Profligate and free-living country western singer Bad Blake (Jeff Bridges) seems to have lived his life on his own terms: one night stands and bouts of heavy drinking. Reduced to singing in bars in the remote American Southwest, he meets a young journalist named Jean Craddock (Maggie Gyllenhaal). He becomes flattered by her interest in him, despite the fact that he has thrown away every opportunity in his life to be a success personally and professionally. Yet, even a last chance at love and compassion cannot cause Bad Blake to reform his desperate lifestyle. Even a chance to team up with his former friend Tommy Sweet (Colin Farrell) only makes Bad Blake swallow a bitter pill.