Paul Giamatti and Thomas Haden Church make an odd couple of long-time friends who spend a funny, revealing and sometimes touching time together during a tour of California�s wine country in Sideways, the new film from the director of About Schmidt.
Giamatti plays sad sack, Miles a teacher and aspiring novelist who still has not recovered from his divorce two year earlier. Church is Jack, a washed up actor who is about to be married but, before he takes the plunge, he wants to have a final fling, so when wine connoisseur, Miles takes him on their vineyard visit, Jack intends to enjoy his �last taste of freedom� between slurps of Chardonnay � or whatever, because to Jack all wine tastes the same. Although they have been friends since college, the neurotic, unhappy Miles and the easy-going Jack could not be more unalike. Miles envisions a quiet time of wine sipping and golfing; Jack sees their trip as a weeklong party and an opportunity for him to sow a few last wild oats. Because he believes Miles has been �officially depressed for, like, two years� he is also determined to help his old friend re-discover fun.
When Jack hooks up with free-spirited vineyard worker, Stephanie (Sandra Oh), he conveniently neglects to tell her of his impending marriage. Miles finds a possible romantic soul mate in Maya (Virginia Madsen), a waitress whom he has seen on other wine trips and whose knowledge of wine matches his own. The ever-helpful Jack, in an effort to boost his friend�s image, tells the girls that Miles� book is about to be published. With their relationships already based on a couple of lies, things are sure to go askew.
As the days pass and the foursome discovers more and more about each other, the exceptional ensemble cast of Sideways creates a group of ordinary, believable people whose lives, loves, lost dreams and aspirations are so keenly, often humorously, observed that they become memorable.