A film by Alexander Payne
"Sideways" is a road trip, a buddy movie, of sorts. Jack (Thomas Haden Church) is getting married in one week and his friend Miles (Paul Giamatti) is going to take Jack out for a week to have a good time. Miles is taking Jack on a wine tasting trip in California's wine country. It is one last "hurrah" before Jack gets hitched. They begin when Miles is late picking up Jack and they get an even later start when Miles decides they have to stop by and see his mother. They have dinner and spend the night, but the real reason is apparent when we see Miles steal nearly one thousand dollars from his mother's dresser. Apparently this will fund their trip. Finally, the next day they are on the road and ready to start tasting some wine.
Miles is somewhat of a depressed personality. He still broods somewhat over his divorce two years prior, and he was never a bubbly, upbeat personality. Jack is a good friend to Miles, and as a wedding present from the groom, Jack intends on making sure that Miles "gets some" on this trip. While Jack is earnestly trying to do what he views as being the best for Miles, he isn't entirely altruistic here. Jack wants one more fling with another woman (or two) before he gets married in a week.
Miles and Jack meet Maya (Virginia Madsen) and Stephanie (Sandra Oh). Jack and Stephanie hit it off right away and begin a very physical relationship. Miles and Maya discuss wine and some literature, and discuss more wine and Miles struggles to rise above his depression even though he is interested in Maya and Maya is clearly interested in him. All of these relationships and pairing up (perhaps even hooking up) is seen through the discussions of wine and the tasting of wine and the flat out drinking of wine. Wine works its way all through this movie and helps to explain so much of this movie. Too many obvious cliche and analogies comparing wine and "Sideways" easily come to mind, and while appropriate, they don't feel quite right to use (though the temptation to mention how this film will age like a fine wine is just too great).
There is a wonderful conversation between Miles and Maya where Miles is explaining why it is exactly that he is so obsessive about the pinot wine. He describes it to Maya, but it is obvious he is also talking about himself, and this is clear to Maya, as well. This is one of the best examples of how wine runs through this film and should there be Academy Award nominations for "Sideways" this scene may be one used on the telecast.
"Sideways" has this wonderful flow and pacing to it. Everything works so well and the wine analogy does not wear thin at all. Each of the four main actors work so well together that this movie could almost approach film perfect. The only problem is that the two male leads are not very sympathetic. They can be likeable at times, but Miles stole money from his mother like a punk kid, and Jack is looking to cheat on his fiance the week before his wedding and still intends on getting married. Alexander Payne does a great job telling this story and it is a very good movie, but these defining behaviors for Miles and Jack show them in a not very sympathetic light, that they may deserve whatever might happen to them. It almost becomes a moral quandary in praising the film and the story and the acting in what is essentially a "buddy" movie while at the same time not celebrating what it is that these men did and are. The reverse is true as well, in condemning what they do, I do not want to suggest that "Sideways" is of a lower quality in filmmaking. It isn't. "Sideways" is quite good. The characters aren't.