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How Michael R. Jackson’s big, Black queer show 'A Strange Loop' is transforming Broadway

Michael R. Jackson’s electrifying Broadway debut is an intensely personal look at the mind's carousal of self-sabotage.
Michael R. Jackson and Jaquel Spivey in "A Strange Loop."
Michael R. Jackson and Jaquel Spivey in "A Strange Loop."Beowulf Sheehan / Marc J. Franklin
/ Source: TODAY

For playwright Michael R. Jackson, the question “what’s in a name?” has several responses. 

His meta-fictional, merry-go-round musical “A Strange Loop” packs as much into the title as it does onto the stage. Earning the 2020 Pulitzer Prize for drama — a rarity for musicals — it’s also the most-nominated show at the 75th annual Tony Awards this Sunday, June 12, having cinched 11 nominations.

Also a composer and lyricist, the 41-year-old began crafting the idea in his early 20s, working as an usher in Broadway theaters night after night. Based on Jackson's own experiences coming of age during that time, the musical describes itself as a "big, Black and queer ass American Broadway show.”

According to audiences and critics, it’s all that and more. Variety called it "both a raw and unflinching interrogation of identity and the most furiously entertaining show on Broadway," while the Washington Post praised it as Broadway's best new musical.

“Strange loops are sort of about self-reference and paradox — starting in one place and ending up right back where you started, even though you think you’ve gone the distance,” Jackson told TODAY.

The luckiest loop? How the show “manifested itself onto a Broadway stage when it’s about someone trying to get onto a Broadway stage." It sounds sequential, but for Jackson, getting it there was a long, arduous process that took almost two decades.

Jaquel Spivey as "Usher."
Jaquel Spivey as "Usher."Marc J. Franklin

What's contributed to the electrifying presence of “A Strange Loop” and its sweeping success is also a list of very well-known producers, including RuPaul and Jennifer Hudson.

“I’ve loved Jennifer for years,” Jackson said. “She’s always been my cousin in my head, so it was nice to have my cousin helping produce this.”

Over 18 years ago, Jackson began to write the musical that’s become his breakout hit, as the industry still struggles to represent people like him on its stages.

Played by Jaquel Spivey in his Broadway debut, the protagonist is a 25-year-old theater usher who’s also writing a play about his life. Fighting the commercialism of conglomerates like Tyler Perry and Disney, "Usher" struggles being a Black, queer writer writing about being a Black, queer writer. The show profiles him through this process while answering his thoughts — played by a talented Greek chorus of six actors each representing different parts of him — in their brutal honesty. From self-loathing to sexual ambivalence, they leave nothing out of the protagonist’s conflicted inner world that harbors resentment flowered from his homophobic, religious family.

“A Strange Loop” gives an unflinching glance at a young man becoming in a world as conflicted as his own inner life. Despite covering intensely personal situations, the play still appeals to audiences as completely universal. “For some people, the show is a mirror, and for other people the show is a window, and both of those experiences are coexisting right next to each other,” Jackson said.

Michael R. Jackson.
Michael R. Jackson.Zack DeZon

How much of the show is about Jackson himself? 

“I would say it’s emotionally autobiographical in that I have felt everything that Usher has felt, but it’s still different than saying this is my life, because there are things that happen in the soul that are super heightened and theatrical,” Jackson said.  

While the time it took Jackson to complete the musical and get it on a Broadway stage was transformative for him, there are some givens that stayed the same: his dedication.

“I didn’t let it go for a couple of reasons,” he said. “One was because I had no plan B whatsoever. I was already working a day job that I hated, so what would I do with the rest of my time?” 

“We have to actually talk about the work in a real way and not just celebrate its presence.”

michael r. jackson

Throughout the years of workshopping and adjusting, Jackson did find time to rethink his approach and find “some distance from it.” That time and space made it possible to “really write about it as a piece of art.”

Amid all that change, what stayed? Jackson said no matter what, the "thing that has remained constant is that the story has always been about an usher that’s a 25-year-old Black gay man." 

“A Strange Loop’’ is coming at a time of change in the Broadway community, where Black protagonists like Jackson’s and his no-holds-barred approach to storytelling is a newer phenomenon. A 2019 report by the Actor’s Equity Association found that just 8% of the organization’s nearly 52,000 actors and stage managers nationwide are Black.

The cast of "A Strange Loop."
The cast of "A Strange Loop."Marc J. Franklin

But Black representation on Broadway has seen an upward trend that’s worth noting. In 2021, seven plays by Black playwrights with predominately Black casts debuted. Jeremy O’Harris’ “Slave Play” led audiences through a look behind the deep-rooted sexual politics of interracial relationships. With other works like a revival of “For Colored Girls Who Have Considered Suicide…” and the new show “Thoughts of a Colored Man,” the Broadway stage is set for a new guard confronting old traumas. 

But does this really spell change? 

For Jackson, he insists that “only time will tell’’ what this moment means for the industry. “I don’t know if I can call this moment change or not, because it’ll only really be changed if it sustains itself, which is a strange loop; it has to continue in order for it to really be a change. It has to become the status-quo,” he said.

“It’s more than the work just being there and being celebrated, of course," he continued, adding, “we have to actually talk about the work in a real way and not just celebrate its presence.”

Success and accolades are one thing, but when it comes to the praise that has made it all worth it, Jackson is quick to answer whose support has meant the most to him.

“My mom and dad,” he said. “Their acknowledgement and their love of the show means more to me than anything else.”