Sideways (2004) 2h 7min.
Miles is a divorced man and a failed writer who teachers junior high English. He decides to take his best friend, somewhat famous actor Jack, on a weeklong drive through California's wine country. There they explore their failures and question their relationships. Jack, who is about to get married has an affair with a woman and wonders whether he should call off his wedding. Miles questions whether he made the right choice while trying to form a relationship with the woman's best friend, a waitress at a restaurant that he frequencies often when visiting that part of the country.
Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen