New England premiere of ‘Strange Loop’ opens in Boston this weekend

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"A Strange Loop" playwright Michael R. Jackson. Photo Beowulf Sheehan

[This article appears in the March/April 2024 print issue of Boston Spirit magazine. Subscribe for free today.]

“A Strange Loop,” a musical about a theater usher named Usher­—a Black, queer man who is writing a musical about a Black, queer man, ad infini-tum—took Broadway by storm and earned the Pulitzer Prize and two Tony Awards for its creator, Michael J. Jackson. That may strike many as a joy-fully unlikely phenomenon. But “A Strange Loop” continues to have a life well beyond New York, resonating with audiences most recently in London and soon arriving in Boston, where it will have its New England Premiere.

Boston audiences will get to see “A Strange Loop” in a co-production of SpeakEasy Stage Company and the Front Porch Arts Collective April 26–May 25 at the Wimberly Theatre in the Calderwood Pavilion, 527 Tremont Street, in Boston’s South End.

“I started working on ‘A Strange Loop’ as a personal monologue when I was 23 years old. At that time, it was a kind of personalized testimony of what it felt like to be a young, fat, Black, gay man in the world,” says Jackson, now 42 and readying his latest show, “Teeth,” for its off-Broadway opening at Playwrights Horizons. 

“A Strange Loop,” he says, “was not something I ever expected anyone to see. I did not plan on it being a musical, and when it did become a musical, I didn’t think it would get produced anywhere. My highest aspiration was maybe off-Broadway. So when it got a production [at Playwrights Hori-zons in 2019 before heading to Broadway in 2022], that was the pinnacle for me, especially how well received it was. … At the heart of it, it’s about a human being trying to deal with himself. Everybody experiences that, so it goes to the universal.” 

Maurice Emmanuel Parent, co-founder and co-producing artistic director of Front Porch Arts Collective, will direct “A Strange Loop.” He’s had a long artistic relationship with SpeakEasy Stage, directing productions such as “Choir Boy” and acting in many shows including “The Scottsboro Boys,” “Bootycandy” and “The Color Purple,” which earned Parent a Best Supporting Actor in a Musical award from the Independent Reviewers of New England (IRNE) in 2015. 

“A Strange Loop,” says Parent, is “a beautiful piece of art” that thrilled him from the moment he saw it on Broadway.

“My jaw was on the floor. I could not believe that something this honest and open and unapologetic was not only on Broadway but there wasn’t any empty seat in the theater and it was a very mixed crowd,” he says. “[Jackson] has said that the show is a mirror for some and a window for others. I saw it as a mirror,” says Parent who, like Usher, is “a Black, gay man raised in the church,” which represents “refuge and safety for some and trauma and pain for others. There are lots of loops in the play; there is the family and church as home, connection and expression with gospel music in the show but also judgement and harm.”

That judgement also extends into queer culture. “A Strange Loop” is brutally honest about Usher’s experiences with “fat shaming and lot of the exclusions that are just as isolating and ostracizing in queer spaces,” notes Parent.

Jackson, who holds a BFA and MFA in playwriting and musical theatre writing from the NYU Tisch School of the Arts, created his emotionally autobiographical “A Strange Loop” out of his lifelong love for musical theater. Like Usher, he was also “once an usher in back of the theater ringing bells and dreaming of having a show on a stage somewhere. I just kept doing it because I loved it… I am as much a consumer of theater as a creator of it,” he says.

Jackson’s follow-up to “A Strange Loop” was last year’s off-Broadway musical “White Girl in Danger,” a sharp satire on race and soap operas. His newest creation, “Teeth,” is a dark comedy based on the cult classic movie of the same title. Jackson wrote the book and lyrics, and collaborator Anna K. Jacobs wrote the book and music for the show, described as centering on “Dawn O’Keefe, an evangelical Christian teen with a powerful secret not even she understands—when men violate her, her body bites back. Literally.” 

“Anna has a different entry point [into the material]. While I am not an evangelical girl with teeth in her vagina, spiritually I am,” says Jackson. “Yes, my entry is through the religious aspect—religion and sexuality battling each other was a story I knew well from growing up in the church. Once I started working with Anna, it became clear that this was a piece for us and also clear that I should not do the music. I didn’t have the musical language to tell the story, and I wanted to work with a female composer who I thought could supply that language, and Anna was it.”

While his personal passions and individual sensibility imbue all his projects, it’s particularly gratifying that a work as personal as “A Strange Loop” has moved so many audiences while making its mark on the culture.

“It always heartens me when I hear from people that it inspired them to write their own story and push the boundaries of the form,” Jackson says. “I love the arts, I love theater, I love musical theater and I want to live in a world where there are more challenging and entertaining works out there that are making space for other people to make space for other people on the stage.”

More: speakeasystage.com

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