Jack Doroshow is a walking hot dog. It’s a warm Saturday afternoon in October, weeks before Halloween, and the 75-year-old wears a costume that turns him into a mustard-slathered wiener in a bun. He’s ambling with a sleek rosewood cane from the crowded corner of 15th and 5th in Manhattan, through Madison Square, and up to Bryant Park. Curtis Carmen, Jack’s boyfriend of 34 years, wears a cardboard box, with a cartoonish hot dog drawn on it—he’s a “conceptual hot dog.” This procession has nothing to do with Halloween. And Jack, with his coke-bottle glasses, Gray Asics sneakers, baldhead topped with the dome of this wiener, all dressed up in that hot dog guise… Jack smiles with the enthusiasm of a young man. It’s a nearly crooked, wolfish grin that spreads to his eyes, suddenly bright with the punch line of a joke, bright as his flawless teeth. When asked, “Where are you going?” He replies with his Philly-by-New York City accent, “The grocery store.”

As loud as Jack’s costume is, the hot dog is of the more understated of his dress over the years. Jack is known the world over as Mother Flawless Sabrina, an archetype of drag culture before RuPaul discovered pumps and Paris is Burning was even conceived. When Sabrina started doing drag in the ‘50s, she was a blonde with thick makeup, huge whorls of eye shadow, strings of pearls, sometimes oversized glasses, often smeared lipstick, and, in the early days, she wore the clothes of a housewife. As she travelled outside of her native Philadelphia more and more, her style evolved a bit.

“It was never about how I looked,” Jack says. “It was more about what I felt comfortable in. That just meant I sometimes dressed like an old lady from the time I was about 14.”

Between 1956 and 1967, Jack held at least 46 drag contests a year across the U.S. They were well attended, often the center of publicity, and almost just as often raided by the police. His first contest was called Miss Philadelphia, and gained enough notoriety that he took the show on the road. Eventually, he’d want to establish a coordinated states-wide championship. After using the phrase Miss Camp America (in reference to “campy” not “sleepaway”) Jack garnered a lawsuit from the Miss America Pageant. Jack then ran these contests under the name The Nationals Academy. At its height, the Nationals had more than 100 employees on its payroll. That drag contest is now called the Miss Fire Island Pageant and still exists to this day.

“In these little towns where we did the shows, we faced a lot of aversion,” Jack says of his smaller contests. “But it wasn’t until I would go into the communities and speak with the leaders we’d get them on board. They thought we’d be bringing in troupes of Queens to do the shows—that wasn’t so. It was the members of the community who wanted to participate.” Jack would offer a donation to a charity for community leaders to allow the contests to go on. Even still, there was public opposition, even if the law wasn’t involved.

Eventually, word would spread about the opulence and attendance of these contests. The judges for the Nationals became quite high profile, Judy Garland, Truman Capote, Gloria Swanson, and Eartha Kitt among them. By the time Sabrina moved to New York City in 1967, the movie director Frank Simon had caught wind of this thriving drag underground. With the help of producer Si Litvinoff (Clockwork Orange, The Man Who Fell To Earth, etc.) he would follow a group of drag queens as they prepared for the contest and throughout. The film, called The Queen, featured Monique, Dorian Corey, Crystal Le Belja, Mario Montez, Rachael Harlow, and International Chrysis. It also features a lot of jealousy, in-fighting, and conspiracy; in a time where these contests were just burgeouning, the stakes seemed higher than ever for these young drag queens.

Film critic Judith Crist called The Queen one of the best films of the decade. It broke box-office records, for a documentary film of its kind. It showed at Cannes in 1968, where the winner of the contest chronicled in the film, Rachel Harlow, became the darling of press photographers. But Sabrina was still the star, the facilitator of the entire spectacle—this was her baby. As a result of her new filmic notoriety, she would later be hired as a “special consultant” on films like Myra Breckenridge, Midnight Cowboy, and Butch Cassidy and the Sundance Kid. I’m still not exactly sure what this title means, even after knowing Jack for a few years.

