Dez Duron on Making His Broadway Debut in ‘Maybe Happy Ending’ and the Role He Was Meant to Play

Dez Duron brings to Broadway the same timeless quality found in the jazz standards he performs night after night—rich with feeling, grounded in craft, and resonant beyond their final notes. As Gil Brentley in Maybe Happy Ending, he channels the charm and emotional clarity of a classic crooner, yet delivers it with an immediacy that speaks to modern audiences. It’s a performance that bridges eras, breathing new life into a role that feels as though it’s always been waiting for him.

Maybe Happy Ending is the kind of original musical that sneaks up on you—tender, transporting, and quietly profound. Set against a backdrop of memory and melody, it tells a story of unexpected connection, second chances, and the quiet courage it takes to open your heart again. Under the direction of Tony Award® winner Michael Arden, the production unfolds with striking visual poetry and a score that’s as layered and expressive as the emotions it stirs. At its core, it’s a meditation on making the most of the time we’re given—and in that space, Dez finds his rhythm, delivering a portrayal that’s both emotionally grounded and musically precise.

Pop Culturalist caught up with Dez to talk about making his Broadway debut in Maybe Happy Ending, stepping into a role that felt destined, and preserving it all through a cast recording that captures the soul of the show. He opens up about the songs that shaped his journey, the lessons he’ll carry forward, and how this chapter has deepened his love for storytelling—on stage, in the studio, and beyond.

PC: It’s so rare to get an original musical on Broadway these days that isn’t based on existing IP. Maybe Happy Ending feels like such a breath of fresh air. Even if you’re not familiar with it at first, there’s an accessibility to the show that draws you in and makes you want to revisit the cast recording or see it again. As an artist yourself, what was it about the production and the musical composition that spoke to you?
Dez: Right off the bat, it was the songs. My character’s whole thing is the singing, and my very first rehearsal was a music session—even before the table read. I fell in love with the score immediately. I remember calling my family and saying, “They did it. They wrote real standards. These songs sound like they’re straight out of that era.” Frank Sinatra would’ve been banging down their door if he were still around.

This is funny—I didn’t realize it at the time—but Darren [Criss] told me that David Foster came backstage after one of our shows, and we all got to meet him. It was such a cool moment. But apparently, he said, “Gil Brentley—I miss that guy. I’ve got to check out his music.” And Darren goes, “He’s not a real person, dude.” [laughs] That just shows how authentic and timeless the music is.

And then there’s the story—it’s so original, but it doesn’t feel out of reach. It feels familiar in the best way, like something you’ve heard before, but told in a completely new light. I remember all of us having a really emotional response at that first table read. I’m just so excited to be part of this world. The way they invite you into it is seamless—there’s no heavy-handed exposition or “make sure you remember this” kind of thing. It’s all slipped in naturally. You understand the rules of the world, what drives each character, and where the story’s heading. The writing—both the script and the music—is just brilliant.

PC: That’s such a huge compliment from David Foster—that he thought your character was a real person.
Dez: I think it was really more about the songs. He was like, “The music’s so great, I need to check out this guy’s catalog.” But there is no catalog! [laughs] It’s just five songs. The writers are just that brilliant.

PC: I haven’t stopped thinking about the show since I saw it on Tuesday. There’s such an introspective quality—it really makes you reflect on the life you’re living and how fleeting time is. What’s the biggest thing you’ve learned about yourself through this experience? How has being part of this company made you a better person?
Dez: There are so many themes in this show—purpose, love, loss, living each day to the fullest, redeeming lost time, mending broken relationships. And depending on the season I’m in, something different always hits me. But I really love being part of a show that resonates so deeply with people. Even my dad called me after he saw it for the first time—two weeks later, actually—and said, “Man, I can’t stop thinking about it. We have a shelf life. What do I want to do with my life?” It gave him this new energy to go out and make every day count.

That’s what I want to carry with me: love deeply, live fully, and make the most of the time I have.

Darren said something beautiful one night after we finished our Broadway Cares/Equity Fights AIDS curtain call—he said this is a show about taking care of each other. It’s about asking, “How can I love the people around me better? How can I show them I care?” And that’s really stayed with me. Making people feel seen, loved, and supported—that’s the kind of purpose I want to hold onto.

