Pearly Mae Bailey was born to a minister father, Joseph, and a mother named Ella Mae. Initially, her parents expected her to be a boy, so when a girl was born, they affectionately nicknamed her "Dickie". She had an entertainer brother, Bill Bailey, who would go on to make a name for himself in the industry.
Pearly Mae spent her early years in Washington D.C., where she received her primary education. She began her career in show business at a young age, frequently appearing on stage at the Old Howard theater in downtown Washington.
As she grew older, she toured the Pennsylvania mining towns as a dancer and later transitioned to singing in Vaudeville. Her big break came when she starred alongside Nat King Cole in the film adaptation of W.C. Handy's life story, "St. Louis Blues".
However, her greatest achievement in the world of theater was her iconic role in the Broadway musical "Hello Dolly".
