Legendary Host Dashaun Wesley Isn’t Done Championing Ballroom Culture

In Elite Daily’s series Rent-Free, celebrities unpack the one thought, memory, or unforgettable pop culture moment that'll always live in their head. In this piece, we chat with Legendary star Dashaun Wesley about the one Rihanna song he’s obsessed with.

Allow me to paint you a dreamy scenario: It’s dark, oppressively loud and hot, but you’re just seconds away from shimmying to “B*itch Better Have My Money” and “Where Have You Been?” before hundreds of thousands of screaming fans. Nope, you’re not Rihanna herself — you just happen to be one of her insanely talented dancers. Fun, right? While it sounds like an other-worldly, idyllic event, that was a reality for Dashaun Wesley, the host and MC of HBO Max’s Legendary. Long before teaching the world what it means to “battle” or “serve face,” he performed with RiRi during her 2016 Anti World Tour.

And it was during that experience that Rihanna’s hit song “Work” landed a permanent spot in his brain. “It replays in my mind rent-free because every time I hear it, I go back to throwing on a catsuit and getting ready to jump on stage,” Wesley tells Elite Daily, explaining the beloved jam was his cue to prepare to perform “Take Care,” the 2011 Drake collaboration included in her setlist. “I just remember being kneeled down under the stage about to rise on the ramp as soon as ‘Work’ finished.”

Of course, that behind-the-scenes memory isn’t the only reason Wesley loves the song. “I love the melody. I have a Caribbean background, so the type of vibe that the song gives is so good,” he says. “The music and the video reflect an underground bashment party — and everyone’s dancing and comfortable and free and in nice clothes. It takes me back to those moments.”

Today, he looks back on that tour — and his singer-turned-mogul boss — fondly. “We always called her boss lady, the best boss ever,” he says. “She was always so loving and giving to those around her. She said hi to us. She gave us hugs. She spoke to us. Yes, she was Rihanna, the superstar. But as my boss, she was saying, ‘Hey Dashaun, what’s up?’ and hugging me. That was surreal.”

Dashaun fell in love with dance — and underground ballroom culture, specifically — as a teenager in late-1990s New York City, where he started venturing off to the West Village and the Christopher Street Pier with friends to watch people gather around boomboxes and take on a style of movement he hadn’t heard of: vogue. “I loved the energy, I loved the vibe, I loved the camaraderie, I loved the competition,” he says. “I was like, I have to have this in my life. So I came back every day to learn.”

Wesley’s tenacity paid off. He moved on to compete with the dance group Vogue Evolution and eventually make appearances in reality competition shows like MTV’s America’s Best Dance Crew. In 2020, he made his debut on Legendary, one of very few TV shows that highlights not only the range of diversity within the LGBTQ+ community, but the history of ballroom culture and the artists who, for decades, have helped bring it to the mainstream. Following Season 2’s finale this June, HBO Max green-lit the series for a third season.

He leads the show alongside a dynamic panel of judges that include Leiomy Maldonado (his former Vogue Evolution co-member), Jameela Jamil, Law Roach, and Megan Thee Stallion, all of whom he’s grown closer to. “Season 1 was us getting to know each other. Season 2 was like, ‘Oh my god family, where you been? It’s been so long! Let’s go have fun.’ I love every judge. We all bring something different,” he says.

There’s an organic chemistry Wesley and the judges riff off, which is why so many of the one-liners and sassy remarks he makes on the show don’t feel forced. “People ask me, ‘How do you come up with the chants? It’s supposed to happen on the whim, on the spot. The more natural it is, the more people can connect to it. You have to deliver these little moments of authenticity,” he says, joking that the teleprompter on set also comes in handy.

As a child of the ballroom scene, Wesley knows the real definition behind well-known terms such as “fierce,” which he says has taken on a different connotation in pop culture. “In ballroom, we look at the word fierce as a bad thing. So if you walk up to someone in ballroom and say, ‘Oh my god, you look so fierce!’ we don’t take that too lightly,” he says. “Before ballroom became mainstream, a lot of people were mimicking what we were doing. So it’s our responsibility in the community for people to know exactly where we’re coming from.”

Especially during Pride Month, Wesley feels a responsibility to pave the way for kids just like him looking to make a living out of their love of dance. “I want my community to receive love due to this,” he says. “When I was growing up, I didn’t have anybody to look up to. There wasn’t an openly gay Black man representation-wise that wasn’t so cliche, or didn’t face the stigmas we heard back then. I know what I didn’t have, and I know what I would have done if I did have it. So why not be an example if I can provide that for anyone after me?”

Outside of Legendary, Wesley plans to continue pursuing projects that bridge LGBTQ+ communities together. “Now y’all see the balls, we see Pose. What else can we get? There are so many opportunities for our stories to be told,” he says. While details remain scarce, Wesley hints that he’s venturing into music and possibly “starting something of my own.” A joint project with RiRi, his former boss? Let me dream big on his behalf.