I write history—another way of saying half my life I live in the past.

It’s not a bad place to live, either. Anything good that’s ever happened is there.

That life I live at a desk halfway between two posters, both gifts from my dad. Behind me is a wall-size reproduction of Otto Dix’s Sailor and Girl, the cover art of a favorite novel, the mad and carnal Sabbath’s Theater, won at auction from the estate of the author, Philip Roth. On the opposite wall hangs a considerably smaller poster of Jim Bailey, the greatest Judy Garland impersonator who ever lived. I’m in the middle.

My job, simply stated, to turn back the clocks, to raise the dead, is impossible.

Writer Sam Wasson talks Jim Bailey with Alta Live.

Facts alone don’t do it. Even when you’re fortunate enough to believe you “know” what happened, you can only “know” it in quotes.

There are facts, and then there is truth. And then there is writing the truth. You can’t even know your own past. I’m supposed to write someone else’s?

I love the epigraph from Roth’s The Facts: A Novelist’s Autobiography, in which Roth quotes one of his characters, Nathan Zuckerman, who serves as the author’s fictional alter ego: “And as he spoke, I was thinking, the kind of stories that people turn life into, the kind of lives that people turn stories into.”

My dad piled the whole family—me, mom, younger sister—into the car and drove us east down Sunset. He didn’t tell any of us where we were going. Leaving Brentwood, all we knew was he was grinning mischievously and we were heading to dinner. But the farther east he drove—a new driver myself, I didn’t know there was anything “after” Beverly Hills—the fewer restaurants I could identify, until finally we crossed La Brea on Hollywood Boulevard.

“Where are we?” I asked.


Of course, it didn’t look like Hollywood, at least not how I had imagined it. In the 1990s, the Walk of Fame was shadowed and lurid and forbidden, a noir sideshow you wouldn’t want to visit with your parents. Which is to say, it was beginning to look like my father—a Dada Clark Griswold—was taking us, his family, to pick up a hooker.

This article appears in the Winter 2022 issue of Alta Journal.

We pleaded for him to tell us where we were going, but he kept his mouth shut from the parked car to the front of the Hollywood Roosevelt Hotel. “This is where they had the first Oscars,” he said as we entered the lobby, before, following his lead, we turned a hard left (or was it right?) into a dark room with about a dozen lamplit bistro tables and one small stage. This was (according to the menu at our table) the Cinegrill. It was a nightclub.

“What’s a nightclub?” my sister asked. She was about 15; I was around 17. It was a question anyone of our generation could have asked without embarrassment.

“We’re going to have dinner and see a show,” my father said by way of explanation.

“What show?” my mother asked.

My father only smiled. My sister, being so young, out so late in such a strange place, and with neither her uninformed mother nor her enigmatic father to reassure her, started to cry. At this, my mother shot a disapproving glance at my father, but the table lights went down before the argument could erupt, and into the follow spot that waited on the curtain stepped Judy Garland.

Garland nervously welcomed everyone to the Cinegrill with a self-deprecating remark about this not being the Palace (or something like that) and started singing one of those songs from the Judy at Carnegie Hall album my father played all around the house, sometimes nightly, as he cooked dinner in the kitchen. And when I say all around the house, that’s exactly what I mean, because there were speakers in almost every room. This was how we knew dinner was ready: I would be doing homework in my room when, without warning, “The Man That Got Away” or “Zing! Went the Strings of My Heart” would interrupt my long division, and minutes later we would be gathered in the kitchen to see my father carrying the salad bowl to the table, singing aloud.

My dad was a jazz-vocals fan, as was I, and in our house no line was drawn between Frank Sinatra, Ella Fitzgerald, Louis Armstrong, the canonical singers of the Great American Songbook, and Judy Garland, who, for reasons I still can’t explain, was never to be heard on our beloved jazz station, KLON. If Garland was played more often than Sinatra in our house, it was partly because my dad, a straight Jewish doctor who once dressed as Garland for Halloween, couldn’t resist belting alongside her, or hammily doing her signature moves, which, unlike clubby jazz singers’, are so fun to imitate. Mick Jagger and David Byrne got airtime at my house for the same reason, but Garland, being the greatest entertainer in the history of entertainment—a rare superlative that isn’t controversial—was our all-the-time sound.

