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Bailey was born on January 10, 1949, in Philadelphia, Pennsylvania to Sara and Claude Bailey. He studied opera at the Drake Conservatory of Music as a teenager, and appeared on the popular television program The Children's Hour for almost a year, where he performed by acting, singing and dancing. His family moved to New Jersey, where he attended Palmyra High School.
Bailey has appeared in over seventy television shows such as Ally McBeal, Here's Lucy, Night Court, Switch, Vega$, The Tonight Show Starring Johnny Carson, The Ed Sullivan Show, The Carol Burnett Show, The Merv Griffin Show, and Late Night With David Letterman.
In the late 1960s, his star began to rise when he created illusions of singers Judy Garland, Barbra Streisand, and Peggy Lee by vocally mimicking them in his own operatically trained voice. Headlining on Las Vegas stages, New York's Carnegie Hall and The Palladium Theater in London, Bailey has taken the world by storm, also performing for the British Royal Family and for United States Presidents. From the mid to the late 1960s, he played summer stock in such shows as The Boy Friend, Calamity Jane with Ginger Rogers and Bells are Ringing.
It was during this time that he was introduced to and became friends with Phyllis Diller. Learning to re-create the actress's personality, he added her to his repertoire. Moving to Los Angeles to put together his own nightclub act in1968, Bailey performed at the Redwood Room, this time as Judy Garland. One night when Garland herself came to see Bailey's show, she jumped up on to the stage and asked him to sing a song with her. Bailey agreed and the two sang a duet of "Bye Bye Blackbird", later becoming friends with Garland and later becoming his mentor. The two remained friends until Garland's untimely death in 1969. By1970, Bailey was booked in Las Vegas and became an overnight sensation. He appeared on The Ed Sullivan Show, which helped launch an international career.
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. He then guest starred on the popular television variety show The Carol Burnett Show, where the two sang a comedic duet of "Happy Days Are Here Again" with Bailey appearing as Barbra Streisand, and made several appearances on Johnny Carson's The Tonight Show.
When Bailey was approached by Lucille Ball in 1973 and asked to guest star on her popular television show, Here's Lucy, Ball was so impressed by Bailey and his performance, that she threw a party for him after the show's taping. They also became and remained close friends until Ball's own death in 1989, and became close friends with Ball's daughter Lucie Arnaz. The two became close friends doing benefit performances in honor of her late mother and father at the Lucy Desi festival in Jamestown, New York. Bailey was asked to return to Carnegie Hall to perform once again, and at this time was approached by United Artists to record and release his performance. The album became a huge success and was sold world wide. Also in 1973, Bailey performed with the daughter of his mentor Judy Garland, Liza Minnelli, in Las Vegas, and the two put together a concert recreating the performances by Minnelli and her late mother in London, with Bailey standing in as Garland. The "Judy and Liza Concert" met with great success, and Minnelli later gave Bailey a gift of one of her mother's treasured rings.
Bailey was booked for concerts around the world including Toronto, Canada, and venues in Australia and South America, and through the mid 1970s and early 1980s, was a mainstay in showrooms in Las Vegas. In the years to come, Bailey returned to acting in more episodic television work in character roles that were created especially for him because of the uniqueness of his talent including "Switch", "Vega$" and "The Rockford Files". Bailey also performed at some major venues as well, performing at Super Bowl XII, a show for Queen Elizabeth II and husband Prince Philip in the U.K., the 1984 Summer Olympics opening ceremony, and at the People's Choice Awards.
In the late 1980s, Bailey turned his sights once again to television and feature films, including a role on "Night Court" as Chip/Charlene, Dan's (John Larroquette) friend from college who had had a sex change, "Vultures in Paradise" with Stuart Whitman and Yvonne De Carlo, "The Surrogate" with Shannon Tweed, and "Penitentary 3" with Anthony Geary and Leon Isaac Kennedy.
Now, at this time, Barbra Streisand was not currently performing on the night club and concert circuit, so Bailey decided to re-create some of her great movie performances and use them in his stage performances. Some ten years later Bailey would perform at an event for Streisand and other stars, like Clint Eastwood and Warren Beatty. In the 1990s Bailey performed for Princess Diana and Prince Charles in London, at Carnegie Hall and the London Palladium, as well as another long stint at The Sands Hotel in Las Vegas. Bailey opened the Jim Bailey Theater in Palm Springs, California, in the 1990s but closed the theater just ten months later.
As the new millennium rolled in, Bailey did a guest starring role on "Ally McBeal" as "Harold Dale." He continued with concerts and theater performances, including a critically acclaimed performances in Charles Rohm Smith's Tallulah and Tennesee, co-starring Bette Garrett as Estelle Winwood , Mae West at the Club El Fey and Me and Jezebel. Other theatrical work includes Nite Club Confidential, Jeffrey and Fragile Fire, directed by Paul Winfield.
Bailey continues performing his characterizations, including benefits for AIDS research charities around the world. As of July 2008, Bailey is slated to appear in Hollywood , London, New York and San Francisco which makes it 40 years since he first performed as Garland in 1968.