Crosby helped Bailey in turn by introducing her to Paul Whiteman in Los Angeles. She sang with Whiteman's band from 1929 to 1933. Whiteman had a popular radio program for Old Gold Cigarettes, and when Bailey debuted on it with her version of "Moanin' Low" on August 6, 1929, favorable public reaction was immediate. However, Bailey's first recording with Whiteman did not take place until October 6, 1931 when she recorded a song called "My Goodbye to You". Her recording of "All of Me" with Whiteman the same year was a hit in 1932.