While Bessie Smith spent a great deal of money on her own family, she also made sure she traveled in style. She bought a custom-made railroad car for her and her troupe when they traveled. The car was a lavish affair, with two stories, a full kitchen, four bedrooms and a bathroom, and when Smith and her troupe traveled, it became a mixture of hotel, bordello, and saloon. The railroad car was especially convenient in the smaller Southern towns, where segregation forbade blacks from sleeping in most hotels. Smith's summer tent show, Harlem Frolics, was doing brisk business, as was its follow-up, Mississippi Days.In May 1925, Smith recorded "Cake-Walking Babies", the first electronically recorded record and the first song Smith ever recorded using a microphone.

In late 1926, Jack Gee began having an affair of his own with one of Smith's chorus girls. Smith found out about the affair while on her way to Ozark, Alabama for a show. Gee met the car at the station, but when the train pulled up, Smith pulled out a gun and began shooting. She missed Gee by inches, and he ran down the tracks in the opposite direction. Smith demanded that the train move on without Gee. Bessie's anger did not, however, mean that her own infidelities came to an end. Around this time, Bessie had begun a particularly intense affair with one of her chorus girls, a young woman named Lillian Simpson. Simpson was a classmate of Ruby Walker's and, like Walker, found show business irresistible. Walker convinced Smith aunt to give Simpson and audition, and although Smith had no openings in the chorus, she felt obligated to take Simpson on the road because Simpson's mother had once worked for her. Once on the road, Smith and Simpson became lovers, and their affair was especially intense. After one heated argument, Simpson threatened to kill herself, and Smith found her a few hours later with her head in an oven. Simpson survived, but the affair ended because of Simpson's terror of Gee's reaction if he were to find out about the affair.

Gee did eventually find out about Smith's homosexual affairs when he caught her in a Detroit boardinghouse in flagrante delicto with a young dancer named Marie. Chaos ensued and Smith locked herself in Walker's room while Gee cursed and threatened to kill her. After Gee left, Smith gathered her troupe and they quickly packed their bags and headed towards the railroad car. An hour later, with all the lights out, they quietly made their escape from Detroit.

Meanwhile, some of Smith contemporaries were making the transition from the TOBA circuit to Broadway and Hollywood. Ethel Waters, a thin blues singer with almost European features, had landed coveted roles in Broadway musicals and even auditioned for roles in Hollywood. Waters's light skin made her a desirable in white circles. Smith, on the other hand, was unable to make this crossover, even though, at the time, she was considered the most talented blues singer of her time.

Occasionally, however, whites tried to win Smith over, with mixed results. One particularly famous episode occurred at the New York home of Carl Van Vechten, a wealthy white music critic and photographer who was known among the artists and musicians of the Harlem Renaissance. In the winter of 1928, when Smith was at her peak, Van Vechten convinced her to attend one of his cocktail parties. Smith was skeptical, but decided to attend. When Smith arrived, she struck many at the party as being crude and vulgar, but after being persuaded to sing, she left her audience dumbstruck by her voice. Van Vechten would become one of Smith's most enthusiastic supporters, but she would continue to view white society with mistrust. For many in her black audience, Smith's rejection of white society and the fact that she had become successful by relying almost entirely on African-American was a point of pride, and seen as a triumph.