‘A Strange Loop’ Broadway Darling Michael R. Jackson Feels Pride — For Himself

It’s June 2022, and Michael R. Jackson has a lot to be proud of. His musical “A Strange Loop” leads the Broadway awards-season race with 11 Tony nominations and stands poised to net the top musical trophy plus several others for him and his collaborators. The show has become a New York media darling; ticket sales have spiked from all the attention; and film and TV projects beckon alongside his ongoing theater work.

But whether Jackson feels anything like capital-P Pride remains up for debate.

“It’s a question I’m asking myself, and I haven’t figured out the answer,” the 41-year-old writer-composer-lyricist says. “I guess the pride I feel is more of an individual one, in the sense that for many years I measured myself against other people’s idea of how to be gay or how to live in the world. I don’t really do that anymore, which I feel good about, but I also feel a little in my own lane about it.

“In a very general way I support the advocacy of pride, particularly things that are helping kids, but there definitely is a corporate feel to it that I don’t resonate with,” he continues. “The other night I went to an event where they were cheering their sponsors, and it’s just very bizarre to see queer people cheering banks and oil companies and weapons manufacturers. But I guess that’s inclusion!”

It’s an answer that embraces ambivalence, complexity and discomfort — and that’s punctuated by a skewering wit. You can say the same of “A Strange Loop,” his kinda-sorta autobiographical show about a queer Black man writing a musical about a queer Black man writing a musical. As the protagonist, Usher, wrestles with ambition, expression, shame, lust, self-loathing and parental expectations, he shares his complicated, cutting feelings about everything from homophobic Christian teachings to the white gaytriarchy to Tyler Perry. Nothing and no one escapes his gimlet eye, especially not Usher himself.

“Michael is so honest and so vulnerable in his work, and he has this ability to push an audience into really kind of shocking, sometimes ridiculous places but keep them rooted in a nuanced sense of character,” says Stephen Brackett, the Tony-nominated director of “A Strange Loop,” who has known Jackson since 2010 and worked on the show for a decade. “Michael knows how to make an impact with these moments that make part of your brain go, ‘Oh my God, I can’t believe he’s going there.’”

“Strange Loop” cast member John-Andrew Morrison, now up for a featured actor Tony, adds, “The thing that has been thrilling to see over the years is that at one point in time Michael was a little more sensitive and shy, but now he’s stepped into this confidence in himself as an artist and as a speaker and as a gay man in a way that’s really met this moment.”

Morrison has been attached to “Strange Loop” since 2008, and Jackson has been working on the show since it began life in 2003 as a monologue he wrote “as a life raft for myself” called “Why I Can’t Get Work.” Throughout its many evolutions, the show picked up long-term collaborators like Morrison and Brackett and their fellow nominee L Morgan Lee, the featured actress contender who is the first openly transgender performer to be nominated for a Tony.

“Everybody was willing, time and time again, to come back, work on it for free, maybe get some Popeyes chicken and then do a reading in a porn factory,” Brackett recalls. “I think people have a sense of feeling seen in this piece that they haven’t felt working on other shows.”

Over all those years and all the developmental work with organizations like Ars Nova, the Lark, Musical Theater Factory and P73, Broadway was never on the radar. It wasn’t until the 2019 Off Broadway premiere at Playwrights Horizons — where the show became a critically lauded buzz magnet — that Jackson says he and his collaborators started to think seriously about the possibility of a commercial move.

Awards from the New York Drama Critics Circle and the Pulitzers added further momentum, but by that time the pandemic had intervened to push back the timeline. After a pre-Broadway run at Washington, D.C.’s Woolly Mammoth in late 2021 and a handful of springtime COVID disruptions, “A Strange Loop” finally opened at the Lyceum Theater on April 26.

“I think a lot about what it means to really spend your time on a piece of art trying to make it as good as it can be,” Jackson says. “Something happening immediately doesn’t mean that it’s good. Something taking a long time can be worth it. When I’m watching people react and have emotional responses to the show, I know that part of what they’re responding to is that we took our time, whether they know it or not.”

Now those reactions include the Broadway audience member from Georgia who told Jackson he found solace in the show, or the man who said seeing “A Strange Loop” with some of his family members inspired conversations with relatives who hadn’t accepted his being gay.

“I never think of myself as an activist, but I do believe in the power of art,” Jackson says. “And in a way ‘A Strange Loop’ does connect to pride because the show is expressing itself without fear, so much so that it’s not afraid to show even the shame. I often hear a lot of gay men say, ‘Oh, we need to move away from stories about shame or the closet,’ and my response to that is always complicated because that might be somebody’s story. Why should they have to hide the ugly parts, if that’s part of who they are? This is a show that exposes all of the parts of its protagonist, even the parts that may make some gay or queer people uncomfortable.”

“A Strange Loop” heads into the Tony ceremony on June 12 as the show to beat, even if it remains an open question whether Tony voters — not to mention the national network of Broadway road presenters — are ready to welcome a musical with an opening number that gleefully announces, “There will be butt-fucking!”

Whatever happens onstage at Radio City, Jackson has a lot on his plate. Following a stint in the writers’ room of Boots Riley’s upcoming Amazon series “I’m a Virgo,” he’s at work on a horror movie for A24 and is developing a TV series for ABC Signature. Plus, he’s got a workshop this summer of his stage musical “White Girl in Danger.”

He’ll be picking future projects carefully. “Particularly as a Black artist, I want to be and I have to be free,” Jackson says. “I want to make art that is as challenging as it is entertaining. I want to piss everybody off and I want to delight everyone, and people can throw tomatoes or not like it, but I don’t want that to stop me from continuing to work. I want to build an audience, and I want people to engage with my work and to think about it and to come back to it and to love it and to hate it and to criticize it and to reread it. And, and, and, and, and. That’s what I’m fighting for.”