A Strange, Yet Familiar, Loop

“What I find heartening about this theater is that it’s the same kind of theater I’ve performed in,” muses JonMichael Reese ’05. “You show up and put on a show. That simplicity is beautiful to me.”

For Jon-Michael, putting on a show has always brought him joy, but “simplicity” may be an understatement. The theater in question is the Lyceum Theater on Broadway, one of the oldest surviving Broadway venues. And the show is not just any show, but the Pulitzer Prize-winning hit, A Strange Loop, winner of the 2022 Tony Award for Best Musical, of which Jon-Michael is an original cast member.

A Strange Loop follows the story of Usher, a queer, Black man writing a musical about a queer, Black man writing a musical. The term “strange loop” is a cognitive science term coined by Douglas Hofstadter. In his book “I Am a Strange Loop,” Hofstadter described it as, “Despite one’s sense of departing ever further from one’s origin, one winds up, to one’s shock, exactly where one had started.”

The success of A Strange Loop has been a dream come true for Jon-Michael, and the culmination of more than two decades of hard work in musical theater — a journey that began at Tatnall.

“What is so special about Tatnall and Dr. Chipman, Mrs. Crawford, Mr. Neidig, and so many others,” he remembers, “is that they made us feel like their peers, never like students or children. I’ve always carried that with me.”

After graduation, Jon-Michael continued his pursuit of musical theater at Carnegie Mellon’s School of Drama before moving to New York City. His early beginnings included notable roles such as a “villainous, diva-fied Thomas Edison” in Nikola Tesla Drops the Beat and artist/ activist James Baldwin in Jimmy and Lorraine. He also joined the second national tour of Book of Mormon, which was a first taste of the kind of juggernaut show that A Strange Loop would later become.

“It’s weird to say that I started small, but that’s exactly what happened!” Jon-Michael continues. “In hindsight, I had a total lack of awareness about how much confidence I had as a 22-year-old, but that sort of naive ambition got me pretty far. But theater is such an unstable business — it taught me to cherish my time with the people in the show.”

Despite the uncertain nature of the industry, JonMichael cherishes the variety and the opportunity to try many things at once. He credits Tatnall for helping him develop such a valuable perspective.

“I cherish those shows we put on,” he reflects. “The fact that I did A Doll’s House as a high school student blows people’s minds. The variety of shows was astounding, and it made me want to do everything. I still want to do everything!”

The path to A Strange Loop began when Jon-Michael did a workshop for the show’s writer, Michael Jackson, who had been developing the story into a musical. It helped Jon-Michael realize that who he worked with was more important than what he was working on. When the show came to Broadway, he jumped at the chance to audition for an understudy role. Not long after, A Strange Loop took off.

“The scary thing about an actor’s life is that it’s not linear,” he says. “It’s all about making connections. It’s about finding the artist that you enjoy making art with. I loved my time in Michael’s workshop, so it was a dream to be a part of his vision for the show.”

A Strange Loop closed in 2023, and Jon-Michael will head back to search for his next mountain to climb. This time, the uncertainty may be less daunting, for within the rise of A Strange Loop, Jon-Michael rekindled something elemental about his life as an actor — strong relationships with teachers and mentors who want to see HIM.

To me, what is so special about Tatnall and Dr. Chipman, Mrs. Crawford, Mr. Neidig and so many others, is that we never went to acting class we put on shows.

—Jon-Michael Reese ’05