Movie Review: Sideways (2004)

A tender yet funny drama about middle-aged men dealing with life's disappointments, Sideways excels as a quest for joy when all options for happiness appear exhausted.

Failed writer Miles (Paul Giamatti) and his friend Jack (Thomas Haden Church), a has-been actor, head out for a week-long trip to California's wine country to celebrate Jack's upcoming wedding to Christine. Miles is broke, lonely, and deeply depressed due to his divorce two years prior, and his lack of success in getting his book published. Meanwhile, Jack is not really sure he wants to get married, and is more interested in having sexual flings than tasting wine.

Miles and Jack settle at a motel amidst all the wineries. At the Hitching Post restaurant, they connect with waitress Maya (Virginia Madsen), who vaguely knows Miles from his previous trips and is herself nursing scars from a recent divorce. At a local winery, they also connect with server Stephanie (Sandra Oh), and Jack is immediately attracted to her. Miles and Maya start a tentative courtship based on their mutual love of wine, while Jack and Stephanie engage in a passionate affair. But with plenty of deception and half-truths generated by Jack's selective interpretation of the truth, trouble lies ahead for both men.

Written and directed by Alexander Payne, Sideways finds humour in the ordinariness of middle age pathos. The film honours the achievement of nothing where many men wallow, as both Miles and Jack have little to show for lives half lived except failed attempts at happiness and false expectations of a better future. The film stays focused on the men, their fading hopes and divergent attitudes towards the future, as Miles is weighed down by the past while Jack is intent on living for today.

Despite the odds they find suitable mates in wine country. Maya is just as emotionally scarred as Miles but is handling it better, while Stephanie is enjoying a life of carefree adventure. The relationships take on the colours of the men, as Miles and Maya proceed slowly and carefully, Jack and Stephanie rush into physical intimacy with wild abandon, and the outcomes carry echoes from the past into the future.

Payne's writing is stellar, and the film stands on the shoulders of the sturdy yet complex friendship Payne creates between Miles and Jack. Although a study in contrasts, the foundations of the relationship are clear: Miles is downbeat but smart, Jack is a dense optimist. They complement each other, and both are at crossroads in life where they need each other, warts and all. Miles needs Jack's encouragement to have any chance to move past his depression, and Jack needs Miles as a logic check against his impending marriage. Miles can't always trust himself because of his depression, and he wonders how much he can trust Jack, who is, after all, an actor, albeit a fading one.

The film uses wine as shorthand for depth of sophistication, if not exactly intellect. Wine is portrayed as a tragic ending worth celebrating, the more convoluted the plight of the fragile grape, the more worthwhile the taste. Wine and whine are also companions, Miles' endless laments about his failure in love, life and publishing matched only by his eloquent descriptions of all things related to wine and winemaking.

In the two lead role, Paul Giamatti and Thomas Haden Church create an enduring pair of friends. Giamatti has never been better, and in Miles finds the perfect role to suit his persona: cerebral but flawed and weighed down by luggage of his own making. Church is the perfect foil, and gives Jack a bounciness stemming from an inability to admit that with fading looks and creeping age, Jack's bright future as an actor is firmly behind him. Virginia Madsen turns Maya into a rich, complex red, while Sandra Oh mimics an in-your-face blast of popping champagne.

Sideways finds the sorrow and the laughs that come when forward momentum is well and truly lost, life starts drifting sideways, and it is suddenly apparent that for now, sideways is better than backwards.

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