Sideways

Miles Raymond is an unsuccessful writer, a wine aficionado, and a divorced and depressed middle-aged English teacher living in San Diego. He takes Jack Cole, his soon-to-be-married actor friend and former college roommate, on a road trip through the Santa Ynez Valley wine country. At the beginning of this trip, he stops to see his mother before the day of her birthday. While there he steals a thousand dollars from her secret stash. Though Jack is still recognized on occasion, his acting career appears to have peaked years earlier, when he had a role in a popular TV soap. He now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business. Miles wants to spend the week relaxing, playing golf and enjoying good food and wine. However, much to Miles' consternation, Jack is on the prowl and wants one last sexual fling before settling into domestic life.