As the 1967 Nationals grew near, Jack approached the Muscular Dystrophy Association, pitching the big contest as a charitable fund-raiser—the organization bit. By a stroke of luck, the society in turn attracted Lady Bird Johnson and Sammy Davis Jr. as co-sponsors. Somehow, Robert F. Kennedy became attached to the project as well. But, as the scope of the contest solidified, all the sponsors jumped ship, though Jack says Kennedy was very supportive. As though the contest could be damned by the perceived perversion of the philanthropic mainstream, it still managed a huge grip of all-star judges. The list included Larry Rivers, Andy Warhol, and George Plimpton.

This all happened in a time when the consequences of this kind of exhibitionism and behavior were grave and punishable. Sure, in the ‘50s and ‘60s, it was common for men to dress as women in film and television. Tony Curtis and Jack Lemmon by 1959 had donned full drag in Some Like It Hot; Tootsie and Bosom Buddies were not far behind. In mythology and folk tales, cultures have used men in drag as a mechanism of narrative for thousands of years. The all-masculine Achilles himself was dressed in drag (albeit by his mother) to prevent his draft into the Trojan War. Even J. Edgar Hoover was rumored to have cross-dressed. But, in conservative post-McCarthy public America, this behavior was a crime, one punishable by imprisonment. At least three pieces of “male” clothing were required to be worn, by law. In some states, cross-dressing was a felony. Jack and his contestants would often sit in jail cells dressed in drag, suffer police raids, and sometimes be escorted to state borders. 14 states still have such laws.

Jack doesn’t even know how many times he was arrested while running these shows. Referring to the judges who convicted him, he says:

“A man in a dress convicted me of being a man in a dress.”

I was led to Jack after I went to cover, for New York Press, an outlaw art show in a gallery in Dumbo where the power was out, in the summer of 2010. I met a young artist and filmmaker there named Andrew Shirley. During film school in the late ‘90s, Shirley met the man named Curtis Carmen—by then Carmen was dating Jack. I called Jack to get to Curtis to fact-check something about Andrew and a film he made, featuring Jack, called Chickenpox. Jack told me just to come over if I wanted to talk. Things spiraled out of control from there. Once, after a long conversation and the light outside his Upper East Side apartment dimmed, Jack gave me a sweater. I’ve been visiting him there for years.

At the beginning of this summer, I invite myself over one afternoon in May. It’s just at that New York tipping point where heat intersects humidity in a painful way. The door is unlocked when I show up and I let myself in without knocking. There, Curtis, tan and shirtless in shorts and sandals, and Niko Solarios, a young, Los Angeles-based artist in shorts and cowboy boots and a bowler, are installing an air conditioner into the window behind Jack’s desk. “Thank you so much,” Jack effuses as he scuttles around the room. “I’m so lucky to have you do this for me.” Without hesitation, Jack takes me into the bedroom to watch a new video he’s featured in. It’s a split-screen, a recreation of a ‘60s Miss America Pageant acceptance speech, with Jack’s interpretation of the words and costume on the right side and the original on the left. It is bizarre. Jack’s knowledge of the absurdity of the situation lends to a kind of beyond-camp commentary on the proceedings that makes it both hilarious and sad. Curtis leaves and Nico and I sit on the south side of Jack’s desk, making inquisition of his thoughts. At some point, Jack pulls out a massive freebase “glass dick” pipe. He offers us some and I ask what it is. “I have no idea,” Jack says. “I’m an old fart.”

Jack is obviously different than most men of his age (nearing the age of my grandfathers) and this goes beyond the scope of his chemical ingestions. He lives and talks a philosophy of self-ownership so positive and effusive you just have to go along for the ride.

“You’ve got no fucking choice, kid. You do whatever you need to. This is all your thing. This is all you’ve got.” He tells me this within minutes of meeting me three years ago, appraising my creative drive, after I ask if I can take some pictures and notes. I’m overwhelmed by the state of his ivy-covered flat at East 73rd street—in a good way. It’s a Beaux-arts gilded-age of New York building that sold about three years ago for $18.5 million. Jack has lived there since he moved to New York, saying he was installed by the notoriously pederast French diplomat and author named Roget Peyrefitte, back in 1967. I point to the Picasso hanging on the wall above the fireplace, a painting as large as my bathroom.

