By Jessica Doherty

A Strange Loop is a musical twenty years in the making. Michael R. Jackson, now 43, began writing the show when he was around the same age as the 25-year-old protagonist, Usher, a Black gay man who is trying to write a musical about a Black gay man who is trying to write a musical about a Black gay man.

‘[A Strange Loop] compresses twenty years of thought into a character who is experiencing these things in a discreet amount of time,” he said. “It reflects both the present moment and a whole lifetime of thoughts at the same time.”

Throughout the show, Usher grapples with his thoughts—portrayed by a Greek chorus that assumes many different characters throughout the show. He struggles with self-hatred, his sexuality, his religion, his race, his career, and his relationship with family— to name a few.

It may sound autobiographical, but Jackson assures it is not—the show is less about the moments that are directly from his life and more about the moments that bring Usher to his ultimate moment of clarity at the end.

Part of Jackson’s entry to theatre was through the church—both as a pianist for services and through the inherent theatricality of Sunday services. There, he learned a lot about music and Black musicality, which heavily influenced the show’s songs and themes.

“I am a Black theatre artist, and that means everything and nothing,” he said. “As a Black artist, I have a complex and sometimes contradictory experience and that is part of being alive and being human.”

In its one-hundred-and-forty-minute runtime, explores a lot of these contradictions as well as the intersections of different aspects of Usher’s identities with both seriousness and humor.Jaquel Spivey (Usher) in A Strange Loop. Photo by Marc J. Franklin

In the song “Exile in Gayville,” Usher’s forays on dating apps begin with short  snippets of “the sexual marketplace” that then sends him into a spiral of self loathing. In “Tyler Perry Writes Real Life,” his thoughts transform into various Black  historical figures like James Baldwin, Harriet Tubman, and Zora Neale Hurston call  him a race traitor for not writing a gospel play for Tyler Perry. A major pivotal moment  for Usher follows in a fervent ballad-turned-gospel chorus, “Precious Little Dream /  AIDS is God’s Punishment.” At the end of the holy commotion, Usher tells his mother,  “You wanted a gospel play / Well, this is the only way I knew how to do it.” 

These vignettes came from a personal place for Jackson, stemming from many points in his yearslong creative process. “As a young 20-something, I got so lonely and angry and sad and scared but also very creative,” he said. “I took all of my demons and made art out of them.”

Jackson never thought his “Big, Black, Queer-Ass American Broadway Show” would make it to Broadway, but it did, earning many accolades like the Pulitzer Prize for Drama in 2020 and the Tony Award for Best Musical in 2022 along the way.

L to R): L Morgan Lee (Thought 1), Jason  Veasey (Thought 5), John-Michael Lyles  (Thought 3),
  in A Strange Loop. Photo by Marc J. Franklin

“I’m really grateful to have had all those years to spend thinking about ‘myself,’” he said. “I’m not the same person that I was when I began writing it, and, in other ways, I’m exactly the same person I was when I began writing it.”

But he said the show’s success wasn’t all “lollipops and roses.” He had made his dream come true— what’s next? “Particularly after A Strange Loop, I’ve been casting my gaze outward to the world,” he said. “I got a lot of attention, and, getting that attention, was its own strange loop.” His second musical, White Girl in Danger, satirized melodramatic Lifetime movies and daytime soap stories. The protagonist, Keesha, breaks free from the “Blackground” she is relegated to in the soap opera town “Allwhite.” While it is a different subject than A Strange Loop, he considers the musical to be somewhat of a sequel, as it reflects where his mind went after his journey with his first show. He’s also currently working on a horror film with A24 and Ari Aster and a “coming-of-rage-musical-comedy" closing this month at Playwrights Horizons based on the cult classic film Teeth.

Despite varying topics, the throughline of his work lies in how he challenges preconceived notions. “I’m always trying to push the boundaries of form as much as possible to connect with audiences and to communicate ideas that are maybe a little challenging, but also reflective of the human experience, the things that we maybe don’t like to talk about.”

He knows that this is not an easy task in the current political and artistic climate.

“I feel that we are entering, or re-entering, a more conservative time, artistic and culturally,” he said. “I also believe that it will be harder for me to do some of the things I want to do...but it won’t be impossible.”

As social media silos continue to grow, Jackson finds the act of bringing people together to the theatre in a truly inclusive way even more challenging.

“There are all these movements to segregate everything in order to make things more inclusive, but I think that it’s doing the opposite,” he said. “But the art form is supposed to be something that literally everyone can access, but we don’t talk much about form, we talk a lot about content, and the content dictates exclusivity rules.” Some people have come up to Jackson to talk to him about the show and make a point to say that, as a person who does not fully align with Usher’s background that they enjoy the show despite it not being for them. But Jackson argues that it is for them— and it is for everyone.

And so, Jackson finds a new loop beginning. “I see my future being, in many ways, like how it started, with a lot of struggle... but eventually getting to a place where I can share my art with audiences and let them decide what they think about it.”