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Sideways is a 2004 comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. Adapted from Rex Pickett's 2004 novel of the same name, Sideways follows men in their forties, portrayed by Paul Giamatti and Thomas Haden Church, who take a week-long road trip to Santa Barbara County Wine Country. Payne and Taylor won multiple awards for their screenplay. Giamatti and Church, as well as actresses Virginia Madsen and Sandra Oh, playing local women who become romantically involved with the men, all received accolades for their performances. Sideways won the Academy Award for Best Adapted Screenplay, and was nominated for four other awards. Miles Raymond (Paul Giamatti) is an unsuccessful writer, a wine-aficionado, and a depressed middle school English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole (Thomas Haden Church), on a road trip through Santa Ynez Valley wine country. Miles wants to relax and live well. However, Jack wants one last sexual fling.
Jack (Thomas Haden Church), on the other hand, covers his with several layers of restless horniness. Jack is a washed-up actor about to marry Christine (Alysia Reiner), and he's Miles' best friend from college, who doesn't understand why Miles can't just get over his divorce. Or his oft-rejected novel. Or his increasing dependence on wine, or the accompanying feeling that, as a middle-aged man, he has long ago peaked. Jack and Miles embark on a trip through California wine country, as a last hurrah for Jack's bachelorhood. Miles want to drink fine wine and play golf; Jack wants to drink anything and pick up women.
Miles and Jack meet Maya (Virginia Madsen) and Stephanie (Sandra Oh) on their trip, and soon we're watching a pair of vastly different pickup styles; Jack is heedless, and Miles heeds everything he can, as long as it's negative. Payne's films are often more a series of interrelated situations than a breakneck plot; after these four characters are introduced, the screenplay (by Payne and his collaborator Jim Taylor, adapted from the Rex Pickett novel) allows them to roam around a bit.
Sideways lacks the unique satiric vision of Election and About Schmidt, and covers less inspired, fairly typical midlife crisis material. Some will deem this a step in a more humane direction from Payne and Taylor, who have been accused (as nearly as all satirists are) of condescending to their characters. Sideways isn't as sharp or fresh as either of those films, but I applaud their refusal to repeat themselves in choosing a subject painfully aware of his own limitations, and Giamatti brings all of his twitching gravity from American Splendor into a less eccentric, more recognizable character. Church, a sitcom veteran, has the broader part to be sure, but he takes the time to really figure out Jack - to let the character's childishness come into focus as the movie goes on (Jack starts out by acting like a teenager, and regresses).
No doubt he was helped by Payne, a skilled, unshowy director, especially with comedy - watch how he keeps the victim of a mild beating just offscreen to subtly amplify the humor. The male-bonding wildness comes in unexpected bursts; the typical comedy-drama will start with the comedy, and then turn serious, while Sideways has the comfortably erratic rhythms of life. Payne holds back some of the biggest laughs in the movie, allowing the audience to get to know the characters before delivering funny payoffs.
But Sideways still ventures into more conventional territory than he's previously seen. Payne has never used devices like montages, soft-focus scenery, and dialogue dubbed over driving shots before; when they turn up here, the film feels imprecise. Payne's previous films made us look at our lives, because so many of the characters refused to do so themselves. Miles is a touching character, but his journey is slight in a way that even retirement-hazed, Hummel-toting Schmidt's was not; as vivid as his depression is, I never felt like he was in any real danger.
It feels churlish to complain that Sideways is merely a good film when, in fact, it has little, observant details and big, earned laughs that many directors would take several films to rack up. Not a false note is struck throughout the cast, even when Madsen has to talk through an extended metaphor. Most movies aren't better than Sideways - it's just that Payne has directed several that are.
The lovely DVD includes deleted scenes, a silly commentary from Giamatti and Church, and a behind-the-scenes featurette.