So it was that, depending on where Garland was in her Carnegie Hall set, dinner tasted like suicide or ecstasy, and I came to see, over many nights, what makes a great artist great: the willingness to live and the willingness to die so that we, in the audience, don’t have to. There is something Christlike in that, but more so for Garland, who “died” and was “reborn” so many times in her career that one of her biographers, Gerald Clarke, could convincingly title a chapter “Resurrection.” But the themes of life and death are more than just organizing principles in her story; they are—as my ears understood before I did—the subject of her work. At its best, each Garland number is a “To Be or Not to Be,” the life force against the death wish, loud and clear. Which is why she will never die again.

So it was only half surprising to see her alive and singing at the Cinegrill, 30-some years after her death, resurrected by an illusionist so gifted that my sister had to be assured by my mother that the person onstage wasn’t the Judy Garland but only someone pretending to be Judy Garland. And that person “pretending” was simply too good, too convincing as Garland, for my sister to believe what my mother was telling her. To my sister, this meant either my mother was lying or my mother was crazy, both intolerable to her young imagination. Overcome with frustration and no small amount of terror, my sister fled the Cinegrill shortly after the show began, certain she had seen, if not a ghost, something dead that was pretending to be alive.

I, on the other hand, was just amazed, and not because this performer, Jim Bailey, a man, had transformed into a woman. I’d seen Tootsie; I’d seen Linda Hunt in The Year of Living Dangerously. That gifted actors have the ability to inhabit genders other than their own was not news to me. This was something different. Bailey’s performance was beyond impersonation, beyond homage, but I couldn’t—and still can’t—find a classification for it. Deeper than Rich Little, a well-known impressionist of Bailey’s era, and far more scrupulous than anything you’d see on Saturday Night Live, it was not parody. Nor was it comparable to Hal Holbrook’s famous evening as Mark Twain or, later, Meryl Streep channeling Margaret Thatcher, or anyone else, really, who has played a figure from real life. What was truly amazing—and I think singularly so, for I have never seen anyone do it since—was to encounter, in addition to something akin to Garland’s giant talent, the talent to re-create her talent. Seeing Holbrook as Twain, you did not experience the writer writing, his moment of creation; you got, instead, the actor’s affection for his subject and Twain’s words, the product of his creation. As Garland, Jim Bailey—to extend and mix the metaphor—was writing Huckleberry Finn right there, live.

I did not understand then why this was so important to me. I did not understand why, after the show, I felt I had to encounter this human individual, Jim Bailey. But somehow my father, who was similarly knocked out by what had just transpired, recognized my own stupefaction and, with his characteristic openness and charm, managed in short order to locate Bailey’s manager, Steve Campbell, present for the occasion, and win me an invitation to Bailey’s dressing room atop the Roosevelt Hotel.

I have only a few memories of the meeting. The first is of me waiting, alone, in the sitting area of Bailey’s penthouse dressing room as he took off his makeup and wondering what I was doing there. I had nothing to ask him and nothing I could think to say other than “You’re cool” or “Wow, you’re cool.” The next is an image: his shadow on the dressing room door as he, presumably, sat at the mirror, turning back into Bailey and making congenial small talk with me in a voice that sounded at first like Garland’s and then like Garland’s impression of a man, presumably him. Then, finally, the pressure of Bailey’s hand as I shook it. It was cold; this memory returned to me only days ago, when I was telling a friend about this piece and she told me about the time she met Garland backstage at a performance in Hartford, Connecticut, and shook her hand. It felt to my friend, she said, like a cold dead bird.

Twenty years later, moving into my new house, I found, in an old box, the poster I had forgotten Bailey had signed for me that night and was faced with the question of where to hang it. I had art; I had photographs of friends and family; I had movie posters. They would naturally go in the living room. That seemed far too intimate a place for Bailey, an act I loved, but whose poster, displayed so prominently, could be misconstrued as an ironic touch, and that felt to me like dishonoring his memory. I hung it in my office almost by default, not knowing that, in fact, it was the perfect place.

jim bailey
Jim Bailey spent his career impersonating Judy Garland.

Jim Bailey was born in Philadelphia in 1938. “I wanted to sing,” he said. Studying opera, he learned the difference between a “head voice” and a “chest voice” and a “throat voice,” methods that had been taught to him. What couldn’t be taught, much less understood, was how he could hear a sound in his mind and then, via the techniques gleaned at opera school, reproduce it with startling accuracy. But to Bailey—who would appear, early in his career, on and off Broadway, in Chicago, and, finally, in Los Angeles—this ear for mimicry was a party trick, a way to get laughs, and also to hide. An underemployed nightclub singer and closeted gay man with the sensitivity of an artist, he found appearing at social functions embarrassing. It was quickly apparent to him that it was easier to survive the night not as himself but as his friend Phyllis Diller, who came to any occasion pre-adored.

