Sasha Colby isn’t just a performer—she’s a powerhouse of creativity, resilience, and raw truth. Raised in Hawaii, she found early support in Ms. Noguchi’s art class and her childhood dance studio. From those roots, she’s spent her life using art as both survival and celebration. Whether with a paintbrush or a fierce strut on stage, Sasha creates space for people to be their full, vibrant selves. As a proud Native Hawaiian and the first trans woman to win RuPaul’s Drag Race, she brings unapologetic authenticity to everything she does. Her current Stripped II tour? It’s not just a show—it’s a revolutionary invitation to connect, imagine, and recharge.
Windy City Times: Hello, hello! How are you?
Sasha Colby: Wonderful, wonderful. I’m doing okay—it’s a rough one today.
WCT:Great. Tell me about the upcoming tour this fall.
SC: This is Stripped 2. Last year’s Stripped was my first real entry into expressing my thoughts and my mind on stage. Stripped 2 continues that theme—same minimalist format, no overproduction, just a blank canvas and the freedom to tell stories.
People buy tickets expecting a drag show, but they leave realizing it’s something more. It’s abstract storytelling mixed with performance. This time, I’m creating a fantastical world on stage—an hour and a half where people can forget their troubles, recharge, and maybe leave with a little hope in humanity again.
The first Stripped was about my own life; this one includes broader queer and trans stories—universal experiences that others can connect with.
WCT:Beautiful. You’ll be performing in Chicago at Thalia Hall, and at Seattle’s Moore Theatre.
SC: Yes! I’m actually in Seattle half the time. I live in L.A., but I’m here a lot.
WCT:You’re in a polyamorous relationship, right?
SC: Yes—just three of us: Ben and his partner, Lee. We’re all dating each other.
WCT:A little triad! I bet you’ve gotten advice from Derrick Barry.
SC: (Laughs) It takes a village to love a drag queen.
WCT:So what’s the secret to making it work?
SC: Lots of communication and checking in. Polyamory still carries stigma, but for me it’s about strong, honest connections and autonomy. I’ve been in relationships where I had to hide parts of myself—especially my drag. Being poly and often long-distance allows me to maintain love and connection without losing who I am. We just check in, take a “poly pulse,” and keep moving together.
WCT: Love that. Congratulations—you’re the first trans woman to win the mainDrag Racecrown!
SC: Yes! It’s such an honor. I watched the show from its first season as a working queen who’d already won Miss Continental, never knowing if there’d be space for someone like me. Now seeing so many trans women thriving on Drag Race—it’s amazing.
WCT:It’s incredible how many queens are coming out as trans now.
SC: Exactly. When the world shows acceptance, it’s easier to be authentic. Trans people have always existed; now we’re finally visible.
WCT:And you’re also the first Polynesian winner.
SC: Yes, I’m the first Native Hawaiian on the show—and to win representing Hawai‘i is surreal. The Pacific Northwest feels like home too; there are so many Polynesians in Portland, Tacoma, and Seattle. It’s beautiful seeing people who share my roots feel seen.
WCT:I also read you have Irish heritage.
SC: Yes, my mom’s half Irish. I recently got to visit Belfast and Dublin—and let’s just say my Irish side definitely shows when I drink!
WCT:Same here! That’s why I try to avoid it.
SC: (Laughs) Double trouble—Irish and Hawaiian!
WCT:Another fun fact—you’re Chappell Roan’s drag mom!
SC: Yes! She called me out at Coachella last year. We started talking, then I saw her perform at Seattle’s Block Party. Watching that crowd sing “Pink Pony Club” together—it was magical. She’s such a strong, sweet example of queer resilience. She even sent me Mother’s Day flowers!
WCT:That’s so lovely.
SC: It is my day!
See Sasha Colby this Friday, Oct. 10 at Thalia Hall, 1807 S. Allport St. For tickets, please visit Sasha’s website at sashacolby.net.