Jim Bailey didn't start cross-dressing because of any suppressed fantasy. As the singer and actor explains, he had to do it. His penchant for perfection demanded it.
"I was at a party," he recalls. "Phyllis [Diller] is a friend of mine, so I knew her mannerisms, and at a party one night I started tossing out some of her one-liners, doing her voice. Someone said, 'You should put her into the show.' I was working as a singer and worked on this for six months and decided to unveil it at a club in L.A. I knew I didn't want to just do it in a tux and fright wig. I wanted to present the entire picture, and it was successful."
Word of his dead-on impersonation of the caustic Diller spread, and soon a club owner asked Bailey to fill in for Diller when she had to cancel a performance. "People thought I was really her," says Bailey. "One thing led to another, and then Judy Garland came, and then Barbra [Streisand] and Peggy Lee, and all of these women."
Bailey has appeared in guest spots on nearly 80 TV shows and had roles in a few movies (Blind Rage, Zelig). As a singer he's performed at New York's Carnegie Hall and in the top Las Vegas show rooms. But the combination of his singing and acting skills with his uncanny ability to impersonate female voices and apply makeup have made him a female illusionist without peer.
In fact, when he did Barbra Streisand for Barbra herself, it was she who led the standing ovation. And since adding the impersonations to his own act, Bailey's reputation has brought in offers for theatrical productions featuring famous women -- he's portrayed Mae West and Tallulah Bankhead, among others.
He won't jump at any female role, though. He has to feel as if he can really pull off the character believably. "I guess the voice really has to be there. That's the most important thing," he says. "The makeup you can work on."
When the producers of Me & Jezebel sent him the script for the show about Bette Davis, Bailey liked it but pondered one more thing before accepting: "I had to know whether I would be able to deliver this particular character."
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Bailey decided he could, and he will portray the late actress beginning this week at the Wilton Playhouse. The comedy is based on the true story of Davis' 1985 run-in with a Connecticut woman named Elizabeth Fuller. A friend of Fuller's called at the last minute asking her if it would be OK to bring someone along to a dinner party with whom the dinner guest had been childhood friends. That someone was Davis. The friend with whom Davis was staying had to leave town for an emergency a couple days later, during a hotel strike in New York, so Davis called Fuller to ask if she could spend a few days with her.
"She ended up staying for a month, taking over the house, and taking over their lives, but it's very funny," Bailey said last week. "Right now we're rehearsing scenes, learning the words, blocking the show. But at the same time I'm thinking about Betty in my mind: What will she do physically in this scene?"
As had been the case with Diller, Bailey had some personal experience to go on. "I met Bette before she died," he says. "I had dinner with her with some friends, so I was able to observe the way she sat and smoked and drank and held the glass. I never knew I'd be doing her, but those are the kind of things I just filed away."
Using those memories, along with research, "I'm going to present Miss Bette Davis in rare form," he says, "and I'm hoping to get as close to Bette as I can."