More often than not, if the composer and playwright Michael R. Jackson was in or near the Lyceum Theatre after a performance of his sui-generis hit musical, “A Strange Loop,” during its recent Broadway run, fans and critics would gather around him, not just to have their Playbill autographed but to continue the conversation that the show had started. Usually, it takes an activist star, like Jane Fonda—or whoever is playing Aladdin—to cause a post-performance commotion outside a theatre. But a writer? A theatre nerd who wasn’t Lin-Manuel Miranda? A self-described “outsider’s outsider’s outsider” and a former usher for “The Lion King”? The protagonist of “A Strange Loop,” which closed in New York in January and opens at London’s Barbican in June, is, according to the script, a “fat, Black queer” man named Usher, who can barely support himself as he attempts to write a musical about the “strange loop”—the cycle of hope and rejection that his heart seems trapped in. Not exactly what you’d expect to be a box-office success. If anything, “A Strange Loop” is a show-biz story—complete with references to Stephen Sondheim and Scott Rudin—but it’s a show-biz story about how there is, in effect, no real stage to frame, let alone contain, an artist with Usher’s sensibilities (which is to say, Jackson’s): that is, until Jackson remade the American musical with “A Strange Loop.”
The show earned Jackson, who is forty-two, the 2020 Pulitzer Prize for Drama and the 2022 Tony awards for Best Musical and Best Book of a Musical, among other honors. Ironically, in the show Jackson’s stand-in, Usher, is hassled by his agent for his artistic “integrity,” which deprives the agent of commissions and barely allows Usher to eat. Where, the agent wants to know, is the material that can be translated into capital? Why can’t Usher ditch the purity bit and ghostwrite some gospel plays for Tyler Perry? In other words, play racial volleyball: serve one Mary McLeod Bethune, then go in for a Frederick Douglass kill. But Usher can’t even find the net. Sitting in his cramped apartment, Usher is visited by his (embodied) Thoughts—ensemble members who play the voices in Usher’s head, as well as multiple minor characters. Thought No. 3, as Usher’s agent, doesn’t get very far with the Perry pitch:
Despite his resolve, Usher is visited by other Thoughts, who call him a “race traitor” and an “ass licker,” because he won’t play along. Then, suddenly, the Thoughts transform into the Ancestors. Entering one by one, they declare themselves to a startled Usher:
Then all the Thoughts sing in unison:
Whenever I saw the show, folks in the audience waved their programs like New Testament pages as the Ancestors appeared, releasing us from the bondage of acceptable onstage Black behavior, which often involves a performance of Black Invincibility—never mind the yoke, we are ennobled, and will survive. By casting off and lampooning this ethos, Jackson was following in the tradition of artists whose work was a critique of race-as-entertainment, and a refusal to play into stereotypes. These works include George C. Wolfe’s “The Colored Museum” (1986), Suzan-Lori Parks’s “Fucking A” (2000), Thomas Bradshaw’s “Southern Promises” (2008), Robert O’Hara’s “Barbecue” (2015), Danai Gurira’s “Familiar” (2015), Donald Glover’s “Atlanta” (2016-22), Jackie Sibblies Drury’s “Fairview” (2018), and Michaela Coel’s astonishing television series “I May Destroy You” (2020). Jackson, Wolfe, and the rest explore how Black history and pop culture have made and remade the worlds of their imaginations—and, by extension, our own.
One evening before the world shut down, Jackson and I had dinner at Orso, in midtown, a favorite of show-business folk. Jackson is brown-skinned, with a beautifully shaped head and large eyes framed by glasses that are habitually smudged—they sometimes make him look like a kid who knows a lot and is just off to the library, beyond excited to learn more. The playwright was filled with his usual verve. I was raised to reveal as little as possible when white people were around, and to never talk about race in their presence. But Jackson, I found, didn’t hold back, and, when it came to sex and race, spoke his mind with great vigor and considerable volume. He didn’t seem to notice that a number of white diners turned to look at us during our conversation. And he didn’t notice my discomfort and anxiety—they can get us; they can always get us—as he talked about whiteness in a “white space,” because I didn’t tell him.
It was the spring of 2019, and Jackson’s new show, “White Girl in Danger,” was in a workshop. (Because of the pandemic, the show was postponed until this spring; it opens at Second Stage on April 10th as a co-production with the Vineyard Theatre.) Jackson—who wore a T-shirt with lines through the words “imperialist,” “white supremacist,” “capitalist,” and “patriarchy,” until you got to the name of the late theorist bell hooks—talked about the transformative effect of theatre. “You have to do self-inquiry,” he told me. “You have to know what is actually for real, not just some lame-ass, woke-ass political statement that you haven’t really thought through. Tell the truth.”
One piece that spoke to Jackson was Arthur Miller’s “Death of a Salesman.” “I saw it when I was nineteen years old,” he said. “I don’t know anything about being an old white man in the forties. But the idea that you’re worth more dead than alive . . . However they did it, that idea communicated from that stage to my Black gay ass going to N.Y.U. . . . I wept. I felt sympathy and empathy for this man. And what I wanted to do in ‘A Strange Loop’ was to flip it. Can I make some old white man feel empathy for this young, Black, gay, musical-theatre writer? Can I get them to understand that this is about the human condition?”
