James Winston, an easy-going real estate salesman, lives life to the fullest. His carefree attitude often upsets his older brother Charles, a sportswriter who compulsively plans every aspect of his personal and professional life. Much of their time is spent hanging out at their neighborhood sports bar with longtime friends Mitchell Ford, a junior high school teacher who is unlucky with women, and Dusty Canyon, a television weatherman whose sense of fashion is as far off as his weekend forecast.