Student Blog: Jagged Little Thrill: The Thrill of Nick Healy & Jagged Little Pill with Dillon Klena

You don’t always need to be prescribed a pill to heal. Sometimes, all it takes is a night in the theater. A story that reaches you, a performance that lets something inside lift, loosen, or breathe again. Jagged Little Pill is exactly that kind of art, healing, challenging, and transformative. And for Dillon Klena, it became a personal journey, one that would leave a lasting legacy on the show and on himself.

Dillon’s earliest memory of Jagged Little Pill dates back to middle school, when he heard “You Outta Know” on the radio and listened to it with his parents. That song became his introduction to the album, a gateway to the music that would later define so much of his life. His first memory of the musical itself was watching the character of Nick Healy, originated by his older brother Derek Klena, perform with a cello in the first adaptation of the show. Although that particular scene did not make it into the final production, the memory became the spark for what would grow into an incredible personal and professional journey.

One of Dillon’s fondest memories with the show was turning twenty-one during the first preview of Jagged Little Pill on Broadway. Outside the stage door, he shared his first toast with Derek, unaware that he would soon step into the very role his brother had originated. Dillon has witnessed the show through every iteration from its Off-Broadway tryout in Boston, to multiple Broadway performances, to getting to lead the national tour as Nick Healy. Dillon first experienced Jagged Little Pill at nineteen, watching his brother as Nick, and four years later, at twenty-three, he stepped into the role himself on the national tour.

Interestingly, Dillon did not immediately connect with Nick. When watching the show, he related more to Phoenix. “Since Nick was a huge part of Derek, he became a huge part of our family.” When Dillon embarked on the national tour, he began connecting to the character and the story on a deeper level. “Watching my brother go through the process of the show and then stepping into it knowing that background was extremely helpful as a kid dealing with the show and its themes,” Dillon recalls.

Playing Nick was never part of Dillon’s initial plan. He assumed Phoenix would be the role for him. At nineteen, he first saw his brother as Nick, and by twenty-three, he was performing as Nick himself. His journey began with a self-tape audition for Phoenix as a quick replacement on Broadway. He didn’t hear back, but a few months later, he received a request to audition for Nick for the national tour. Excited and shocked, Dillon poured his heart into the self-tape, submitting it with care. A month later came a callback for both Nick and Phoenix. Dillon attended the in-person callback, performing a dance call for Nick and reading sides for both characters. For the final callback, he was then asked to focus on Phoenix material while keeping Nick in his back pocket. On his final callback day, Dillon performed one Phoenix scene, one Phoenix song, and then delivered all of the Nick material, fully showcasing his ability to embody both characters. 

The moment Dillon officially booked the tour was unforgettable. While seeing Company on Broadway with his Best Friend, he missed two calls and then received texts from his agent. At intermission, he checked his phone to find the message: “Dillon. Call me!!!” He immediately returned the call and learned he had booked Jagged Little Pill. He then called his mom to inform her of the news and then Derek and the two had scheduled dinner to celebrate and discuss the show and the character. Derek had helped him with one of the audition scenes, offering guidance and advice, a quiet passing of the torch that made the achievement even more meaningful.

Stepping into a role previously played by his brother brought unique challenges. Dillon had done this before in Dog Fight with Eddie Birdlace, but Nick was different. With Phoenix, he had no familiar template but with Nick, he had Derek’s interpretation as a reference. Yet this familiarity helped him find his own voice in the role. Dillon embraced the emotional journey of the character by using his personal outlooks to help shape his unique portrayal of Nick. 

In Jagged Little Pill, Dillon encountered moments where the legacy of his brother became strikingly tangible. During costume fittings, he was asked to try on every costume Derek had worn as Nick on Broadway. Every piece still had Derek’s name tag, and when Dillon tried on Derek’s shoes, he discovered that they fit perfectly. He then went on to wear those very shoes when he embarked on tour and walked in his brother’s literal shoes, a symbolic and profoundly moving gesture. The fact that the name tag already read “D. Klena” was an unplanned bonus; it was as if the role had been waiting for him to step into. Dillon wore those shoes throughout the first year of the tour until they broke as that year came to an end. Receiving a new pair marked the start of the second year of tour, a moment where he could fully step into the role himself. It was a beautiful, symbolic passing of the torch, showing that while he honored the path Derek had carved, he was now claiming Nick as his own.

Another artifact carried equal emotional resonance: a prop notebook that Nick uses toward the end of the show. Many props on the national tour were the same as Broadway’s, and Dillon discovered that the notebook had been used by Derek. Inside, Derek had written in it as if it were a diary, documenting moments in his life throughout his time with the show. One of the things Derek had written was, “Dillon’s NYC Debut Baby” when Dillon was performing in New York at the same time in Starry: The Musical. Reading it for the first time now playing Nick on tour, Dillon was moved. He even called Derek from his dressing room, and began reading aloud what his brother had written to see if it “clocked in for Derek,” and Derek immediately recognized it. This shared artifact created a moment of connection across time and stage, blending mentorship, family, and legacy into the very props of the performance as if this story had already been written for the two of them in the pages of this very notebook. By the end of the tour, Dillon had filled all the pages himself, keeping the notebook and the shoes as cherished artifacts, a beautiful reminder of the personal and professional journey he shared with Derek, and of stepping into the role of Nick Healy. 

The national tour rehearsal process began at New 42 Studios in New York City, with two to four weeks of preparation before traveling to Louisville, Kentucky, for previews and two weeks of tech. The tour's opening night was at the Pantages Theater in Dillon’s hometown of Los Angeles. This was a full-circle moment, performing before an audience filled with people that had watched him grow up. Dillon reflects on the importance of touring productions as many communities don’t have access to Broadway-level theater, and national tours often provide the first exposure to these transformative performances. Opening at the Pantages allowed him to witness firsthand how touring theater inspires children and communities alike; years earlier, he had been one of those children sitting in the very seats of the Pantages, moved by countless touring productions, and now he was the one standing on that stage.

The tour was full of firsts for Dillon: his first national tour, his first experience performing eight shows a week, and his first time seeing the world through the lens of touring with theater. The show’s progressive themes, addressing identity, trauma, and social justice gave Dillon the opportunity to advocate for communities and amplify voices that might otherwise go unheard. Audience members often expressed gratitude for bringing the show to their cities, reinforcing the social impact of the production.

For Dillon, the greatest joy was performing. Traveling, connecting with audiences, and telling a story that matters. Touring enriched him as both an actor and a person, allowing him to see the similarities and differences of the show across the country and immerse himself in the variety of life experiences around him. Each performance was a privilege, a chance to inspire, heal, and challenge audiences and Dillon never took that responsibility for granted.

Dillon has been one of my greatest inspirations, and the Klena family have been such bright lights, not only in my life but in the theater community. Getting to have the honor of knowing Dillon personally and witnessing his journey become what it is today has been beyond impactful. In the end, Dillon Klena’s journey with Jagged Little Pill is more than just a story about stepping into a role, it is a testament to the power of art to heal, connect, and transform. It is about family, legacy, and the quiet magic of walking in someone else’s shoes while discovering your own— and it is even more special when that someone is your older brother. Every performance, every city, every shared stage door moment reaffirmed that theater is more than entertainment, it is a lifeline, a mirror, and a catalyst for change. For Dillon, for audiences, and for anyone who has ever felt the music and the story of Jagged Little Pill stir something deep inside, the show is proof that sometimes the most powerful prescription is not a pill at all, but a jagged little story that is lived and felt in the hearts of those who take the journey.