The war did not affect Bessie Smith's burgeoning career, and the scope and quality of her performances continued to grow. In 1915, Smith joined Ma Rainey on tour with the Rabbit Foot Minstrels, and in 1916, Smith traveled with Pete Werley's Florida Cotton Blossoms Minstrels Show and Silas Green's Minstrel Show. Between 1918 and 1919, Smith appeared as a singer, dancer and male impersonator in her own show, the Liberty Belles Revue, in Atlanta. In the early 1920s she performed in New Jersey with the Charles Johnson Band at Paradise Gardens. Smith worked at Horan's Madhouse Club in Philadelphia from 1920 to 1923, and she appeared in the musical "How Come" at the Dunbar Theater in Philadelphia in 1923.

These were formative years for Smith. Her years of touring had helped her build a huge fan base, despite the fact that she had not yet recorded a single song. If her name was on the show's billing, people would line up for hours in order to buy tickets. Around this time, Smith married a man named Earl Love, who came from a wealthy Southern family. Very little is known about Love and the circumstances of the couple's meeting and marriage. All that is known is that they married in 1920 and that Love died soon after. Smith told people that Love died in the war, but this was never confirmed.

In 1920, Smith moved to Atlantic City to perform in various shows there. Around this time, Mamie Smith's "Crazy Blues" was released and became an enormous hit. It was the first blues record recorded by an African-American to hit the mainstream market. Record companies had previously believed there was little money to be made in African-American communities, but the popularity of Mamie Smith's recording sparked a mad rush by recording companies to put out blues records.

Shortly after Mamie Smith's "Crazy Blues" was released, Bessie Smith met Sidney Bechet, a talented young saxophonist, during a stint in Washington, D.C. Their friendship turned to romance as they spent time together on tour, and Bechet remained an important musical collaborator for Smith for years. Prohibition went into effect in 1920, and many music clubs went underground. The Blues became a staple of these illicit speakeasies.

In 1921, Smith moved to Philadelphia. While there, she auditioned for two record companies: Okeh Records and W.C. Handy's Black Swan Records. Both record labels turned Smith down because her voice was "too rough," a thinly veiled euphemism for "too black." Smith would face this kind of veiled discrimination for years, sometimes from other African-American performers. Lighter-skinned African-Americans were granted many more opportunities in show business because they more closely resembled whites, and the dark-skinned Smith was frequently passed over for jobs because she wasn't light-skinned enough. These early experiences haunted Smith for the rest of her life, and she became extremely hostile toward lighter-skinned blues singers and those African-Americans who, after moving during the Northern Migration, joined white society in their new cities. Smith had no desire to join white society in the way blues singer Ethel Waters had. Smith was also, by this time, notoriously moody and obscene, and already an alcoholic.

In 1922, during a stint at Horah's Cabaret in Philadelphia, Smith met Jack Gee, a strikingly handsome night watchman. On Smith and Gee's first date, Gee got into an altercation and ended up in the hospital with a gunshot wound. Smith visited him every day for five weeks. When he was released, they moved in together and embarked on what would be the longest-lasting and most volatile relationship of her life.

At this time, Smith had not yet recorded a song. After the success of Mamie Smith's "Crazy Blues," record companies saw that there was quite a bit of money to be made in what were then termed "race records" and sent scouts to Southern cities to find talent. Frank Walker, the head of Columbia's Race Records, convinced Smith to travel to New York for an audition. Jack Gee pawned his watch and his night watchman's uniform in order to buy Smith a red dress to wear to her first recording session with Columbia. She arrived at the studio with her friend and pianist Clarence Williams on February fifteen, 1923. Throughout the session, Smith was so nervous that Frank Walker had to schedule another session.