In “White Girl in Danger,” Jackson continues to examine how humanity gets categorized—by race, gender, and class—and what those straitjackets feel like when you try to break out of them and reach for something like freedom. In this musical, which he began to write in the fall of 2017, Jackson, an inveterate fan of soap operas, has created a soap-opera town called Allwhite, in which Meagan, Maegan, and Megan—three versions of the same whiteness—can’t leave the house without encountering . . . danger. At the start of the show, as the three girls strike dramatic poses, a “Blackground Announcer” tells us:
The drama centers on maternal revenge, premarital sex, and—a huge plot point—a Black girl named Keesha Gibbs, who lives in Blackground but wants to cross over to Allwhite. Why can’t she, too, live in a white wonderland? Why should she be relegated to Blackground, with its back-burner stories of police brutality and its history of slavery? Keesha wants to be involved in the real shit, the white-girl stuff that puts you at the center of your own story. Keesha’s mother, Nell, who tells it like it is (and who may or may not have been inspired by the “sassy” character played by Nell Carter in the eighties sitcom “Gimme a Break!”), doesn’t want her daughter to leave. While running away, Keesha sings:
Keesha is a little disingenuous when she claims that she’s jettisoning herself out of Blackground for her people. What she really wants—what her internalized racism considers the ultimate prize—is a white man. In some ways, she’s the flip side of Usher: all shaky, heteronormative id. In “A Strange Loop,” Usher sings about his envy of white girls, who, unlike him, seem free to pursue their dreams:
Part of the brilliance of “A Strange Loop” lies in the conflict between Usher’s self-awareness and the demands of the gay (and musical) marketplace. Toward the middle of the show, Usher sings about the way our identities, no matter how seemingly fixed, are made up of mismatching parts that we are always trying to hold together—or vomit up:
At one point in “A Strange Loop,” Usher hooks up with a white “Daddy” type (played by a Black actor) who doesn’t nurture; he just commands. In that terrible room, there is a gap between what our hero wants—love—and what he engages in, or allows, because of his silence: race play. It’s a terrifying moment, and, if you’ve spent any time in that room, the acts that Jackson describes aren’t as disheartening as his soulful acknowledgment of where the desire for love can lead you—straight to the crooked island of the loveless.
During a series of long talks that Jackson and I had after the Off Broadway run of “A Strange Loop” ended, in 2019, and before it opened on Broadway, in 2022, I thought about the fact that love—or the hope of love—plays such a strong part in the stories that his characters tell. It’s reductive to read either of his two musicals as a literal transcription of his life. But, like any powerful artist, he borrows from what he knows—himself, and the world that made him—the better to make and remake his world onstage.
Jackson was raised in Detroit, the much loved younger son—he has an older brother—of Henry and Mary Jackson. His parents had been born in the South and, while still young, emigrated north. Henry worked for many years as a police officer and, after that, as a security consultant for General Motors; Mary worked in accounting for the same company. Jackson’s family was “very, very, very involved” in the church, he told me. He has played the piano since he was eight, and accompanied two choirs at the church. “My mother was the church financial secretary for more than thirty years, my dad was a trustee, and my brother and I went to vacation Bible school every summer—and so you knew people’s business, and the drama and all that,” Jackson said. “Every Sunday you show up, and you play your part in the church play. I always feel like I learned about theatre from church.” He also attended plays with his mother. “I’ve always been a fan of theatre,” Mary Jackson said. “Mr. Jackson wasn’t. So Michael was always my date.”
“I grew up in a Black city and a Black family,” Jackson said. “I went to Black schools. I went to Black churches. I went to Black family reunions. Almost everything I did was Black, Black, Black. It was so Black, to the point that I thought the whole world was basically that. And because of that I rebelled against it. No different than when a white person would rebel against their own upbringing.” Children, of course, don’t generally get to pack up and leave, but they can enter the world of their imaginations. The imaginary places Jackson most loved to visit were soap operas. His great-aunt Ruth, who babysat him before he started kindergarten, would dip snuff and then turn on “Days of Our Lives” or other popular serials. He thrilled to that world, with its weird coincidences, plot twists, and outrageous wealth and misfortune. After he started school, his aunt would keep him up to date. “I would call her on the phone, and—you can ask my mom—I’d be, like, ‘Aunt Ruth, what happened?’ And then she would fill me in, and we would be, like, ‘Oh, my God, can you believe Vivian buried Carly alive? . . . But I also liked the other stuff, like Jack and Jennifer making love for the first time.”
