One humid July evening in 2010, my agent called to ask if I’d be willing to leave Chicago for a spot opening up in the revival of La Cage aux Folles. I had been in Chicago for over three years at that point, and had more or less stopped auditioning. But the idea of being able to say (to whom, I wasn’t sure) that I had done not one but two Broadway shows still had the appealing ring of achievement to it, even if it meant I’d have to do some seriously strenuous choreography dressed as a French showgirl eight times a week as one of the Cagelles in La Cage aux Folles.

For the La Cage audition, my agent told me to be prepared to learn a dance combination or two, sing sixteen bars of a traditional musical theater song, and perform a routine in full drag to a recording of “It’s Raining Men.” The audition was to be the following morning at ten, and my agent seemed to assume I was in possession of a trunk overflowing with heels, a room in my apartment reserved solely for wigs, and a fully choreographed routine and developed drag persona ready to perform on a moment’s notice. I was in possession of none of the above.

I’m the swing at Chicago, which means I am at the theater every night like the rest of the cast. But unlike everyone else, whose bodies are put through the grind of performing eight shows a week, I either watch the evening’s performance or sit in my dressing room for two and a half hours, doing things like reading, watching TV, or, on that humid night in July, working on my drag persona. That is, unless one of the ensemble guys is out sick or on vacation or is injured in the middle of the performance. Then, of course, I throw on my costume, run down the six flights of stairs, and get myself onstage.

When the Chicago overture began that night and I was alone in my dressing room, I sat down at my spot in front of the light bulb lined mirror, opened my laptop, and began searching YouTube for clips of drag queens doing their drag-show thing. To be honest, drag queens had always scared the shit out of me. They were often so abrasive, so hostile toward their audience, and all that garish makeup, those games of illusion, had a way of making me queasy. The few times I’d been to drag shows, I’d been reminded of the jitters I felt as a seven year old, watching my older cousin play soccer. Sitting in the bleachers, I had always been terrified I’d for some reason be forced to join in and play the game, too. Just as I’d always known I was embarrassingly terrible at soccer, I’ve always held the deep-seated belief that I’m just not man enough to convincingly pull off dressing like a woman.

I started looking around my cluttered, triangular dressing room for something to either inspire or save me from that audition. But between the crumbling plaster walls, the mildewed plastic shower stall in the corner, the harsh florescent lights, the racks of faded mesh costumes, and the sealed shut, blacked out window that faced a parking garage, I was finding neither inspiration nor salvation. I started wondering if I really wanted a second Broadway show all that badly.

I closed my laptop, ready to call my agent back and cancel the audition appointment. Then my eyes fell on the stack of books I kept on my dressing room table. Beneath volumes of John Cheever and Chekhov short stories was a copy of Me and My Shadows, a memoir by Lorna Luft. Ms. Luft is the woman who has spent her life unfortunately known as Judy Garland’s other daughter. A friend of mine was the book’s editor and had recently given me a copy (which, I am not ashamed to admit, had made me really, really excited). I had always had a thing about Judy. When I was growing up, family-bonding time had, after all, included renting old MGM musicals, eating oversized bowls of popcorn, and shushing each other for singing along with the songs and reciting the dialogue to the movies we’d seen again and again and again. More than once or twice, I had faked elaborate illnesses to stay home from school to watch a Fred Astaire or Gene Kelly marathon on AMC. But it had always been all about Judy Garland for me; that vulnerability, that impeccable comedic timing, and, of course, that voice.

I flipped through the photos of Ms. Lorna’s memoir, then reopened my computer and found Judy doing “Get Happy” in her black blazer and fedora on YouTube. It had been years since I’d watched that clip, but obsessive viewings of the That’s Entertainment series in my adolescence seemed to have stuck with me. Somehow, the choreography came galloping to the front of my brain and out my limbs as if I’d been rehearsing it every day for years. I then pulled up a recording of “It’s Raining Men” and danced Judy’s choreography to its disco beat. Suddenly, without a wig or makeup or heels, I was doing drag, and I found myself thinking, inexplicably, of my father.

