During a walk along the Great White Way this winter, I saw something peculiar: two marquees advertising two Michael Jacksons. On 52nd Street, at the Neil Simon Theater, where “MJ: The Musical” has been running since December, there’s a graphic of the King of Pop in his iconic early ’90s pose: fedora perched low, obscuring his face; shirttails flying in the artificial wind; white glove; high-water pants; sparkling socks; feet en pointe. Seven blocks away, at the Lyceum Theater on 45th Street, another sign bore the name “Michael Jackson” and an illustration of a 20-something Black man’s head in semi-profile, with six tiny bodies floating around his face and hair. This image advertised “A Strange Loop,” the playwright Michael R. Jackson’s Pulitzer Prize-winning metafictional musical, which premiered on Broadway in April.
“It’s a strange loop,” Jackson told me on the phone when I mentioned the coincidence. He chuckled, his buoyant, lisp-tinged laughter calling to mind fluttering shirttails. “See what I did there?” He stopped, started again, wanting to clarify. “When I say that, I mean that, my whole identity as a person just in the world, has always been sort of tied to that man, because of our names. That’s been both an annoyance and a help.”
Jackson has embraced the absurdity of the coincidence — his website name and Instagram handle is “thelivingmichaeljackson,” for example. “Certainly whenever my name is mentioned, the ghost of him appears somewhere. But we’re two very different artists working in two very different traditions.” He paused, punctuating his thinking with ellipsis, his voice relaxed and slowly propulsive, as if his sentences were bridges he was building as he walked over them. “And yet, there’s something about his legacy that is invoked whenever my name comes up. There’s a certain excitement that comes up, and maybe I’ve been able to utilize that. I think that’s true. And I think that maybe it’s given me a certain kind of confidence, perhaps, as somebody in the entertainment world because ‘Michael Jackson’ stands for pop excellence and razzmatazz and razzle-dazzle, and that’s certainly something that I aspire to in my own work.”
“A Strange Loop,” which is being marketed as a “big, Black, queer-ass American musical,” is in part about how identity is cobbled together out of the flotsam of pop culture: how the faces we present to the world are neither organic nor stolen, but co-opted, borrowed and reshaped in the borrowing. Jackson relishes the playfulness at work in these kinds of appropriations, and the show bristles with references as varied as Bravo’s “Real Housewives” franchise; the writing of bell hooks; Dan Savage, the advice columnist; “Hamilton”; Stephen Sondheim. The title carries its own layers of reference: to Liz Phair’s 1993 song “Strange Loop” and to the work of Douglas Hofstadter, the scholar of cognitive science and comparative literature. In his 1979 book “Gödel, Escher, Bach: An Eternal Golden Braid,” Hofstadter coined the term “a strange loop” to describe the recursive nature of selfhood and intelligence.
The show is a product of Jackson’s own vicissitudinous loops: his fits and starts of success and failure, when he was working, for five years, as an usher at “The Lion King” and “Mary Poppins” while revising his own play over and over and over again, trying not to give up. Jackson says that the show is not autobiographical but “self-referential,” though the parallels between him and his protagonist are striking. The story concerns Usher (played with vulnerability, charm and delicacy by Jaquel Spivey), a 25-year-old “fat American Black gay man of high intelligence, low self-image and deep feelings.” Like his creator, Usher works as an usher for “The Lion King” and shares his name with a pop star. (In the memory palace of his mind, his relatives are named for “Lion King” characters: His mother and father are called Sarabi and Mufasa, his niece is Nala, his ne’er-do-well brother is Scar.) He “writes stories and songs and wants desperately to be heard.”
Usher is trying to develop his own musical — about a Disney usher who’s writing an original musical about an usher who’s writing a musical, and so on — as he deals with the impositions of his mind, which are personified as six Greek-chorus-like “Thoughts” who voice his desires and cutting internal commentary. The Thoughts (played by L Morgan Lee, James Jackson Jr., John-Michael Lyles, John-Andrew Morrison, Jason Veasey and Antwayn Hopper) are “a spectrum of bodies that are Usher’s perceptions of reality inside and out.” They “come in many shapes and sizes. But they are all Black. And they are as individual in expression as they are a unit.”
