A Pulitzer winner at the worst possible time, 'A Strange Loop' is Broadway-bound

Of all the terrible times to win a Pulitzer Prize for drama, the worst was surely April 2020. Every theater was shuttered and dark when playwright Michael R. Jackson's shattering debut musical, A Strange Loop, took the prize.

"It was pretty surreal," Jackson admits. "My producers got on Zoom and got everyone involved on the production together, and they sent me some champagne."

More than a year later, A Strange Loop is finally gearing up for Broadway. Jackson sat down for an interview with NPR at the Woolly Mammoth Theatre in Washington D.C. where the show recently opened to rave reviews. It explores a young playwright's meta-journey—a "portrait of a portrait of an artist," in the words of the main character.

"It's about a black, queer man writing a musical about a black, queer man who's writing a musical about a black queer man who's writing a musical about a black queer man," the playwright's stand-in, Usher, explains to a sympathetic Broadway tourist. Usher is literally a theater usher, showing out-of-towners to their seats to The Lion King—a job Jackson actually held while writing this musical. (Don't for a minute think it's accidental that a playwright whose name is Michael Jackson chose Usher as a sort of nom de théâtre.)

"The piece is not autobiographical," Jackson tells NPR. "I call it self-referential—which is to say, I drew on personal experience to write a lot of it, but it's not an apples-to-apples relationship to my life."

Michael R. Jackson grew up in Detroit. His father was a police officer, and his mother worked in finance for General Motors. Jackson was an aspiring child actor who also played piano in church. He loved writing fiction, and a teacher in high school encouraged him to consider screenwriting, since his stories were so cinematic. Scripting soap operas sounded like fun, so Jackson applied to New York University's playwriting program.

"I loved musicals, but I never thought about writing them," he says. He ended up studying musical theater as a graduate student at NYU, he says, simply because it was his most interesting option after college. The obsessive challenge of creating musicals is fundamental to what makes A Strange Loop so... meta.

Jackson's musical kaleidoscopically draws on influences ranging from Stephen Sondheim to Kirsten Childs to George C. Wolfe, and owes a peculiar debt to the rocker Liz Phair. One of her songs even inspired the musical's name.

"Liz Phair is unabashedly herself and who had her own voice and her own music," Jackson explains. Listening to Phair's music in high school helped teach him to channel rage into art. "Weirdly, Liz Phair helps me get there," he says, patiently. "She did. Tori Amos did. Joni Mitchell did." (You can watch Jackson's paean to these artists in the song from his musical called "Inner White Girl.")

"From the moment I heard the music for A Strange Loop, I thought Michael R. Jackson was a genius," says Woolly Mammoth Theater artistic director Maria Manuela Goyanes. That moment dates back to when Jackson was workshopping the show in its very early stages.

Goyanes has launched other risky musicals, including a little show called Hamilton, when she worked at the Public Theatre in New York. "I feel like A Strange Loop is a musical for people who don't like musicals," she says. "It doesn't work like a normal musical at all."

Normal musicals don't come with trigger warnings about racially fetishized sex, child abuse and racist stereotypes. Nor do they devote numerous over-the-top musical numbers dragging Tyler Perry for his history of producing lowbrow entertainment containing messages of homophobia and HIV stigmatization.

"He didn't see it. He heard about it," Jackson allows, when asked about Perry's reaction. "He called me to congratulate me when I won the Pulitzer, which I think was a really nice thing to do. I mean, he also told me that he was gonna beat my ass if he ever saw me."

More recently, Jackson has been working on two other projects. One is a musical adaptation of Teeth, a 2007 feminist-black-comedy horror film about a born-again Christian teenager who finds herself suffering from an unexpected case of vagina dentata. He's also going back to his earlier ambitions by working on an original musical inspired by soap operas, titled White Girl In Danger.

And at last, A Strange Loop is expected to open on Broadway in 2022. That is, unless the pandemic shuts theaters again, in a strange loop that nobody needs—especially not Michael R. Jackson.

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