And adore her—or him?—they did. So much, in fact, that Bailey began to reconsider his whole act. He was working nights at some insurance company. Where had that gotten him? “I kept thinking, ‘God, there’s got to be some way. I’ve got to do this.’ Because I knew I could do it,” he recounted in one of several interviews with public access talk show host Skip E. Lowe. “And I thought that if I did [Phyllis Diller], I couldn’t just do it in a fright wig and a tuxedo. I was really going to have to go all the way and do it. But you see, in my mind I never looked upon it as ‘Oh my God, I’m going to wear a dress; that’s female impersonation.’ I never thought about it that way. I thought about it as character acting.” The term “female impersonation” never satisfied Bailey, nor should it have. Impersonation is a function of technical or even neurological assets, like being able to hear a tune and then immediately replay it, and “an impression,” Bailey would say, “is something that lasts for a few seconds and then it’s gone.” There was no name for what he wanted to try.

Whatever you call it, he certainly did it: Phyllis Diller, Barbra Streisand, Mae West. But his Judy Garland? Even Bailey acknowledged it was a cut above. With total solemnity, he would confess, “I become her.”

One night in 1965, when Bailey was appearing as Garland at the Redwood Room, a club in downtown L.A., a waiter told him before showtime not to freak out, but Judy Garland was in the audience. (“No, she’s not” was Bailey’s response.) Taking a peek through the curtains, he saw for himself: Judy Garland, sitting there in a giant hat. As Bailey would tell it, he had no time to be nervous. The curtain opened and he was off and shortly thereafter he heard her laugh: he was out of the woods. When the show ended, she stood up, tossed her giant hat on the chair, and joined him onstage. “You know, darling,” she said, throwing an arm around him, “I never realized I was that pretty.” The audience leapt to their feet, and the curtains closed, leaving Jim and Judy alone. Only she seemed to anticipate that there was more to come. “Well,” she said to him. “What should we do now?” The curtains opened—again, he had no time to be nervous—and Judy said, “Let’s sing something.” “Bye Bye Blackbird,” a cappella, poured out of them, and the crowd went insane.

Backstage, after the show, Judy and Jim talked. “Would you call me?” she asked as she left.

Me? he thought. I’m going to call Judy Garland?

Two days later, he got up the nerve.

“Miss Garland’s residence…” It was Alma, the housekeeper.

“I’m calling for Miss Garland. This is Jim Bailey.”

“Oh! She’s been expecting your call.”

Expecting his call?

The phone was handed off.

“Jimmy!” Judy bubbled. “I want you to come by the house.”

“Well, I was going to go to the beach today—”

“The beach? Why would you want to go to the beach?”

He did not go to the beach.

A friendship developed and, given Garland’s feeling for adoring gay men, perhaps more. It was told to me—and here is a mystery, yet another obsession within this obsession—that after Garland was fired from Valley of the Dolls, she and Bailey shared a sensitive moment, and Bailey felt they were on the lip of going further. They didn’t. But one could easily see Garland falling for him. In 1967, Bailey was not yet out of the closet, and Judy Garland loved love; that is, the Judy Garland version of love, which went something like, You’re swell, please rescue me. Considering the possibilities is, for me, as hypnotic and dizzying as endlessly twisting a kaleidoscope.

It was only a matter of time, then, before she started answering his questions with demonstrations. On these occasions at Garland’s home, she would giddily cue him to put on the Carnegie Hall record, then scurry over to her place at the top of the stairs and make her Carnegie Hall entrance, going through the entire concert, of which there is no film, move by move, Esther Blodgett performing for Norman Maine in their living room. Garland died not long after, in 1969. She was only 47.

In 1970, Bailey appeared as Garland on The Ed Sullivan Show, and it was said that many who tuned in that night were distressed to think they were watching a rerun.

The next year, he appeared as Garland with Liza Minnelli at the Flamingo in Las Vegas. The Hollywood Reporter wrote of opening night with an almost religious awe: “It was an incredible one-of-a-kind, once-in-a-lifetime performance…. When [Bailey] called Liza ‘my little girl’ and she called him ‘Mama,’ a collective lump rose in the throat of the overflowing capacity audience…. What might have been maudlin was magical. What might have been spooky was sensational.” They received 10 standing ovations over the course of the 30-minute performance. For the finale, a solo, Jim-Judy sang “Somewhere over the Rainbow,” and “there was a hush and stillness over the crowd that was absolutely eerie; many openly cried.”

