Miles and Jack have been best friends since college. They've seen each other through a lot of times, both good and bad. Neither has come even close to achieving the career goals they have sought. Miles (Paul Giamatti) wanted to be a novelist, but makes his living as a teacher. Jack (Thomas Haden Church) wanted to be a famous actor, but his biggest recent roles are for voice-over work in TV ads. In fact, Jack is about to marry into money. He and Miles take one last road trip - a week-long excursion through the wine valleys of southern California. They also find some time for golf. The trip is more of interest to Miles, as he knows wines well. Miles goes to taste wines, while every wine tastes good to Jack. As we learn more about these two friends in "Sideways," the more these friends seem to be opposites who attract. Miles is quiet and introspective, while Jack is more outgoing and fun-loving.
Jack enjoys the trip, but he really wants it to seem more like a week-long bachelor party. When they stop for supper at one of Miles's favorite restaurants, Jack learns that the divorced Miles enjoys dealing with Maya (Virginia Madsen), a waitress there. Jack suggests that Miles should spend some of the week getting to know her better. Miles assures Jack that Maya has been married for some time. However, Maya has gone through a divorce since Miles's last visit. Maya learns of some of Miles's plan for the week, and is invited to join. At a vineyard where tasting is done, Jack strikes up a friendly conversation with Stephanie (Sandra Oh), their tasting server. Friendly conversation turns to a friendly evening with the two couples. Neither Jack nor Miles tells the ladies about Jack's impending nuptials. That secret eventually becomes known, and threatens to destroy any good that may have come during that week.
"Sideways" is a bittersweet examination of several lives, and the directions those lives went, and where they didn't go. This film from director Alexander Payne is thematically similar to his previous film, "About Schmidt." However, Payne and writing collaborator Jim Taylor used different source material for each picture. "About Schmidt" was based on a novel by Louis Begley, while "Sideways" was based on a novel by Rex Pickett. Each film with a man's place in his own life, and the compromises that are made to subsist. While Miles and Jack deal with compromise and subsistence, each finds divergent ways to keep their true interests alive. Each knows this, and each has their reasons for not revealing their interests. One man would hurt those closest to him, while the other has seen little interest in his private endeavors. Still, Miles and Jack know that life would be worse if they didn't keep their interests alive. In one week's time, they manage to find ways to add to Maya and Stephanie's tales of woe in relationships.
As Payne slowly reveals his characters' stories in the same ways grapes reach ripeness in a vineyard, I became much more interested in the story of Miles and Maya than the one of Jack and Stephanie. Miles and Maya have a chance to continue as a couple, and physical intimacy isn't their starting point. Giamatti and Madsen are captivating in their roles as the marital casualties Miles and Maya. They see their lives slipping away without distinction. Yet, they find the opportunity for distinction as they learn that they have common interests in wine and literature. When Maya speaks of vintage wine to Miles, she could just as easily be describing the situation the main characters are facing. They feel they may soon be reaching a peak in their lives, and so many years are already behind them.
They don't seem to realize that the best could soon be coming. Through most of the movie, Miles awaits word on the fate on an unpublished novel that his agent is shopping. Although Miles speaks bitterly about his ex-wife Victoria (Jessica Hecht), he has never minded dealing with Maya. Giamatti conveys the regrets of Miles very well. His sad eyes and tone convey the regrets of his life, as well as the desire to belong that he fears may never come to him. Whenever he sees Maya, Miles has a look that says he wished Maya had come along before he'd ever met Victoria.
I like Church and Oh in their roles, but they seem more like comic relief than characters. Jack is a complete hedonist. He may be getting married, but any woman who wants to go to bed with him is fine, too. He has no guilt about leading on women. When things go predictably wrong between Jack and Stephanie, Jack concocts a wacky explanation to cover his tracks for his fiancee and her family. When Stephanie learns the truth about Jack, she throws a typical hissy fit, going ballistic in the parking lot where Miles and Jack are staying. Church and Oh do have funny moments, but Jack's carpe diem attitude eventually grows tiresome. It never occurs to him that Maya might be more special than the sexual conquest Stephanie is to Jack. Ultimately, Jack is not there to patch the hurt he helped to create. What a guy!
"Sideways" may be a forty-something version of "About Schmidt," but it's still a film with plenty of life of its own. Four people ponder the paths their lives did not take, and may never take. These people keep asking themselves, "What if?" That question, though, is now viewed from older eyes, so it's now a "What if?" of a different sort. There's always something new to try, and relationships to create. Life may have never reached the expected peaks for the characters in "Sideways," but they learn slowly that there's some good in the places they go, as well as in the places they are.
Life doesn't go sideways. Miles, Maya, Jack, and Stephanie have merely accepted that illusion.
In this intoxicating, intelligent comedy, director Alexander Payne (Election, About Schmidt) serves up one of the best movies of the year (Entertainme...More at Buy.com Marketplaces
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