|Bailey was born in Southampton County in southeastern Virginia, to Joseph and Ella Mae Ricks Bailey. She was reared in the Bloodfields neighborhood of Newport News, Virginia.|
She made her stage-singing debut when she was 15 years old. Her brother Bill Bailey was beginning his own career as a tap dancer, and suggested she enter an amateur contest at the Pearl Theatre in Philadelphia. She entered the amateur song and dance contest and won and was offered $35 a week to perform there for two weeks but the theatre closed during her engagement and she wasn't paid. She later won a similar contest at Harlem’s famous Apollo Theater, and decided to pursue a career in entertainment.
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. Early in the television medium, Bailey guest starred on CBS's Faye Emerson's Wonderful Town.
Her support of female impersonator Lynne Carter led him to credit Bailey with launching his career.
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. Though she was originally considered for the part of Annie Johnson in the 1959 film Imitation of Life, the part went to Juanita Moore, for which Moore received an Academy Award nomination.
Bailey in a 1968 Ed Sullivan Show performance.
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.
Pearl Bailey died at Thomas Jefferson University Hospital in Philadelphia on August 17, 1990. Following an autopsy, Dr. Emanuel Rubin, professor and chairman of the Department of Pathology at Jefferson Medical College, announced the cause of death as arteriosclerotic coronary artery disease with significant narrowing of the coronary artery. She is buried at Rolling Green Memorial Park in West Chester, Pennsylvania.
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