In what was perhaps the capstone of Bailey’s career, he re-created Garland’s spectacular Carnegie Hall concert, the capstone of her career, at no less than Carnegie Hall itself.

Liza Minnelli—in what has to be the ne plus ultra of rave reviews—told Bailey if he ever stopped performing, she would never see her mother again.

jim bailey as judy garland
Philip Burke

If in his lifetime Bailey remained only a performer’s performer, it’s because of how we have misconstrued the Judy Garland Story. In countless biographies and the popular imagination—the chicken and the egg—Garland is characterized by the theme of victimhood. She was a victim, the story goes, of her mother, of drugs, of men, of MGM. While there is truth to this, victimhood cannot be the biographical thesis statement of one who performed with such vitality and strength. She was, in addition, the life of the party. One need only check her appearance on The Jack Paar Program in December 1962 for confirmation of a spontaneous wit, warmth, and general loveliness to match the suffering we all know she endured. So why—all the way through the recent Oscar-winning Renée Zellweger incarnation—do her biographers (with the notable exception of John Fricke) favor suffering? It must be because on some level it serves us, the audience, to know that the giants get suicidal too. But death is only half of the Christ story—or the human story, for that matter. “I saw her in all different kinds of moods,” Bailey would say to Skip E. Lowe. “I saw her happy, I saw her sad, I saw her kind, I saw her nasty. She was a human being.”

That’s how he played her.

It came through best onstage. Live, interacting with the audience, Bailey could actually improvise, with journalistic fidelity, as Judy Garland. That alone was incredible. But Bailey could go even further. By “improvise,” I am not referring only to Bailey’s capacity to quickly recall his subject’s complete and detailed history, to trot out her old Munchkin and Mickey Rooney stories, which he could do as naturally as she did; I mean, Jim Bailey could improvise new material in her spirit. Spirit—a thing deeper than body and mind. I don’t have another word for it, and no one can explain how to come by it. This was his second miracle. Engaging with the audience, person to person, as Garland did so brilliantly, Bailey re-created the Garland we can only know fleetingly on records or see in movies, a “real” Garland, the documentary Garland, not the singing star but the woman. I don’t know how that was possible.

“I think she really has become a part of me,” he said. “She does live through me in many ways.”

Bailey did Garland for 40 years. But the more he did her, and the better he got—rather, she got—the more he had cause to wonder whether, in doing Garland, he wasn’t doing himself. Would they ever want him for him? What he may not have known is that his doubt mirrored Garland’s own relationship with her genius. She always suspected it wasn’t her they wanted, but “her.”

jim bailey as judy garland, liza minnelli, barbra streisand
Clockwise from left: Bailey performs as Garland with the singer’s daughter Liza Minnelli; two legendary performers—Shirley Jones, left, and Ann Miller, right—with Bailey as Garland in 1992 at the Hollywood Roosevelt Hotel; Francesco Scavullo portrait of Bailey as Garland; in addition to Garland, Bailey embodied many other famous female performers onstage, including actor-singer Barbra Streisand.
Courtesy of Steve Campbell; Getty Images; © International Center of Photography and Francesco Scavullo Trust Beneficiaries

The pandemic threw me off the research I was doing for my next book, a kind of biography, and with more time on my hands than I knew what to do with, I went down a YouTube rabbit hole one night that ended with Jim Bailey as Judy Garland. Compelled by a strange old force, I got in touch with Steve Campbell, Bailey’s manager. I’m not sure what I expected to come of it. Surely, there were questions. What had happened to Bailey in the years between his farewell performance in 2013 and his death in 2015? The biographer in me wanted an accounting. But writing biography, I’ve learned, is often just an excuse to get next to a mystery. The mystery can be talent; it can be character; it can be—and almost always is—something felt but unknown in the biographer.

Biographers, we aren’t so much detectives as unrequited lovers of ghosts—Dana Andrews as Detective Lieutenant McPherson in Laura. We start with the mystery, the “something happened,” and end up possessed by a thing more mysterious than what psychologists call the presenting issue. We’ve all heard nuns speak of “the calling” and mystics of “channeling”; that’s a little too wispy for my taste, but in their intensity of concern, they do undergo something like what I think I’ve felt, a transformation of awareness. Whether it’s real or imagined, living in another’s headspace, trying to think as they do, one can seemingly end up, if not thinking someone else’s thoughts, seeing through their eyes. And in that sense, becoming them—a little.

