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Musical tastes began to change around this time, and the kind of blues that Bessie Smith sang began to wane in popularity. Swing and jazz music were now popular, and the blues had fallen out of favor. In 1933, Prohibition was repealed. Although Richard Morgan remained financially comfortable, Smith was finding it more and more difficult to make ends meet. In 1933, Smith approached Okeh Records, which had turned her down in 1921 because her voice was "too rough." She recorded some songs for the label, including "Do Your Duty", "Gimme a Pigfoot" and "I'm Down in the Dumps." During these sessions, Smith recorded with some of the top jazz musicians of the day, including trombonist Jack Teagarden, clarinetist Benny Goodman, and pianist Buck Washington. But Chicago was quickly becoming the center of a more guitar-heavy, male-dominated blues culture. Talking pictures had also begun to siphon off some of the audience for live music, revues and vaudeville shows.

Smith seemed ready to make the transition from blues singer to jazz and swing singer as she started to revamp her look and substituted sleek evening gowns for her usual outfits. She also began adding songs to her set like "Smoke Gets in Your Eyes," and frequented jazz clubs in Harlem and in Philadelphia. She was even billed as "The Queen of All Torch Singers." In 1935, Smith played the Apollo Theater in Harlem, replacing an exhausted Louis Armstrong. The owner thought Bessie's chorus girls were too dark-skinned, but Smith refused to perform without them, even though she desperately needed the job. The owner relented. In 1936, Smith appeared in place of a sick Billie Holiday at a jazz club in New York called Connie's Inn. She performed a strict jazz and Tin Pan Ally set. Meanwhile, Smith's drinking escalated. She was rarely sober. Smith's last club appearance in New York took place in 1936 during a jam session at the Famous Door club on 52nd Street.

In September 1937, Smith accepted an engagement with Winsted's Broadway Rastus Show. On September 26, 1937, she was on her way to a performance outside of Memphis, Tennessee. It was around three in the morning, and Smith and Richard Morgan were barreling down the dark country road in their Packard. A truck was parked on the shoulder with its lights out, and Richard crashed into the parked vehicle. Smith's arm was nearly severed in the accident. What followed next is unclear. It is known that Smith did not arrive at a hospital until 11:30 a.m., seven hours after the accident occurred. A few minutes after the accident took place, a white doctor who happened to be driving down the same road stopped to tend to Smith. As he was taking care of her, another car carrying a white couple crashed into the back of Richard Morgan's wrecked car. It is at this point that the stories begin to diverge. One version of the story maintains that the white woman in the second car, who was only slightly injured, was rushed to the hospital in the ambulance that had arrived to take Smith away. Another story maintains that Bessie was indeed rushed to a hospital, but was turned away because she was black. In fact, this version of the Bessie Smith story was immortalized in Edward Albee's famous play, "The Death of Bessie Smith." As a result, Bessie Smith has often been heralded as a martyr to the racism of the American South. John Hammond, one of Bessie's producers at Okeh Records, wrote an article soon after Bessie's death that furthered this version of events. Still others speculate that Smith was taken to G.T. Thomas Hospital for Blacks in Clarksdale, Mississippi, about a mile from the scene of the accident. There, she received a blood transfusion and her arm was amputated. Despite these efforts, she died of massive internal injuries. Bessie was forty-three years old.

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