Interview: Tyler Jordan Wesley of THE OUTSIDERS at Orpheum

Let’s start at the beginning. How did you discover your love for the arts?

I’ve always been in love with musicals and movie musicals—whether it was Disney, Hairspray, or Dreamgirls. I remember sitting in front of the TV, memorizing every line word for word, and knowing from a young age that this was what I wanted to do. In middle school, I started taking drama and acting classes seriously. They were just electives at first, but I knew I had to be in drama. I did it all three years of middle school.

In high school, I took it even more seriously. I’m from Hopkins, South Carolina, but I went to school in Columbia. During my junior year, I attended the South Carolina Governor’s School for the Arts and Humanities—a school that Danielle Brooks and Patina Miller also attended. It was such an honor to be accepted. The program wasn’t focused on musical theater; it was strictly acting. Up until then, I’d been involved in musical theater, performing in productions like The Lion King, Fiddler on the Roof, Shrek the Musical, and Into the Woods. But I said goodbye to all of that my junior year to focus on acting.

Then the pandemic hit. I had left home to attend the Governor’s School, which was a boarding school about two hours away. We lived on campus, took general education classes in the morning, and focused on acting in the afternoons. COVID interrupted all of that. Around that time, I started talking to my teachers about pursuing musical theater in college. My voice teacher, Candace Dickinson, told me about Texas State University’s musical theater program and encouraged me to keep an eye on it. I did, auditioned, got in, and spent the last four years there. I just graduated this May—and now I’m here, feeling so grateful and excited.

Congratulations! That’s so exciting. Since your transition from education to professional performance happened so quickly, can you tell me about your audition experience for The Outsiders?

My final semester of college was a whirlwind. I was going through that classic senior-year existential moment—wondering, “What am I doing? Am I making the right choices?” It felt like I was stepping into the abyss of adulthood, accountability, and responsibility in a whole new way. I’d felt something similar when I started college, but leaving it was different.

I saw the open call for The Outsiders on Instagram around February or March. A bunch of my friends sent it to me and encouraged me to audition. At the time, they were only casting for Johnny Cade and Ponyboy. I was excited and sent in a tape just to see what would happen.

Meanwhile, I was juggling a lot—our school’s production of Guys and Dolls, our senior showcase, catching up on classes, and directing our Black History Month showcase. I’d also just directed a concert version of Jesus Christ Superstar. My brain was bouncing all over the place.

I didn’t hear back until April, when they put out a call for Dally. I auditioned again and waited about three weeks. Then I got callbacks for both Johnny Cade and Dally. After another couple of weeks, I was called back for a final audition for Dally. In mid-May, on the night of my senior showcase, I got the call offering me the role.

What an incredible way to celebrate! Before we dive deeper into the show itself, I’d love to hear any advice you have for young artists making the leap into professional theater.

One of the best pieces of advice I’ve received—and something that’s really stuck with me—is to remember that you are the puzzle piece. Casting directors and creative teams have seen countless versions of a character. Trying to be what you think they want doesn’t serve you.

It’s easy to say, but hard to practice—especially when you’re caught up in the momentum of wanting to book the job, find stability, and stay committed to your artistry. It gets complicated. But as much as you can, stay rooted in the joy and creativity that drew you to this art form in the first place.

That’s how you give yourself the best shot—not just at booking the job, but at having fun and feeling proud of your work. If you walk into the room and do what you can do, rather than what you think you should do, then even if you don’t get the job, you’ll know you left your best foot forward.

You touched on this earlier—the idea that casting directors have seen so many different interpretations of these characters. What was your preparation like for playing Dallas? With the movie, the book, and now the Broadway production, how did you craft the Dallas that Omaha audiences will see?

I actually didn’t read The Outsiders in middle or high school like so many others did. My first connection to the story was through the musical. I remember being in my sophomore or junior year of college, listening to the cast album, and showing it to my mom. I told her, “This is a show I could be in one day.” I specifically remember playing “Run Run, Brother” for her, and she said, “That sounds just like you.”

When the audition call went out, I wasn’t super familiar with the material, so I wanted to absorb as much of it as I could. I’m a very visual person, so I started with the movie before reading the book. I watched it two or three times and really studied what Matt Dillon brought to the role. In my mind, he’s how a lot of people fell in love with Dally—he’s the first visual interpretation of the character, even though the book came first.

I also studied Joshua Boone’s performance and tried to learn as much as I could from him. I haven’t reached out to Devonte Moody, who played Dally at La Jolla, but I tried to expand my research as much as possible. I read the book to get into S.E. Hinton’s mind and understand how she envisioned Dallas. Then I brought myself into it. I looked at the character through the lens of my own life—thinking about who Dallas might be if he existed in my world, who he reminded me of. Through all of that, I crafted the version of Dallas that America will soon see. I hope he inspires people.

Is there a part of the show—whether you’re on stage or watching from the wings—that you especially look forward to each night?

A part? Laughs. Honestly, I’m just excited for people to experience the full scope of the show. But if I had to choose, “Throwing in the Towel” is one of my favorite moments. Seeing the three brothers on stage, going through this larger-than-life moment—it’s a true test of faith, love, and care for each other, and for themselves. It’s so nuanced and gut-wrenching, and it means a lot to me personally.

I have an older brother, and I’ve had the privilege of growing up with both of my parents. But there’s something about that brotherly bond—looking out for each other, teaching each other how to navigate the world. My brother answered so many of my questions growing up and helped shape the man I’ve become. Getting to tap into what he might’ve felt at a similar age means a lot to me. I love “Throwing in the Towel.”

What is it about this show and this material that you think really resonates with audiences, especially within the Broadway community?

The Outsiders has this multigenerational pull. No matter your age or where you are in life, there’s something in it you can connect to—something that feels like home. A big part of that is the theme of “finding the words.”

Watching Ponyboy go through this tragic, beautiful time in his life, he’s trying to find the words to explain it. Darry, his older brother, is trying to find the words to connect with Ponyboy and help him see the world as he needs to. Dally—my character—struggles to find the words to connect with others because of the life he’s lived and his worldview. His biggest moment in the show is defined by his inability to find the words. He doesn’t know how to express himself, and that leads to a pivotal decision.

Even on a broader level, S.E. Hinton wrote this book at 16. She was trying to find the words to connect with people through her own experiences in Tulsa. That act—finding the words—is so important at every stage of life. It’s what life is about: recognizing what you’re feeling and understanding what you need from others. I think that’s beautiful.

Any final thoughts for Omaha audiences who haven’t yet clicked the “purchase tickets” button?