Jerry Jeff Walker made this first solo album primarily to discharge a contractual obligation to Vanguard Records. His rock band Circus Maximus had just broken up. Walker, who had already signed with Atco on the basis of massive New York City airplay for his demo of "Mr. Bojangles," chose to honor a commitment to the label, partly because it gave him a chance to record some of his older, pre-rock material.
The resulting album, recorded in Nashville with some of the same musicians who had recently backed Bob Dylan on BLONDE ON BLONDE, is fun in a period sort of way. There are (as the title suggests) lots of songs in which Walker talks about being a ramblin' sort of guy, along with some hippie-esque observations about changes we all go through ("Shell Game"), and of course an ode ("Gertrude") to the inevitable whore with a heart of gold.