* AwesomeDearBoy: Creator/GeorgeClooney was so eager to work with Creator/TheCoenBrothers, he signed on without having read the script.
* BreakawayPopHit: The film's cover of "I Am a Man of Constant Sorrow" became a minor radio hit.
* CastTheExpert:
** 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.
* TheCastShowoff:
** That's really Creator/TimBlakeNelson singing the lead vocal on "In the Jailhouse Now".
** Defied by Creator/GeorgeClooney. 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.
%%* {{Defictionalization}}: The Soggy Bottom Boys.
* DyeingForYourArt: Creator/GeorgeClooney 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.
* HalfRememberedHomage: Though they based the story on ''Literature/TheOdyssey'', Creator/TheCoenBrothers admitted to having never read it; instead they based the script on [[PopCultureOsmosis adaptations they read or saw as kids]], particularly the 1954 movie version starring Creator/KirkDouglas.
* NonSingingVoice: Dan Tyminski, a member of Music/AlisonKraussAndUnionStation, 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.
* ProductionPosse: Creator/JohnTurturro, Creator/JohnGoodman, Creator/CharlesDurning, Creator/HollyHunter, Creator/StephenRoot, Creator/MichaelBadalucco, Creator/GeorgeClooney, and Creator/TimBlakeNelson have all appeared in other Coen Brothers films.
* WhatCouldHaveBeen: Creator/JKSimmons auditioned for multiple parts, but backed out when the one character the Coens were leaning toward casting him as was too similar to ''Series/{{Oz}}'' and turned it down. He would work with the Coens many times down the line.
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