Usher must reconcile the seeming contradictions of his life. He is gay but was raised religious and taught that homosexuality would send him to hell. He uses Grindr but considers himself a feminist — someone who can see through the race- and body-shaming that frequently occur on dating apps. He yearns to be himself and pursue his own artistic inclinations yet feels pressure to pay his parents back for their support by ghostwriting a Tyler Perry play. In the musical’s scintillating, uproarious opening number, “Intermission Song,” Usher declares that he wants to “subvert expectations Black and white, from the left and the right, for the good of the culture.” This idea of subverting expectations — of presenting art that grinds the gears of easy understanding to a halt — is crucial to Jackson’s work.
Jackson overlooking the set at the Lyceum Theater in April.Credit…Malike Sidibe for The New York Times
One day, Jackson and I sat together in a Chelsea diner and discussed a play we’d both recently seen (a period piece that Jackson asked me not to name). He detected in the show the urge in many contemporary works of art to retrofit current attitudes onto historical matters. “Everybody keeps trying to speak to the moment,” he said, and punctuated his words by tapping the menu on the table, improvising his own percussive track. “There’s so much presentism in so many works, particularly the ones that are dealing with historical issues. I’m kind of like, Why is there this weird rewriting of history so that it can flatter you and validate you? Why can’t we just tell stories about these people as they were and whatever their positions and attitudes were? I think that that’s actually a lot more powerful, because then you can understand how other people lived and thought and dreamed and made mistakes or whatever. I keep seeing all of this stuff that’s like, This is just like right now, and I’m like, No it isn’t!”
The show we discussed treated almost every white character as evil but didn’t give that behavior any emotional or psychological foundation. Yes, racism is ridiculous, but the people who subscribe to it don’t feel that way; if characterization is to be believable, it has to accurately and seriously portray even the views that belong to abhorrent people. Otherwise you get what Toni Morrison called “harangue passing off as art,” and characters who are mere vehicles for political arguments. “There’s a nuance that I feel is being lost in this moment in time, particularly in the arts, in the theater especially, that I am personally at war with,” Jackson said.
Jackson is dead set against contemporary virtuousness: a puritanical need for fixed, context-repellent delineations of right and wrong; the performance of utmost certainty, all the time. “A Strange Loop” is dedicated to feelings of uncertainty, presenting, with vivid detail, the internal logic of a character who’s fighting with himself. The self is arguably everyone’s first and most recurrent battleground, and Jackson stages internal chaos that far outstrips arguments you might find between partisan politicians or on Twitter.
One of Usher’s Thoughts is called “Your Daily Self-Loathing,” and as you’d expect, it regularly reminds him of how worthless he is. Another Thought is the supervisor of Usher’s “sexual ambivalence”; others represent his loving mother’s religious upbraiding and his father’s confused, macho judgment; others stand in for student-loan collectors and an opportunistic agent. With all of this at play, Usher has to find a way to assert his own value or to “fight for his right to live in a world that chews up and spits out Black queers on the daily,” but first he has to find some peace with his flaws, whether real or imagined.
It took Jackson decades to achieve the kind of clarity that Usher yearns for and to distill it into this play. “The only reason why I come to any of these conclusions is because I spent almost 20 years working on one piece of art,” Jackson said. “And the exercise of that forced me to have to really be thoughtful and really be open to changing my mind. I’ve changed my mind so many times with new information coming along.” This thought eventually took him to a Joni Mitchell lyric, from her 1985 song “Dog Eat Dog,” which he quoted to me after breaking into an improvised medley of her deep cuts: “Land of snap decisions/Land of short attention spans/Nothing is savored/Long enough to really understand.”
Jackson, who is 41, was born and raised in Motown. Growing up “middle middle-class” in Detroit in the 1980s and ’90s, he had what he calls “a normal external childhood.” His father was in the police force for 27 years before he retired to work as a security consultant for General Motors, and his mother worked in the accounts-receivable department of the automotive manufacturer American Axle. His brother, who is four and a half years older, took him to see horror-comedy films like Rusty Cundieff’s “Tales From the Hood.” They all went to First Glory Missionary Baptist Church, where his mother was a secretary and his father a trustee. Jackson sang in the main choir and played piano for the Sonshine Choir (for little kids) and the Inspirational Choir (for older women). He appreciated church as kind of a workshop; it gave him a chance to hone his craft. “It was just a place for me to play music and to teach songs, and it was almost like I was playing in a jazz club or something. I was building my musical chops playing in front of an audience and for choirs every Sunday.”
Pop culture suffused his life. He attended Cass Technical High School, where the legends of alumni like Diana Ross, Lily Tomlin, Ellen Burstyn, Jack White and Kenya Moore haunted the hallways. Jackson’s preteen bedroom was covered with autographed photos of his favorite celebrities that he’d sent away for: Macaulay Culkin, Jasmine Guy, Kadeem Hardison, Anna Chlumsky, Emilio Estevez and Tim Allen, or “whoever was on some TV show or movie I was watching.” In high school he drafted award-winning poems and worked on a literary journal. Even then, his thinking resisted easy judgment and retained the right to take its time. In a passage in his journal marked by strikethroughs and scribbled-out ink, he wrote about O.J. Simpson’s 1997 civil trial for the death of his ex-wife Nicole Brown: “I don’t know how I feel. At first, I thought he was innocent. Then during the civil case, I thought he was guilty — in both cases I didn’t care whether he did it or not. I resented the fact that people assumed he was either totally capable of murder or not capable of murder.”
While his external circumstances were comfortable, internally he was struggling with accepting his sexuality. When he came out to his parents at 17, they confronted him; Jackson says his father asked his son, passive-aggressively, if he was attracted to him, a moment Jackson reprises in “A Strange Loop.” (He’s on really great terms with his parents now.)
It was around this time that Jackson was first introduced to what he calls “white-girl music” after his cousin studied at Interlochen Center for the Arts in 1995 or 1996, and brought back Tori Amos’s albums “Little Earthquakes” and “Under the Pink.” “I was just sort of coming out at that time and trying to figure things out, and that music hooked me right in. The language is very riddlelike, but the music underneath it is so complex and lush and complicated, and I just kept listening. And then the second track comes on: ‘God, sometimes you just don’t come through.’ And I was like, ‘Oh, yeah,’ because I was raised in church, and I was having a lot of questions about that.” Amos’s music “met me right where I was at that moment in time. And because I was also writing, it gave me permission to start saying things that I was thinking or feeling or wondering about in like a profane sort of way. And so I began copying her immediately just trying to find my voice.”
He also loved Liz Phair and Joni Mitchell and considers the three songwriters his own private religious triptych: Mitchell is the mother, Phair is the daughter and Amos, Jackson’s “first love,” is the Holy Spirit. “These white women singer-songwriters inspired me to be my truest, rawest self,” he told me. For “A Strange Loop,” Jackson wrote “Inner White Girl,” an ingenious paean to the emotional and lyrical freedom those women employ in their music: “Black boys don’t get to be cool, tall, vulnerable and luscious/Don’t get to be wild and unwise/Don’t get to be shy and introspective/Don’t get to make noise, don’t get to fantasize.”
