When High Heels Make the Man
How drag performance helped me backhand demons and toxic masculinity
Once upon a time there was a magical pair of shoes. No, not those glass slippers from that retrograde tale telling girls to sit around and wait for polished mediocrity to show up. No. I’m talking about a REAL PAIR OF MAGIC SHOES.
Okay so it’s 2011, I’m back at my old beach sharehouse, and one morning I wake up before everyone else and head upstairs to the airy living room with its view of the ocean, when I notice, parked next to the couch, a GARGANTUAN pair of six-inch heels. Now! I know right away that they belong to a woman named Teresa, because after once getting our flipflops mixed up, Teresa and I learned that we have the same size feet — only I’m six feet tall, while Teresa is maybe five-seven, which means that Teresa would literally hold up well in the middle of a hurricane.
Feeling curious, I sit down and strap them on. But when I push up off the couch, my knees are so much higher and I rise unsteadily, like a colt finding its legs, stumbling and wobbling, still rising until…
Most women don’t need me to explain the following — only please imagine, Women, experiencing this transformation for the first time at forty. Because once I’m finally standing straight up — aside from now being taller than most shooting guards in the NBA — my calves and lower quads engage, pitching me forward as my posture rolls, like a wave, into perfect alignment. I feel powerful and (ironically) aggressive — like a beer-muscled nineteen-year-old looking for a fight. Taking a tentative step, feeling balanced and rooted, I fix my eyes on the horizon and then I walk clear across the floor.
I’m not sure I can convey just how spectacular this felt, but I grew up with two brothers who both possess superior athletic ability, and so I thought that I was experiencing, for the first time, what it felt like to be a natural.
Nevertheless, I filed away my secret talent until a few years later when I attended a knock-down drag show in Baltimore, at a place called Club Hippo. Watching those queens take center stage reminded me of being at The Golden Gloves — because just like boxers, they were trotting out there with a lot more than just a certain set of skills. There was attitude, bravado and a stylish arrogance that I loved. (I especially loved the occasional stumble, because the recoveries displayed a talent and comic improvisation that morphed into its own graceful flow.)
Standing there, I airily imagined trying drag myself, even confessing this left-field desire to my date; thirty seconds later, doing drag felt as fantastical as training to become a super middleweight. Aside from knowing nothing about clothes and makeup, I questioned whether a straight person should even be stepping (or strutting) into queer space. And since there is no group more self-limiting than straight, white males — no other demographic even comes close — I counted myself out. (Funny how it keeps coming back to boxing…) But after watching another queen stumble, I thought to myself, I bet I can walk in heels just as well as her.
Fast forward to Halloween, 2017. The new Wonder Woman movie is out and women are spontaneously organizing watch parties, even taking young girls in an expression of solidarity and resistance to our country’s first Orange-American president, and I thought — amid the parade of superheroes bound to come out — that it might be fun to dress up as Wonder Woman, replacing her red boots with red, six-inch heels.
Two days and $38 later, the Evil Empire delivered the goods just in time. After putting on the costume — including the Lynda Carter wig — I stood barefoot before my mirror and…
I thought I looked ridiculous.
I then questioned the wisdom of a man dressing up — dare I say, “appropriating” — this icon of female power. Maybe, I thought, I should just don khakis and a tan shirt along with a red winter cap and be a match.
But then I strapped on my second pair of magic shoes.
Rising up from my bed, I could feel those teams of leg muscles once again engaging, transforming my posture. I thought to myself, No matter what, you’re going to be dead relatively soon, so you might as well go for it.
Later, at Dogwood, a local bar, I won the costume contest.
After strutting out of there clutching a basket of craft beer and swag, I moved on to The Denning’s Point Distillery where a DJ had the dance floor pumping. Until he cut the music for their costume contest.
I won forty bucks.
Back at home, having known both the Thrill of Victory and the Agony of da Feet, I stripped out of my costume and collapsed. The following morning, I got a kick out of seeing the gold wrist bands in a heap among two crumpled twenties. Luckily it wasn’t a rough night because the last thing you want — after going out dressed like a woman — is to not recall why you’ve returned home with a net profit.
Nevertheless, performing in drag still remained a flighty and distant fantasy. Then, earlier this spring, I went to a drag show at The Roosevelt Bar, situated at the end of Beacon’s Hudson Valley Food Hall. Hosted by Andramada, her show was happening every Friday night, capping off a watch party for RuPaul’s Drag Race. Last year, the pandemic had screwed me out of a properly epic fiftieth birthday party; at the time, I just let it go, thinking, we don’t have the time to make up everything and we all just need to move forward. But on the cusp of turning fifty-one, I felt like that was the wrong answer. Were this not a polite column, I might even say that that was the wrong fucking answer. My fifty-first birthday was in four weeks, and as it fell on a Friday, I thought it would be fun to re-do my fiftieth by inviting people to celebrate with me at The Roosevelt during the drag show; two seconds later, I wondered if I could be IN the show.
