Sideways 3 Chile follows the further adventures of Miles Raymond (played by Paul Giamatti in the now cult movie Sideways) and, to a lesser extent, his friend Jack. It's now ten years later, and Miles is a successful author, but he's still searching for something; depression has him, once again, in its taloned grip. Offered a chance to travel to the antipodean country of Chile and visit their wine regions for a magazine assignment, Miles, his world turned upside down by bad financial investments and even worse luck with relationships, happily agrees. A somewhat cynical Miles finds Chile, its people, and its spectacular and vastly diverse wine regions to be a life-transforming journey. The Sideways trilogy is now complete.