Owl Hollow sits on a hill surrounded by trees in Hazelwood. With rubble from demolished row houses scattered around it, the house feels far from the glimmering skyline, but it’s only a short bus ride away.

The yard looks a little like the apocalypse happened here, but years ago, and now the people have moved on. In a fire pit burn the remains of cereal boxes, coloring books, and fruit crates, waiting to consume damp, winter-swollen logs. Hula hoops, rusted typewriters, and worn, faux-leather couches litter the yard. People perch on anything they can find, enjoying the late afternoon sun and mugs of tea. From inside the house, the blare of guitars leaks through the poorly-insulated siding. From the street below, rap music bumps gently. The wind gusts sharply, though it’s already April, and I tuck my notebook into my bag and head into the house.

I walk through the kitchen, where a few people have gathered around a curry-scented pot of stew, and into the living room, red and gold with afternoon sun. On the burgundy walls hang instruments, paintings of faceless people, dream-catchers, and shelves upon shelves of books. On the floor, Josie Ashkar sets up her merchandise. I sit down opposite her, introducing myself by my online handle, the only way we’ve communicated until now (hers is @princessjafar). We give each other our chosen names, but not our last. She doesn’t know mine, and at this point, I don’t know hers. First names only. They’re all that matter.

I look down at the table, on which she’s arranged her collection of memorabilia and nostalgia items, mostly from the 90s. I ask what she’s vending; she replies, “I usually say I’m selling back your memories.”

She’s a vintage curator, the kind you usually find on Instagram or Etsy, but today she’s vending at a local house/DIY venue, which is hosting a “Psychedelic Garden Party.” She’s dressed for the occasion, with pink trousers, a blue, white, and pink striped shirt, and a vintage, royal purple McDonald’s cap over her long, dark hair. Outside near the fire, a clown in turquoise silk and white lace sells terrariums and potted plants. A local band tunes a guitar behind me; someone taps keys on the piano. In front of me, however, is the Princess Jafar Bazaar: an arrangement of old newspapers, Happy Meal toys, trading cards, and clothing.

Princess Jafar is Josie’s stage name, which she uses for any professional, performative, or protective situation, which can range from a business meeting to a confrontation with a homophobe. Inspired by the animated Disney movie Aladdin, Princess Jafar is a villain crafted to mirror the “large-scale, graphic” approach Disney takes to its branding. Not only is this drag queen persona designed to grab the attention of millennials missing their youth, she’s also meant to challenge the current narrative about what drag can be. Josie sports a full beard while performing as Princess Jafar, and often forgoes any makeup or body padding. “Drag,” she tells me, “is not confined to a bar. It’s a tool of expression that anyone should feel free to explore.”

She’s much more interested in creating something big, like Elvira, “who not only played the role of entertainer, but also created the content to support” her role. Josie also cites Peewee Herman and Hulk Hogan as examples of entertainers on whom she models herself. She wants people to believe in her persona, “a local villain and media mogul.”

How does she get them to believe? High production value, of course. She’s in the process of making Princess Jafar and the Great Space Chase, which will feature local, underground filmmakers and creators. Josie compares the film to ensemble classics like The Wizard of Oz or The Muppets Movie, as it’s about “trying to find something that’s been inside you the whole time.”

Josie’s work as Princess Jafar also includes a 2018 Pittsburgh Arts Council grant, which awarded her $14,000 to produce four live performances of The Princess Jafar Show: a live variety show inspired by the same 90s nostalgia she’s selling today. The show struggles with contemporary issues, such as workers rights and social justice, from the perspective of a trans Disney Princess of color. So far, she’s produced a few episodes of The Princess Jafar Show at the Kelly-Strayhorn and Glitterbox Theatre’s.

The scope of her art ranges from live productions to hip-hop music, portrait photography to video production. Throughout her career, Josie’s documentary work has been exhibited around the world, including in The National Queer Arts Festival in San Francisco. More recently, she focuses on video direction for local Pittsburgh artists, as she tries to bring others’ creative vision to the forefront. In March 2018, she hosted the first “Princess Jafar Workshop,” a two-day conference featuring 14 local artists. By platforming queer women of color artists, Josie provided them an uncommon opportunity.

