Alright – so today we’ve got the honor of introducing you to Summer Orlando. We think you’ll enjoy our conversation, we’ve shared it below.
Summer, looking forward to hearing all of your stories today. Are you able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen?
I’m Summer Orlando, New England’s premier theater drag queen and illusionist, I am known for my Broadway-quality costumes, show-stopping performances, live singing, comedic timing, and amazing event hosting skills. Hosting duties include bachelorette parties, anniversary celebrations, Weddings, Pride events, and birthday parties for all ages. I perform throughout CT, NYC, Florida, Internationally, and everywhere in between!
I’m a full-time drag entertainer and have been performing for over 10 years. My first experience with drag came in college when I was in a production of “The Rocky Horror Show”. If you are unfamiliar the actors have to wear the clothing of the opposite sex and wear makeup. I did not make a pretty woman back then, but with time and practice, it got better. A local drag queen named “Marita Bonita” saw me in the show and offered me an audition at a drag club in Hartford CT, called the Polo club. I aced the audition and was put in theme shows, When I made the move to New Haven and made friends with the drag community there, that’s when things got serious and after a few years guesting in other people’s shows, I teamed up with another local drag queen and we created an empire over the last 5 years. After 8 years of working with as a duo, I made the decision that I would go a lot father and be more successful with my personal dreams and goals if I continued solo. Now I perform in prestigious theaters, wineries, breweries, and honestly everywhere you wouldn’t expect to see a Drag Queen. It’s my love and my passion. I have been so grateful for all the amazing opportunities I have been given through this platform. Sometimes I have to pinch myself as I’m making a living truly living my dream. I am about to turn 33 and the world is my oyster.
I definitely have had some bumps along the way. From being disowned by my father over 15 years ago when I came out of the closet, rebuilding family dynamics, and quitting my food service job to take a chance on myself and be a performer full time. Lived paycheck to paycheck for many years as a starving artist, and scrounged up the money to pay my bills. We all start somewhere and need room to grow. I’m happy to say I’m in a place now where I can live semi-comfortably and I have loving family and friends as my biggest cheerleaders. The road is a lot more paved these days.
I began taking on bigger projects, one of my most notable accomplishments being in 2017. I produced, directed, and starred in a fully licensed production of The Wizard of Oz. I made history as the first male actor to ever play Dorothy in a licensed production of the show worldwide. This groundbreaking performance took place at the Hole in the Wall Theater in New Britain. The show was a phenomenal success, garnering attention from BroadwayWorld.com, which came up from New York to cover the story. I was featured in newspapers and received a Ruby Slipper Award, a very cool recognition of achievement.
I have my own production company “Summer Orlando Productions LLC” where I produce the show I’m most known for “Hocus Pocus Live: an all new parody musical. Celebrating 9 years of sold out performance. My biggest year for Hocus Pocus Live came in 2022, following the show’s immense success and buzz. I received an unexpected call from Disney, inviting me to be a look-alike for Bette Midler. While doing a theater residency in Fort Lauderdale, performing various themed shows, I had to leave early from my final performance to fly to Rhode Island. Disney wanted me for a Sanderson look-alike contest, and I shot scenes with Bette Midler, Kathy Najimy, Sarah Jessica Parker, and several RuPaul’s Drag Race stars; Ginger Minj, Kimora Hall and Cornbread. Disney was so impressed with my uncanny resemblance to Bette Midler that they decided not to feature me in close-up shots with Midler to avoid confusion. Despite the adjustment, I felt incredibly honored. I appeared in three scenes, including the Sanderson look-alike contest, and was part of a bewitched dancing crowd. The experience was surreal, especially when Bette Midler and the other witches flew overhead on cranes, making it a magical and unforgettable time.
I just got back from a 2 month theater residency in PV Mexico and straight off the Broadway Cruise with Sixthman and Norwegian, I was the first drag queen to ever perform on the “Broadway Cruise”. I like to manifest things for myself. I see myself continuing to tour the world, visit new places,more cruise ships, making long-lasting business relationships, Creating a US tour for Hocus Pocus Live, Bringing the show Off- Broadway and connecting with a producer that wants to help that journey, Writing and produce some more original works for the stage, Doing a Broadway show, more movies, Being the first male “Friends with Winifred ” in the Hocus Pocus Villain Spelltacular in Disney World, and honestly whatever else falls in my lap. I love a challenge and don’t mind the work and the longgame it takes to get there.
Summer, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Many people have a misconception about drag shows, that drag means seedy clubs, 21 and over, with a drag queen who is dirty, sexual, and raunchy.
I like to flip that misconception on its head by introducing performance art where all ages, from six to sixty, can come to enjoy drag for what it is; interactive, fun, and full of surprises!
They include jokes, live singing, games, audience participation, giveaways,
celebrity impersonations, and much much more.
Summer is New England’s Number one Character impersonator and looks alike and I think what sets me apart from most drag queens is though I do a little lip-syncing I mainly sing life, including as the celebrities and characters I impersonate.
Summer Orlando is New England’s premier live-singing drag entertainer — a powerhouse performer and dazzling international queen known for Broadway-belting vocals, razor-sharp wit, and show-stopping glamour.
She made worldwide headlines when she was handpicked by the producers of the film Judy to appear as their official Judy Garland meet-and-greet look-alike during World Pride in New York City.
A historic trailblazer, Summer is the first male actor ever honored with the role of Dorothy in a licensed stage production of The Wizard of Oz in the world. She is also the producer and creator of the acclaimed stage tribute “Hocus Pocus Live!!!”, and her spot-on portrayal of Winifred Sanderson earned her the ultimate recognition — she was handpicked by Disney to appear in “Hocus Pocus 2” . Summer is the first drag entertainer to perform on “The Broadway Cruise” with Norwegian Cruise lines.
From casinos to cruise ships, theaters to cabarets, Summer is a crowd-favorite host, vocalist, and celebrity illusionist whose performances pack houses and turn first-timers into lifelong fans. Catch Summer January/February 2026, in residency in Puerto Vallarta, Mexico with her hit show “Broadway Queen.” and for monthly drag bingo at Mohegan Sun
One thing’s for sure:
Where Summer Orlando goes, the spotlight follows.
Can you share a story from your journey that illustrates your resilience?
During the 2020 pandemic when the world shut down and my in person shows were cancelled. I pivoted and switched to virtual shows every Saturday on Facebook and Youtube. I learned how to use editing software, greescreen, and livestreaming, to continue to work and pay my rent and bills. It was a scary time, but I made it work and got through it and kept creating new and engaging virtual opportunities that kept me going until socially distant outdoor shows were allowed to happen.
What do you find most rewarding about being a creative?
The connection with the audience. There’s something magical about stepping on stage, creating a character, and watching people light up, laugh, sing along, or even feel a little more confident about being themselves. Drag is more than just costumes and glitter; it’s storytelling, celebration, and a reminder that creativity can bring people together. When someone comes up after a show and says they forgot about their worries for a while or felt inspired, that’s the moment you realize the art actually meant something and that’s incredibly rewarding.
Contact Info:
- Website: https://www.summerorlandoproductions.com
- Instagram: https://www.instagram.com/misssummerorlando/
- Facebook: https://www.facebook.com/MissSummerOrlando
- Youtube: https://www.youtube.com/@SummerOrlando
- Other: Tiktok: https://www.tiktok.com/@misssummerorlando
www.hocuspocusliveofficial.com
