The song was first performed in concert on October 19, 1971, in Minneapolis, Minnesota at new keyboardist Keith Godchaux's first appearance with the band. In the song's earliest performances (c. 1971–72), Weir sang all of the vocals. By the time the 'Europe 72' version was recorded, (at the Olympia Theater in Paris on 5-03-72), Weir and Jerry Garcia were switching up the vocals - as they had on April 26th when 'Hundred Year Hall' was recorded. The song appeared in both the first and second sets until the band's short hiatus in 1974-1975. After re-forming, the song almost exclusively appeared in the first set. After Brent Mydland joined the band in 1979, the song almost exclusively opened the band's first set. The band also often extended the jam after the second verse after Mydland's joining, often extending the song to over six minutes. Dead and Company have also further extended the song, often adding an abstract opening jam prior to the song's first verse.[1]
Bob Weir stated in a 2004 interview that the song's lyrics were partly based on John Steinbeck's novel Of Mice and Men.[2] The song's themes include riding the rails, the Great Depression, and hobo (homeless) camps of the era. Jack Straw is also—perhaps coincidentally—the name of the original plantation owner, who lived controversially with his gay lover, Peter Ochello, in Tennessee Williams's play Cat on a Hot Tin Roof.[3]
