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Otis Lee Crenshaw
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Comedian Rich Hall (of Sniglet fame... hmm... is fame the right word here? Never mind.) plays this Tennessee-born country singer with seven ex-wives and over 12 jail terms. His songs include the prison rape ballad "He Almost Looks Like You" -- "when he sneaks off with other men/He almost looks like you." From the straight to video Otis Lee Crenshaw: Live (2001).
There's also a CD and Rich toured in character with an entire Otis Lee show.
Backup band: The Black Liars, bassist Rev. Alvy Ronson (Damian Coldwell) and guitarist Orson Carson (Christian Reilly). The Black Liars also have their own solo CD, The Black Album.