SIDEWAYS tells the story of Miles (Paul Giamatti), a failed novelist, and his soon-to-be married friend Jack (Thomas Haden Church), a washed-up actor. To salute the remains of their youth, the two men take one last road trip in the week before Jack’s wedding. A serious wine enthusiast, Miles is determined to educate his friend on the region’s beloved Pinot Noir wines before the week is out.
Jack indulges his best friend’s passion for the grape but is mainly interested in living his last week of bachelorhood to the hilt. Trouble ensues with wine and women (played by Virginia Madsen and Sandra Oh) and the duo comes to some profound realizations as they come to terms with maturity.