Chatmon moved to Hollandale, Mississippi in the early 1940s and worked on plantations in Hollandale. He started playing again in 1960, playing mostly blues music. In the same year, he recorded songs for Arhoolie Records. He went on tours in the 1960s and 1970s and played for many festivals such as the Festival of American Folklife in Washington, D.C. in 1972, the Mariposa Fest in Toronto in 1974, and the New Orleans Jazz and Heritage Festival in 1976.