Earlier this season, Kyle Ramar Freeman was seen as the Lion in the Schele Williams-directed Broadway revival of The Wiz after playing the same role in the musical's national tour. Now, the gifted actor can be seen Off-Broadway in the long-running hit musical Titanìque at the Daryl Roth Theatre.

The Miami native is playing the Iceberg in the irreverent send-up of the blockbuster film Titanic, and the casting marks a theatrical homecoming of sorts for the performer. Freeman played the same role in the live-stream concert of Marla Mindelle, Tye Blue, and Constantine Rousouli's musical comedy, which was seen on Stellar in 2021 prior to the Off-Broadway premiere.

Freeman, however, is probably best known to theatre audiences for portraying the role of Usher in Michael R. Jackson's Pulitzer Prize and Tony-winning musical A Strange Loop, first as an understudy on Broadway and subsequently as the lead in the musical's West End premiere. He has also been seen in the national tours of Once On This Island and Joseph and the Amazing Technicolor Dreamcoat.

In the interview below for the Playbill series How Did I Get Here—spotlighting not only actors, but directors, designers, musicians, and others who work on and off the stage to create the magic that is live theatre—Freeman recalls a joyful night with the cast of The Wiz and how A Strange Loop changed him as a performer.

Where did you train/study?
Kyle Ramar Freeman: American Musical and Dramatic Academy.

Was there a teacher who was particularly impactful/helpful? What made this instructor stand out?
Absolutely. Mrs. Irene Pasteris was my elementary music teacher, and she played a pivotal role in my musical journey. She was the first person to recognize my singing talent and encouraged me to pursue it further. Her belief in my abilities gave me a strong foundation to build upon and truly shaped my passion for the arts.

What are the challenges/rewards of joining a production that is already running like Titanìque?
Joining a running production comes with its challenges, as you essentially have to jump onto a moving train. Everyone has already established their roles and routines, and fitting into that can be tricky. Fortunately, the cast and creatives have been incredibly welcoming, allowing me the freedom to make my character my own. I’m also grateful to have been part of a previous performance right after the pandemic, which makes revisiting Titanìque even more special for me. I’m so proud of how the show has evolved.

How demanding, emotionally and/or physically, was playing Usher in A Strange Loop? Did you notice any difference in reaction between Broadway and London audiences?
Portraying Usher in A Strange Loop has been the most challenging experience of my career, both emotionally and physically. It's like running a marathon that never seems to end. Throughout the journey, I learned to become a better performer, to stay present, and to detach from the heavy themes in ways I never expected. The role stretched, challenged, and ultimately liberated me in the most beautiful way. I’m incredibly grateful to have been part of this story and to share it with audiences in both Broadway and the U.K.

Interestingly, the reactions to the show were somewhat similar; American audiences tend to respond more vocally, while U.K. audiences are a bit quieter. However, the interactions after the show were consistently heartfelt, with people expressing how moved and challenged they felt, and how grateful they were for the new perspectives we offered through our work.

Do you have a dream stage role or stage acting partner?
I don’t have a specific dream role in mind, but I aspire to create original characters in musicals and plays that I build from the ground up. My goal is to contribute meaningful art to the world and inspire others, especially those who look like me, to create their own work. As for collaborators, I have a long list, but I’d love to work with Jordan Cooper, Keke Palmer, and Debbie Allen. There’s a unique magic that these Black creatives bring to the entertainment space, and I feel drawn to their work. I’m confident that I will have the opportunity to collaborate with them in the future.

Can you share a favorite experience—either on stage, backstage, or at the stage door—from your recent Broadway work in The Wiz?
One of my favorite memories from The Wiz was touring the country with our company. We always found a way to make long, exhausting travel days entertaining, which made those experiences fun. However, a standout moment for me was getting ready for the Met Gala with my friends. It was such a special experience that reminded us of our hard work and the privilege of being in a situation that most people never get to experience. Plus, we looked fantastic while doing it (shout out to Tanner Fletcher), which made it all the more exhilarating!

What do you wish you knew starting out that you know now?
What I wish I had known when I was starting out is that what you think you want at any given moment isn’t always what you need. I learned that if I had gotten my desires on my own timeline, it could have jeopardized my career and led to burnout sooner than I anticipated—ultimately because I was not prepared for it and needed to gain an understanding of who I was and what I contribute in this business. Everything that has happened has prepared me for where I am now. It's important to be happy for others and celebrate their achievements, because when your time comes, it will be so rewarding and so sweet, and you’ll receive just as much love.

What do you consider your big break?
For me, my big break was simply moving to New York City. I always knew that once I arrived, I would have the opportunity to make my mark and pursue my calling. While career achievements are certainly important, the fact that I made it here and have been able to stay is what I truly consider my biggest break.