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Bailey was born in Southampton County, Virginia, to Rev. Joseph and Ella Mae Bailey, and raised in the Bloodfields neighborhood of Newport News, Virginia. She made her stage-singing debut when she was 15 years old. Bailey's brother Bill was beginning his own career as a tap dancer, and suggested she enter an amateur contest at Philadelphia's Pearl Theater. She entered, won first prize, later won a similar contest at Harlem's famous Apollo Theater, and decided to pursue a career in entertainment. Bailey, costumed in the role of Butterfly, gauges the applause following her performance of the song "It's A Woman's Prerogative", July 5, 1946. Sustained applause required her to take another bow

Bailey began by singing and dancing in Philadelphia's black nightclubs in the 1930s, and soon started performing in other parts of the East Coast. In 1941, during World War II, Bailey toured the country with the USO, performing for American troops. After the tour, she settled in New York. Her solo successes as a nightclub performer were followed by acts with such entertainers as Cab Calloway and Duke Ellington. In 1946, Bailey made her Broadway debut in St. Louis Woman. Bailey continued to tour and record albums in between her stage and screen performances. In 1954, she took the role of Frankie in the film version of Carmen Jones, and her rendition of "Beat Out That Rhythm on the Drum" is one of the highlights of the film. She also starred in the Broadway musical House of Flowers. In 1959, she played the role of Maria in the film version of Porgy and Bess, starring Sidney Poitier and Dorothy Dandridge. Also that year she played the role of "Aunt Hagar" in the movie St. Louis Blues, alongside Mahalia Jackson, Eartha Kitt, and Nat King Cole. In 1967, Bailey and Cab Calloway headlined an all-black cast version of Hello, Dolly! The touring version was so successful, producer David Merrick took it to Broadway where it played to sold out houses and revitalized the long running musical. Bailey was given a special Tony Award for her role and RCA made a second original cast album.. That is the only recording of the score to have an overture which was written especially for that recording. The following year, she sang the national anthem at Shea Stadium, prior to game 5 of the 1969 World Series. During the 1970s she had her own television show, and she also provided voices for animations such as Tubby the Tuba (1976) and Disney's The Fox and the Hound (1981). She returned to Broadway in 1975, playing the lead in an all-black production of Hello, Dolly!. She earned a B.A. in theology from Georgetown University in Washington, D.C. in 1985. Later in her career, Bailey was a fixture as a spokesperson in a series of Duncan Hines commercials. Bailey was born in Southampton County, Virginia, to Rev. Joseph and Ella Mae Bailey, and raised in the Bloodfields neighborhood of Newport News, Virginia. She made her stage-singing debut when she was 15 years old. Bailey's brother Bill was beginning his own career as a tap dancer, and suggested she enter an amateur contest at Philadelphia's Pearl Theater. She entered, won first prize, later won a similar contest at Harlem's famous Apollo Theater, and decided to pursue a career in entertainment. Bailey, costumed in the role of Butterfly, gauges the applause following her performance of the song "It's A Woman's Prerogative", July 5, 1946. Sustained applause required her to take another bow

Bailey began by singing and dancing in Philadelphia's black nightclubs in the 1930s, and soon started performing in other parts of the East Coast. In 1941, during World War II, Bailey toured the country with the USO, performing for American troops. After the tour, she settled in New York. Her solo successes as a nightclub performer were followed by acts with such entertainers as Cab Calloway and Duke Ellington. In 1946, Bailey made her Broadway debut in St. Louis Woman. Bailey continued to tour and record albums in between her stage and screen performances. In 1954, she took the role of Frankie in the film version of Carmen Jones, and her rendition of "Beat Out That Rhythm on the Drum" is one of the highlights of the film. She also starred in the Broadway musical House of Flowers. In 1959, she played the role of Maria in the film version of Porgy and Bess, starring Sidney Poitier and Dorothy Dandridge. Also that year she played the role of "Aunt Hagar" in the movie St. Louis Blues, alongside Mahalia Jackson, Eartha Kitt, and Nat King Cole. In 1967, Bailey and Cab Calloway headlined an all-black cast version of Hello, Dolly! The touring version was so successful, producer David Merrick took it to Broadway where it played to sold out houses and revitalized the long running musical. Bailey was given a special Tony Award for her role and RCA made a second original cast album.. That is the only recording of the score to have an overture which was written especially for that recording. The following year, she sang the national anthem at Shea Stadium, prior to game 5 of the 1969 World Series. During the 1970s she had her own television show, and she also provided voices for animations such as Tubby the Tuba (1976) and Disney's The Fox and the Hound (1981). She returned to Broadway in 1975, playing the lead in an all-black production of Hello, Dolly!. She earned a B.A. in theology from Georgetown University in Washington, D.C. in 1985. Later in her career, Bailey was a fixture as a spokesperson in a series of Duncan Hines commercials.

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