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Jimmy Rodgers' version of "In the Jailhouse Now" was recorded February 15, 1928, and features Rodgers on vocals and guitar. Rodgers included his famous yodel throughout the song. He recorded a sequel titled "In the Jailhouse Now—No. 2" in 1930, which follows the misadventures of a man named Campbell.
Prior to 1930, several different versions of it were recorded and copyrighted. The earliest is Davis and Stafford's 1915 version, which has verses about a man named Campbell cheating at a card game and a corrupt election. In 1924, Whistler's Jug Band from Louisville, Kentucky, recorded it under the title "Jail House Blues," which was the same title as a famous blues tune by Bessie Smith but was, in fact, the same song as "In the Jailhouse Now".
In O Brother, Where Art Thou?, "Delmar" (Tim Blake Nelson) sings a rendition, with "Pete" (John Turturro) yodeling between the verses, prior to the Soggy Bottom Boys' main number, "Man of Constant Sorrow". The other "Soggy Bottom Boys" songs are lip-synched, but Tim Blake Nelson sings his own vocals on this song, while Turturro's yodeling is actually performed by Pat Enright of the Nashville Bluegrass Band.