Around 1915, the Raineys toured with Fat Chappelle’s Rabbit Foot Minstrels. Shortly after, they then became known as the “Assassinators of the Blues” with Tolliver’s Circus and Musical Extravaganza.
After she separated from her husband in 1916, Rainey later toured with her own band, Madam Gertrude Ma Rainey and Her Georgia Smart Sets, featuring a chorus line and a Cotton Blossoms Show, and Donald McGregor’s Carnival Show.