Her brother, Al Rinker, started to perform as a singer with Bing Crosby in Spokane and became a member of The Rhythm Boys.

[5] Bailey's great-grandfather, Bazil Peone, was a head speaker and song leader of the Coeur d'Alene at the turn of the 20th century.

His ability to create indigenized Catholic hymns helped guide the tribe during difficult times of active colonization by Jesuit missionaries.

[8] The family often hosted Saturday night gatherings, creating small music and dance hall in the home for local ranchers with both Josephine and Mildred at the piano.

[7] Josephine died from tuberculosis at the age of 36, threatening Mildred's ability to remain connected to her native family and traditions in a way that she was able to while her mother was alive.

She married and divorced Ted Bailey, keeping his last name because she thought it sounded more American than Rinker,[5] which was of Swiss (German) origin.

[3] 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.

[9] 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.

Whiteman had a radio program for Old Gold Cigarettes, and when Bailey debuted on it with her version of "Moanin' Low" on August 6, 1929,[10] favorable public reaction was immediate.

[13] She was Whiteman's female vocalist through 1932 (recording in a smooth, crooning style) but left the band later that same year over salary disagreements.

Bailey was part of an all-star session with Benny Goodman's studio band in 1934 featuring Coleman Hawkins, Dick McDonough, and Gene Krupa.

[21] Bailey sang lead vocals on "Darn That Dream", recorded by Benny Goodman and His Orchestra, which reached number one for one week in March 1940 on the U.S. pop chart.

[22] (Vocalion releases only) [23] The 2023 American historical drama miniseries "Lessons in Chemistry" used Bailey's 1940 recording of "Wham (Re Bop Boom Bam)" as its opening theme song.