It’s Halloween circa 2001. Under the moonlight’s glow, a chorus of giggles and rustling polyester costumes weave a symphony of anticipation. Children skip through neighborhoods, threatening mischievous tricks in exchange for sugary treats. Older thrill-seekers join in on the festivities. They don skimpy clothes in the name of a costume as they take shots of cheap liquor. Among the young adults searching for fun, one stands out, adorned with a flowing blonde wig and a baseball jersey. She carries a bat on her shoulder as she struts to her destination. But this isn’t just a random Jane Doe enjoying a night of spooky merrymaking. This is the birth of drag legend Sasha Colby.

“It was Halloween, probably that same year I saw [my first] drag show,” the latest winner of RuPaul’s Drag Race says as she recounts her first outing. “I’m like, well, I’m going out on Halloween in drag.” A smile forms as she reflects on one of the first moments she truly felt like herself. “I made my own outfit. Really slutty 2000s Y2K moment. It was hot...I had a trucker hat. It was giving Paris Hilton vibes. I cut a jersey, and I made the bottom a skirt. It had a little crop top. I was really feeling like The Pussycat Dolls.”

It was only a few months prior to this late-October fête that Colby had attended her first drag show. Instantly, she was captivated. She sets the scene in Hawaii, where she was born and raised: the show was a 40th birthday celebration for one of the area’s more iconic queens. Colby was only 17 then, so she had to sneak in, unbeknownst to her ultra-religious Jehovah’s Witness family. This was the first time she watched performers transcend the gender binary, but it was also the first time she saw who these performers were—underneath the glam, under the layers of makeup and teased 40-inch wigs. Several of these queens weren’t just performing femininity onstage for the entertainment of others, but instead expressing themselves as women in their everyday lives. 

“There were so many trans girls,” the ageless superstar explains, “So many trans performers, and I was like, ‘You can look like that?’ I already felt trans. I already felt like I was supposed to be a girl at five. When everyone’s hair started growing, I had to cut mine. I just always hung around with girls, and I knew, but I just never thought being trans was an option.”

Colby soon became a regular at the weekly drag shows the bar hosted. To test out the waters before becoming an entertainer herself, Colby began performing as a background dancer for other queens. Having taken years of dance classes, this came naturally to her. But she didn’t want to blend in. Her thirst for performance art wasn’t even close to quenched.

It’s not uncommon for a new performer in the drag scene to have a timid first performance. They stand in the middle of a bar’s small stage, shuffling their feet as they miss words to the campy pop song they are lip-syncing. If they’re oh so brave to wander into the audience, they shakily grab dollar bills from bar regulars. Colby’s first performance couldn’t have been any more different.

Picture this: an 18-year-old Colby takes the spotlight in a white bikini and a skirt long enough to cover the entire stage. The skirt’s billowing fabric hides her two best friends as her background dancers. As the enchanting melody of a slowed-down rendition of Amber’s 1999 sensation “Sexual (Li Da Di)” fills the air, Colby’s lip-syncing prowess takes flight. In a mesmerizing display, her supporting dancers emerge, yet she commands the spotlight. Her stage presence captivates the audience, their eyes steadfastly fixed upon her, utterly transfixed. From the moment she steps into this spotlight, she knows she doesn’t want her womanhood to end on stage. She doesn’t want to return to a life that feels inauthentic. “I didn’t know if I was trans or not. But I knew I never wanted to take the drag off.”

Being surrounded by happy trans women in the drag scene changed Colby’s life. Her drag mother, Cassandra Colby, helped her navigate her transition. “I just saw good examples of trans people,” she recalls. “‘Oh, you don’t have to have this awful life that the media portrays and religion makes you scared of?’When I saw an example of a really great, well-rounded, healthy, happy trans woman, I was like, okay. I feel safe. I want to do that.”

As soon as Colby turned 18, she moved to Las Vegas to begin her transition and elevate her drag. For years she struggled to get by. “I was broke,” she says. “I was poor for quite some time.” In her youth, she imagined herself being a background dancer on cruise ships, or for Madonna or Britney Spears, but after coming out, she realized that there was “no space” for trans women in the scene at the time. As soon as she realized drag was something she could do as a career, she didn’t turn back. She had no Plan B. Even on days when she considered getting a part-time job to help make ends meet, hours later, she would book a gig out of town.

A few years after her debut, Colby started performing in drag pageants and quickly made a name for herself. After securing the title of Miss Continental in 2012, the drag world’s equivalent of Miss America, Colby’s ascent to success was cemented, firmly establishing her status as a drag legend. Relocating to Chicago, she swiftly became an iconic performer to seek out. It was no surprise that when it was announced she would be a contestant on the 15th season of RuPaul’s Drag Race, she would make it to the top. And make it to the top she did, winning the competition earlier this year after a spirited final lip sync for the crown against fellow queen, Anetra.

It wasn’t until a few hours before the competition’s finale that Colby considered the idea that she might not win. “It was wild because I never entertained any other idea,” she shares. “But at that moment, I had to be like, ‘Are you okay if you don’t win? Are you gonna go crazy? Are you gonna faint, like, what’s gonna happen?”’ she explains. “And I told myself, ‘You better not be a sore loser. You better be a good loser if you lose, if you don’t win.”’ Luckily, she didn’t have to brave a smile when she was announced runner-up. Instead, she describes her reaction to winning as “anticlimactic” and like “crying a little puddle.”

Being crowned America’s Next Drag Superstar has already changed her life. “Drag has been my only source of income, my only life source, so it is like my entire life. But with this Drag Race thing, it’s like I can now actually live and play this game of life and maneuver with such ease,” she says. “That’s not a common thing for a trans person, especially a trans person of color, especially somebody that comes from this small, little town. For me to be celebrated and show my love for drag—this is at the core of why I wanted to do Drag Race. It’s like, I’m not trying to compete to do anything. I’m showing you this as my love letter. I’m showing you my love for drag and why this is the only thing I know.”

After 20 years as a drag queen, winning Ru Paul’s Drag Race has undeniably solidified Colby’s revered status as an icon in the world of drag. But as the world of drag and trans culture becomes increasingly politicized and weaponized, the mission isn’t over. Colby is emboldened to show not only her talent with her new platform, but the humanity underneath it all, the possibility. Something she didn’t have when she was younger and walking to Halloween parties looking like Paris Hilton’s doppelgänger or dancing behind drag queens at her local bar. With two decades of dedication under her belt and more to come, Sasha Colby is a burning star of wonder and awe. 

Photographed by Easton Schirra at The Only Agency.

Styled by Todd White at Opus Beauty.

Written by Audra McClain 

Hair: Ricky Fraser at The Only Agency.

Makeup: Preston Meneses

Flaunt Film: Isaac Dektor

Market Editor: Hannah Griffin 

Styling Assistant: Marie Dor

Production Assistants: Cerys Davies and Khami Auerbach

Location: Bubble World Los Angeles