When Illness Hit, Tony-Winning Strange Loop Creator Saved Show by Going on: 'Not in My Wildest Dreams'

Michael R. Jackson steps into the role of Usher in A Strange Loop
Michael R. Jackson steps into the role of Usher in A Strange Loop

Jimmy Wilson, Theo Wargo/Getty

Life is imitating art for playwright and songwriter Michael R. Jackson.

After winning the 2020 Pulitzer Prize for Drama and the 2022 Tony Award for Best Musical for A Strange Loop, Jackson is closing out his first Broadway endeavor with another milestone moment.

On Saturday, the 41-year-old writer made his Broadway performance debut in his very own show when cast members fell ill and the production was almost forced to cancel its weekend of shows. With only one week left on Broadway before A Strange Loop plays its final performance on Jan. 15, Jackson knew the show(s) must go on.

"We didn't want to cancel any more shows than we already had," Jackson tells PEOPLE following the whirlwind weekend. "And so it was floated to me the idea of: How would I feel about doing a concert version? And I couldn't totally wrap my brain around it."

He adds, "Not in my wildest dreams."

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Michael R. Jackson steps into the role of Usher in A Strange Loop
Michael R. Jackson steps into the role of Usher in A Strange Loop

Jimmy Wilson

Still, it happened. Jackson took the stage in the lead role of Usher, a queer Black man who works as an usher at the Broadway musical The Lion King. It's a part Jackson knows all too well, mirrored after his own life before he found recent success on Broadway and in the theater industry.

"I was nervous, but I also weirdly had an excitement," Jackson explains.

Before the shows on Saturday, the writer went into the rehearsal room with music director Rona Siddiqui and director Stephen Brackett. Though Jackson has performed much of the show's material before in concert, he wanted to iron out any uncertainties before taking the stage at the Lyceum Theatre.

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The show was pared down from its original staging. The actors sat at chairs, and Jackson had a music stand with him. Still, the audience was electric, he says.

Before going on, Jackson thought, "People are coming to see a Broadway show, and we're gonna do this reading, and it's with me in it. So I kept bracing myself for people to boo or something like that, but the minute they announced that I was going on, and I walked out, it was kind of thunderous applause."

Things became particularly emotional when Jackson sang the words, "I am the story's writer." He began writing his autobiographical Strange Loop when he was in his 20s. After a stint Off-Broadway in 2019, it eventually transferred to Broadway in 2022, receiving critical acclaim.

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"That first performance, that moment especially was an incredibly powerful and emotional moment for me. And I think some of the audience started to hear when I sang those words that first time. I got very choked up," Jackson tells PEOPLE.

"But I just committed to the words of it and just tried to tell the story to the best of my ability and be truthful in singing the song. It was a very emotional moment for me because it was like I was talking to my 23-year-old self who started the show, and he could have never imagined where we would end up."

With only a week left on Broadway, Jackson says that going on in his show at the last minute felt "like a sense of completion" for him.

Michael R. Jackson steps into the role of Usher in A Strange Loop
Michael R. Jackson steps into the role of Usher in A Strange Loop

Jimmy Wilson

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"It felt like the universe was giving me the closure that I need," he says. "I got to be Usher and remember what the experiences were like that I drew upon to write the show — but from such a different older and wiser experience and not feel the trauma or the low self-esteem that I was feeling when I was writing through them as a younger person."

He adds, "To know that the little Black gay boy with a low self image would get to take stage and tell the emotional version of his story and that he would be applauded for it — it was just a really powerful thing for me."

Jackson's next project, White Girl in Danger, will begin performances Off-Broadway March 15 at the Tony Kiser Theater.