Once again, those self-limiting demons came for me. This time, however, I beat them back with the notion that I now possessed another skillset, having been the front man in a few musical projects, and that doing drag would really just combine two things I’ve already done. Unfortunately, those demons questioned, once again, my stepping into queer space. But then I realized that drag — which is truly having its moment — was conversely stepping into straight space, particularly in the form of drag brunches. (After all, is there anything straighter — or whiter, for that matter — than brunch?) The more I thought about it, the more performing in drag felt like raising a middle finger to so much of what I resent in our culture. Because as far back as 1987, I KNEW, in my bones, that masculinity was broken. Particularly as my high school (and our broader culture) held up as paragons far too many men and boys whom I knew were sexist — and frequently racist — pieces of shit. They further trucked in standard-issue homophobia where “gay” was the worst possible pejorative, which back then further implied being stupid and weak. Sometimes it felt like a considerable percentage of straight men were guided by a persistent and omnipresent fear of ever being perceived, even remotely, as gay. (Only how durable is your masculinity if you’re afraid that it might get canceled because you chose the wrong color shirt?)
I wish we had invented the term “Toxic Masculinity” back then so that I could have named what I saw and felt. Unfortunately, my negativity toward these people (and some institutions) led to my feeling gaslit, particularly by people in positions of authority who told me that I had a bad attitude. (In all fairness to those apparatchiks, I did have a bad attitude. But that bad attitude allowed my own sense of manhood to develop in opposition to the crummy, default model that I saw — and frankly still see — all around me.)
Unfortunately, my imperfect manhood was unaware that I was full-on working the repression game myself — at least until April when finally, at long last, I gave the possibility of trying drag full conscious consideration.
Twenty seconds later, Domina Tricks was born.
I just saw her, fully formed in my mind’s eye — shiny, tight black dress, spiky hair, and — as per her name — clutching a riding crop.
I went to Marko, the owner of The Roosevelt, to ask if I could reserve the open loft upstairs on the Friday of my birthday; then I approached Andramada to ask, humbly, if she’d consider having me as a performer. Both of them loved the idea and so I invited friends and family to my 50.1 party. And while they all knew they were coming to a drag show, I thought it would be fun if none of them knew I’d be in the show, treating them to a reverse-surprise birthday party.
My first number came to me immediately: Blondie’s “Call Me.” So did my second, Patty Smythe’s “The Warrior.” Once I began to imagine choreography, however, something in me questioned whether these forty-year-old songs were good choices. But this just opened the door for those self-limiting demons. Only this time, they didn’t just come back for me — they brought all their friends.
I knew, consciously, that those demons are always ready to fight to the death to keep me in my comfort zone, as their only interest, ever, is to maintain the familiarity of the status quo — even when it is fruitless or miserable. (This also applies to a lot of jobs, institutions and governments.) And so I beat them back by reminding myself that I LOVED those songs. And then I began finding the same answer over and over: Just be and express who you truly are and whatever it is that burns uniquely inside of you. And then doing drag felt, once again, like a bold and glorious rejection of the self-limiting, straight, white-male model. And without getting too lofty over here, sometimes it feels like our world is being strangled to satisfy the degenerate excesses of such a small group of men, men who, instead of experiencing their power and self-worth through self-expression and generosity toward all, vainly grasp for it through a relentless and psychopathic desire to take more and more — more than they’d ever possibly need — at the expense of virtually everyone else and everything. That our cultures still venerates and celebrity-worships so many of these selfish and destructive men is a major part of what remains toxic and broken in contemporary masculinity. So doing drag, for me, feels like pitching a glitter-crusted stone at an ongoing and evil construct that we so desperately need to change.
So there I am. It’s Friday, April 22 at The Roosevelt Bar, and while I’ve successfully kept the self-limiting demons at bay, I’m now trying to hide my nervousness while celebrating with friends and family. And once Andramada began warming up the crowd, I slip away with my friend, Leslie, into Marko’s back room, where I get dressed while she applies my makeup, finishing my garish, purple eye shadow just in time for Domina Tricks to run around the corner. The intro to “Call Me” comes over the sound system and my heart begins pounding as I trot out there, swinging my crop, making it halfway down the Hudson Valley Food Hall before my friend Adam had to actually inform my parents, to their astonishment, that Domina is me. Coursing with adrenaline, much of my prepared choreography went out the window as I collect bills and interact with the crowd, getting down on my hands and knees and crawling like a cat before running back to the middle in time to toss a handful of bills in the air during the song’s pivotal moment.
I just can’t recall the last time I had so much fun.
Later, during “The Warrior,” I stumbled. BUT! I didn’t fall, kept my flow, and just kept going.
I made $138.
And I love that I keep getting paid for dressing up in drag. And I’m — I mean, Domina Tricks, is about to ride again. She’ll be performing at Drag Brunch at Mama Roux in Newburgh (hosted by the wryly hilarious Victoria Bohmore) on Sunday, September 25. You can reserve a spot here. Come on out — Mama Roux’s brunch is pretty spectacular before you even get to all of the main dishes.
👉 Please SUBSCRIBE to get John Blesso’s latest right in your own damn inbox every other Sunday morning!
