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.
For her performance, she won a Donaldson Award as the best Broadway newcomer.
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 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 Victor 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.

A passionate fan of the New York Mets, Bailey sang the national anthem at Shea Stadium prior to game 5 of the 1969 World Series, and appears in the Series highlight film showing her support for the team.
She also sang the national anthem prior to Game 1 of the 1981 World Series between the New York Yankees and Los Angeles Dodgers at Yankee Stadium.

Bailey hosted her own variety series on ABC, The Pearl Bailey Show (January – May 1971) which featured many notable guests, including Lucille Ball, Bing Crosby and Louis Armstrong (one of his last appearances before his death).

Following her 1971 television series, she  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!.
In October 1975, she was invited by Betty Ford to sing for the Egyptian President Anwar Sadat in a White House state dinner, as part of Middle-Eastern peace initiative.

She earned a degree in theology from Georgetown University in Washington, D.C., in 1985 at age 67.
Here she was a student of Wilfrid Desan.

Later in her career, Bailey was a fixture as a spokesperson in a series of Duncan Hines commercials, singing "Bill Bailey (Won't You Come Home)".
She also appeared in commercials for Jell-O, and Westinghouse.

She also did some free-spirited commercials for Paramount Chicken.

In her later years Bailey wrote several books: The Raw Pearl (1968), Talking to Myself (1971), Pearl's Kitchen (1973), and Hurry Up America and Spit (1976).
In 1975 she was appointed special ambassador to the United Nations by President Gerald Ford.
Her last book, Between You and Me (1989), details her experiences with higher education.
On January 19, 1985, she appeared on the nationally televised broadcast of the 50th Presidential Inaugural Gala, the night before the second inauguration of Ronald Reagan.
In 1988 Bailey received the Presidential Medal of Freedom from President Reagan.
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. For her performance, she won a Donaldson Award as the best Broadway newcomer. 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 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 Victor 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.
A passionate fan of the New York Mets, Bailey sang the national anthem at Shea Stadium prior to game 5 of the 1969 World Series, and appears in the Series highlight film showing her support for the team. She also sang the national anthem prior to Game 1 of the 1981 World Series between the New York Yankees and Los Angeles Dodgers at Yankee Stadium.
Bailey hosted her own variety series on ABC, The Pearl Bailey Show (January – May 1971) which featured many notable guests, including Lucille Ball, Bing Crosby and Louis Armstrong (one of his last appearances before his death).
Following her 1971 television series, she  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!. In October 1975, she was invited by Betty Ford to sing for the Egyptian President Anwar Sadat in a White House state dinner, as part of Middle-Eastern peace initiative.
She earned a degree in theology from Georgetown University in Washington, D.C., in 1985 at age 67. Here she was a student of Wilfrid Desan.
Later in her career, Bailey was a fixture as a spokesperson in a series of Duncan Hines commercials, singing "Bill Bailey (Won't You Come Home)". She also appeared in commercials for Jell-O, and Westinghouse.
She also did some free-spirited commercials for Paramount Chicken.
In her later years Bailey wrote several books: The Raw Pearl (1968), Talking to Myself (1971), Pearl's Kitchen (1973), and Hurry Up America and Spit (1976). In 1975 she was appointed special ambassador to the United Nations by President Gerald Ford. Her last book, Between You and Me (1989), details her experiences with higher education. On January 19, 1985, she appeared on the nationally televised broadcast of the 50th Presidential Inaugural Gala, the night before the second inauguration of Ronald Reagan. In 1988 Bailey received the Presidential Medal of Freedom from President Reagan.
Pearl Bailey