Johnson married Virginia Travis in Penton, Mississippi, in February 1929. He lost both his sixteen-year-old wife and baby in childbirth in April of 1930. He returned to Hazlehurst where he studied blues guitar under Ike Zinnerman. Zinnerman was evidently accomplished on the instrument, but he was never recorded. Not much is known of him other than that he was born in Grady, AL and that he told his wife that he learned guitar by practicing sitting on tombstones at night in the graveyard.
Also while in Hazlehurst, Johnson met Calletta "Callie" Craft, ten years his senior and mother of three small children. They were married at the Copiah County courthouse in May 1931. Once he thought he was ready to begin his life as a bluesman, he packed up Callie and the kids and traveled to the delta. Callie, however was not a strong, healthy woman. She became ill in Clarksdale and called for her family to come get her and take her back to Hazlehurst. Robert, evidently, had deserted her. Neither she nor her family ever saw Johnson again and Callie died a few years later.
Robert returned to Robinsonville where he encountered Willie Brown and Son House. He astounded the bluesmen with his improved abilities. Son House said, "When he finished all our mouths were standing open. I said, 'Well, ain't that fast! He's gone now!'" This quick, unexpected improvement of ability gave rise to the idea that he had made a pact with the devil, a myth that Johnson was quick to exploit.
He spent some time in Helena, AR, a wide open gambling and drinking town and a hotbed of blues performers in those days. There he met most of the well-known bluesmen of the day and influenced most of them. He didn't stay in any one place for very long, however. It seems that traveling was an end unto itself for him. He was always ready to go anywhere.
By the mid-'30s, he had been a professional bluesman for quite a number of years. He contacted H.C. Spiers in Jackson, MS. Spiers had a record store and a small recording studio. He was also somewhat of a talent scout and quite a number of musicians had recorded for Paramount on his recommendation. He had just entered into an agreement with American Record Company, and after Johnson auditioned with him, he put him in touch with Ernie Oertle of that company. Oertle decided that Johnson would record in San Antonio. In November 1936, Johnson recorded a number of tunes, including "Terraplane Blues" which probably got the most radio play during his lifetime. He returned to record more tunes in June of 1937. In all, he recorded 29 tunes, some with more than one take.