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The Skyy’s the Limit: An Interview with Jenna Skyy

The Skyy’s the Limit: An Interview with the Reigning Queen of Drag

The Skyy’s the Limit: An Interview with Jenna Skyy 73



“The further we go in this industry, the more doors you realize are there waiting to be kicked down.”


In the almost 10 years I’ve known Jenna, there have been many doors – open, closed, barred shut, those that are stuck or unhinged, and one’s still waiting to be discovered.


And then there are the doors that she has created.


And the one’s she has opened for so many others – including myself.


Here is my first public piece of writing honoring, reflecting, and celebrating my drag mother, mentor, and best friend Jenna Skyy.


On drag origins:

“My first time in drag (like drag in the sense that I was actually going to do this – and NOT Halloween drag but “bitch, I’m gonna be FAMOUS” drag) I went to a city preliminary pageant at the Roundup Saloon.  My friend (and ultimately that night my drag mother) was hosting the pageant so I felt safe in my first outing.  I wore jeans I bought from some trendy boutique store at the mall and a sweatshirt I had chopped up and made Greek letters for on the front (trying to look sorority phish).  The letters were Beta Theta Upsilon (ΒΘΥ)…clever huh!?  I think I had pink pumps from Payless and a little purse from Ross. Looking back on that night, I didn’t know what I was doing or what I wanted.  I still wonder what I imagined all this would be at that time. I certainly would not have imagined what it has become and still find myself having surreal moments when I realize where this path has led. I think in the beginning I was looking for something in my life – something I could own, could work toward, goals to set and chase.  I think…this was just going to be food for my soul and when I was full, I’d be done.”


This is the first time I met Jenna circa 2006 at the Dallas PRIDE parade.

Screenshot (95)

(photo by me)



The next time we saw each other we hated one another. Hate turned into respect and respect turned to (a small) like. After agreeing to put up with each other for the sake of our art, we did our first performance together at Rydell High Gaybingo in April 2008. She’s going to kill me, but here’s the YouTube link. It’s a reminder to everyone (including us) that EVERY queen’s journey starts somewhere.


On drag as art:

“Certainly drag is an art form – a culmination of them really. Its creative expression fusing so many layers and mediums of art and performance into one presentation, one showing.  I define drag as all the possibilities I can’t typically do becoming reality. Through drag, I get to be an actor, a model, a rock star, a vocalist, a dancer, a boss, an entrepreneur, a business owner, a designer, a choreographer, a bitch, a diva, a sister and hopefully an inspiration.  When you get caught singing along to the radio in your car at a stop light – really servin’ the kids – you get embarrassed.  When you get caught singing along to the radio in a drag show, you get tipped!”


Since that kismet summer nights moment in 2008, we’ve made A LOT of art together. Here are just a few of my favorites.


  • Geisha Gaybingo – Click here  for the video.
  • Roller Boogie Gaybingo – Click here for the video.

But the most magical and by far the most meaningful was Bollywood. One year after Rydell Highing, we found our groove and a piece of art that would later become Jenna’s trademark. Bollywood was made up of the best pieces of all of us – Manny, Jenna, and myself. We all knew it was good, but we had no idea – at the time – just how fucking brilliant it really was.  


Five years after putting that piece together for Gaybingo Dallas, Jenna would transform it and take it onto the USofA stage as the FIRST of twelve talents final night.


She won with a perfect score in talent. And drawing number 1. And her first time competing in the system. Completely blowing any stigmas of what can or cannot be done. She was good. She was really fucking good.


On hearing her named called:

It was like being asleep in a dream that you actually got to see finish.  You know how when you’re dreaming and its good, how often you will wake up before you get to the end of the dream? Yea, this wasn’t like that.  I totally got to the end . . . and I was awake. Every emotion ran through me in an instant.  Relief, elation, exhaustion, happiness, joy, fear, calm, and comfort because Layla LaRue was right there with her arm around me. Excitement. It really was perfection.

Screenshot (89)

(photo by Ben Earley)



I was bawling.


I felt like I had won all over again. And really I had. Just the year before we had been sitting in the audience with intention. Hers being on that stage. Me creating my own within it. We had taken this picture before arriving at final night 2013.

The Skyy’s the Limit: An Interview with Jenna Skyy 74

(Photo by Tyler Curry)



(Photo by Ben Earley)

(Photo by Ben Earley)


One year later and on that exact night, we took this one.


From sitting in the audience watching with the intention of becoming, we became it.


It’s one of the top 5 moments of my life and it’s sealed in drag history forever.  


On advice for those seeking & those wearing crown:

To someone seeking:

“Look well beyond the pageant.  There is a role when you win that requires skills that have little to do with the actual categories for which you tirelessly prepare.  What you do TO prepare though – how you manage your time, budget your resources, maintain your relationships, your image, your brand, how you communicate, how you listen, how you react – all these skills that get you on stage final night these skills will most certainly be most relevant. And judged when you do get it. Focus on developing those skills. And most importantly, know what you want to take away from this experience – beyond the title. Memories, experience, a trip with friends, new friendships there’s more to this effort than just winning.”

To someone who is crowned:

“Social media will not define you.  YOU will define you.  We celebrate the qualities unique to each title holder so be unique.  Everyone has an expectation of what a titleholder should be . . . but you hold this title, have your own expectations.  Bring your own shoes.”


She is one of the smartest people i know and one of the most generous with her advice. This Saturday she graduated with her MFA in music education. i am so proud of her. There is nothing she can’t do.


On what comes next:

“I live in Dallas so I fully intend to take part in the national pageant every year in some capacity.  My strengths have always been administrative so those are skills I want to share with the system and the national event where needed.  I enjoyed my time this year, so I will likely throw my wig back into the ring in the future.”


And she will. And you can bet that whatever she decides to do she will slay.


One door closes and another one opens. There will always be endings and beginnings, growth and changes. The only true constant is and will always be us.

(Photo by Musico Roots)

(Photo by Musico Roots)

It’s been one hell of a ride and I am ever so thankful that I got to live in this moment like we live our life – side by side.


Congrats on a stellar year. I love you.



Article by Brandi Skyy

Brandi Amara Skyy is a writer, drag artist, and entrepreneur. You can find her blogging away about drag and creativity at When she’s not behind a computer, you can find helping others live and be their art or onstage to the kids.

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