Jim Bailey's illustrious career began in the early 1950s, when he started acting and singing on the Nationally Syndicated show The Children's Hour. He then went on to study Opera at the Philadelphia Conservatory of Music.
By the late 1950s, Bailey had moved to New York City and transitioned to Theater, both On and Off Broadway, regional, and summer stock productions, including The Diary of Anne Frank and The Boyfriend.
His breakthrough role came in 1962 with the Broadway musical Fly Blackbird, co-starring Robert Guillaume, which won two Obie Awards. He continued to perform in various plays and musicals, such as Wildcat, The Bells are Ringing, and Calamity Jane with Ginger Rogers.
In 1964, Bailey discovered his knack for mimicking and added Judy Garland, Barbra Streisand, and Phyllis Diller to his repertoire. This talent caught the attention of Judy Garland and Phyllis Diller themselves, who became mentors and friends.
Bailey's career spanned television, movies, and theater, with headlining performances at major concert venues worldwide, including Carnegie Hall, the London Palladium, the Dorothy Chandler Pavilion, and the Hollywood Bowl.
He has also performed in Europe, Australia, Canada, South America, and South Africa, and has appeared at numerous award shows, including the People's Choice Awards.