It wasn’t my father’s many appearances on the community theater stages around Maryland that I was recalling. Rather, I was hearing his words and directives as he coached me for a role in Adventure Theater Summer Day Camp’s production of Joseph and the Amazing Technicolor Dreamcoat. I was nine years old and playing the Pharaoh, an Elvis inspired character that got to sing a killer rock song at the beginning of Act II. Nearly every day of that three-week summer session, I would come home from camp, dunk my head in the bathroom sink, then sculpt my hair into a pompadour with a squirt of Dep gel the size of five stacked quarters. I would then run through my song, choreography and all, six times in front of the mirror until my dad yelled up to tell me it was time for dinner. After dinner, I’d ask him to help me work on my moves, and the coaching would begin.

“It’s the element of surprise,” my father said to me. “Let’s try it again.”

I was standing on my bed, my sister’s hairbrush clasped in my right hand like a microphone. My five-year-old brother, Max, stood at the foot of the bed, aping my swiveled stance. My dad pressed play on the boom box and a steady descending baseline from the original Broadway cast recording of Joseph pounded out. I began popping my knee in time to the music, my lip curling up. My dad had told me that the trick to being a great performer was to surprise the audience: just when they think they can predict who you are and what you’ll do, you give them a spasm, a shift that springs from stillness, and bam, you’re entirely reinvented in their eyes.

I sang along with the recording, the Mississippi drawl I’d gleaned from repeated listenings of “Jailhouse Rock” sticking to the tune automatically. I ended the song on one knee, swinging my arm into a triumphant fist pump on the final button. My brother and dad applauded while I sat down on the bed, wiping sweat from my forehead and neck.

“That was better,” Max said, jumping up and down on my bed. “I thought that was really better.”

“Good, Briny,” my dad said. “Let’s take it from the verse again. This time remember: focus your gaze, find that stillness.”

I knew that if I absorbed my dad’s advice, I could make my performance great. But it had been my experience that the perfect costume could elevate any performance from great to legendary. I figured that whatever Carol, Adventure Theater’s bobbed costume mistress, had cooked up for me that year would help me focus and find something close to that perfect stillness.

“The Pharaoh is the king,” Carol said later that week, handing me a gold sequined vest in the theater’s mothball-scented dressing room. “That’s why Andrew Lloyd Webber is a genius. Do you get it? Pharaoh? The King? Elvis is the King? Genius.”

I was starting to put the vest on over my t-shirt when Carol said, “Try on the whole shebang, no T-shirt under that vest. Let’s get the total effect.”

Moments later, I moved out from behind the dressing curtain and stood on a square platform before the three-way mirror. The gold vest twinkled above my bare torso and reached just below my bottom ribs. I was a chunky nine-year-old, and my stomach hung over the black spandex biker shorts Carol had given me. I sucked in my belly button and, fingers shaking, began to button the gold vest.

“No, no,” Carol said, slapping my hand away. “Give the people what they’re paying for.”

I turned from side to side, taking in my image from every angle of the three-way mirror. There he was, a little Jewish boy from Potomac in a sparkling sequined vest and black spandex shorts, standing in front of a mirror, thinking he was Elvis.

“And now for the final touch,” Carol said, bending down to help me into the rhinestone-studded gold platform shoes she held. I slid my feet into the shoes and teetered for a moment before finding my balance.

“Look out, Adventure Theater,” Carol said. “Elvis has officially entered the building.”

On the day of the Joseph performance, I stood upstage center on an elevated platform, hidden by a network of overlapping bamboo fans. When I finally heard my cue—a descending bass line plunked out from the piano in the orchestra pit—the bamboo fans parted to reveal Elvis in spandex and a sequined gold vest, standing with feet wide, chin down over the right shoulder, holding a microphone. I snapped my head to the audience and sang the verse through a curled lip. Blinded by lights and glittering harem girl outfits around me, I couldn’t see the faces in the audience, only blurred outlines of heads bobbing and swaying to the music.

The number sailed by, every movement and vocal lick I’d been rehearsing with my dad came tumbling out in perfect, dynamic succession. As I jumped from the elevated platform in my gold platform shoes, I strode through my choreography, sure of my footing, fully believing myself to be the king. Finally, the tempo slowed to half time for the big finish. I got down on one knee, sang the last notes with everything I had, then pumped the air with my fist. The lights bumped to a white heat and the audience leapt to their feet, screaming and applauding, as I remained frozen in my final pose. Over top of the applause, I heard my dad’s familiar, sustained, Woooohooooooo. I turned my head to the audience to smile and say into the microphone, “Thank you. Thank you very much.”

