A week-long tour of California’s wine country brings together two old friends on an unexpected adventure and leads to a few interesting love interests. Miles (played by Paul Giamatti) and his freshman roommate from college, Jack (Thomas Haden Church), set out on a boys' week on the town in Northern California for a last few days of freedom for Jack before he ties the knot.
Miles’ passions focus around the finer things like fine wine and great literature. Unfortunately for Miles his career as a school teacher does not help support his high cultured interests. He’s a mopey character whose expectations are as low as his failed marriage of years before and whose only relief is a bottle of Xanax.
Jack, on the other hand, is a man who seems to have not matured a day since rooming with Miles in college. His interests seem to have stayed the same since those days as well. Though engaged, Jack still loves the occasional intimate company of a waitress or bartender. While Miles focuses on the complexities and diversities of fine wines, Jack’s main objective is to get drunk and find a cute lady to shack up with.
Even though it’s Miles who should be showing Jack a good time, Jack is the one left having to chaperone his morose friend who can’t seem to have any fun if his life depended on it. As their “wine tour” begins they meet a waitress and a wine server who they spend the next few days with exploring the restaurants and vineyards of wine country. Jack and his new lady friend Stephanie (played by Sandra Oh) immediately hit it off, while the antisocial Miles, disenchanted from his divorce, is hesitant to get too close to her counterpart, Maya (played by Virginia Madsen.) Through their mishaps and outrageous antics during their week in California wine country, Miles learns to be true to himself and finds that he must get past the ghosts of his past and move on with his life. An outrageously funny and smart comedy-drama, Sideways (directed by Alexander Payne) depicts a clever set of misadventures that are heartbreaking and comical all at the same time.