Factual error: When the escapees are hiding in the movie theater, the door opens and a deputy steps in, silhouetted by the light behind him. The movie is set in the 1930's, but the shotgun the deputy is holding appears to be a 1960's model Remington pump. (01:05:40)
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.
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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