Born in West Philadelphia, Bailey demonstrated his affinity for his specialty at age 11 when he won a school talent contest singing Garland's "You Made Me Love You." He studied opera at the Philadelphia Conservatory of Music, and broke in his act playing small clubs in New York's Greenwich Village. He graduated to larger clubs and Las Vegas hotels, the London Palladium, Carnegie Hall, "The Ed Sullivan Show," "The Carol Burnett Show," "The Tonight Show" and other TV appearances with a drag act that included impersonations of Phyllis Diller, Barbra Streisand and Peggy Lee. He memorably duetted with Liza Minnelli, playing her mother. He was known for meticulous costuming and preparation, which led to his doing only a single impersonation per show.
He dreamed of playing Broadway, and in 2001 landed a commitment from the Shubert Organization to open his biographical revue, Judy Garland Live! at one of its theatres on Oct. 16 of that year--50 years to the day after the real Garland opened a legendary stand at the Palace Theatre. The production was far along, with Joey McKneely signed to direct and choreograph and Ann Hould-Ward (Beauty and the Beast) providing the costumes. But after repeated delays the production failed to complete its capitalization and was finally "indefinitely" postponed.
A statement on Bailey's website Tuesday read, "Heaven is getting a fabulous show tonight with standing room only! Rest in Peace Our Sweet Prince."
Watch a clip of Bailey's Garland, below: