(Photo by Preston Meneses)
There’s a reason Sasha Colby is billed as your favorite drag queen’s favorite drag queen. She probably is.
The entertainer has captivated audiences for over two decades, discovering the art form at 17 and never looking back. She met her drag mother Cassandra Colby soon after, who helped cultivate her craft and introduced her to the drag pageantry circuit.
It was never the same. Colby won Miss Continental in 2012 and amassed a significant following long before competing on the 15th season of “RuPaul’s Drag Race” last year, becoming the first native Hawaiian trans person to ever win the reality competition.
Her reign as America’s next drag superstar ended in April but gave Colby her largest audience yet. Last year she emceed a Pride reception at Vice President Kamala Harris’ residence with GLAAD, launched a new ponytail line inspired by her iconic looks and this February embarked on a 22-city, solo North American tour.
Next up, the entertainer headlines St Pete Pride’s Friday Night Concert at Jannus Live June 21, bringing her meet-and-greet to St. Petersburg for the first time. Watermark spoke with the one-time Orlando resident beforehand about what fans can expect.
WATERMARK: What drew you to performance and drag?
Sasha Colby: I don’t know if I was drawn to it or it just kind of happened. I guess it’s been a product of my Y2K generation, watching [MTV’s Video Music Awards] and “Total Request Live” and seeing pop stars; there was a lot of heavy dancing required to be an artist back then. That was something that I aspired to be and then I actually joined dance, which really incubated and nurtured my love for performing, dancing and drag.
Who were some of your influences?
My drag influences were pop stars like Janet Jackson, Madonna and Whitney Houston. They gave goddess energy and that’s something that I was drawn to naturally. But also, a lot of the women on my island that I grew up with — these beautiful Hawaiian women, beautiful trans women. I just love a strong, powerful woman and those are the women I grew up with in my family. So those traits have always stuck with me and that’s what I like to exemplify when I’m on stage. Maybe she has a crack or has been through things, but at the end of the day she’s always strong and powerful.
What led you to pageantry?
I think what led me to pageantry was that before “Drag Race,” the only way you could make a living doing drag was to get into the pageantry system. I remember watching Miss Florida pageantry as a kid — back in the 80s and 90s, it was the biggest national pageant held in South Florida in South Beach that a lot of trans women would be in — and watching Continental, watching all these pageants. That’s what really sparked it.
It gave you a sizeable fanbase before “Drag Race.” Why was season 15 the right time for you to compete?
With the trans experience being put into question these past couple of years and the overall climate being very trans exclusionary, I felt there needed to be a moment of queer and trans joy and couldn’t think of a better platform than “Drag Race.”
Historically drag has been a fringe art form that allowed everyone and anyone to express themselves — which is not how it’s always been shown — so I wanted to present my drag on a national platform and raise awareness for this important message. I’ve been involved in the drag community for a long time, so going on the show when I did was really spurred by the need to help shed a light on the trans experience.
Why is that representation so important?
It’s really important to see strong, powerful, queer stories … and just having trans stories being told is really important. Unfortunately, it’s kind of a fad, it’s a cool thing to be doing, and a lot of people can read the book or turn on the show, and then they get to turn it off and go back to their pretty privileged lives … I want to see even more stories about happy trans people that have lived their lives and are full and complex and have great relationships.
What do you think comes more naturally for you, performing on stage or on screen?
I think I like performing on stage a lot more than screen. Screen is like a magnifying glass, it’s really up close and personal. It’s a different way to capture art in that medium and for me, I feel like I’m most effective live in a space where I can create a whole world.
What has international fame taught you about yourself as an artist?
It’s really cool, because drag is a passion of mine. It’s really personal for me to go on a show like “RuPaul’s Drag Race” and bear the love that I have for this art form and then to get recognized. It’s beautiful but it’s wild, because it’s something that I didn’t intend to be the spokesperson for. This is all just a really amazing cherry on top; a huge cherry on top. (Laughs.) I don’t know how to do anything else — all I know how to do is drag and tell stories, and hopefully connect people through performing.
How do you think “Drag Race” has changed the state of drag?
