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Jim Bailey Has Passed Away

| Jun 8, 2015
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bailey060815Renowned gender illusionist Jim Bailey passed away on May 30 due to complications from pneumonia. He was 77.

Bailey was from Philadelphia, Pennsylvania. He was born on January 10, 1938, in Philadelphia, Pennsylvania to Sara and Claude Bailey. He had one brother, Claude. As a teenager he studied opera at the Philadelphia Conservatory of Music. In the 1960s he was active in the local theater scene and performed in local clubs doing a straight singing act. After meeting and becoming friends with Phyllis Diller, Bailey moved to Los Angeles where began to mimic Diller at parties. She became his first female character, soon followed by another singer who would become a good friend, Judy Garland. Doing Garland let Bailey take advantage of his impressive vocal skills. He went on to add Barbra Streisand and Peggy Lee, among others, to his act, and he appeared on several television programs including  The Carol Burnett Show, The Ed Sullivan Show, The Tonight Show, Here’s Lucy, Night Court and Ally McBeal.

When he was interviewed in 1997 in the Advocate Bailey was asked how he’d like to be remembered. He replied, “OK — I don’t want to be remembered as one of those guys who wore a dress and pretended to be female. I want to be remembered for the uniqueness of the art form I created. Not just lip-synching, not just wearing dresses, but singing, acting, the makeup, the details — the full monty.”

If anyone was the “full monty” it was Jim Bailey. Here is a video of him performing Judy, Barbra, Phyllis, Peggy and Marilyn.


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Category: Impersonation, Obituary, Transgender History


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  1. cuban legend cuban legend says:


    I was very lucky to have seen the very talented Jim Bailey perform a few times, first in San Francisco and then once in Phoenix ….my late dear mom Tila, my partner Paul and I went to see his marvelous transformations as: Judy, Peggy and Barbra and he sang always with an orchestra and sometimes with less musicians if he was booked at a smaller venue, but always he sang LIVE and did it very well too.

    I even interviewed Jim many years ago in SF for the USA Judy Garland Fan Club and then many years later for my own website.

    Thank God, there is You Tube now where anyone can see many of his videos.

    God bless him!,
    David de Alba

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