Otis "Bad" Blake (Jeff Bridges) is a 57-year-old alcoholic singer-songwriter who was once a country music star. He now earns a modest living by singing and playing his guitar at one-night stands, in small town bars, in the southwestern United States. Having a history of failed marriages, Bad is without a family. He has a son, aged 28, with whom he has not had contact in 24 years. He is mostly on the road performing, staying in cheap motels and traveling in his old car alone. The film opens with arrival at a bowling alley for a show.
Enter Jean Craddock (Maggie Gyllenhaal), a young journalist after a story, divorced and with a four-year-old son, Buddy (Jack Nation). She interviews Bad, and the two enter into a relationship. Jean and her son become a catalyst for Bad beginning to get his life back on track. In doing so, he lets himself be pushed into renewing a professional relationship with Tommy Sweet (Colin Farrell), a popular and successful country music star he once mentored, and plays as the opening act at one of Tommy's concerts, despite his initial balking and wounded pride at being the opening act to his former student. He asks Tommy to record an album with him but Tommy instead suggests that he concentrate on writing songs that Tommy will sing solo.