job simply by being luminous, which she does exceedingly well. But she’s also got to convince us that she’s smart, capable, and driven…yet sensitive enough to be attracted to a neurotic schlub like Miles. Maya is both Miles’ ultimate woman and his unattainable fantasy at the same time (or so he thinks; he seems completely oblivious to the near-constant “hey, I’m interested” signals she throws him). Maya, like Miles, is also somewhat broken: she’s coming off of a painful divorce and to her, Miles represents everything her ex-husband wasn’t and couldn’t be. As much as she clearly likes Miles, she’s tentative and conflicted.

Jack and Stephanie are, in many ways, the anti-Miles and Maya. While Miles and Maya both listen to their heads too much, spending hours on end talking, Stephanie and Jack fall into bed almost immediately. Stephanie wraps her heart around the shallow but loveable Jack; she’s needy yet passionate, emotionally fragile, more than a little irresponsible (we see her mother caring for Stephanie’s six-year-old more than we do Stephanie), yet an unforgiving warrior when injured. (This might be a good place to interject the fact that I don’t normally find Sandra Oh particularly attractive, but wow, she’s smokin’ hot in this movie.)

Church digs his way out from the cinematic detritus that is his recent film career to find a part perfect for his smooth egotism; it’s not hard to imagine that the once-famous actor Church is playing is a minor-chord variation on himself. Church reveals all in this movie–literally–as a man wildly out of touch with himself and what he truly wants. Jack is everything a woman like Stephanie could want–charismatic, wild, passionate, caring–and yet at the same time he disgusts her: he’s a liar and a cheat. Church, who (like Madsen and unlike Giamatti) was nominated for an Oscar for his work, brings both sides of Jack to life and finds surprising depth in a character that initially seems like one-dimensional comic relief.

Payne’s previous movies have been kind of hit-and-miss with me. I loved the hell out of the exuberant Election but was unimpressed by the bleak melancholy of About Schmidt. Payne’s complex characters usually don’t find themselves in situations too far removed from the mundane–he seems more intrigued by examining the “real world” reactions of his characters to situations just outside their comfort zones. Miles Raymond’s comfort zone barely extends past his skin, if even that far, so Payne doesn’t have to push far with him, and the results he gets satisfy like a velvety smooth Zinfandel.