She toured with a West Coast revue and finished in California where she obtained work at radio station KMTR and at a speakeasy in Bakersfield called The Swede's. With the help of her second husband Benny Stafford, Bailey became an established blues and jazz singer on the west coast of the United States. According to Gary Giddins in his book "Bing Crosby: A Pocketful of Dreams, The Early Years 1903–1940", she found work for her brother Al Rinker and Bing Crosby, who had started performing in Spokane, Washington. They had traveled from Spokane to join her in Los Angeles. Giddins says Crosby heard about Louis Armstrong from Bailey, who urged him to hear Armstrong if Crosby was to be a serious jazz singer. She also played Crosby records from her collection by Ethel Waters and Bessie Smith.