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O Brother, Where Art Thou?
In the summer of 1937, three convicts – Pete, Delmar, and Everett – escape from a Mississippi chain gang to retrieve a buried treasure hidden by Everett before the area is flooded to make a lake. The three are assisted by a blind man driving a handcar on a railroad, who prophetically tells them they will find a different fortune than the one they seek. The trio then travels to Pete's cousin, Wash, who breaks off their shackles, feeds them, and allows them to sleep in his barn. While they are sleeping, Wash reports them to Sheriff Cooley, who torches the barn with his men. Wash's son helps the trio escape. Pete and Delmar get baptized in a river the next day, but Everett refuses to join them.
The group then picks up Tommy Johnson, a young black man who claims that he sold his soul to the devil in exchange for the ability to play the guitar. In need of money, the four stop at a radio station, where they record a rendition of " Man of Constant Sorrow " as the "Soggy Bottom Boys". That night, the trio parts ways with Tommy after their car is discovered by the police. They then briefly fall in with outlaw George "Baby Face" Nelson, who has been robbing banks and killing cows, but after becoming depressed, George gives the trio his cash and walks off. Unbeknownst to the trio, their radio recording becomes a major hit.
Near a river, the group hears singing and finds three women washing clothes. The women give them corn whiskey and they lose consciousness. Upon waking, Delmar finds Pete's clothes lying next to him, empty except for a frog. Delmar is convinced the women were sirens who transformed Pete into a frog, and so takes the frog with them. Later, one-eyed Bible salesman Big Dan invites them for a picnic lunch, then mugs the men and kills the frog.
On their way to Everett's hometown, Everett and Delmar glimpse Pete working on a chain gang. They arrive in town in the midst of a campaign rally for Homer Stokes, the challenger in the upcoming gubernatorial election. Everett confronts his wife Penny, who told their daughters that he was hit by a train. He gets into a fight with Vernon, her new suitor and Stokes' campaign manager. While recovering at a movie theater, Everett and Delmar encounter a group of prisoners including Pete, who warns them that an ambush has been set up at the treasure site.
That night, they sneak into Pete's holding cell and free him. Pete confesses that he gave up the treasure's location to the police under torture, but Everett then confesses that he made up the treasure to convince the men he was chained with to escape with him, so that he could stop his wife from getting remarried. Pete, enraged, fights with Everett until the trio stumble into a Ku Klux Klan rally, presided over by Homer Stokes as its Grand Wizard, and find that the Klan has captured Tommy to lynch him. The trio disguise themselves as Klansmen and attempt to rescue Tommy, but they are unmasked by Big Dan. Chaos ensues as the trio rush Tommy away and cut the supports of a large burning cross, which falls on Big Dan.
Everett persuades Pete, Delmar, and Tommy to help him win his wife back. Disguised as hillbilly musicians, they sneak into a Stokes campaign gala dinner that she is attending and perform "Man of Constant Sorrow", unaware that the Soggy Bottom Boys are famous. The crowd is electrified, but Stokes recognizes them from the KKK rally and interrupts the performance. When he demands the group be arrested and reveals his white supremacist views, the crowd runs him out of town on a rail. Pappy O'Daniel, the incumbent governor, seizes the opportunity to endorse the Soggy Bottom Boys, grant them full pardons, and hire them as his "brain trust". Penny agrees to remarry Everett as long as he finds her original ring. The group then encounters an exuberant George Nelson as he is paraded through town by a mob on his way to be executed.
The next morning, the group arrives at Everett's cabin in the valley, which Everett had previously claimed was the location of the treasure. They are ambushed by Sheriff Cooley and his deputies, who have been lying in wait. Dismissing their claims that they had received pardons, Cooley orders their hanging. As Everett prays to God, the valley is flooded, killing the officers and saving the group, who survive by floating on top of their own coffins. Tommy finds a ring in the flotsam and they return to town, but when Everett presents the ring to Penny, she claims it is not hers and firmly insists that she will not marry Everett without the original ring. As Everett belligerently pursues her, the blind handcar driver passes by on the railroad tracks.