Anderson was born in Laurens, South Carolina, and raised in nearby Greenville and Spartanburg. He joined Dr. William R. Kerr of the Indian Remedy Company in 1914 to entertain the crowds, while Kerr tried to sell a concoction purported to have medicinal qualities. During this time Anderson occasionally worked with Blind Simmie Dooley in the Spartanburg area, recording with him in 1928 for the Columbia label. In the 1950s Anderson toured with Leo “Chief Thundercloud” Kahdot and his medicine show, often with the harmonica player Arthur “Peg Leg Sam” Jackson, who was based in Jonesville, South Carolina.

Anderson was recorded by the folklorist Paul Clayton at the Virginia State Fair in May 1950. He recorded an album in the early 1960s and performed at some live venues. He appeared in the 1963 film The Bluesmen. He reduced his activities in the late 1960s after a stroke. Attempts by the folklorist Peter B. Lowry to record Anderson in 1970 were not successful, although apparently he could occasionally summon up some of his past abilities. A final tour took place in the early 1970s with the aid of Roy Book Binder, one of his students, taking him to Boston and New York City.

He died in October 1974 of a heart attack, at the age of 74. He is interred at Lincoln Memorial Gardens, in Spartanburg.