Bessie Smith was a rough, crude, violent woman. She was also the greatest of the classic Blues singer of the 1920s. Bessie started out as a street musican in Chattanooga. In 1912 Bessie joined a traveling show as a dancer and singer. The show featured Pa and Ma Rainey, and Smith developed a friendship with Ma. Ma 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 following in the south and along the eastern seaboard.  By the early 1920s 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 (no relation).

In 1933 she recorded for the last time under the direction of John Hammond for Okeh. The sessions featured white Jazz musicians Jack Teagarden and Benny Goodman. Despite having no record company Smith was still very popular in the South and continued to draw large crowds, although the money was not nearly as good as it had been in the 1920s.

Bessie had started to style herself as a Swing musician and was on the verge of a comeback when her life was tragically cut short by an automobile accident in 1937. While driving with her lover Richard Morgan (Lionel Hampton's uncle) in Mississippi their car rear-ended a slow moving truck and rolled over crushing Smith's left arm and ribs. Smith bled to death by the time she reached the hospital. John Hammond caused quite a stir by writing an article in Downbeat magazine suggesting that Smith had bleed to death because she had been taken to a White hospital and had been turned away. This proved not to be true, but the rumour persists to this day.