With so much focus on the amazing Caitlyn Jenner story, there’s been a lot of discussion involving gender identity and sexual preference and masculine and feminine presentation. Amid all this, Jim Bailey has died, at age 77. For those of you too young to remember, Jim was a phenomenon. He was most often called a female impersonator, or a gender illusionist. He would perform uncannily precise and loving, full-drag versions of Streisand, Garland, Peggy Lee and Phyllis Diller, among others. He didn’t lip-synch, as he was an astounding vocalist. During his heyday, especially in the 1970s, he appeared on every major TV variety and talk show, and he was a Vegas headliner. He became friends with his idols, including Diller and Liza Minelli, and he’d perform with them. He was rarely asked about his sexuality, although sometimes ignorant talk show hosts would find it necessary to assure the audience that Jim was “all man.” Through all of this, Jim maintained great dignity and commanded respect for his gifts. He was part of a grand theatrical tradition, of men playing female roles, which stretches from the ancient Greeks through Shakespeare and the English music halls, right up to RuPaul’s Drag Race.
Here’s how I knew Jim: he was especially beloved in San Francisco, where’d he’d sell out the swankiest night clubs. When my play Jeffrey was first performed there, Jim was cast to play the central role of Sterling, an acerbic and great-hearted interior designer. The play’s director, Chris Ashley, and I, first arranged to meet with Jim in a lounge at JFK, because he was touring. As we approached, Chris asked me how we’d recognize Jim. Then we heard his voice, very assertively asking, “Where’s Barbra’s head? WHERE’S BARBRA’S HEAD?” When we found Jim, he was standing amid a stack of deluxe luggage, and searching for the styrofoam stand which held his Barbra Streisand wig.
Jim couldn’t have been more gracious or more excited about doing the play. He appeared on the first day of rehearsal in perfectly tailored black pants with a black cashmere turtleneck sweater and a second black cashmere sweater tossed over his shoulders. He’d already had his script bound in black calfskin, with the title of the play embossed in gold. As rehearsals progressed, there was a problem: while Jim was eager to act, when he wasn’t costumed as one of his legendary divas, he was lost. As Carol Channing or Judy, he was brilliant, but acting in a more ordinary range just wasn’t his sort of thing. He eventually left the production before we opened, which was sad but necessary. The sublime Peter Bartlett, who’d already played Sterling in New York, generously flew in and triumphed.
Jim was a fascinating man, and he’d battled many obstacles and slurs. He always wore a decent amount of make-up, even on the street, and his hair was always immaculately colored and immobile. Out of drag, he seemed even more like a regal, delightful leading lady from the Golden Age. He wasn’t a relic; he was one-of-a-kind. I don’t think Jim was transgender, but I bet he would’ve been a huge fan of Caitlyn Jenner’s, because not only is Caitlyn beautiful and compassionate – she’s a star.
