Chatmon played guitar and other instruments in Hollandale, Mississippi in the 1930s. He played with his brothers sometimes in a band called the Mississippi Sheiks, and may have been a songwriter, though the Mississippi Blues Trail is unclear about that.
He also picked cotton to make a living, and played in the clubs of Hollandale with many of the blues big names. He got a chance at a bigger stage during the folk and blues revival of the 1960s, and played festivals all over the country. I’m assuming that’s when this fun cut was recorded. There are some Alan Lomax recordings and films from 1978, too.