As I watched myself in the dressing room mirror nearly twenty years later, reaching up with splayed fingers like Judy Garland, leaning back with the microphone for a long note like Judy Garland, rocking my hips over bent knees like Judy Garland, wobbling slightly and gesturing with crooked elbows and loose wrists like Judy Garland, I could hear my dad’s voice telling me to focus my gaze, to plant my feet, to find that perfect stillness. It was odd, and a little unnerving, that though I knew my dad was sitting in his office overlooking Farragut Square, reviewing legal briefs and facilitating transactions, he was also reflected back at me in the dressing room mirror, helping me become a chorus boy who was man enough to perform in drag.

The audition for La Cage aux Folles went better than I could have anticipated. I can-canned with a flexibility I didn’t know I still had; I leapt in the air and landed in the splits wearing the black strappy heels I’d borrowed from Chicago. I sang my sixteen bars of music (wearing loafers, not heels), and, when it was time, I put on my black blazer and black fedora and got ready to do Judy. I told myself it would be better to look like I wasn’t trying too hard, so I didn’t wear makeup or a wig or even the black pantyhose I’d brought along. I did my Judy impersonation in front of not only the creative team and the casting directors, but also the dozen or so other guys auditioning who were, by and large, in much more involved states of dress than I was. One guy wore a full-on Geisha costume; another did a flamenco routine in a fringe skirt with a rose in his long, black wig. Others went the more wild and raunchy drag queen route, wearing huge, teased wigs, and glittery tube tops while accosting their audience of auditioners with lap dances and pelvic thrusts.

When it was my turn to take the floor, I was clammy with nerves, but hoped my visible trembling was adding authenticity to my Judy impression and perhaps making up for my half-assed costume. As “It’s Raining Men” wailed from the rehearsal room speakers, I found it impossible to, even for a moment, focus my gaze or find any kind of stillness at all. My mind kept leaving the audition room to think about my dad.

I often wonder what kind of performer he would have been had he dedicated his life to music instead of to us, his family. He had been an oboe student in the competitive conservatory at Oberlin, but had packed up his oboe after graduation, gotten a Masters in social work, and, after marrying my mother, went to law school so he could provide for her in the manner to which he thought they ought to become accustomed. His oboe sat locked in its case next to the upright piano at our house for years, then was buried in the storage room, where it remained while he built his law practice, shuttled us to and from dance classes and rehearsals, and coached us on our endless string of performances.

I’ve tried to picture my father seated on stage, illuminated by a single spotlight, playing his oboe and swaying to its rhythms. Would he have been flashy and demonstrative when he played? Or would he have been subtle and subdued, allowing the music to speak for itself? I don’t think I’ll ever know for sure. He has refused to play that oboe for as long as I can remember, claiming that the squeaking would be unbearable to our trained ears. But the last time I was home in Maryland, I did notice that my father’s oboe, still in its closed case, had made its way out of the storage room and was sitting next to the antique upright piano in the living room. I didn’t ask him if he’d started playing it again. I figured that if he had, it was something he was doing, finally, just for himself, in his own rare moments of stillness.

When I finished my Judy routine, I wobbled over to the side of the rehearsal room, allowing the next guy to strut his glittery, shimmery stuff. I leaned against the wall, panting, my ankles throbbing.

In the end, I didn’t get that role in La Cage aux Folles. It went to the one guy at the audition whose agent had failed to tell him to wear drag, a cute little blond with a muscley body who had simply stripped down to his underwear and shaken what he had to offer for the creative team.

I went back to Chicago that night and the boys in my dressing room agreed I would have been miserable doing jump splits in heels eight times a week, and that it was good I hadn’t booked the job. When the stage manager called places, I opened my collection of Cheever short stories and the rest of the boys descended the six flights of stairs to the stage, ready to do yet another performance.

The reality that I might never do another Broadway show began to sink in. My mind started sorting through options of what else I could do with my life. Maybe I’d look into psychology; maybe I could be a professor of English; maybe I could find some rich dude who wanted to buy me things. I thought for a moment of what it would be like to go to law school. Then I thought back to one night when I was nine or ten years old, sitting around the dinner table with my family. My dad was telling us about some negotiation he was handling for the commuter rail agency in LA, and how they’d spent two full hours that day arguing over one single word of the agreement. When he had finished speaking, I looked at him, shook my head and said, “Daddy, I will never, ever be a lawyer.”

My father had looked back at me with his broad, easy smile and said, “That’s a good thing, my boy. I think that’s a very good thing.”