Sideways

Sideways is a poignant and humorous tale of two middle-aged buddies, Miles (Paul Giamatti), English teacher and wine-connoisseur, and Jack (Thomas Haden Church), an actor, going on a road-trip of California’s vineyards one week before Jack is getting married. Miles is the kind of person who can instantaneously kill the most swinging of parties; he’s a depressed, self-absorbed loser who’s unsure of where is life is heading. Jack is almost his alter-ego, a party animal, who wants one last week of freedom (read “sex”) before settling down into what promises to be a very opulent life.

In Miles and Jack, director Alexander Payne gives us two characters difficult to sympathize with, at least initially. Miles is not one of those interesting, lovable loser-types, the kind the audience roots for. He steals from his mother when he’s short of cash; he lies easily, gets drunk all the time and cannot stop talking about wine. Neither is Jack one of those lovable goofy guys whom everyone easily forgives with a shrug. He comes off as a selfish person, lucky to be where he is in life, seemingly prepared to throw it all away and hurt everyone around him, just to satisfy his cravings.

But our opinions begin to change as the week unfolds and we get to know the two better, especially Miles, who is the focus of the movie (Giamatti features in pretty much every scene). Miles goes around most of the time feeling like a heel, facing constant rejection and disappointment before eventually meeting Maya (Virginia Madsen), whose interest in him gives him some sense of redemption even though he is not sure he deserves it. Jack meanwhile has his dreams answered in Stephanie (Sandra Oh) who appears to be one of those hot, “easy” girls, just looking for a good time and just what the doctor ordered as far as he is concerned.

Even though we never really understand that Maya sees in Miles, their relationship helps bring out some of his nicer sides, especially as we contrast his behavior with Jack’s and, thus, begin to like him a little, kinda... In their first double date, Jack easily slips into infidelity with Stephanie, while Miles mumbles and fumbles his way through, unable to move from the subject of wine. Miles’ timidity compared to Jack’s temerity also provides a lot of the humor in the movie.

Overall, Giamatti gives a terrific performance as Miles here, a kind of depressed version of Kevin Spacey in American Beauty and it is quite surprising that he did not get a Best Actor nomination. Both Virginia Madsen and Thomas Haden Church definitely deserve theirs though and the only reason that Sandra Oh didn’t get one is we don’t get to know her as much as Maya (Much of her action with Jack takes place off-screen).

NOTE: I spent quite some time wondering why the movie was titled "Sideways". While I can think of a lot of low-level metaphorical explanations, I've been unable to come up with anything satisfactory!