How Chicago became a 'safe haven' for the drag queens who call it home
For the first time in her life, Kylie Lefever feels like she belongs.
She and her drag persona, Kylee Hunter, moved to Chicago in 2022. She'd been living in Florida at the time, and performing had gotten too hard. The vitriol and legislation targeting the state's drag performers and the larger LGBTQ+ community had become too much for her, she said.
So she came here, looking to grow her career and put down roots after living like a nomad for much of her adult life.
"It's the first time I've really had a safe space or had a place where I could be myself and people weren't judgmental or people didn't try to conform me into what they wanted me to be," the 32-year-old said, tearing up. "Whatever I was bringing to the table was good enough. And I've never felt that in my life before. Like in anything I've ever done."
Lefever is just one of many drag performers who've found a home in Chicago's booming drag scene. The city is not only a premier place to practice the art; it's become a haven for drag queens, several performers told the Sun-Times.
"Chicago is a safe haven and it's the land of opportunity," said Anthony Taylor, who performs as The Vixen. "There's enough room for a new queen to come in and make space."
Watching Chicago drag history unfold
Drag in Chicago dates back to at least the late 19th century. After the 1893 World's Fair, people from around the city would gather in spaces like The Dill Pickle Club on the Near North Side to see performers put on their shows. From political fundraisers to cabarets, the scene only grew in the decades that followed.
Matthew Harvat, 59, has watched the scene evolve and grow for more than two decades. He first started performing in 1995 while working at Roscoe's Tavern in Northalsted. The bar, a longtime performance space for drag queens, was doing an all-staff drag show for charity.
The show was called "Boyz II Women," and everyone from the bouncers to the barbacks performed.
Up to that point, Harvat had resisted drag. He had been encouraged by other drag queens many times to give it a try — he was a theater kid with high cheekbones. Though his upbringing told him it was "too gay" and "emasculating."
But, taking inspiration from actors like Tony Curtis and Jack Lemmon who did drag in "Some Like It Hot," he decided to give it a try. He borrowed a dress and a fur. His future drag mother did his hair and make-up. And then she got on stage and performed Natalie Cole's "I Got Love On My Mind."
"I thought, if I'm gonna do this, I'm gonna do it right," he said. "When I turned around, there was a collective gasp from the crowd, because she looked pretty!"
Harvat's career blossomed from there. He started performing regularly as Circuit Mom at clubs and bars to bigger and bigger crowds.
"It was very meteoric," he recalled. "I was bringing a little production to my performances, like costume changes and back-up dancers. Not a lot of people were doing that in Chicago at the time."
When it comes to drag entering the mainstream, "RuPaul's Drag Race" made it all possible, becoming a household name over 16 seasons.
"Drag itself started getting more social acceptance through RuPaul. RuPaul really is a pioneer in this whole thing," Harvat said. RuPaul's influence was everywhere, down to the types of wigs queens wore. No more shake-and-go wigs, it had to be a lace front.
The series blew open doors to greater acceptance in popular culture. Lefever said she first saw a drag queen while watching "Drag Race" with her college roommates. After growing up in a conservative household in rural Lancaster, Pennsylvania, that was an awakening for her.
"I already knew I was gay. Little did I know that was just the beginning," she said.
With more acceptance came more ways to practice the art. There are seemingly limitless options for drag styles: pageant queens; comedy queens; camp queens; punk queens; avante-garde queens; bearded queens.
And Chicago helped lead the way.
"Chicago was at the forefront of different types and styles of drag that really came forward with flames and arrows and cannonballs and glitter and unicorns," Harvat said, pointing to the late legendary drag queen JoJo Baby as a leader of the city's scene.
These days, there are ample ways to watch a drag performance in Chicago, Harvat said. Venues like Roscoe's, Hydrate and Sidetrack have regular shows. Even the Walnut Room, the posh restaurant on the top floor of Macy's on State Street, recently hosted a drag brunch.
"It's everywhere," Harvat said. "You can't swing a lace front wig in this town and not hit a drag queen."
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Leaders in the scene have worked to make Chicago drag more inclusive. The Vixen, 33, who starred in Drag Race's 10th season, has worked to make the city a place for local Black queens to thrive, particularly with her popular drag show Black Girl Magic, which she started in 2016.
At one point, she, DiDa Ritz, Lucy Stool and Shea Couleé — now all well-known performers — were among the few Black queens performing on Chicago stages.
"There were very few times that we were in the same room. We were still being tokenized on the lineups and separated," said Taylor, who currently lives in New Orleans. "Once we had those opportunities to be in the same room, above everything, we realized how good it felt to just be seen and have that camaraderie with someone who understands the struggles that you're facing in the community as well."
These days, it's easier to find more than one Black queen at a show's line-up, a point of pride for The Vixen.
"When I started producing shows, the thing I wanted to hear at any show and the thing that has always touched me is ... is, 'I came because I knew you would be here and I knew it would be okay,'" she said.
"I think a lot of drag queens in Chicago have become that beacon," The Vixen said. "And because there's so much variety in the types of drag in Chicago and depending on the queen, you know your freak flag is safe."
Rock Evans, who performs as Miss Toto, moved to Chicago from Miami in 2019. They saw Chicago as a place to advance their career, and to be around "like-minded people" who'd push them to learn more about themselves and the art form.
As Miss Toto, she started out as a "bodybuilder gender-bending monster." Now, her persona is more complex, blurring more aspects of femininity into her performance.
"Chicago was in its Renaissance at the time and it really felt like — and I still think this is true — like the epicenter of the drag scene," Evans said.
They now feel a sense of belonging among Black queens working in the city.
"I wanted to be surrounded by specifically Black drag artists because they do exist in Miami, but I was finding much more community and friendships with the Black queens that existed here," Evans said.
Chicago became a place to grow for Evans. For Lefever, too. The scene welcomed them and built them up like so many queens before them.
"Chicago really has their scene down," Lefever said. "I had my opportunity to lay a foundation and get some contacts built, but the opportunity that I have now is really to take full advantage, on an income and artistic level, of everything this city has to offer."