PC: Beautifully said. This is also your Broadway debut—congratulations, by the way. You’ll always be the actor who originated the role of Gil on Broadway, and hopefully this production runs for many more years to come. What’s played the biggest role in helping you shape your interpretation of the character? And as you think about future Gils, what do you hope actors take away from your portrayal?
Dez: Gil is such a wonderful character because so much of who he is lives in the material itself—especially in the music. For me, it was shaped song by song. At the table read, I had this specific image in my head: Gil was a cool cat, kind of like Frank Sinatra. But then we got to “Jenny,” which is this big production number where you’re hitting your marks, doing choreo—it needed that for the show. And suddenly, I thought, “Okay, maybe he’s not just Sinatra. There’s a bit of Sammy Davis Jr. in there too.”

Then you get to a song like “Why Love,” and suddenly it’s more introspective. You learn that Gil plays the piano, writes his own music—it made me think of Nat King Cole. So over time, I kept shaping him based on what the story needed, what the music demanded. Each number added a new layer to who he is.

What’s also so cool about playing Gil is that there’s a lot of room to make him your own. You can really create your own backstory—there’s a lot of space for interpretation. I’ve made up a million different versions of Gil’s story in my head. For a while in Atlanta, I imagined that Gil wrote every single one of these songs—that he was the composer behind it all, deeply invested in this story. And that kind of mystery is fun. You get to fill in the blanks and draw from whatever inspires you.

But there are clues, too—especially in “A Sentimental Person.” It points to a life dedicated to his craft. Gil’s incredibly talented—he writes songs, plays piano, arranges strings. I can say that because I didn’t write the music and I’m not actually a composer, but Gil is. [laughs] It suggests someone who spent most of his life focused on his career, and only found love later in life. “Why Love” hints that he may have even lost that love.

But I just love him. He’s a good guy. And the fact that his ghost reappears to help Oliver break free from the chains of his programming—to help him experience love—that speaks volumes about who Gil is. He’s lived a full life, and now he’s paying it forward.

PC: You can feel how deeply this character sits within you.
Dez: I love Gil. I want to be Gil. He inspires me deeply—so yeah, I really do love him.

PC: I feel like this is the perfect role for your Broadway debut. You actually answered my next question a bit, but there’s so much juxtaposition in this musical—and you really get to explore that in the different numbers. “Why Love” is so haunting and subtle, while “Jenny” is bold and expressive, not just vocally but in your facial performance too. How different is the preparation to tap into those contrasting mindsets, especially given that this is a one-act musical?
Dez: I was actually just asking Marcus [Choi] this same thing—I was like, “How do you shift from character to character like that?” And he said, “Well, the work’s been done in the rehearsal room.” And that’s true to a degree. You’ve run it so much by the time you’re performing, your brain just clicks into gear. I’ll even hear the lobby music in the hotel and be like, “Boom—we’re getting ready for ‘Jenny.’”

The thing about playing Gil is that you’re always Gil. Whatever mood he’s in, it’s still him. “Jenny” is like he’s on one of those old variety shows—he’s got one shot, one song, and he wants to make this moment count. He’s written it, choreographed it in his head, built the whole performance. And even though he’s nervous, he’s still Gil. I imagine Julie London just sang some smoky, sexy version of “I’m in the Mood for Love” before the commercial break. Dean Martin cracks a few jokes, and then—“Here’s up-and-comer Gil Brentley with his hit song, ‘Jenny.’” That’s the energy. I’m stepping out trying to crush it, trying to prove myself. There’s a youthful hunger in that moment—like, “I’ve got it, too.”

Then you’ve got something like “A Sentimental Person,” which is a completely different shade of Gil. It’s way more vulnerable. I’m often looking directly at people in the audience, and that can be a little scary—because sometimes when people feel seen from the stage, they don’t know how to react. [laughs] But other times, it leads to really beautiful moments. That song feels like something you’d hear at the end of the night in a quiet jazz bar. It’s personal. It’s like, “This is my truth. I’m in love. That’s scary. But I think you’re in love, too—and that makes me feel a little more okay.”

So yeah, it’s always Gil—but it’s Gil in different phases of his life, with different motivations driving him.

PC: That’s so funny. During “A Sentimental Person,” I noticed you picking out different people in the audience. That must feel really special for the people you choose—it’s fun to hear about the different reactions.
Dez: It’s honestly so much fun. I said it “sucked” earlier, but it doesn’t—it’s just funny when people feel perceived while they’re in full observer mode. You can see them shift. Sometimes it’s really joyful, like they’re thrilled to be part of the moment, and other times it’s more like, “Wait…are you looking at me?” [laughs] But I love that about Gil. He’s not just performing—he’s watching the story unfold with you. He gets to be present in that moment alongside the audience, and that’s a really beautiful thing.

PC: I feel like that works so well for this production too because it’s so immersive—without giving anything away for those who haven’t seen it.
Dez: Yeah, exactly. They’ve built the set in a way that feels more and more expansive as the show goes on. You almost feel like you’re being drawn into it, because it just keeps opening up—without spoiling anything, it really grows by the end.

And Gil becomes more involved in the story, too. He starts off as just a guy on a record player, but eventually, he has these really special moments with Oliver—watching the story unfold from the apartment above. It’s fun. The team did such a great job pacing everything out and letting the world build naturally around you.

PC: As you just said, what makes theater so special is that every night is unique to that audience—and that’s true for your performances as a musical artist as well. How different are those experiences? And how has the comfort of performing your own music on stage translated into your Broadway debut?
Dez: It actually translates a lot—especially because of the character. But it’s also a very different experience from other musicals I’ve done, where there’s this clear fourth wall. That doesn’t exist for Gil. There’s no barrier—no protection. I’ve been instructed to treat the audience as my audience, so it’s about having the confidence to look people directly in the eye.

That wasn’t hard for me, thankfully, because of the shows I’ve been doing for the past four or five years—setting up shop in a jazz bar or transforming an event space into one. It’s just me, a mic, and the band. We’re riffing, feeling the room, and really feeding off the energy in an interactive way.

That experience definitely prepared me for this. It helped me tap into Gil’s mindset—especially in the earlier part of his career, when he’s just showing up, singing his heart out, and feeling everything in real time. I’ve tried to bring that spirit into the character as much as I can.
PC: You belong on that stage. I know it’s not your song, but there’s a lyric in “Where You Belong” about Oliver being James’ anchor. Who have been the anchors in your own life—the people who’ve grounded you and helped you get to where you are today?
Dez: That’s a great question. I have an amazing family. I’m one of seven kids, and I have two parents who love me deeply. They taught me how to be musical—both my mom and dad are songwriters and wonderful singers. My family definitely keeps me the most grounded… and the most humble. [laughs] It’s hard to ever feel like a big deal when you’ve got six siblings. It doesn’t matter what I post in the group chat. I could be like, “We just performed on The Tonight Show,” and it’ll be the big news for maybe two hours—then someone shares a baby picture and that’s that. It brings you right back to real life. So yeah, my family is absolutely an anchor for me.

I also have close friends out here who are in it too—who are going through the same grind. That shared experience can be such a grounding force. It reminds you that what you’re feeling is normal, that you’re not losing it, that you shouldn’t give up just yet. Having people to bounce ideas off of, to talk through the highs and lows with—that’s so important. And honestly, that can be one of the hardest parts about being a music artist. In a lot of ways, it’s lonely unless you’ve found your people.

That’s one of the things I really love about Broadway. We’re all here together. I can walk into Helen [J. Shen]’s room between shows, and we’ll just sit on the couch and talk. I’ll share what I’m feeling, and usually, she gets it. There’s this sense of camaraderie that’s so special. But if I had to name one true anchor—it’s my family.

PC: That chemistry among the cast really comes through on stage. What I love about the cast recording is how it captures the experience of being in the theater. Can you talk a bit about what went into making that happen and how you ensured that sense of continuity from stage to studio?
Dez: That’s all Will Aronson, Hue Park, and Deborah Abramson. They’re incredible. They worked so hard throughout the entire recording process—it was a real sprint for them. We all watched them pour so much care and thought into figuring out, “How do we want this to be remembered forever?”

One of the things that’s amazed me about developing a new musical is how open-handed the process is. There’s this mindset of, “I created this thing, but I’m willing to change it if it makes the story stronger.” There’s room for critique, for deeper exploration, even for cutting songs if they no longer serve the piece. We actually cut an entire number during the Atlanta run before we moved to the big stage. That willingness to stay flexible, and then pivot into, “Okay, now how do we preserve this for good?”—watching that unfold was really cool.

For me, singing these songs night after night, they start to evolve a bit. Especially since my songs lean into jazz, I’ve been given a lot of freedom by Will and Hue. But I always want to honor what they wrote. I’m constantly like, “Please give me notes if something’s not exactly how it was written,” because I want to make sure we’re being true to their vision.

So going into the studio was like going back to the drawing board—asking, “How did these songs begin? What did we discover along the way? What layers have we added through Gil’s arc?” It was about finding what best serves the story now, and what emotional depth we could pull out. The beauty of recording is that you’re not confined to the physical demands of the stage anymore—so I could really focus on the emotional storytelling. Where can we dig in vocally? How can I express what Gil is feeling now that I’m not, say, running away from Oliver after something just happened—without giving any spoilers. [laughs] It was really about telling the story of the song as fully as I could.

PC: Anyone who sees you in this will immediately want to catch one of your live sets with your original music—the vocals are incredible. There’s also such a powerful thread in the show about memory. With this being your Broadway debut, what’s a moment from the experience so far that you’ll carry with you?
Dez: Thank you. There have been so many. It’s funny—I almost texted the cast today just to say, “I love you guys.” We’re sharing so many beautiful memories together.

One that really stands out is our first preview. Almost my entire family was there. During “Jenny,” we actually had a show stop—I was alone on stage when it happened. I walked off, and because the audience was mostly friends and family, they started cheering and clapping like crazy. When I came back out, they clapped again. I sat down—more clapping. [laughs] It was just such a fun, surreal moment. And then taking that first bow… it was electric. Helen [J. Shen] and I were both making our Broadway debuts, and the energy from everyone around us was nothing but pure encouragement. There was no patronizing, no “I remember my first time” kind of vibe. We were fully supported—told to take it all in and really feel how special it was.

So when it finally came time for that first bow, we just exploded. As a creative, you hold your breath the entire time. You’re constantly thinking, “Is this really happening? Is this actually going to happen?” You brace for disaster right up until the curtain goes up or the lights come down. There are so many twists and turns in this industry. So when we finally took that bow, it felt like this giant exhale—a dream realized.

And then Tuesday night, we had another show stop for a medical emergency in the audience. Thankfully, we’ve been getting updates from someone in the band, and she’s doing great—I’m so relieved. But in that moment, being told to walk back out on stage and just figure it out… I had to steady myself. And what ended up happening was this really calm, special moment that I got to share with Darren and Helen. It was once-in-a-lifetime. I hope we never have another show stop—because no one wants that—but looking back, I’m just like, “Golly, that was wild.”

PC: I think it actually heightened your performance—there was such humility and earnestness in the way you came out when you drew the short straw.
Dez: I kind of lied a little bit. [laughs] During previews, we knew there was a chance we might have some stops—there’s just so much going on in the show. So the plan was: if anything happened, I’d be the one to go out. But I didn’t think it would actually happen. Even when we did have stops, they were only a couple of minutes long. That plan felt like it was from a whole other era.

So when I was in my dressing room and suddenly heard, “We need Dez Duron on deck right now,” I was like, “Oh my God. This is it.” [laughs]

The crowd was wonderful. I immediately felt like they knew I was stepping out on a limb, and they were incredibly supportive. My biggest priority was making sure everyone felt comfortable—that I wasn’t just out there wasting their time. I genuinely wanted to entertain them for those ten minutes and help reassure them that everything was going to be okay.

But honestly? It was fun. That’s our job. That’s live theater.

PC: You did a fantastic job. Outside of Maybe Happy Ending, you’ve mentioned that being part of this production—and being in a city surrounded by so many artists—might give you more time to focus on your own music. Is there anything you can share about what fans can expect on that front?
Dez: I really want to start turning my focus in that direction. I’m not sure if it’ll be all original music right away. Given the role I’m playing on Broadway and what people might expect from me, I think it might start with some jazz covers—and maybe even jazzified versions of Broadway songs. But getting my original music out there is definitely the goal. That’s the next chapter… even if it should’ve been the focus a while ago. [laughs] I’ve just been enjoying the ride so much.

But yes, I’m always writing. With every show I do, I try to bring in new songs, test things out, see how they feel in the room. We’ve got some Joe’s Pub shows coming up in September that we just locked in. I’ll also be performing in Bryant Park on August 8th—and that set will include some originals.

We’re still figuring out the details. The dream version of the show—which depends on the budget, of course—would have six horns and big arrangements. Just bangers. Songs you know, songs you love. A big band sound that makes it feel like a real event. I want it to be something where you can come out, throw a frisbee around, and enjoy some live music that really swings.

To keep up with Dez, follow him on Instagram, Spotify, and Apple Music. Pick up your tickets to see Maybe Happy Ending today. Stream the cast recording here.