Born Mildred Rinker in Tekoa, Washington, Bailey retained the last name of her first husband, Ted Bailey, when she moved to Seattle to bolster her singing career. With the help of her second husband, Benny Stafford, she became an established blues and jazz singer on the east coast. in 1925 she secured work for her brother, Al Rinker and his partner Harry Lillis "Bing" Crosby. Crosby helped Bailey in turn by introducing her to Paul Whiteman. She sang with Paul Whiteman's band 1929 to 1933. In the mid 1930s, she recorded with her third husband Red Norvo.

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