Finally, trans performer Sasha Colby’s persistence pays off, with a ‘Drag Race’ win

Sasha Colby wears a gown and sits in a rooftop garden.
Sasha Colby moved to L.A. nine years ago to be on “RuPaul’s Drag Race.” She finally made it to the show this year and won — the first trans performer to win a regular season.
(Yasara Gunawardena / For The Times)

Compared to her 14 predecessors, Sasha Colby has had the longest road to capturing a crown on “RuPaul’s Drag Race.” The first trans woman champion of a regular season, Colby arrived in Los Angeles nine years ago with hopes of eventually getting on the competition series after spending a good chunk of her 20s in Chicago — a city where in 2012 she made a name for herself winning the most prestigious drag competition besides “Drag Race,” the Miss Continental pageant.

The Hawaii native competed for that esteemed title four times over seven years. That process taught her valuable life lessons such as figuring out her brand, a skill she says definitely helped her with “Drag Race.” However, it was her approach to a staple of any pageant, the question-and-answer session, that changed her life.

Every time Colby reached that particular moment in the pageant, she feared people would judge her if she was too forthcoming. It was shame over an addiction to meth from the ages of 19 to 23 that she didn’t want to discuss. Colby says, “When I finally did win was when I finally spoke it, and I said that I was battling a drug addiction, and the positivity that came out of that and finding sobriety through that.


The attendees and drag queens of RuPaul’s DragCon LA didn’t disappoint when it came to serving looks this year and reminded us of the self-actualizing power drag can have.

May 13, 2023

“I realized that the most powerful thing is showing your vulnerability to make other people stronger,” Colby says. “And I really try to do that a lot with myself and my story and my presentation on ‘Drag Race.’ And I feel that it’s really this connection that a lot of people make when I travel. [Fans are] just bawling to me, and it makes me feel good that other people can find strength in what I was once ashamed about. Isn’t that exactly what being trans is, too? We’re walking with this shame of something that’s actually our biggest gift.”

Despite being called “every drag queen’s favorite drag queen,” Colby began to wonder if she’d ever get a chance to compete on the global “Drag Race” platform. Although a number of contestants had come out as trans while on the show, the first trans winner, Kylie Sonique Love, won the “All Stars” edition of the program in 2021, almost 10 years after Colby won Miss Continental. Colby admits that at times she wondered if it was time to get a day job.

She notes, “There were moments where I was like, ‘Maybe I’ll just be happy choreographing for my sisters that have been on “Drag Race,” or maybe I could be a part of at least the machine if I can’t be on the show yet.’ So, that was definitely something I was thinking of. But I mean, I’m just so stubborn. I could not see myself doing anything else, and thank God my stubbornness paid off.”

Sasha Colby cups her face in her hand as she leans on a low wall.
“There were moments where I was like, ‘Maybe I’ll just be happy choreographing for my sisters that have been on ‘Drag Race,’ ” Sasha Colby says of nearly giving up her dream of being on “RuPaul’s Drag Race” herself.
(Yasara Gunawardena / For The Times)

Colby says her OCD seeps into her drag process and when she got cast on the program it was as if she was an athlete training for the Olympics. “This was my World Cup, and I treated every aspect, my body, mind and spirit. I tried to make everything pristine and at a point where I could compete and have a lot of self-confidence. And just getting the package ready? Yeah, I put myself through it.”


Noted for her talent as a dancer and live performer, even her most ardent fans were curious how Colby would tackle some of the other key aspects of “Drag Race,” in particular the improv and acting challenges. Participating in a comedy musical with Season 9 winner Sasha Velour a year prior gave Colby a bit of a boost. She also took advantage of living in L.A. by recruiting her best friend’s husband and his colleagues, members of the Groundlings, to prepare for the notoriously difficult celebrity impersonation challenge, “Snatch Game.” It all clicked, and Colby steamrolled through the competition.

Although she jokes about the joy of the show’s $200,000 cash prize, she is well aware of the responsibility of not only winning “Drag Race,” but also being the first regular season trans winner. Especially in this political climate where a public drag ban was passed in Tennessee and anti-trans laws are going into effect in conservative states across the country.

Despite an ongoing culture war, L.A.’s thriving drag scene is bursting with queens, kings, things and rebellious spirit.

June 6, 2023

“I think trans personalities, trans celebrities, people who are in the spotlight and happen to be trans, our lot in life is kind of to be the teacher, to be the activist,” Colby says. “And for me, I don’t want to completely be the activist girl where all I’m talking about is the negative statistics. I would love our allies to do research about that so we don’t have to keep on saying it. Maybe allies could start speaking for us, which would be great.”

She also finds it odd that something so personal and so niche to the queer community as drag has become a political issue. “I guess it’s a sign that ‘RuPaul’s Drag Race’ has been so pivotal in this last decade of pop culture,” she says. “But it’s very weird to know that something that you take as yours, something that the cishet community practically forced queer people into making as their own art form [is under attack].”

And with a glimmer of optimism, Colby adds, “I am blindly manifesting, blindly just hoping” that all the laws that are passing won’t stand up in court. “There can’t be that many bigots in the world.”