Bailey’s greatness was in his ability to convey Garland’s greatness. That makes him a medium, hers. That may even be the biographer’s job, manifesting. It’s impossible—there is no way, out of the facts of historical life, to bring back the dead, to turn back the clocks. But what is the point of telling the story if we can’t feel it? History must be a feat of conjuring too. We must feel emotional proximity to the lives of the spectacular dead. But how does that happen?

I don’t know. Only art knows. I know that.

I want to get next to my subject’s goodness. It doesn’t have to be moral goodness, though it can be. Mostly, it’s talent. I try, through research, to be present at the creation, to will myself, via all the information I can gather, to observe, then re-create the emotional and aesthetic effort of the masters. Art comes from somewhere; it has a beginning. I first find it in childhoods, then I watch it. I watch it build, moving forward. Watching it move, it moves me. It travels me backward through time and space alongside him or her, those who necessarily risked so much to create so much, staying alive accruing goodness until they couldn’t. Then they die and I find someone else.

jim bailey as judy garland
Bailey in his dressing room preparing to perform as Garland in Palm Springs.
Peter Palladino

Last summer, I drove out to Palm Springs to meet Campbell, who was also Bailey’s partner for a decade, as so many of Garland’s chief collaborators were hers. Campbell was as you would hope a companion of Bailey’s, or Garland’s, to be: a great laugher, up for a good time, devoted. The house Campbell shares with his partner, Rock Hall, also a fan of Bailey’s, is all high ceilings and glass tables, with bright white sofas and walls, like a snow globe in the middle of the desert.

And then there is the guest room: a bed, a bathroom, a whole wall climbing with Bailey show posters and memorabilia. Pointing from poster to poster, Campbell sketched out for me the shape of Bailey’s biography. An ideal source, he knew my admiration for Bailey was pure and answered my every question, save the most important one, the one no one—certainly not me—would ever ask: How did he do it?

We opened up the wine and got to talking. I got the facts. I learned from Campbell that Ian McKellen, after he saw Bailey re-create Garland at the Palladium, insisted that Bailey not refer to himself as an illusionist, because “illusions aren’t real, and what Jim was doing was real.” I learned that Garland gave Bailey one of her rings. I learned that as Bailey aged, Garland aged, his repertoire deepened, and his telling of her story took on mortal shades—“she got older,” Campbell explained. I thought he was stating the obvious until I realized he was talking about Bailey in character, no longer “he.” As older Garland, “she could get darker,” Campbell said. “She would surprise them,” meaning audiences, “with things the rest of us didn’t know were true about Judy until much later.” Bailey knew what wasn’t yet public information. Exactly how he knew these truths he couldn’t possibly know was a function of his talent—but how did he know? “Now it’s all come out, books and movies, everyone knows everything about Judy, but it wasn’t like that then,” Campbell says. I learned that Bailey was a drinker, that in the end, he got into pills, and Campbell, for all his love of and admiration for the artist and the man, got burned-out looking after him. I learned that all along Bailey wondered whether it was him or Garland the people really loved, and whether, if it wasn’t him, he had wasted his talent. Her songs, he didn’t make them his own. But who else could do that? His was a life devoted to the art of history—and indeed, as he practiced it, as I hope to practice it, it is an art. For bringing the dead back to life takes more than good reporting; it requires communion with ghosts—wise ghosts. Though I didn’t yet know who I was to become in my professional life, seeing Bailey at 17, some part of me must have known I would try to do on the page what he did on the stage that evening: the impossible, raise the dead.

We ended up in the living room finishing the bottle and listening to a recording I didn’t know existed of Bailey doing Judy at Carnegie Hall. I was glad to have the wine working in me, helping me to see, a little less clearly, exactly where I was, which wasn’t Carnegie Hall for Bailey’s performance or, 30 years earlier—for what has been called the greatest night in show business history—Carnegie Hall for Judy’s.

Opposite my signed Jim Bailey poster, I sit at my desk, staring every day with stage-frightened eyes at just one of the thousands of pages of notes I have collected for a book about Francis Ford Coppola. They tell me he was born on April 7, 1939, in Detroit, Michigan; as a boy, he had polio; his first favorite movie was The Thief of Bagdad…•

L.A.-based writer Sam Wasson is the author of several acclaimed works of nonfiction, including Fifth Avenue, 5 A.M.: Audrey Hepburn, Breakfast at Tiffany’s, and the Dawn of the Modern Woman; Fosse; and, most recently, The Big Goodbye: Chinatown and the Last Years of Hollywood.