‘A Strange Loop’ brings queer Black representation to the stage

Celina Colby

Celina Colby is an arts and travel reporter with a fondness for Russian novels.... VIEW BIO

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When Dorchester native Kai Clifton saw “A Strange Loop,” it was the first time he had ever seen a queer Black character represented at the heart of a musical. After years of studying and participating in theater, Clifton finally felt like he belonged. Now, coming full circle, Clifton plays the protagonist Usher in the Speakeasy Stage and Front Porch Arts Collective performance.

“I remember being so captivated because I was seeing a fat Black queer person in the front, singing this beautiful song and hitting these high notes and it just looked so beautiful,” says Clifton. “I had never seen anyone who looks like me in that light.”

Now Clifton has the opportunity to provide that representation for a new generation of young theatergoers.

Kai Clifton, foreground, is backed up by his “Thoughts.” PHOTO: NILE SCOTT STUDIOS

The Tony Award and Pulitzer-Prize winning musical, written by Michael R. Jackson, centers on Usher, a protagonist grappling with his desires and identity and the pressures and judgments of the outside world. While attempting to write a musical, Usher battles with self-doubt, interacting with a sassy and outspoken cast of characters that represent his thoughts.

The musical began as a written monologue in which Jackson tried to work through his own emotions. Over the course of nearly two decades, that monologue evolved into “A Strange Loop.”

Produced in tandem by Speakeasy Stage and Front Porch Arts Collective, and directed by beloved local talent Maurice Emmanuel Parent, the show is a hilarious romp of a musical that exposes the soul of a young artist and serves an intensely personal and important purpose in representing the Black queer community.

“I think about my ancestors,” says Clifton. “I think about all of the queer people who have come before me who would have loved to see a show like this that represents them and represents what they go through and what they experience.”

“A Strange Loop” runs at the Wimberly Theatre in the South End April 26-May 25.

This production is an affirming full-circle moment for Clifton. Not only is it his first lead role in a production, it will be on stage at the Wimberly where he grew up watching local theater. Clifton was influenced by actors like Parent who paved the way for Black representation in the Boston theater scene. Now he joins their ranks.

“I’ve lived here my whole life and not only has Boston shaped who I am as a person, but it’s shaped my artistry,” says Clifton. “I love Boston audiences. I think they’re so progressive. I think they’re very smart and they want to be changed. They want to see work that’s bold. To be a part of that feels so amazing.”