Participants paid $200 for the workshop, modeled on TedX events, but more intimate. The 15-20 person class size allowed up-and-coming artists to develop personal connections with the bigger names in Pittsburgh’s arts scene. janera solomon (who styles her name like bell hooks), the executive director of the Kelly-Strayhorn Theatre in East Liberty, has connections with the August Wilson Center, says Josie, so she was a perfect fit. She also emphasized that Anne Mulgrave from the Greater Pittsburgh Arts Council was a big draw for those seeking grants.

I pause for a moment to take down notes, asking her to repeat herself for a quote. She thinks for a minute, and my partner appears with cookies for us to try, fresh out of the oven. “It’s rose-flavored,” he says, and we try not to burn our mouths on the sticky filling. I had almost forgotten we’re at a garden party; Josie and I had been talking for nearly an hour, the little world of Owl Hollow happening around us. Josie is careful about words, and seems grateful for a moment to gather her thoughts. When I finish my cookie, she rephrases or revises a few times on the particularly pithy quotes. I am happy to oblige — after all, she’s creating something cohesive. Disney press releases go through revisions, so why shouldn’t she edit herself? She understood how she wanted me to see her, and she put that forward. As she told me before, she’s great with an audience.

But what about audiences who aren’t already in the palm of her hand? That’s harder. In tiny DIY venues populated by queer people and punk rockers, she has no problems. But at a performance marketed to the public (read: straight, cis gender people), the vibe can be somewhat different. I bring up performances at Ace Hotel or the Carnegie Museum of Art, where the audience is drawn through advertising, rather than word-of-mouth. Josie brings up the Valentine’s Day Third Thursday evening at the museum, because her monologue hadn’t gone as she planned. She didn’t bomb, but some of the audience seemed like they didn’t quite get it. She got a few laughs, but nothing compared to what she’d seen the weekend before.

“It wasn’t the material,” she tells me, as she’d done the same jokes at an experimental gallery’s Valentine’s Day erotica event. Evidently raunchy jokes about gay dating apps can only go so far.

I first met Josie at the Valentine’s Day party she’s talking about. I arrived late, and I rushed to find a seat in the Hall of Sculpture, where a small stage waited, replete with folding chairs, block speakers, and pink paper hearts. On the right side of the stage sat a diverse crowd of six — the evening’s lovely contestants, and on the left dallied a staff member. This event’s big draw was a game called “Match 412,” hosted by a queer, Black entertainment group called True T PGH. Through their annual Galaxy Ball, True T PGH raised and reinvested over $20,000 into local queer communities of color over the last four years. They specialize in community outreach and protecting and promoting ball culture (think voguing, a la Paris is Burning) in Pittsburgh, but Third Thursday drew a pretty different audience than a house ball might.

CMoA’s evening events draw all sorts of people — parents on date night, college kids, and up-and-coming yuppies — likely because of their diverse, experience-based offerings. Tonight’s explicitly queer event made no difference in who attended, but the rain kept many away.

Like all good theatre, this drag show started late.  Princess Jafar, a statuesque queen in a baby blue sailor suit, stood off to one side of the stage. Her blonde wig contrasted against her dark beard and brown eyes, and she didn’t bother with makeup.  She chatted idly with an acquaintance, absentmindedly adjusting her pink beanie while another True T host set up the sound system. I hadn’t met her yet, but even then she struck me as an unconventional queen — long, lean, elegant, but dressed rather plainly. No sequins, no glitter, but a magnetic persona nonetheless. She seemed at ease with the small crowd. The audience members buzzed, and their voices echoed through the cavernous hall. Above, finely muscled sculptures observed the little crowd of 30 spread out on the white, marble floors, the same type of marble used in the Pantheon.  High art surrounded the room on all sides — ancient architecture, radical photo galleries, and contemporary installations. But on the ground, a crowd waited to see a different kind of art.

