Ulysses Everett McGill (George Clooney), a suave, fast-taking convict, escapes from incarceration in Mississippi during the Great Depression. He is chained to two other prisoners, slow-witted Delmar (Tim Blake Neslon) and hot-tempered Pete (John Turturro), so the three must escape together. Everett convinces them that he has hidden $1.2 million after robbing an armored car, and promises to split it with them. They hitch a ride with an elderly blind man on a railway handcar, and he foretells that they will indeed find a treasure, though it may not be the one they seek.
They travel on foot to visit Pete's cousin, Washington Hogwallop, who removes their shackles and allows them to sleep in his barn. However, the trio is awakened by the authorities after Hogwallop turns them in for the reward. The barn is set ablaze, but Everett, Pete, and Delmar escape with the help of Hogwallop's rambunctious young son (who drives them out of the fiery barn in a car). They continue their journey, and encounter a religious congregation in the midst of a mass baptism. Pete and Delmar are drawn in and are baptized as well, but Everett resists. They later pick up a hitchhiking young black guitarist, Tommy Johnson (Chris Thomas King), who claims he sold his soul to the devil in exchange for musical talent. They hear that the nearby WEZY radio station pays people to sing into a can, so they pay a visit to the blind disc jockey (Stephen Root), and sing a version of "Man of Constant Sorrow" with Tommy accompanying them. Calling themselves The Soggy Bottom Boys, they are paid cash and leave satisfied. However, unbeknownst to them, their record becomes wildly popular around the state, with no one knowing the identity of the band.
That night the police track them down and find their car near their campsite. Everett, Pete, and Delmar part ways with Tommy as they escape. The next day, they meet famed robber George Babyface Nelson (Michael Badalucco), on the run from police, and accompany...
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