The first time Billy Wilson saw a female impersonator, he was a little freaked out.
“I remember seeing my first drag queen on stage and I was like, oh my gosh, that’s so scary,” he said. “Why would anyone want to do that?”
But 14 years later, the Roanoke resident is one of the top female impersonators in the country. Earlier this month, he traveled to St. Louis , where he donned dresses, put on “the face” of Jessica Jade, his persona, and beat out 51 other competitors from across the nation to become Miss Gay America 2014.
For Wilson, the win culminated nearly a decade of preliminaries and pageants, for which he estimates he has spent about $100,000. For someone who nearly quit after a disastrous first national pageant, it was a chance to finally see his perseverance pay off.
“I always say that the things we want most in life come with the most sacrifices,” Wilson said in an interview last week.
A busy year is beginning for the 32-year-old radiologic technologist. Wilson said he has appearances booked in Louisiana, Ohio and Oklahoma in November. Next year, he will appear at Miss Gay America preliminaries nationwide.
The pageant’s owners will pay for his travel, motel rooms and most meals on those trips. Combine that with a monthly stipend and the money he won in St. Louis, and it could add up to $60,000 in prizes, Wilson said. That still won’t cover the money he’s put in — this year alone, he spent $14,000 on wigs, dresses, dance outfits and makeup .
“This is a very expensive hobby,” he said. “And if you compete in pageants, it’s even more expensive, cause you can’t go there with just cookie-cutter stuff.”
Going out, dressing up
It’s a hobby that started with a dare.
Wilson moved in with a roommate after graduating from Glenvar High School in 1999. He began frequenting The Park, which hosted monthly female impersonator talent competitions.
At the time, his roommate was dating Miss Gay Roanoke, who went by the name Diondra Dee. One night, Dee suggested putting Wilson “in face” — applying makeup to change his features.
“And I was like, ‘Uh, I don’t know, that’s kind of weird’,” Wilson said. “As a dare, I finally let her do it. And I remember we finally took pictures, and I was like, ‘Oh my gosh, this looks really good’.”
His friends persuaded him to enter a talent contest at The Park, where Wilson lip-synced to Britney Spears’ hit “Oops! … I Did It Again.”
“I didn’t win, but I made tons of money” in tips, he said. “Everybody went crazy. The audience loved it. It was kind of like an addiction, and I’ve been doing it ever since.”
Wilson had always wanted to be on stage, to have the spotlight, but he was afraid that people would hear his voice and see his mannerisms, then make fun of him.
“I think hiding behind the mask as Jessica Jade … kind of gave me that sense of being on stage that I had always wanted,” he said. “I became successful at it, and it kind of just carried through over the years.”
Pageant life
After winning a Miss Gay America preliminary at The Park in 2004, Wilson had a rough experience at his first national pageant. A car breakdown outside Little Rock, Ark., backup dancers quitting at the last moment, even a broken gas nozzle on the way out of town conspired against him.
“I vowed I would never come back to Miss Gay America, and the pageantry was just not for me,” he said.
But he monitored later competitions from his computer, perusing “every little detail” online.
“I was a little heartbroken and a little out of place that I wasn’t there. So I finally got myself back together and I went back. And each year, I spent more money than the previous year to hopefully get me closer to winning,” he said, with a laugh.
All the while, his crew grew larger (10 people traveled with him to St. Louis this year), his costumes fancier and his productions more elaborate. He travels every year to Chicago to rehearse with his backup dancers.
It took four hours to prepare his dress and makeup for the evening gown competition, and he had to submit to lengthy interviews.
“At Miss Gay America, they want, like, a business man,” he said. “This is considered a job. You’re traveling all over the country representing their contest, overseeing all these preliminaries, doing interviews, promotional stuff, charities.”
Performances and preparation preclude a private life.
“I always joke and say that Miss Gay America has been my boyfriend for the past 10 years,” he said.
He has decided he’s not going to date anybody who is attracted to him in drag.
“To me it’s like acting,” he said. “It’s like theater. I’m not doing this because I want to be a woman. It’s never been that. It’s like another job. It’s like acting.”
What’s next
As the clock struck midnight Friday, Jade took the stage at The Park — the recently closed gay disco given new life by new ownership — for a Halloween homecoming. The venue’s management, which plans to open full-time next year, declined to allow a reporter and photographer access to the event.
Today, Wilson is scheduled to make an appearance at a filming of the Lifetime show “Dance Moms” at Roanoke Civic Center. Wilson said that the show’s star, Abby Lee Miller, wanted him to speak to girls who aspire to compete on the Lifetime TV show.
“She heard my story about competing so many years at Miss Gay America and not giving up on my dream,” Wilson said.
It’s a story that Wilson would not have told publicly 10 years ago. Since then, attitudes toward homosexuality have improved, though not completely.
After WDBJ (Channel 7) aired a short piece on Wilson and his win, the station posted a link to Facebook. Many commenters congratulated Wilson, but several others were critical both of the station and Wilson’s way of life.
Wilson said that he long ago got over worrying about what other people think. His time in drag has been empowering in multiple ways. For one, money he made doing shows helped him pay his way through Virginia Western Community College, where he learned his trade.
“Life is too short to have to deal with people judging you for what you do,” he said. “Be happy. Do whatever makes you happy.”
Wilson can never again compete for his title. He might consider trying other pageants, though he feels like Miss Gay America is the best of the female impersonator crowns. For now, that is his focus: Hoping people will remember Jessica Jade as a great Miss Gay America.
“I think eventually I will retire from entertaining,” he said. “It’s hard on the body doing this — I mean the dancing, the prep work, the traveling. But I think I’ll always be involved in some capacity in the art form.
“Maybe I’ll come back as a judge at the national pageant or at preliminaries over the years. I’ll help teach the new girls coming up the makeup and costuming. It’s been such a huge part of my life for so long, it would be hard to walk away completely.”
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