NOTE: This spoiler was written by Gus.
Bad Blake (Jeff Bridges) is a broke-down country music singer past his time. Bad unhappily arrives in a small town bowling alley to set up for a gig he'll be playing for some local fans and small pay. After he has a quick drink and smoke at the bar, he makes a stop at a gas station for some of his favorite whiskey. He heads back to his motel room and begins to drink. His manager/agent Jack Greene calls him and they argue back and forth, Blake accusing him of not getting him good venues, Greene criticizes Bad for not writing new material in over ten years.
Blake arrives at the bowling alley that night and drinks a bit before playing. Every couple of songs, he takes a break, drinks some more until eventually he can't play anymore and completely abandons the show, running to the nearest trashcan to puke. The next morning, he wakes up in his hotel room with a woman from the bar. He leaves as she sleeps.
Blake makes his way to Santa Fe to play another gig in a small bar. There he meets Wesley, a piano player. He tells Bad about his niece, a reporter, who would like to meet and interview Blake. Bad Blake tells Wesley to send her over to his motel room.
Hours later, Bad sits on his couch watching television and is interrupted Jean Craddock, Wesley's niece. She interviews him and he asks her to come back later, after his show, to continue. Blake plays his show that night, which turns out fine. Blake and Jean continue their conversation earlier, as their relationship flourishes, Bad begins to fall for Jean.
Bad plays another show, which this time Jean misses out on. She arrives late and they go back to his room, where eventually they begin to kiss and sleep together.
Bad meets her four-year-old son, Buddy and cooks breakfast for them.
Jack Greene, his manager, calls him later to inform Bad that he got him a gig with an audience of 4,000 people in Houston. Bad is excited to hear this, but finds out that he will be opening the show for Tommy Sweet (Colin Farrel), a young, very famous country singer. Blake meets Tommy at a restaurant later and they discuss old times, when Tommy was in Bad's backup band. Bad had helped Tommy with songwriting, and sort of became his mentor. After Tommy made it famous, he never stayed in contact with Blake until now.
At the show, Bad arrives to little applause until Tommy comes out to support him. The crowd goes wild. Tommy/Bad sing a duet. Later, Bad watches from afar as Tommy plays his show of modern country music, which Bad feels has no flavor.
Bad calls Jean and tells her he will be driving over to Santa Fe to see her. As he is driving he falls asleep and crashes his truck. A bystander helps him. Bad wakes up in the hospital, not remembering what happened until he speaks with the doctor. The doctor says Bad is in very poor shape, and needs to stop drinking and smoking so much. He heads back to Jean's place and has a couple of good days with her and Buddy, her son. Bad travels back home and gets a call from Jean that she won't have to work for the next four days. Blake invites her over his home in Houston, where they spend a good couple of days together, and Bad starts to write a new song, inspired by Jean.
Bad reveals to Jean that he has a son he hasn't seen in twenty years. She suggests that he calls his son and try to reconnect. Bad does, but his son wants nothing to do with him. One day, Jean goes out and leaves Bad with Buddy at home. Blake takes buddy to play at the park and then to a mini-mall in Houston. At the mall, Bad orders a drink at the bar. Buddy begins to wander around the place as Bad speaks with the barkeep. When Bad starts to call out Buddy's name, there is no answer. Blake tells a security guard and is taken to the security waiting room. Jean arrives, angry at Bad and worried sick about Buddy. Eventually, Buddy is found and he is okay, but Jean is infuriated with Bad, accusing him of drinking heavily and not looking out for Buddy. Jean leaves as Bad tries to reconcile with her, but fails.
Days later, Bad meets up with his friend Wayne (Robert Duvall). He tells Wayne of his drinking problem and Wayne vows to help him. They go fishing one day, and another to an Alcoholics Anonymous meeting. Blake continues to write and perfect his new song, which was inspired by his love for Jean. Bad goes without drinking for nearly two weeks, and decides to try and smooth things out with Jean. He arrives at her home, and she doesn't seem happy to see him. Jean also tells him she can't forgive him for what happened with Buddy, and if Bad loves them so much, to stay away from them as far as possible. Bad leaves in a sad state as the screen fades to black.
Sixteen months later.
Tommy Sweet is at a concert playing the song Bad Blake wrote for him (the same song Blake has been writing throughout the movie). Blake and his manager Jack Greene are backstage, happily watching. Jack hands Blake a royalty check with a large sum on it. Bad thanks Jack and heads out of the backstage area. Outside, Jean is waiting to interview him. He is happy to see her, but notices she is wearing a wedding ring. Jean says, "He's a good guy," to which Bad replies "You deserve one." Bad then hands Jean the check he just received, and tells Jean it’s for Buddy, once he turns eighteen. Jean tries to refuse but Blake pleads with her and she accepts. They end up sitting on a bench, talking, as the song "The Weary Kind" plays over the end credits.