Guy Anabella: The Legacy Begins

Guy Anabella Reflects on Her Historic Win and the Power of Pretty Girls Who Are Strong

When Vision Drag Artists and Buddies in Bad Times Theatre announced their first-ever Pride Legacy Pageant, it promised a new tradition rooted in excellence, creativity, and community. On stage, eight talented performers brought drag, drama, and daring to life—but only one would walk away with the crown. Enter Guy Anabella, the powerhouse performer, professor, and poet who stunned the judges with her vibrant butterfly fantasy and original song, “Pretty Girls Are Strong.”

In this exclusive interview, Guy breaks down her history-making win, her inspirations, and the artistry behind her drag—one that fuses Caribbean celebration, gender-defying strength, and unapologetic beauty. As the first-ever Pride Legacy winner, she’s not just wearing the crown. She’s redefining what it means to earn one.

THISisDRAG.com: Guy, congratulations on being crowned at the first-ever Pride Legacy Pageant! How does it feel to have won the title?

Guy Anabella: It feels correct! Honestly, I’m deeply honoured. I don’t take the title lightly. This is the first-ever Pride Legacy crown, and I want to set the tone for what it means. I hope this pageant becomes a new tradition every Pride, and I can’t wait to cheer on next year’s winner from the front row.

TiD: What were your initial thoughts and emotions when you were announced as the winner?

GA: I try not to expect anything, but in that moment? Pure gratitude and pride. I had worked so hard in the month leading up to the pageant. So to hear my name being called and realizing that all my effort paid off? It was emotional. Still feels a bit surreal.

What were your thoughts when you first learned that you would be competing in this pageant?

Not gonna lie, I was nervous! I’ve never done a pageant before so I didn’t know what to expect. But once the nerves subsided, I decided it was time to lock in and give it my all.

What were your thoughts about the rest of the contestants?

I thought it was an incredibly strong cast, with each of them bringing a very unique and different perspective to drag. It was a celebration of how diverse, creative, and powerful drag can be. I knew I had to push myself to stand out because of this iconic lineup.

TiD: Who did you expect to be the biggest threat?

GA: Every single one of them was a threat in their own way. Here’s the tea:

• Sucka brings camp and comedy, which I love. I’ve performed with her before and knew she’d give something very Willow Pill-coded and gobble the stage.

• Sevynn—I didn’t know her beforehand, but the minute she hit that pole? I knew she was one to watch. Fierce, sweet, and strong.

• Sahira is absolutely stunning. Like me, she weaves her culture into her drag, and I’m obsessed with artists who have a message.

• Midas—I’ve seen her perform in Toronto. A stunts and fashion girlie. I knew she was one to watch—and rightfully so, as she was in the Top 2!

• Masisi has international credits, hunni! Drag Race Holland and Queen of the Universe. I was nervous. Her runway and live vocals had me shook. Such a radiant, regal energy.

• Betty Baker had me gagged when I saw her do “Turn the Beat Around” at Drag Brunch Saved My Life. That performance is easily one of my top 3 drag performances ever. Camp, kicks, comedy—I was living!

• Molly Kewl is an education queen like me! Her aesthetic is giving “Bill Nye meets Decora,” and it’s so smart, so fresh. I knew she was going to do something shocking.

What can you tell us about your Legendary Moment runway look?

I knew I wanted to serve something Caribana-inspired. That’s my aesthetic through and through: vibrant, cultural, over-the-top. This was a pageant, so I wanted to go bigger. I told myself: it has to be impactful. I want people to gasp.

When I saw Anna-Lisa Ragu’s design, I was shook. The colour palette was dreamy, and the giant bouncing butterflies… I was in awe. That was the biggest backpack I’ve ever worn—and trust, it felt like it too—but it was so worth it. Covered in rhinestones, layered with delicate butterfly details… it was so pretty.

The hair was styled by the fabulous Zsa Zsa and matched the look perfectly—rhinestoned to the gods. Fun fact? It was actually a drawstring ponytail that she turned into a hair topper. Out of drag, I’ve got long hair, so I tucked it into a bun and pinned it on to make it look real.

The butterfly is such a powerful symbol for me. It’s all about transformation. Rebirth. Becoming. It feels so queer to me…the way we evolve, challenge norms, and reveal our true selves in colour and light. That’s exactly what I wanted to channel on that runway.

TiD: What can you tell us about your talent number?

GA: When I started thinking about my talent number, I knew I wanted to do something creative… something that would shock people.

I’m a powerlifter and a professor, and people are always shocked when I tell them that. So I thought: what if I leaned all the way in? My early concepts were a motivational lecture in full drag or a live weightlifting stunt onstage. Because we see muscle queens, yes… but can they lift, mama?

I also wanted to challenge myself to make an original song. In a past life, I was a world-renowned rapper. I wrote and performed the original song called “Pretty Girls Are Strong.” I worked with my producer Gavin Whehelan and choreographer Brianne Katz-Griffin to bring it to life—all in a month! But I learned so much about what goes into making a song and performing it. I want to make more music!

The song is about smashing gender expectations, especially the ones placed on women. Society tells you to be dainty, smooth, soft… but what if you’re strong, hairy, sweaty, and pretty? What if you’re all of those things at once?

That’s what my drag is about. I blur gender lines. I honour femininity and strength. The talent number was a love letter to all the people who’ve ever felt like they had to choose between masculinity and femininity... Spoiler: you don’t.

TiD: What does winning this title mean for your future in drag?

GA: It feels like a green light. This title has affirmed that I’m on the right path and that my version of drag belongs in the spotlight. It’s opened doors, but more importantly, it’s opened my own eyes to what I’m capable of. It’s incredibly validating and affirming. I do believe that I was born to do this. And I am not done!

What’s next for Guy Anabella?

So much! I want to get into garment design. I have the vision but I just need to level up the execution. I also want to keep making music! “Pretty Girls Are Strong” is just the beginning. And of course, continuing to blend my professor life with my performer life. Guy Anabella’s just getting started. I’m planning to create some queer creativity courses in 2025! I want to make sure this reign is a successful one.

Do you have anything else that you would like to add?

Your biggest competition is yourself. Sometimes, the hardest part is getting out of your own way. It’s okay to be critical of yourself because that’s how we grow—but it’s even more important to celebrate yourself. You deserve to take up space, to shine, and to be proud of how far you’ve come.
And remember that PRETTY GIRLS ARE STRONG!

From runway wings to lyrical fire, Guy Anabella proved she’s more than a pageant queen—she’s a force for transformation. With a reign ahead and new creative projects in the works, Guy’s legacy is just beginning to unfold. And if this first chapter is any sign, the future of drag—and of Pride Legacy—is in very powerful, very pretty hands.

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By Kevin Blondin