"Is that a Picasso?" I say.

"That's the assumption, although I wasn't there when he painted it,” he says after loading a bowl into a small wooden sneak-a-toke but carefully dancing around the specifics of the hundreds of syringes around his home, parts of sculptures he's created around the room, whether for diabetes or something else I’m not sure. They glisten among hundreds of other artifacts of accumulated interest. Signed books from Burroughs, a copy of Michael Musto’s obituary for Madonna tagged to the wall, stacks of art gifts that he’s featured in, portraits of him in painting, photograph and poem, memos of his own making taped to lampshades and walls and mirrors, a frame by street artist AVOID hanging behind his desk, piles of paintings turned against the wall, florid wigs on dummy heads, the floor a worn oak, a basket of odd and large sunglasses, the previously mentioned hotdog costume, mirrors everywhere, knotty Victorian furniture all about; the bedroom is lined floor to ceiling with books, the bed itself lofted in a nook of curiosity, a flat-panel television angled in the corner king in the center of the room, bottles of Vaseline and lotion on tables everywhere, each of which is technically bedside; every surface of the multi-colored bathroom covered in hand-written greetings from friends and visitors; a sparse, tiny kitchen. This apartment has been open to creatives and intellectuals since he moved there. Visitors of note: Michelle Obama, Lou Reed, Truman Capote. Jack says Capote named Allston’s Ultrasuede while at this apartment, during a late-night salon.

I’m walking around, scribbling in a pad. Jack startles me: “Work!” he yells, and then takes his voice into a feminine drawl. “WOOORK, darling. You’re brilliant, kid, You just always gotta do you. Let me tell you a telepathic joke. Did you get it? No. I have never once thought about what others think about me. ” You get the feeling he would encourage any young creative in this way.

It took me a year to find a full copy of The Queen. I bought it on VHS off a dated-looking website and it took so long to arrive that I forgot I had ordered it. Even worse, as fascinating as I found Jack, I couldn’t find anyone who had ever heard of him. I went to burlesque shows at Mug Lounge and drag contests at Sugarland in Brooklyn. I went to bars like Madame X on Houston. Everyone would know RuPaul and Flotilla DeBarge but never Flawless Sabrina. (Rachel Harlow, the winner of the contest in The Queen, is now post-op and a well-known club owner in Philadelphia.)

Things I did discover: Jack was born in Phildelphia in 1938 (I think). He had a rough upbringing on the Philly streets, but came from a very talented family. His brother was a drummer who won nine Grammys for his work, at times playing with Lou Reed, among many, many others. He died in the late ‘80s, a fact Jack and I bonded over as my own brother died shortly after we met. Jack earned his Ph.D. in psychology from the University of Pennsylvania, which seems to be the source of his unerring confidence; he’s constantly evaluating his environment, the artifacts of culture around him, and coming to the conclusion that the only thing that matters is one’s happiness, which for Jack means total freedom to do whatever he pleases.

“You’ve got no choice in the matter. This is the experience of knowledge. It’s our job to own that we are legends. Each and every one of us,” he says.

I got someone on the phone from Crossdressers International, a “member-supported adult transgendered group focused on support and social activities.” No one there had ever heard of Jack or Sabrina. But Michael Avor, the man I had on the phone, told me to call Joe Jeffreys.

Joe E. Jeffreys Ph.D. is a professor at NYU’s Tisch School for the Arts in theater and the director behind a video verite project called DRAG. He had a hard time overstating the importance of Jack’s life and work, not to mention the conservative, borderline-oppressive environment this drag subculture flourished in.

“In New York City, it was even illegal if you were gay,” Jeffreys tells me. “It was illegal to sell alcohol or serve alcohol connected to the Miss Fire Island Pageant, or to clubs. This was the early, late ‘60s. People would be charged with disorderly conduct. Everyone on these scenes was immediately suspect. Everybody had to have a cabaret card. You had to be fingerprinted and photographed to get one. Even Frank Sinatra objected! I’ve only ever seen one cabaret card. But all the drag queens definitely had them.”