In 1999, Jackson left Michigan to attend Tisch School of the Arts at New York University. Shortly after he graduated, he wrote a monologue, a vehicle for his career anxiety called “Why I Can’t Get Work,” that became the kernel of “A Strange Loop.” He kept writing and developing songs in Tisch’s M.F.A. playwriting and musical-theater program, and after that, all while ushering at the Disney musicals. Later, he worked at an advertising agency. Influenced by “Hair,” Wayne Koestenbaum and Michael Daugherty’s “Jackie O,” Kirsten Childs’s “The Bubbly Black Girl Sheds Her Chameleon Skin” and Stew’s “Passing Strange,” Jackson kept hacking away at the collection of songs and dialogue that eventually became the musical, trying to make something uniquely his own. These were lonely years for Jackson in New York City, when he was alternately not dating and chasing unattainable paramours, hating himself and finding internal armistice, losing weight and gaining it back.
As he aimed to finish “A Strange Loop,” the thing that delayed his progress, he told me, was his own self-loathing. He could not shake the feeling that many things were wrong with him: his gayness, his fatness, his chosen career path. Because the play is so self-referential, Jackson had to figure out his own life before knowing how Usher fares, and therefore how the musical ends. Sometime in 2014 or 2015, Jackson had a breakthrough. During a therapy session, he was engaging in the practice of “tapping,” where you touch various chakras throughout the body and say, “Even though [fill in the blank], I completely and totally accept myself.” That session, he told me, “brought up a sense of grief for my childhood and how sad I had been for a long time — feeling like I didn’t belong or fit in and being able to have compassion for my younger self who was still with me. And having that moment was very powerful and healing in so many ways.”
Gradually, he realized that nothing was wrong with him, and he used this insight to unlock the play’s structure. Usher comes to find that his negative, self-effacing thinking is just a series of spiraling feelings that he has some amount of control over. Those thoughts tell a story, but it doesn’t mean that the story is true. Jackson’s two-decade process of writing “A Strange Loop” — and the many years he spent in therapy — helped him accept his own questing mind and the trouble it sometimes causes him. He’s someone who disdains orthodoxy, someone whose ex ghosted him after saying, “Wow, you’re really not a static thinker.”
Stew, one of Jackson’s influences, told me that “A Strange Loop” is in a “continuum of Black art” that expresses how Black people “are complete people who have every possible thought that could be had.” Jackson himself, Stew said, is in another tradition. “I just felt like his work is so firmly in that line of Black disrupters, of generous disrupters. Artists that are willing to go beyond, you know, and sort of display themselves? I consider that a kind of generosity and a kind of bravery.” Jackson’s close friend Kisha Edwards-Gandsy spoke of the searching, restless quality of Jackson’s intelligence. “I feel what Michael asks everybody is, ‘If you think you know something, do you?’”
One day in mid-March, I arrived in a Midtown Manhattan studio for Day 3 of rehearsals for “A Strange Loop.” The whole space felt like an extension of Jackson’s imagination: A miniature model of the Lyceum’s proscenium was situated in the background, along with a few props, including an empty Popeye’s chicken box. Jason Veasey, who plays Thought 5, wore a green shirt with “Detroit” across the front; Thought 3, John-Michael Lyles, had on a T-shirt that read, “Stay weird and live free,” which could be Jackson’s motto.
The group started rehearsing “Exile in Gayville,” a song about Usher’s relationship to dating apps and a nod to Phair’s “Exile in Guyville.” Jackson, the actors, the associate choreographer, Candace Taylor, and the show’s director, Stephen Brackett, made changes on the fly. “Can I advocate to make a tiny adjustment to get a little bit more quickly into the line?” Brackett asked about the pacing of the Thoughts’ reaction to Usher calling Beyoncé a “pop-culture terrorist” (he was paraphrasing bell hooks). “If Beyoncé comes, I’m not going on,” Spivey joked.
Later, Jackson and the show’s choreographer, Raja Feather Kelly, jokingly compared themselves to each other and to other Black artists.
“If I position you as me in the downtown dance world and me as you,” Feather Kelly said, “in celebrity culture, we are Kanye West, because for so long, no one would give us any attention. And people were like, ‘It’s impossible what you’re doing.’”
Jackson: “But does that mean we’re egomaniacs?”
“I think we have to be,” Feather Kelly said, “I mean, by virtue of needing to be seen and heard.”
