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James William Bailey was born in Philadelphia to Sara and Claude Bailey on January 10th 1949. As a teenager, he studied opera at the Drake Conservatory of Music and was on the popular television show, The Children's Hour.It was at this time he discovered he had a gift for vocally mimicking people. From the mid to late 60s he played summer stock in such shows as 'The Boyfriend' and 'Bells are Ringing'. During this time, he became friendly with Phyllis Diller and started mimicking her. He then moved to Los Angeles in 1967 where he put together his own niteclub act at the Redwood Room. This is where Judy Garland saw him perform. She got up onto the stage with him and they sang 'Bye Bye Blackbird' together. She became fascinated with him and was a mentor-getting him a pay raise. Many nights he spent at her home listening to stories.One night she performed her whole Carnegie Hall Album - just for Jim.The following year, Judy passed away and Jim was booked into Las Vegas and became an overnight sensation. He was also booked onto The Ed Sullivan show.This was groundbreaking because no man in a dress was doing what Jim Bailey was doing; singing as a woman in a serious manner. His appearance was a phenomenon and he was asked back a couple of months later.He was also booked on the Carol Burnett Show and the Tonight Show. He went on to perform at New Yorks' Carnegie Hall, the London Palladium and the Dorothy Chandler Pavillion in Los Angeles. Variety stated at that time that he was 'the hottest thing in show business'.'Here's Lucy' followed in 1973 where he met Lucie Arnaz; they remain friends to this day. He then returned to Carnegie Hall for a couple of nights where the shows were recorded by United Artists for wide release. In Las Vegas in 1973, he and Liza Minnelli put together a concert where they recreated her concerts with her late mother-Judy Garland. She stated "Angels gave this man a special talent". At another time, when she was onstage with Jim, she said "The only comparison I can make with somebody that does something that fantastically brilliant and so unusual is Marcel Marceau".
During the 70's, Jim was a mainstay in the main showrooms in Las Vegas and was booked around the world.
In the late 70's Jim turned to more TV episodic work and guest starred on such shows as 'Switch', 'Rockford Files' 'Streets of San Francisco' and 'Vegas', creating original characters which were written especially for him because of the uniqueness of his talent. Apart from numerous Tonight Show appearances, he also did all the variety shows including 'The Dean Martin Show', 'The Merv Griffin Show',The Bob Hope Specials, 'Chuck Barris Gong Show', 'The Mike Douglas Show' and 'The David Frost Show'. Jim was considered TV's top impressionist.
In the late 70's to mid 80's, Jim was asked to headline the Superbowl Halftime in 1978, do a command performance for Queen Elizabeth and Prince Phillip and perform at the 1984 Olympics Opening Ceremony.His also performed on the People's Choice Awards and won the Las Vegas Entertainer of the Year 4 times. At this time, Barbra Streisand was not doing the niteclub circuit so Jim recreated some of her great movie performances for the stage.He also did a month-long season at The London Palladium.
In the late 80's, Jim turned his sights onto television and feature films, which included a ground breaking performance as a sex change on 'Night Court' and feature films that were not major successes including 'Vultures in Paradise', playing eight roles,'The Surrogate' and 'Penitentiary 3'. In the 1990's, he did a command performance for Princess Diana and Prince Charles and played Carnegie Hall and the London Palladium and Las Vegas and Atlantic City in the Main Showrooms.
He toured extensively in the 90's and one summer portrayed Barbra for Barbra Streisand and for a group of her famous friends, including Clint Eastwood and Neil Diamond. He once said when Barbra came into his dressing room, she was as sweet as he had always hoped.At this time, he felt he wanted to settle down, so he opened the Jim Bailey Theatre in Palm Springs. After 10 months, he closed it. At the start of the new century, Jim played Harold Dale on 'Ally McBeal' and lots of theatre. He did Charles Rohm Smith's 'Tallulah and Tenesee' co-starring Bette Garrett as Estelle Winwood. The Los Angeles Times said "Bailey as Bankhead conveys the necessary verve and venom. His performance is superb". The Daily News said "Bailey fearlessly rides the fine line between caricature and character much like Robert Morse in "Tru". In "Mae West at the Club El Fey", Gannett News Service said "Bailey's performance is a tour de force of acting." In "Me and Jezebel", the Miami Herald said "Bailey never drops character for a second" and "I didn't know Bailey was such a fine actor". Other theatrical work includes "Niteclub Confidential", "Jeffrey" and "Fragile Fire", directed by Paul Winfield.