Easton was born in Brunswick, Georgia. Around 1920 he joined the Ringling Brothers circus. He then returned to Georgia and was briefly married before heading north on a freight train to Indianapolis, where he settled in 1928. There he met and was influenced by the pianist Leroy Carr and the guitarist Scrapper Blackwell.
By 1931 he had moved to Chicago, where he made his first recordings, as Bumble Bee Slim, for Paramount Records. The following year his song “B&O Blues” was a hit for Vocalion Records, inspiring a number of other railroad blues and eventually becoming a popular folk song. In the next five years he recorded over 150 songs for Decca Records, Bluebird Records and Vocalion,often accompanied by other musicians, including Big Bill Broonzy, Peetie Wheatstraw, Tampa Red, Memphis Minnie, and Washboard Sam.