Rainey was Bessie's mentor and she stayed with her show until 1915. Bessie
then joined the T.O.B.A. vaudeville circuit and gradually built up her own.
By the early 1920's she was one of the most popular Blues singers in vaudeville.
In 1923 she made her recording debut on Columbia, accompanied by pianist Clarence Williams. They recorded "Gulf Coast Blues" and "Down Hearted Blues." The record sold more than 750,000 copies that same year, rivaling the success of Blues singer Mamie Smith. Throughout the 1920's Smith recorded with many of the great Jazz musicians of that era, including Fletcher Henderson, James P. Johnson, Coleman Hawkins, Don Redman, and Louis Armstrong. Her rendition of "St. Louis Blues" with Armstrong is considered to be one of finest recordings of the 1920s.
By 1931 the Classic Blues style of Bessie Smith was out of style and the Depression, radio, and sound movies had all damaged the record companies ability to sell records and Columbia dropped her from its roster.