I eventually find out Jeffreys was actually present during the filming of The Queen. He’d known Jack for years from just being on the scene and from art and critical circles ever since the movie came out. He even worked as an assistant to Simon, the director, and contributed seven minutes of outtakes to an extended version.

“This film is landmark because other films of the time, crossdressing was presented as a sickness, a pathology,” he says. “I would call The Queen an impressionistic documentary. When you look at the subject matter, it was a miracle we even got it released. It was barred and censored in several countries. At times we just thought: ‘We’re not even going to antagonize the censorship board with this film so why even try?’ For the time, there were even things in the film that cross other boundaries. Race moments, for example. A black contestant and a white contestant hug. These are things we don’t even necessarily see anymore because we’re so focused on the sexuality aspect.”

So at least one person knew Jack. And better: he was a contemporary. In time, I would find others who knew him. But, surprisingly, they were all young artists, writers, photographers, and filmmakers—like Shirley—who had been inspired by him. Shirley used him in a feature film he worked on called Chickenpox, an experimental piece of work that’s as hilarious as it is lurid. And it seemed Shirley and the others had run into him in much the same way I had, through a strange network of coincidences and acquaintances.

Solaris has paid out of pocket to take Jack across the world to drag shows of the current age. “I know I could call Jack at any time day or night and he would be there for me. It doesn’t matter how much older he is. He’s got an unbelievable spirit,” Solaris says. Michelle Handelman, a 2011 Guggenheim Fellow and 2010 New York Foundation for The Arts Fellow, met Jack through artist/performer Chris Tanner. The young photographer has had Sabrina sit for numerous portraits. “I would do anything for Jack,” she tells me over email. Another artist, Zackary Drucker is well known in and outside of drag circles; he tells me similar things. The common element running through all Jack’s conspirators is a sense of support. Everyone consistently tells me Jack would do anything to help him or her work, and vice-versa. He never takes money. Jack does it for the sheer joy of the experience.

“I may be an old fart but I don’t look through the rearview mirror,” Jack says. “Everyone is always mentoring me. These kids are so smart.”

Back in the day, Jack had other friends. 'Hunt' was short for S. Thompson, Jim Morrison was too wasted one weekend and Jack ended up not liking him. Abbie Hoffman and the Weather Underground were all right but Jack didn't know what they were up to at the time. He and Brian Goodfellow allegedly bailed Keith Haring out of jail the night he was busted for Crack is Wack, one of the only surviving of Haring's public works. Jean-Michel Basquiat was an incredible force, Jack says. He still sees Yoko Ono when going for walks in the park. He hung out with Patti Smith when she still worked at The Strand, a fact she doesn't hesitate to bring up to Jack today. He was a well-known consort of William S. Burroughs during the years he lived in the Chelsea Hotel. Andy Warhol was always lovely to him.

“Hello Andy, I’m in the Chelsea Hotel,” Sabrina says, punctuating each sentence with a long pause for Andy’s response, a rotary phone pressed to her ear. “Yes Andy, the Chelsea is still standing.” She’s onstage at a gallery show in the Grand Ballroom of the Chelsea Hotel, November 2006. She wears a stringy silver cocktail dress, garish purple eye shadow, mint green bracers, baby blue pumps, and silver stockings. The stage is littered with roses and empty bottles of Jack Daniels. “I know,” she goes on, “it’s beyond human comprehension. No, Andy, it’s not a Shining Palace on a Dark Street no more. Its bright sign has been eclipsed by all of these monstrosities. God, Andy, remember all of the fun we used to have in the lobby. You don’t? Well I do! Yes Andy, I know that Valerie Solanas used to live here in the Chelsea, but I didn’t want to bring that up.”

There are many things Jack tells me that I can’t verify, whether because he was making things up—which never seemed to be the case, given how frank and forthcoming he was—or because the people in question had long since died, or because there was simply no record of his exploits. Jack described to me a situation in 2000, when Hillary Clinton was running for New York State Senate, dressed as an old woman, petitioning signatures for Clinton’s campaign. This particular night would lead to him to start really putting himself out there, in his late sixties. He went to a bar in the East Village, says the “Chubby Chasers” and “Tranny Chasers” steered totally clear of him—this was incomprehensible. It led to him refining his look, putting on fishnets and heels, and going out to pick up these people, just to prove that he could. The money came later. (Jack is a well-known campaigner for Clinton. He’s jaded politically on everyone else, though he did throw a fundraiser or two for Obama.)