A staff member nodded to Princess Jafar, and she flipped her blonde hair, took a swig of her drink, and sauntered to the stage, hips swaying to the loud pop music.  She welcomed the audience, and the cold stone around them sharpened their applause. She started her set with a positive outlook — “I’m cold, I’m depressed, and I’m lonely,” she said, citing after a pause, “snow banks and stilettos don’t mix.” Her monologue shifted to Valentine’s Day, and she asked, “Who needs sunlight when you can get your vitamin D online?” As she related her online misadventures, she recalled seeing Mayor Bill Peduto on a dating app “looking for some shady side piece to get plowed by instead of plowing the streets.” The audience let out a burst of surprised laughter, mixed with a few gasps. Jafar beamed over her microphone, knowing she’d timed the joke just right. She finished out her set with a heartfelt, “Valentine’s Day is within all of you! The anal bead! The dildo! The Fleshlight! Go home, and go fuck yourselves!” and again laughter filled the hall. A few red faces appeared around us. Stage hands appeared to reconfigure the mic, and the crowd hummed once again.

Mica and Lee, the evening’s “Match 412” contestants, sat on the left of the stage with Princess Jafar, while their potential matches sat on the right. Princess Jafar read a statement like “We all know about Becky with the good hair, but what about Becky with the good ______?”  Mica, Lee, and their suitors filled in the blank on their whiteboards, and then a contestant picked three possible matches, hoping they’d written the same phrase. If they did, it was a match; if they didn’t, Jafar asked a new question and the other contestant chose their suitors.

In the audience, people milled about, fetching drinks and chatting while Princess Jafar called out answers.  On the board, Mica wrote “Becky with the good ass,” while the suitors guessed Becky had “good taste in music,” “Spotify playlists,” or “head.”  Those paying attention laughed at “Becky with the good head,” but most seemed uninterested. At the end of the game, no one matched, and many audience members had already wandered off to find entertainment elsewhere.

Fewer than 10 people remained in their seats, and Princess Jafar and the other True T PGH members mingled with those left, chatting with friends or new acquaintances.  The atmosphere transformed from one of forced performance to one of open, authentic celebration. Those uninterested in the performers disappeared, and the stage area became a small party, one whose rowdiness and lewdness made itself at home in dark bars and clubs rather than in the pristine hall of a public museum. Or perhaps, their glamour and ingenuity was too much for the clean, old marble columns and statues. Either way, the music played and our group thought little of setting, perfectly at home with one another. Two femmes danced close, hands entwined, while others looked on cheerily. My partner smiled at them, and together we mingled our way out of the crowd, off to see the evening’s other attractions.

More and more, drag queens are popping up in public spaces. From Drag Queen Brunch to Drag Queen Story Hour to the recent spike in popularity of RuPaul’s Drag Race, mainstream culture seems to have embraced drag as a form of entertainment.  Drag Queen Brunch invites diners to enjoy waffles, coffee, and mimosas while watching a performer sing and do comedy. Drag Queen Story Hours pop up at libraries and bookstores, as progressive parents try to encourage their children to embrace their own gender expressions. The Carnegie Library in Oakland hosts story hours to “celebrate diversity, promote self-acceptance and gender expression and honor each child as an individual.” But can cis, heterosexual Americans view it as art, or is this just a trend that makes them feel progressive?

Regardless of adults’ opinions, the kids are certainly enjoying the exposure. When I meet 12-year-old Max Busch and his dad, Jesse, for a cup of tea in Mt. Lebanon, they tell me the story of how Max came up with his drag name. Max and his mother, Erin Morey, sat on the couch, brainstorming names. They found all the good ones had been taken by other queens, until Erin tried “to say honey suckle while chewing,” Max tells me, and Hunny Chuckles was born. Today, Max wears a t-shirt with a cartoon of Alaska, a drag queen from Erie, PA. He tells me how Alaska used to date Sharon Needles, a queen from Pittsburgh, but that the details of their breakup were revealed on All-Stars, a spinoff of the original Drag Race show starring former contestants. He has a near encyclopedic knowledge of the show — and Jesse often jumps in to add small details Max misses. They began watching RuPaul’s Drag Race with Erin, and soon after, at age 9, Max began dressing up in his mom’s clothes. It seemed a natural progression for him after a school Makeup Club and a make-your-own nail polish kit. Erin encouraged Max by giving him her old clothes, and soon Hunny Chuckles debuted.