Drag is definitely a machine now, and before it was a fringe art form, created for people who were not accepted in society to be able to have a place to play, live and have a safe space. Now it’s all over the country, all over the world. But that grittiness and rawness of drag — that punk idea of drag — has to be found when you go out there, it can’t be really seen on TV. It still goes back to finding those drag spaces where girls are working really, really hard despite the mainstream recognition that drag has.
There are so many hardworking, local drag queens that are unrecognized, underpaid and really are practicing what drag is in its purest form. I think that’s what we have to remember as drag queens: what is your intention of doing drag? To get on “Drag Race” or to do art? A lot of times that decision will help with your longevity, how well you do on “Drag Race” and how successful you are after.
What was your tour like?
Doing “Stripped” was a very fierce experiment. I’ve never had the opportunity to create my own show, curating the people I wanted around me and really pouring my heart out into a project that I didn’t have to compromise for anyone … This was purely just for me and there was so much love from all these cities that I got to go to. I felt exhausted each night but exhilarated at the same time. I can’t wait to do another show like this again in 2025, hopefully.
You also launched a ponytail collection. How did that come about?
Well, you know, I’m known for my ponytails from Continental and “Drag Race” — and I know the power that a ponytail can have. (Laughs.) I wanted to bring that in an affordable, accessible, easy-to-use ponytail for your every day use. I love seeing it being worn at my shows, I love getting tagged when girls wear it. I love it when drag queens get creative with it. It’s really, really fun. We’re now looking at two lengths, there’s a 28 and a 36 inch, and the 36 inch is very nice and lush and gives a little layered effect. We have four colors and we’re also going to expand … so just keep a lookout for the future.
Last Pride you were invited to the vice president’s residence to celebrate. What was that experience like?
It was really nice to be invited. I love GLAAD and they approached me and said that they were looking for an emcee and that I was the first person they thought of. It was really gratifying, sweet and humbling to be put in a place next to so many powerful people; movers and shakers in our government, all of them who are queer advocates or are queer themselves. It was really cool to mingle with the people that are really striving for hope and equality in Washington.
Why are you excited for St Pete Pride?
I have actually never been to St. Pete. I’ve been to Tampa, I lived in Orlando and worked in Jacksonville. I literally have worked everywhere, so to be able to have my first performance in St. Pete be at St Pete Pride is pretty exciting … it’s going to be a great time.
Do you have any Florida memories you want to share?
None that I can legally share. (Laughs.) Just that Orlando has been such a great city, I was there for about two years and worked everywhere. I got to work at Pulse and Southern Nights when it was Revolution, that era, and Parliament House and Hamburger Mary’s and The Brink — and I went all over Florida, being able to road trip it north, south and west to do drag all up and down the state. I still have best friends there that I love to this day.
What can fans expect from your performance here?
They can expect a lot of goddess energy. A lot of sexy and powerful moments, a neck crack or two. A little ponytail flip. All the things that you come to love at a Sasha Colby event — throw me a dollar, it might get stuck in my booty and we’ll have a great time.
Florida has passed a number of anti-LGBTQ+ laws in recent years. What message do you have for your fans?
For Florida, it’s just been such a rough one and being a resident of Orlando for a few years, I still have a lot of friends there that I keep in contact with. It’s a rough time to be queer and to feel all this legislation happening in the state. It’s a hard time, but we just have to band together even stronger as queer people and express our queer joy and find our happiness. Our happiness is with our community, so sticking together and understanding that there is power in numbers, we’ll get through this.
Sasha Colby headlines St Pete Pride’s Friday Night Concert June 21 from 6-10 p.m. at Jannus Live, located at 200 1st Ave. N. She’ll be joined by the 2024 St Pete Pride Royal Court, DJ Manne, Daddy Sparkle, Selena Witaweena, Brianna Summers, Phaedra E. Rose, Dante V. Lane Cardoza, Charlotte Diamond Star, Autumn Vee, Rockell Blu, Kamden T. Rage, Ceazia Giovanni Kreshé, Sky Lemay, Jay Miah, Keirra Ka’oir Summers, Imani Valentino, Burly Nathan, Mr. Vyn Suazion, Daphne Ferraro, Alice Marie Gripp, Mr. Gripp, Jared Vasquez and Yummy’s World.
The event is recommended for those 18+. Tickets are $25 and available at StPetePride.org. For even more information, pick up a print edition of the official St Pete Pride Guide in current issues of Watermark and read the digital version here.
