Pearl Bailey’s remarkable career as a singer and stage and film actress lasted nearly sixty years. When she was twelve years old, Bailey won a five dollars first prize in a talent contest at the Pearl Theater in Washington, D.C. The contest management also promised a chance to perform several shows at the club, which for Bailey meant appearing alongside her brother, the well-known tap dancer Bill Bailey, who was performing there. After a few shows, the club closed and Pearl Bailey never received payment for her first professional theater job.

In spite of this, the little taste of success she experienced winning the contest convinced Bailey to give up her plans to become a teacher and pursue a career on the stage. She joined the chorus line of a vaudeville troupe and began a tour of Pennsylvania’s vaudeville circuit. She soon graduated to solo performances in clubs from Washington D.C. to New York City. When she won another talent contest, this time at Harlem’s Apollo Theater, the music and theater community began to notice Bailey. Audiences, too, were charmed by her trademark performance style, a casual and intimate presentation that made her skillful vocalization seem deceptively simple. Bailey began playing New York’s finest clubs, becoming one of the city’s favorite singers.

In the 1940s, in addition to her successful career as a singer, Pearl Bailey became a popular theater performer. She made her Broadway debut in 1946 in St. Louis Woman, an all-black musical by Johnny Mercer and Harold Arlen. Bailey sang two songs in the show: “A Woman’s Prerogative,” and “Legalize My Name.” Audiences were thrilled by her performance and critics singled out her numbers for praise. That year, Bailey won the Donaldson Award for Best Newcomer on Broadway.

Her next Broadway appearance was a little less auspicious. The show, Arms and the Girl, in which one of her co-stars was a horse, received mixed reviews and wasn’t popular with audiences. Though it was a disappointing way to follow up her first theatrical success, Bailey had a good sense of humor about it. “There was another star in the show, a horse. I mustn’t forget him,” she wrote in her autobiography, The Raw Pearl. “From the beginning there were misgivings about that horse, because they are show stealers, like children. Then, too, you can’t pin down what they might do onstage.”1

After that early misstep, Bailey made many memorable and successful Broadway appearances. Among her most famous roles were Madame Fleur, the West-Indian bordello owner in House of Flowers, a musical written by Truman Capote and Harold Arlen, which also starred a young Diahann Carroll. Her biggest success came in 1967, however, when Bailey played Dolly Levi in the all-black version of Hello, Dolly! Bailey won a Tony award for her performance. The show played for two years and toured nationwide in the 1970s.

Bailey’s popularity as a singer and stage actress led to many offers to appear in Hollywood films. Bailey played Frankie in the 1954 hit film adaptation of Carmen Jones which also starred Harry Belafonte and Dorothy Dandridge. In 1959, Bailey performed with Dandridge again in Porgy and Bess. The all-star cast also included Sydney Poitier and Sammy Davis Jr. During the 1970s, she appeared on several television programs, including her own brief series, The Pearl Bailey Show.

Though she had dropped out of school to become a performer, Bailey didn’t give up on getting a formal education. When she was in her sixties, she went back to school, earning a bachelor’s degree in theology from Georgetown University. She completed her studies at the age of sixty-seven.