Now, that being said, it seems Jack is an incredibly effective example of gay rights activism of the last few decades, a figure both politically and artistically still active and massively influential to this day. And yet, as he ages, he has gone largely forgotten in this canon, not to mention that RuPaul, whom Jack claims to know, has essentially aped his entire pageant format for small-screen profit. (A long-time representative of RuPaul wrote to me saying he had never heard of Jack, but declined to ask Ru directly of Jack’s existence. Whatever kind of veracity that brings to Jack’s claims is unclear.)

Sure, Jack retired from hosting his contest two years before the Stonewall Riots. But the implication of his and other drag and trans-culture figures being even still slightly marginalized points to an overarching theme of hetero-normativity, especially in the accepted images and roles of this struggle. Even when The New York Times is citing the diversity and importance of the gay vote in the 2012 election, it’s not often you see any but two, clear-cut strictly Male or Female people as examples of the issue. Androgyny still flags below the surface. Maybe that’s just where the androgynous want to keep it.



There’s a naked man on stage who moments ago was a clothed woman. On the baldhead of the person is a smattering of duct tape that looks like a strange crown at a glance. But the black-and-yellow bob wig at the feet of the performer reveals the tape’s function. The person has a dollar billed stuffed in her mouth, lips smeared with bright red lipstick. Her cheeks are smattered with red as well, the eyelashes well over an inch long, like black and gold butterflies. A bright gold and black choker. Earrings that look like crystalized dandelions. Jack’s body is taut and muscular, despite his age—this is during a November performance in 2011 at the The Leslie-Lohman Museum of Gay and Lesbian Art. The event and exhibition celebrates Jack’s life and career, the first one of its kind. And he’s made no small fuss of his appearance. Again: his black cocktail dress is in his hand, weakly attempting to cover his penis. His eyes always look so bright. The crowd is not large, but carnivorous. And Jack eats up every second.

It’s much more subdued at home.

Some days, it seems hard for Jack just to function as a man. If you catch him at the right moment, there are sores visible on his face and it’s hard to understand what he’s saying.

“Sometimes I feel like a confused boy trapped in this old-fart body. I was never supposed to be this old,” Jack says on a Tuesday afternoon, walking around his apartment, pouring vodka into a vanilla Ensure at one point. “I’m a bad boy and bad boys were never supposed to live this long.”

He’s in tight black jeans, a pair of black leather trainers, and a garishly adorned windbreaker that could be Givenchy, if I wasn’t quite sure of Jack’s disdain for most identity politics of fashion. “Do you know who made your shirt?” He asks with mock contempt.

He’s looking for something, talking about his age as he walks around. He finds it: an orange bath towel.

“What the fuck am I doing here? It’s a bite of a reality sandwich, man.” It’s early and he still doesn’t have that perfect smile filling his face yet.

It’s a process to put them in. Jack has it down to a science. The towel across his lap. Two white wafers of Sea-Bond, trimmed to fit his mouth, a gob of pink Fixodent between them. A sewing needle pierces the Fixodent-and-Seabond sandwich to seep the goo into both sides. The sandwich goes into a small tub of water to soak. More pink dots of Fixodent on the top and the bottom sets of the teeth. Cleaning up the dripping water with the orange bath towel. The wafers mold into the top of the dentures. Then in the teeth go. It takes about 30 minutes.

He then starts rolling a massive joint. It takes far less time.

“What are you talking about?” He replies when I tell him I have another appointment I need to be sober for. “This is for you to take away. Share it with your friends.” And then there’s that wolfish grin.

When I tell Jack I have to leave, he gets up, gold chains swinging from his neck. He walks around his desk and puts both his hands on my shoulders.

“Hey,” he says to me, entirely too earnest. “Just keep doing what you’re doing. I love you, man.” He gives me a big hug and tells me again that the door is always unlocked. As I head down the stairs, he calls out.

“You’re the boss, applesauce. That’s the majesty of the children.”