“Who is our Pete Davidson? Who is our K.K.W.?” Jackson asked, and Feather Kelly whispered an answer in his ear.
“No, no, no,” Jackson squealed.
“I won’t say that out loud, but tell me I’m wrong,” Feather Kelly said, grinning.
“I won’t tell you you’re wrong,” Jackson replied, cackling.
The most interesting comparison Jackson identified was between himself and Tyler Perry, whose artistic work seems to exist at the opposite end of the spectrum from the playwright’s: Perry is a multimillionaire who boasts about producing films in five days, and Jackson, who is not wealthy, spent 20 years working on one project. In his dramedies, Perry often features Black archetypes without complicating them — the stalwart matriarch (exemplified in his Madea character); the “strong Black woman,” usually portrayed as unhappily lonely; the relative addicted to crack cocaine; the closeted gay Black man. Many of his gospel plays, TV shows and films feature a consistent message about the power of prayer.
Perry’s work is referenced a few times in “A Strange Loop,” as a paragon of commercial success and an object of Usher’s ridicule. In one of the show’s most biting, farcical numbers, “Tyler Perry Writes Real Life,” Thoughts masquerading as notable Black historical figures like Harriet Tubman, Marcus Garvey, James Baldwin, Zora Neale Hurston and someone called “Twelve Years a Slave” castigate him for disliking Perry’s work. Eventually, though, Usher relents to a Thought playing his agent and ghostwrites the ridiculously derivative gospel play, “Show Me How to Pray,” for Perry.
Perry’s stage plays were a staple for Jackson’s mother, who’s still a fan — “If Tyler does it, she’s on it,” he told me. He always felt that Perry’s work wasn’t for him but really started to reject it after watching the 2013 film “Temptation: Confessions of a Marriage Counselor,” in which a young woman contracts H.I.V. after a period of sexual exploration. Jackson has loved ones who died of AIDS (“A Strange Loop” is dedicated to “all those Black gay boys I knew who chose to go on back to the Lord”) and knows other people still managing the illness. He found the film toxic and stigmatizing. Still, although Jackson thinks Perry’s work is “intellectually lazy,” he values the joy his Madea films and stage plays bring to his mother and other family members.
One day in late February, Jackson and I sat down in the conference room of his production office to watch “A Madea Homecoming,” Perry’s latest Netflix feature, which premiered only days before. We could hardly get from one scene to the next without pausing the film to unpack some narrative error or slapdash prop. “These wigs are terrible … I mean, and consistently terrible … he just does not give a damn about the wig work,” Jackson said, with an air of resignation. “I wonder, do any of the actors think this is dumb, or are they all just excited to be there because it’s Tyler?” he asked.
Although he lambastes what he calls Perry’s “simple-minded hack buffoonery,” he also worries he might be capable of something like it, deep down. While working on a horror film for A24, Jackson told me, he compiled a list of his fears to share with the film’s producers Ari Aster and Lars Knudsen. “This film is about my fears, and so I have to write all of them down. Even if those things don’t make it into the movie, they will be in the subtext of it.” One of his fears is that he’s not as advanced as he thinks he is, and that he might not be insulated from the kind of artistic foibles he criticizes Perry for. “Sometimes I worry that I’m a coon. That I think I’m this progressive, freethinking blah blah blah, but really I’m just a coon.” Jackson was referring to a worry shared by many introspective Black people that they are inadvertently performing for a white gaze. “Freedom starts in here,” he said, and pointed to his temple. “I don’t want to live in fear. I can’t live like that. I don’t have a man at home to hug up with. I have to wake up every day alone in my bed and get up out of bed and make something happen for myself. I don’t have generational wealth, I don’t have all this stuff, which means if I want to live, I have to be free.”
