In 1928, Bessie Smith bought her sister Viola a restaurant in Philadelphia in the hopes that the investment might encourage Viola to become financially independent. Around the same time, Jack Gee had the first of many nervous breakdowns, and Smith took time off touring to nurse him back to health. As soon as he recovered, however, Smith returned to drinking heavily and to her string of love affairs, while Gee continued to bear her savagely whenever he managed to catch her doing something wrong.
In 1929, Gee proposed to set up a new show for his wife, which was to be called "Steamboat Days." Smith gave Gee three thousand dollars to begin production while she was on tour, but instead, Gee used the money to set up a show for a woman he'd been having an affair with. The woman, Gertrude Saunders, was a thin, moderately successful blues singer known for her roles in shows led by the bandleader Irvin Miller. Saunders was light-skinned and pretty, which added to Smith's insecurities about the affair. Smith read about Saunders's show in the Amsterdam News while in a Cincinnati dressing room, and Ruby Walker would later report that this was the first time she saw Smith cry. This last betrayal effectively ended Smith and Gee's marriage. A few months later, Smith recorded another hit, "Nobody Knows You When You're Down and Out," whose lyrics eerily paralleled her life.
The year had been a disastrous year for Bessie Smith, but was punctuated by a spot of good news when she was tapped to star in a short film based on her hit song "St. Louis Blues." Kenneth W. Adams and W.C. Handy, who composed the song, had written a short script about a love triangle which featured a musical performance by one of the female characters, played by Smith. Filming began in June 1929. St. Louis Blues was a two-reel short film of the kind shown before feature films at the time. Like "Nobody Knows You When You're Down and Out", the St. Louis Blues was similar to Smith's actual life. The film features a thinner, prettier, lighter-skinned rival who has an affair with the boyfriend of the character played by Smith. Smith's character catches them together, and her boyfriend chooses the other woman. Smith then sings the song "St. Louis Blues" while standing against a bar with a glass of whiskey at her elbow. This was Smith's only film appearance, and the only footage of her singing.
Despite the success of St. Louis Blues, Smith's life continued its downturn. In an act of revenge, Jack Gee kidnapped Jack Gee, Jr. from Bessie's Philadelphia home and brought the boy to the offices of the Society of Prevention of Cruelty to Children (SPCC). There Gee filed false neglect and endangerment charges against Smith. The courts remanded Jack, Jr. to Viola's care, rather than to Smith's. A short while later, Jack Jr. went to live with his biological father, who kept him in the basement and often forgot to feed him. The SPCC then sent the boy to a home in Valhalla, New York. Smith, who had no idea where her adopted son was, grew despondent. Later that year, Smith starred in a Broadway show called Pansy. The show was a flop and closed after three days, even though reviews conceded that Smith's performances were a break in an otherwise bad show.
To make matters worse, Smith missed Ruby Walker terribly. When Gee and Smith split, Walker disappeared with Gee. Walker would later tell Chris Albertson, Smith's biographer, that Gee had forced her to come with him. Walker's friendship was, for many years, the most stable relationship in Smith's life, and without her best friend, Smith was heartbroken.