Cannon's musical skills came without training; he taught himself to play using an improvised instrument made from a frying pan and raccoon skin. He began playing in Memphis in the 1900s with Noah Lewis and Jim Jackson, then started working in medicine shows in 1914.
Cannon began recording in 1927, both alone and with Lewis, Hosea Wood, Blind Blake and Ashley Thompson. By the end of the 1930s, though, Cannon had retired, returning in 1956 to make a few recordings for Folkways.