As a teenager he studied opera at the Philadelphia Conservatory of Music, and was on the television program The Children's Hour for almost a year, where he performed by acting, singing and dancing.

Bailey's fame began in the late 1960s when he created the "illusions" of singers Judy Garland, Barbra Streisand, and Peggy Lee by vocally imitating them in his own operatically trained voice.

Bailey appeared on concert stages throughout the world, including headlining in Las Vegas at hotels such as The Thunderbird, Caesars Palace, The Desert Inn, The Sands, Harrah's, The Dunes and performing at New York City's Carnegie Hall a total of nine times and The Palladium Theater in London a total of 17 times.

[5]From 1966 through to 1968, Bailey played summer stock in such shows as The Boy Friend, Calamity Jane with Ginger Rogers, Bells are Ringing and Wildcat with Gale Storm.

In 1968, Bailey moved to Los Angeles and put together a nightclub act with Michael Greer, performing at the Redwood Room, this time adding Judy Garland to his repertoire.

Bailey's success continued as he appeared for performances at New York's Carnegie Hall, the London Palladium, and the Dorothy Chandler Pavilion in Los Angeles.

Bailey was approached by Lucille Ball in 1972 after she saw him at the Dorothy Chandler Pavilion and asked him to guest star on her popular television show Here's Lucy.

The two remained close friends, doing benefit performances in honor of her late mother and father at the Lucy Desi festival in Jamestown, New York.

He again performed at Carnegie Hall and the London Palladium, as well as another long stint at The Sands in Las Vegas and Harrah's in all of their main showrooms.

In July 2008, Bailey was slated to appear in Hollywood, London, New York and San Francisco, marking 40 years since he first performed as Garland in 1968.

Susie Boyt from The Times wrote "There is nothing camp or stagey about his act—it can scarcely even be described as an act, for Bailey inhabits Garland's persona to such an extent that, well, there she is.