| Miles Faymond, a failed writer who teaches junior high school english takes his best friend, former hot actor Jack on a weeklong drive up to 'wine country' in California. There they explore the nature of their failures and question their relationships. Jack, about to get married, has an affair and wonders whether he should call it off. Miles, recently divorced, questions whether or not he made the right choice. [TRAILER]
STEVEN
SNYDER'S REVIEW
“Sideways’” journey is really a chronicle of expressions: A forced smile, a frustrated grimace, a desperate stare and an optimistic grin.
This is the story of a midlife crisis happening in real time, and the final breakthrough that can only occur when someone has seen and embraced complete despair.
Miles (Paul Giamatti) is that man – the lonely high school teacher who we meet as a wine connoisseur but come to understand as a dejected, heartbroken alcoholic. He is divorced, has failed at becoming a published writer, but is trying to put on his happiest face for a week-long trip into California’s wine country.
He is the best man for Jack’s ( Thomas Haden Church) wedding, and together they have decided to spend the week before the ceremony. Jack is the antithesis of Miles, always upbeat, shallow and the beneficiary of a life that has given him a beautiful bride-to-be and a successful career as a commercial actor.
And so the stage is set for yet another Alexander Payne triumph. The director of such brilliant works as “Election” and “About Schmidt,” Payne is the master of finding the two sides evident in every truth. Although it is common in cinema, life is rarely comprised of moments that are purely good or purely bad, and Payne stands as a breath of fresh air because he is able to find the hidden laughs to be enjoyed amid tragedy and the deep pains that run beneath even the funniest commentaries.
In “Election,” Payne explored the cynical, universal truths about power and envy that can be found in even a high school student council election. In “About Schmidt,” he looked with conviction at the dark side of America’s heartland, which has lost its sense of liveliness or purpose, but ultimately found the small shred of hope that eventually we will all strive for more than life in a cubicle.
You might say that “Sideways” is a step in the optimistic direction for the director. At least this time it is about a middle-aged hero sorting out his life rather than a senior citizen realizing his life has meant nothing.
The story’s road trip develops in the most believable of ways. Miles and Jack swing by Miles’ favorite hangouts (he has clearly taken this alcohol-fueled trip before), taste some wine, and talk about their lives. Yet there is always the feeling that they are simply going through the motions, and that some deeper issues are lurking unsaid and unacknowledged.
Those issues spring to the surface with the arrival of Maya (Virginia Madsen), a local waitress, and Stephanie (Sandra Oh), a worker at a local winery. They go on a number of dates with Miles and Jack, and soon it becomes apparent that for Jack, this week is his time to party before the wedding day, and for Miles, this is his last chance at salvaging his life.
But now I’ve gone and made this sound like a drama, which it really isn’t. “Sideways” is foremost a comedy and while it is occasionally hilarious, it’s more often tragically funny, as we laugh along with the awkwardness of Miles, the ignorance of Jack, and their inability to relate, and as we realize their flaws and fears parallel reality a little more than we’d like to admit.
And it is the sublime fusion of Payne, Giamatti and Church that really makes this atypical comedy grow into a moving affair. Payne keeps the story alive through his balance of laughs and tears. Giamatti, much like “American Splendor” is able to personify in his face, voice and posture the angst that is fueling Miles’ personal hell.
Appropriately, the climax is a simple one, a hopeful promise that if we all keep persevering, the sun will break through the clouds one of these days.
  
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