Bad Blake (JEFF BRIDGES) was once a big thing in the world of country music, but he's now a mostly washed up and alcoholic, 57-year-old performer who plays bowling alleys and bars for tiny crowds of adoring fans who still love his old work. He does too, and would rather spend his time drinking and/or with middle-aged groupies rather than write anything new, much to the chagrin of his manager, Jack (JAMES KEANE), who's always hustling to book his gigs.
He's clearly reluctant to work with his former protege and band-member, Tommy Sweet (COLIN FARRELL), who's now a big thing on the country music scene. He certainly doesn't want to talk about him to Jean Craddock (MAGGIE GYLLENHAAL), a local reporter in El Paso who lands the rare interview. A single mom to 4-year-old Buddy (JACK NATION), Jean just wants the story, but she finds the unkempt star interesting, while he's near-instantly smitten with the much younger woman.
Despite her hesitancy to get involved with any man again, the two become an item. Yet, his drinking and always being on the road -- including eventually hooking up again with Tommy who still idolizes him -- threatens to put a strain on that. With the help of his old friend and bar owner, Wayne (ROBERT DUVALL), however, Bad hopes to prove he's a changed man to Jean and thus allow him to stay in her and Buddy's lives.