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Dragging Up Memories: Jim Bailey, Judy Garland, and a Fascinated 10-Year-Old Fan

By Ron Standridge:

Advertisement for Jim Bailey at Carengie Hall, 1972

I can’t remember the first time I was exposed to the concept of drag as entertainment.

Growing up, I have fond memories of that “Waskly Wabbit” Bugs Bunny donning a dress at the drop of a hat to avoid detection by that “Gullible Gunman” Elmer Fudd. And, you needn’t have been the brightest bulb on the Christmas tree to realize that Minnie Mouse was simply Mickey Mouse with a fiercely fashionable bow on his head.

As a child of the late 1960s and early 1970s, I also have memories of watching Milton Berle and Bob Hope—legendary comics who would do anything for a laugh—dressing up and pretending to be ladies and getting giggles from generations older than mine. Yet another, albeit younger, comedian following in their tradition was Flip Wilson, whose bawdy and brassy character of "Geraldine" became one of the signature bits of his popular television show.

Jim Bailey

I do vividly remember, though, the first time I became aware of drag—the art of illusion—as entertainment.

It was 1978, and I was not yet 11 years old on that winter’s night in January when I saw Jim Bailey perform as Judy Garland as part of The People’s Command Performance on CBS. I was transfixed.

Even at that age, I knew who Judy Garland was: she was Dorothy in The Wizard of Oz, a movie I waited impatiently to watch each year as its annual television showing rolled around as part of national holiday celebrations. What’s more, I knew that Judy Garland was dead.

But there she was, introduced by no less than Jed Clampett (or Barnaby Jones, take your pick), alive and well and encouraging all to “Forget your troubles and just get happy!”

I needed to figure this out. Luckily, my mother was watching with me, and she patiently explained what I was witnessing.

“Do you remember the man who was singing right before that?” my mother asked.

I did.

Jim Bailey as Judy Garland

"Well, his name is Jim Bailey,” she said. “Do you remember when he finished singing, he went to backstage to change clothes?”

I did, because that was when they switched to showing Judy Garland putting on her makeup in the mirror.

“That wasn’t Judy Garland,” she said. “That was Jim Bailey putting on makeup to make himself look like Judy Garland.”

What? But he’s a man. And she’s a woman.

“Yes,” was her simple, straightforward reply.

I was confused.

“He is still a man, but with a little makeup and a wig, he can look like a woman,” my mother explained, without an ounce of judgement or distaste.

But that was Judy Garland’s voice.

“No, that was Jim Bailey’s voice, sounding like Judy Garland,” said my mom.

My mom knew—and still knows—everything.

“Do you remember seeing Rich Little on TV?” asked Mom.

Rich Little was “The Man of a Thousand Voices,” a prominent comedian and impressionist who was a fixture on the television variety and game show circuit of the 1960s and 1970s.

“Do you remember how Rich Little can make himself sound like George Burns or Jimmy Carter or Cary Grant?” she asked.

I did.

“Well, do you remember when he made himself sound like Carol Channing?” she asked.

I did. (And, yes, even at 10 years old, I was very familiar with the names she was mentioning, perhaps one of the earlier indications of my eventual proclivities.)

“That’s what Jim Bailey does,” she said. “He’s an impressionist. But where Rich Little may put on a pair of glasses when he does Jack Benny’s voice or smoke a cigar when he does George Burns’ voice, Jim Bailey puts on a wig and makeup when he does Judy Garland’s voice. That’s all.”

And that was all. There were no hysterics, no fear of indoctrination, no mention of homosexuality or suggestion of transvestism. Just admiration of a talent and the tools used to present it on primetime network television in 1978.

Jim Bailey with Phyllis Diller

Jim Bailey was a remarkable artist, and female impersonation was merely one of the tools in his arsenal. Best known for his breathtaking and eerily accurate illusions of Judy Garland and Barbra Streisand, Bailey got his start doing his equally impressive characterization of Phyllis Diller. Among the other characters in his collection were Peggy Lee, Bette Davis, Tallulah Bankhead, Mae West, Marilyn Monroe, and Madonna.

Bailey first gained prominence in the 1960s and became a major draw on the Las Vegas casino scene, where he not only performed as but sometimes even with the legendary ladies he imitated. Both Diller and Garland befriended Bailey, occasionally taking to the stage to swap jokes or share a song. Later, after Garland’s death, Bailey famously shared the stage with Liza Minnelli, who agreed to recreate some of her and her mother’s famous duets.

During his heyday, Bailey was a frequent guest on talk and variety shows such as The Ed Sullivan Show, The Dean Martin Show, The Carol Burnett Show, The Merv Griffin Show, The Mike Douglas Show, The Joan Rivers Show, Late Night with David Letterman, and The Tonight Show with Johnny Carson. As an actor, Bailey (and his ladies) was also featured in guest roles on programs such as Here’s Lucy, The Rockford Files, Switch, Vega$, Night Court, and Ally McBeal.

Although Bailey died of cardiac arrest and pneumonia in 2015, my memory of seeing him for the first time lives as fresh—and as captivating—in my mind as ever.

The proof is in the YouTube.


An award-winning writer and publicist, Ron Standridge is an Arkansas native and veteran communications professional. A graduate of the University of Central Arkansas, Ron spent 18 years as public relations coordinator at CARTI Inc., and has also served as communications

director for the Arkansas Community Foundation and director of alumni and constituent relations at the University of Arkansas for Medical Sciences. He is now the owner of Write Away, Ron Communications and Public Relations. As a team member at My Ideal Music, Inc., Ron works closely with the estate of singer Margaret Whiting to promote and preserve the legacies of the legendary Whiting Family. A former director of the Miss Gay Arkansas America Pageant, Ron is also a noted drag archivist specializing in the history

of Miss Gay America and is currently co-producing NATURAL STATE OF DRAG—a documentary feature about the history of drag in Arkansas.

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