“In the Jailhouse Now” is a comic song of crime and bad luck whose roots lie in early-twentieth-century vaudeville and the African American blues and jug-band tradition. Versions circulated well before it was a hit; the song was recorded by jug bands and by blues singers including Blind Blake in the 1920s, and one of them, Jim Jackson, copyrighted it before it became widely known.
The song is most closely tied to Jimmie Rodgers, the “Singing Brakeman” and a founding figure of country music, who recorded it in 1928 and again in 1930. Rodgers wrapped the lyric — a rueful catalog of gambling, scrapes, and the jailhouse that follows — in his trademark blue yodel, and his recordings made the song a country standard, often credited to him despite its older history.
The song has been sung across country, blues, and bluegrass ever since. The version heard here is by the Soggy Bottom Boys, the fictional band of the 2000 film “O Brother, Where Art Thou?,” whose hugely popular soundtrack carried the old song to a new audience.