In the 1920s, having already perfected his slide technique, he moved to Chicago, Illinois, and began his career as a musician, adopting the name "Tampa Red", with reference to his childhood home and his light-colored skin. His big break came when he was hired to accompany Ma Rainey. He began recording in 1928, with "It's Tight Like That", in a bawdy and humorous style that became known as hokum. His early recordings were mostly collaborations with Thomas A. Dorsey, known as Georgia Tom. The two recorded almost 90 sides, sometimes as the Hokum Boys or, with Frankie Jaxon, as Tampa Red's Hokum Jug Band.