3 convicts escape jail in the deep south. They are continuously searching for a treasure while being hunted down by the warden. They meet several characters along the way such as a black guitarist who has sold his soul to the devil. They record a bluegrass type song that becomes an instant smash and are constantly thrown off track by various events. The story is based on The Odyssey Homer which details a long journey home. Several of the characters in The Odyssey are represented in the movie such as the cyclops is represented by John Goodman and the sirens are also encountered.
Continuity mistake: There are seven Wharvey Gals. Three on the stage singing, three with the wife, and one that she's holding. One of the girls even says that there are seven of them. Yet in the end, when Everett and his wife are walking down the street, there are only six. One that she is carrying, and five following.
Delmar O'Donnell: You work for the railroad, Grampa?
Blind Seer: I work for no man.
Delmar O'Donnell: Got a name, do you?
Blind Seer: I have no name.
Ulysses Everett McGill: Well, that right there may be the reason you've had difficulty findin' gainful employment. You see, in the mart of competitive commerce.
Trivia: George Clooney (Everett) was going to sing "Man of Constant Sorrow" for the film but his singing voice was very poor so he ended up lip-synching the songs instead. He said "I'm not my aunt [referring to the late singer/actress Rosemary Clooney, best known for her role in "A White Christmas" (1954)]. I decided it would be easier to just do a passionate lip-sync." He was so nervous that the tapes of his singing would get out that he returned to the studio to ensure all the evidence had been erased. The musical director of the film confirmed this but said "George is a very good singer but that style of music is very difficult and one almost has to grow up singing it in order to sing it convincingly. George did a really good version of the tune but it wasn't as good as he wanted."
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