Max surprises me when he says he goes to a lot of drag events. Many, especially Drag Race contestant tours, take place at the Carnegie Music Hall, where kids are welcome to attend. Max also participates in Twinkle, an annual LGBTQ+ talent show for young people. Although Max is one of the younger drag queens or kings in the scene, he certainly is not alone. He’s working to start a Gender and Sexualities Alliance (GSA, formerly “Gay Straight Alliance”) at his middle school. He attends game nights at the Pittsburgh Equality Center downtown, but probably most importantly, he’s an activist. Jesse tells me that there aren’t many performance opportunities for 12-year-old drag performers, and that Max isn’t much of a performer anyhow. In the last year, however, he’s made appearances to defend a municipal anti-discrimination law and a city zoning law that limited drag to urban industrial zones.

The zoning law, which defined cabaret performance as including “male or female impersonators,” was completely unenforced. However, the inclusion of such language opened the city up to discrimination lawsuits, as they were technically not enforcing the rule equally. A Pittsburgh Post-Gazette article on the council hearing features a picture of Max as Hunny Chuckles, sitting across from mom, Erin. The article quotes Max as well, and he states: “I just have to say that drag is for everyone. Drag is art. Art is what you choose to show about yourself and reveal truth.” The provision was amended without opposition.

The municipal anti-discrimination law passed by “an anonymous vote,” Max says, and Jesse corrects, “unanimous.” Max looks furious for a second, and then looks back to me. “Was there any opposition?” I ask. It’s my neighborhood too, after all. “Some Catholics,” Jesse says, and we all shrug, a non-verbal what can we do? One of Max’s quotes from that evening, when he stood in front of the council and his community in full drag resonates now as we sit in Uptown Coffee, a popular meeting spot in the neighborhood’s business district: “We are your friends, we are your neighbors, and we are your family.” At a table across from us, a mother sits with her three children, who jabber and squawk sweetly through cookie crumbs and lemonade. Another table over, a tutor teaches a young boy French. The sense of community is as strong as the smell of espresso here. The unanimous vote isn’t a surprise, but neither is the opposition. Public displays of queer identity are at once normalized and repulsed, even among kids.

Max tells me that kids at school are mostly nice, although one of his friends was recently called a “faggot” by some older kids. Another of his friends is excited to become a drag king, and yet another wants to be in GSA, though Max doubts he’s really gay. “You’re not the gatekeeper,” Jesse reminds him, but Max’s statement reminds me of my conversation with Josie.

“Do you think being gay is trendy?” I ask, and Max replies yes. He is, in every single way, a normal kid. His friends come over to play video games every afternoon. He hates wearing jeans. He wields a Nerf gun with deadly accuracy. And, coincidentally, he’s found something he loves by being exposed to drag — just like he loves Samurai movies and Spaghetti Westerns.

Max is right about the trend. Since moving from Logo, an LGBTQ+ network, to VH1, Drag Race has had record-breaking ratings. Whether new viewers see drag as art or trend seems like an irrelevant question when I think about Max and his friends. As drag becomes normalized, suddenly youth have access to a new form of self-expression. But for people like Josie, who makes part of her living from drag performance, the question is more complex.

“How do we profit off the commercialization of our queerness without selling out?” she asks rhetorically. It’s a serious question for many artists who finally see respect from progressive institutions and their liberal audiences, just as the larger institutional outlook on LGBTQ+ people reverts.  There’s an effort to bring queer performance into traditionally straight space, but is there an effort to protect existing queer spaces?

“We don’t want our positive cultural markers to trend because all trends end,” Josie tells me. We still sit across from one another, a table of cultural artifacts spread before us, ready for purchase. Trends end. Sometimes, someone like Josie becomes a collector: she gathers the scraps from vintage stores, garage sales and attics, and she sells you back your memories. I wonder if, 20 years from now, there will be a table like this spread with artifacts of today’s queer youth, like Max’s Alaska t-shirt, for anyone nostalgic for the days of RuPaul’s Drag Race and Queer Eye. At the end of the interview, Josie hands me a signed Princess Jafar print and a pack of Backstreet Boys trading cards. “Backstreet Boys are back, you know,” she says, and I smile.

Editor & Web Producer: Alyse Horn-Pyatt
Photographs were courtesy of the writer and/or the story subjects.