Bluegrass Hootenanny was the second duet album by Jones and Montgomery, the first being the bluegrass-tinged What's In Our Heart. As the title implies, this second Jones/Montgomery collection brings this sound into focus, a departure of sorts for Jones, who was known primarily for his hardcore honky tonk sound and soulful ballad singing. The album features several bluegrass interpretations of classic country songs written by Bill Monroe, Lester Flatt, and Hank Williams. Jones co-wrote two songs with Johnny Mathis, the rollicking "Jump In The Mississippi" and the plaintive "I'd Dreamed My Baby Came Home", while "Will There Ever Be Another" and "I'll Be There To Welcome You Home" were co-written by Montgomery. The album was a hit, reaching number 12 on the country album chart, although not quite as successful as What's In Our Heart had been, which had risen to number three.
Jones and Montgomery would tour together, with Jones confessing in his autobiography I Lived To Tell It All, "My affections for Melba surfaced almost immediately after we began working. But my drunkenness and the fact that I had a wife did little to make her want to commit to me." Jones also divulged that he had asked her to marry him but Montgomery had begun a relationship with Jones' guitar player Jack Solomon, whom she would eventually marry.