He can even allow himself to embrace the little overlap that exists between him and Perry. Jackson, too, aspires to a kind of populism. “For me, I’m always trying to mix high and low, Black, white, whatever. That’s sort of what I’m interested in is like, everyone is invited to come into this. The piece can be as entertaining as it is intellectually challenging.” Of Perry, he said, adjusting his glasses, “To me, he’s like a right-wing artistic populism, and I’m more of a left-wing artistic populism. I think. I think. I’m making this up,” he finished, cautiously. “A Madea Homecoming” and its ilk make him “want to double down on what I’m doing, in trying to make art that is Black and nuanced and that doesn’t have sacred cows, that’s emotional, that’s intellectual, that’s silly, that’s all the things.”
When Jackson won the Pulitzer, Perry called and playfully threatened to beat him up. Later, Perry texted Jackson a screen cap of the “Strange Loop” cast album as a gesture of support. Jackson texts Perry holiday greetings. The men’s polite acquaintanceship seems like a model for how to disagree about art.
When I finally went to see the show, on a Saturday afternoon in April, I was surprised by how it destabilized me. I stumbled out of the theater bewildered, remembering the bawling of a man who sat behind me. Blinking in the sunlight, I eventually made contact with other wide-eyed women. “That was overwhelming,” one lady told me. “Now, it’s going to make me ask so many questions of my nephew. Like, oh, my God, what is your experience of our family, for real, for real?”
At some point, I saw Jackson standing under the Lyceum marquee. I told him that I’d purchased a refrigerator magnet from the merch table, so that every time I walk by it, I can remind myself to question the narratives that run through my mind, my own strange loops. “We all have them,” he said. Right then we ran into a woman I’d met years ago; by sheer coincidence we had both been at the show. She asked Jackson if he planned to do a performance just for a Black, queer audience. He explained that he’s open to Black theater night, where Black people are specifically invited and encouraged to attend, but he didn’t want to do a “Blackout” night, where the audience is exclusively full of Black patrons. “I believe that it’s important to have as many people as possible with as many different perspectives as possible,” he told her.
Later, on the phone, I asked him if he could elaborate. He’s OK with it if the audience is organically full of Black patrons, like if a church wanted to come and see it. “But I just struggle with the idea that like I’m supposed to create a quote-unquote all-Black space. And yet what I observe is that these all-Black spaces, to me, look like they all sort of come from the same class, and I don’t sense a ton of diversity within the Blackness, which then makes me question the intent of it. I could be looking at it in the wrong way, but I’ve seen the push for a lot of these events, and at the end of the day, they’re just not in the spirit of what I think ‘A Strange Loop’ really is, which is both Black and expansive.” He paused. “I’ve been asked in interviews recently, what do I want audiences to take away from the show, and my answer always is, ‘I want them to be thinking about themselves.’”
The week before opening, Jackson shared with me a few lyrical tweaks he’d made during previews, to make a coda easier for the actors to sing, and to make it clear that his critique of Perry’s work is not a personal attack. But when the play officially opened on April 26, Jackson and company ceased being able to make any changes. The show had to “freeze.” I asked Jackson what it was like for a person who’s worked on a show for 20 years, whose creative philosophy is predicated on resisting being locked in, to freeze? He was sanguine about it, explaining that it’s part of the process. “I think the show is good regardless of whether I get every little thing that I want in there before we freeze, but I’m just trying to get it to be the best that it can be.”
When I consider the heretofore living, breathing document of “A Strange Loop” frozen, I imagine Jackson holding notes for the next restaging, while also hoping the show goes on a long time — that whatever adjustments he has will be superseded by the revolutions in his thinking that will surely take place during its Broadway run, however long it is. The strange loops will continue. “I have a lot of opinions,” Jackson told me, “and my opinions change, and sometimes I don’t know, and sometimes I’m wrong.” He half smiled, showing the gap in his teeth. “But I feel like the world has made it so that, how can I just adhere to one thing?”
Niela Orr is an essayist, a story producer for Pop-Up Magazine and a contributing editor for The Paris Review. She writes The Baffler’s Bread and Circuses column.