By: Sofia Esparza
After eight hours of Zoom meetings, coordinating resident visits and troubleshooting the winter ritual of bursting water pipes, Joshua Bilskemper clocks out of his last shift of the week as a property manager in student housing. He speeds home through 20 minutes of rush hour traffic to take a nap and get a bite to eat.
Then he puts on a wig, glues his eyebrows down underneath makeup and throws on a brightly-colored dress.
He heads to the Gay 90s nightclub in downtown Minneapolis, walks up two flights of red-carpeted stairs to the LaFemme Lounge, and walks backstage to a bubblegum pink dressing room.
Along the left wall hang dozens of intricate costumes bejeweled with gems and sequins. The closet is thick with ruffled sleeves and colorful dresses and the back of the dressing room door is adorned with costume jewelry in every color imaginable. At the center of the room, a studio mirror sits complemented with plaques from competitions and lit by white LED light bulbs that are ideal for doing makeup.
It’s a room fit for a queen. A drag queen.
Bilskemper’s weekends are for hosting and performing under the stage name Alotta Shots with the Ladies of LaFemme, traveling for shows, and pulling in cash tips on stage. But he knows other lives, first as a middle school science teacher and now as a property manager at the Pavilion on Berry apartments in St. Paul since 2024.
Bilskemper, 33, started drag in 2016. For years, his friends tried convincing him to perform drag because of his fun personality, but it was the tragedy of the Pulse nightclub shooting in Orlando, Florida, that finally pushed him to do it.
Bilskemper was on a nearly two month-long road trip around the southern United States when 49 people were killed and 53 injured at the gay nightclub in Florida. It was the second-worst mass shooting in U.S. history. While he was visiting Savannah, Georgia, he stopped by a local fundraiser put together by the LGBT+ community in response to the tragedy.
“There were drag entertainers there, leading the way and they kind of inspired me,” he said. “This is entertainment, but also these people can be leaders with the community and that was something really exciting for me.”
Once he was back home in La Crosse, Wisconsin, he entered the 2016 La Crosse Pride drag competition. He didn’t even have a stage name yet, but he won.
And the next morning, his job teaching seventh grade science awaited him. As his life as a drag queen started to take shape, he realized that it probably was taboo for a small-town teacher. But what finally drove him out of the classroom had more to do with his view on education.
Bilskemper said he defines himself as the teacher who always had animals in the classroom. He brought in turtles, bunnies and snakes. He recalled a time when he brought baby bunnies, two of which went missing by the start of the first period. He spent the class period panicking, just to have some of his students approach him at the end of class and pull out the bunnies from their pants pockets.
“I told them to never do that again. I was one of the few teachers who actually tried to hold kids accountable and help them learn life lessons in the present,” he said. “I just felt like I was the only one that seemed to care, and I can only do so much.”
Bilskemper needed a change from the small classrooms in Grand Meadow, Minnesota, where he started his teaching career, and got a job teaching middle school science in White Bear Lake in 2018, the same year he moved to Minneapolis.
His seventh graders knew about his career in drag and often brought it up to him that they looked up his drag Instagram account.
“I’d always tell them, ‘And what about it?’”
In teaching, you have to entertain and interact with all types of personalities and there’s a level of performance, according to Bilskemper. “If I can entertain 30 eighth-graders, I can entertain a bunch of drunk adults.”
Bilskemper was in drag for two years, competing in weeknight shows, getting small bookings here and there and trying to get his name out there, until he got his first consistent job in drag.
He said he was far from polished when the Gay 90s’ show director reached out to him and asked him to host the Wednesday night amateur drag competition, So You Think You Can Drag.
That gave him a chance to work with the full-time cast of Ladies of LaFemme, the longest-standing drag show in the Midwest. After a year and a half of occasional bookings with the cast and major changes in staffing, he was asked to be a part of the full-time cast.
Three years later, he found that he needed a bigger change than transferring school districts. After nine years in education, he finally resigned from White Bear Lake two weeks before the start of the 2023-2024 school year. In his view, the school administration cared more about students enjoying their time than being reprimanded.
A week before he quit teaching, he was hosting So You Think You Can Drag. He told the crowd that he was desperate for a new job.
“I was doing everything to just get out of teaching because that was so miserable and I hated my life,” he said. “So I was like, is anyone hiring?”
Sure enough, Jess Smith, regional manager of Stadium Village Flats near the University of Minnesota campus, was looking for a new assistant manager. Josh had previously worked as an RA in college and felt up for the challenge.
“I got a napkin and I wrote down my name, number and email and I was just like, here you go, message me, let’s do something.”
He interviewed and before he knew he got the job, he quit teaching. For 24 hours, he thought he was jobless. He was offered the job in student housing two days later.
In November 2024, he was promoted to property manager at another apartment complex within the company. He now spends Monday through Friday doing property walks, speaking with residents and planning outreach events.
His day job has its rewards: He has a steady paycheck, it’s less physically demanding and more likely to see promotions. Drag has become a way to express himself outside the corporate landscape.
“I’m passionate about drag because it gives me an outlet to be creative and to let loose. The more you are a part of it, the more you realize what it can be,” he said. “Whether it’s being a community leader helping to raise money for organizations, providing people an outlet to get away from their crazy and hectic lives or just laughing and enjoying community.”
“You’ve got one shot at this thing called life. It’s important to make the best of it.”
His weekends consist of late-night drag shows in the Lafemme Lounge and trips to Fargo, North Dakota, for performances, where he can make up to $2000 a night.
Doing drag is hard on the body. Performers wear heavy costumes, high heels, and thick makeup underneath bright stage lights for hours at a time. Like many entertainment professions, it is also difficult to maintain a livable wage, Bilskemper said. The five-hour drag shifts he does Thursday through Sunday are in effect another full-time job.
The way he balances both? Naps and mental toughness.
“Entertainment’s one of those things where all eyes are on you and it gives you a glimpse into what famous people are like. You always have to be in a good mood,” he said. “There might be times when I’m hosting and I’m dead tired. But the moment I’m on, it’s ‘Welcome everybody!’ It’s one of those things where you really have to conserve your energy.”
There are lessons to be learned. It’s important to try everything and put yourself in experiences that might be challenging or change your perspective, Bilskemper said, adding that he has grown through performing in drag.
“Surround yourself with people who really appreciate you,” he said. “Don’t allow others to dictate how your path in life should be. Hold your good friends close and appreciate things in the moment. You get one shot at this.”
