Otis Blake (Jeff Bridges) is a singer-songwriter, who used to be a country music star. He is 57 years old, an alcoholic and has a history of failed marriages. He has a son of 28, whom he has not seen in 24 years. He is out on the road, performing in bars, staying in motels and traveling in his old car alone.
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Jean Craddock (Maggie Gyllenhaal) is a journalist who is after a story. She is divorced and has a young son, Buddy. She interviews Blake, and they become close. The relationship with Jean and Buddy motivates Blake to get his life back together. As a consequence he renews contacts with Tommy Sweet (Colin Farrell), a successful country music star he mentored before. Otis asks him to record an album together, but Tommy says his record company demands more solo albums. He suggests Otis to concentrate on writing songs for him, telling him his songs are better than anyone else's.
Otis' drinking gets worse, and he has an accident while driving drunk. The doctor informs him that although he only broke his ankle in the crash, he must stop drinking and smoking, and lose weight if he wants to live for more than a couple of years. Otis' relationship with Jean makes him rethink his life. To make amends, he calls his son, but he only tells him that his mother, Otis' ex-wife, has died, and hangs up on him. And Jean breaks up with him, after Otis loses Buddy briefly at a shopping mall while have a drink in a bar.
Upon losing Jean and her son, Otis decides to quit drinking.
Going through rehab, and with support from his AA group and his old friend Wayne (Robert Duvall), Otis manages to kick the habit. He tries to reunite with Jean and Buddy, but she tells him to leave them alone. After, Otis writes a song, "The Weary Kind", and sells it to Tommy.
Sixteen months later, Tommy plays "The Weary Kind" to an responsive audience. Otis watches backstage and gets presented with a large royalty check for the song by his manager. When Otis is leaving, Jean walks up to him. He offers her the royalty money. Jean refuses it at first but accepts it after Otis explains the song wouldn't exist without her and Buddy. Jean asks if Otis would like to see Buddy again, but Otis declines saying it might be too disruptive for him. The film ends with them walking away, chatting.
Best part of story, including ending:
It's the story of a life that could have been different without booze.
Best scene in story:
At the end where he is spotted by Jean and positions himself to talk to her.
Opinion about the main character:
It took him long to get himself together.