- Awesome, Dear Boy: George Clooney was so eager to work with The Coen Brothers, he signed on without having read the script.
- Breakaway Pop Hit: The film's cover of "I Am a Man of Constant Sorrow" became a minor radio hit.
- Cast the Expert:
- Real-life blues singer Chris Thomas King plays Tommy, and at one point gets to sing (in his own voice) a rendition of Skip James' "Hard Time Killing Floor Blues."
- Many of the KKK extras were from a military formation troupe.
- The Cast Showoff:
- That's really Tim Blake Nelson singing the lead vocal on "In the Jailhouse Now".
- Defied by George Clooney. According to him, he was cast partly because the filmmakers were under the mistaken impression that he could sing, probably because he has several singers in his family. In spite of his best efforts (which included several weeks of singing lessons), his singing voice was not up to snuff, and he was ultimately dubbed by Dan Tyminski.
- Creator-Chosen Casting: George Clooney was The Coen Brothers' first and only choice for the role of Everett. They had been impressed with his performance in Out of Sight.
- Defictionalization: The Soggy Bottom Boys.
- Dyeing for Your Art: George Clooney used period-appropriate, fat-based hair product in his hair throughout production and noted that flies seemed to be more attracted to him because of it.
- Half-Remembered Homage: Though they based the story on The Odyssey, The Coen Brothers admitted to having never read it; instead they based the script on adaptations they read or saw as kids, particularly the 1954 movie version starring Kirk Douglas.
- Non-Singing Voice: Dan Tyminski, a member of Alison Krauss & Union Station, provided Everett's singing voice. Pete's singing voice was dubbed by Harley Allen, and other than for "In the Jailhouse Now", Delmar's singing voice was provided by Pat Enright. The three sirens were also dubbed while singing, as was Homer Stokes.
- Production Posse: John Turturro, John Goodman, Charles Durning, Holly Hunter, Stephen Root, Michael Badalucco, George Clooney, and Tim Blake Nelson have all appeared in other Coen Brothers films.
- What Could Have Been: J. K. Simmons auditioned for multiple parts, but backed out when the one character the Coens were leaning toward casting him as was too similar to Oz and turned it down. He would work with the Coens many times down the line.
http://tvtropes.org/pmwiki/pmwiki.php/Trivia/OBrotherWhereArtThou
FollowingTrivia / O Brother, Where Art Thou?
Go To