Jim Bailey, Impersonator of Hollywood’s Female Icons, Dies at 77

Courtesy Everett Collection
Bailey circa 1970.

He did convincing re-creations of Judy Garland, Barbra Streisand, Peggy Lee, Phyllis Diller and more.

Jim Bailey, a self-proclaimed “character actor” who did spot-on re-creations of such iconic female entertainers as Judy Garland, Barbra Streisand and Peggy Lee, has died. He was 77.

Bailey died on Saturday of cardiac arrest from pneumonia complications at Pacifica Hospital of the Valley in Sun Valley, Calif., said his manager of 27 years, Stephen Campbell.
 
"Heaven is getting a fabulous show tonight with standing room only! Rest in Peace Our Sweet Prince," reads a statement on Bailey's website.
 
A native of West Philadelphia, Bailey performed in nightclubs around the world and in such celebrated venues as the Palladium in London, Carnegie Hall in New York and the Dorothy Chandler Pavilion in Los Angeles. He was a regular in Las Vegas for years, did a Streisand tribute at halftime of the 1978 Super Bowl and put out three albums.
 
At age 11, Bailey entered and won his school’s talent contest, singing “You Made Me Love You,” one of the first songs Garland sang when she was a child star. He later attended the Philadelphia Conservatory of Music and studied opera, then headed to New York City.
 
“I did jazz clubs in Greenwich Village, went on the Playboy circuit, that sort of thing. I wasn’t doing badly, but I needed that gimmick, something to make me different, unique,” he told the Philadelphia Inquirer in a 1995 interview.
 
His first impression was of comedienne Phyllis Diller, to whom he was introduced in the late 1960s, and he hit pay dirt after he heard Garland on the radio and decided to impersonate her. When Garland came to see Bailey's show, she jumped on the stage and asked him to sing a song with her: "Bye, Bye Blackbird."
 
She became his mentor, and Bailey landed a gig on CBS’ The Ed Sullivan Show, dressed and made up as Garland and singing like her. After that performance, the Las Vegas hotels came calling.
 
The showman also guest starred on The Carol Burnett Show, where he and Burnett sang “Happy Days Are Here Again” with Bailey appearing as Streisand. And he played Diller (complete with her crooked smile and signature cigarette holder) opposite Lucille Ball on a memorable 1972 installment of Here’s Lucy.
 
 
In 1973, Bailey teamed with Garland's daughter Liza Minnelli at The Flamingo in Las Vegas to re-create performances by her and her late mother in London. He and Minnelli became great friends.
 
“He becomes these singers to a degree that defies disbelief, and he's an uncanny and as classy an act as you could hope to find,” the London Times once said of him. Wrote the Boston Globe, “If he were to appear at Madison Square Garden instead of Barbra, who could possibly tell the difference.” 
 
Three hours of preparation were required for each of his full-length concerts, so he could only do one impersonation for each show. 
 
“It’s my job to make people believe they’re seeing and hearing Judy Garland,” he said in the Inquirer interview. “Convince them that I’m Judy Garland, Barbra Streisand, take the audience on a magical trip.”
 
On a 1985 episode of the NBC sitcom Night Court, Bailey played a college friend (Chip/Charlene) of John Larroquette’s character who had undergone a sex change. He also appeared on What’s My Line?, The Rockford Files, Vega$The Tonight Show Starring Johnny CarsonLate Night With David Letterman and Ally McBeal.
 
In addition to Campbell, survivors include his brother, Claude.
 
Twitter: @mikebarnes4
 
1 p.m. June 2: Updated with details of death.
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