Things started to heat up even more when Jackson was in fourth grade, and an older cousin let him read her Jackie Collins novels. “ ‘Chances,’ ‘Lucky,’ ‘Lady Boss.’ Lots of tumescence,” he said. “I was deeply into it. And because I lived in a house where I couldn’t look at dirty magazines, or porn, I could read books.” In seventh grade, he got caught at school showing other kids the “good parts,” and his father made him hand the books over. Then Michael discovered Alice Walker’s “The Color Purple.” “I was hungry for it,” he told me.
Jackson attended Cass Technical High School, where his interest in music grew. He sang in a youth choir and was a huge fan of Tori Amos—he saw her as part of a “white girls’ club,” whose members got to express their feelings in song in a way that no closeted boy dare risk. Later, a favorite was Liz Phair, whose seminal “Exile in Guyville” had a seminal effect on Jackson. (One of its tracks is called “Strange Loop”; in it, Phair describes herself as “adamantly free.”) In high school, Jackson, the good church boy, was surrounded by Black queerness—“All these boys fucking each other and breaking up with each other, and all under the radar”—but he felt outside it. I asked him why, and he told me, “Because I didn’t go to the fine-ass-nigga finishing school.” When I suggested otherwise—that he was cute, too—Jackson shut me down: “It’s about being a fine-ass nigga. And I was not that.” He was a bookish nerd, and his parents kept him on a tight leash.
Jackson didn’t come out until he was sixteen, an event that was precipitated by what he refers to as the “trauma” in his gay-teen-age story line. He liked another boy in his school, but the boy told him, over the phone, that he wasn’t interested. Jackson’s father was eavesdropping on the line, and, afterward, confronted his son. “My mother walked home at that exact moment from church,” Jackson told me. “It was the most hilarious and horrifying thing. And then it turned into this whole ordeal about ‘God hates it, it’s worse than murder.’ ” The juxtaposition between who Jackson’s parents are—“They like everything. Every accomplishment I’ve ever had, they’re super proud of me. They used to go on school trips with us. They’re very involved”—and their reaction to his queerness is startling. (In “A Strange Loop,” Usher’s mother’s worry and confusion about her son being gay is deeply touching.) His parents have since come to a kind of acceptance. “Michael was always determined to be Michael,” his mother said. But the family doesn’t discuss the subject. Jackson said, “For me, there’s the added thing—and I feel this about most Black folks—we don’t talk about sexuality. In general.”
In 1999, Jackson, who had been greatly encouraged in his writing by three high-school teachers, enrolled in N.Y.U.’s Dramatic Writing program. He attended a lot of theatre. He also found himself trying to navigate New York’s gay scene. “All I knew was Blackness,” he told me. “And then I came to New York. . . . And the gay people I knew—because I was at N.Y.U.—were white. And those people became my friends. So then we would go to Splash, or to Pieces, or whatever—places that were filled with white people, or people who were interested in white people. So, even if you saw somebody Black, they only had eyes for white people. And maybe the white people had eyes for them because they were some kind of fetish. So then I was, like, ‘All right, I’ll orient myself toward white men.’ And that proved to be disastrous at every single turn.” These white men were even less interested in him than the Black boys from his high school had been, which was “doubly terrible.” He found that he didn’t fit well into what he calls the “gaytriarchy.”
Recently, as pandemic restrictions were lifting, Jackson and I had dinner at an Italian restaurant in SoHo, and he told me about a white guy he met online during those years. They exchanged a few messages, and then Jackson told the man that he is short. The white guy’s response “was, like, ‘Michael, I’m so sorry, I think that we hit the first of the little bumps in the road if we’re going to possibly consider dating. I’ve never dated anybody who was shorter than me, and I didn’t even realize it because you’re such an amazing conversationalist, and I love talking to you, and you’re so amazing over e-mail . . .’ And he was, like, ‘While we’re talking about height, I also should mention that I’m very tall and also I’ve never dated anybody whose penis was not at least the same size as mine, or larger.’ ” Jackson still went out with him. For their second date, the man suggested that they go to a speed-dating event. Jackson agreed. “This is where my self-esteem was,” he said. “He matched with three people, and I matched with no one. Then, after that, we were walking to the train, and he was meeting someone else to go on a date with, who he introduced me to.”
Part of Jackson’s skill as a writer is in describing not just the pockets of pain we live in but the hope that led us there. Early in “White Girl in Danger,” Keesha refuses to be warned against the dangers of the white world. As she talks with her mother, Nell, and Caroline, another resident of Blackground, this exchange takes place:
After graduating from college, Jackson held down a million dead-end jobs, including working as an usher at Disney shows, on Broadway, between 2003 and 2008. He lived uptown, with an ever-changing cast of roommates. One day, the cops came to his apartment. “I’m not afraid of cops,” he told me. “My father was a cop.” But, unbeknownst to Jackson, one of his roommates was allegedly dealing drugs. Rather than find out who was at fault, the cops threw Jackson onto a sofa and cuffed him. He started crying. They soon realized that he wasn’t their suspect, and uncuffed him, but they continued to turn the place upside down, making small talk as they did it. “My apartment was being raided, but they’re having a quotidian conversation about rent, commute, and my nice apartment,” he told me.
Despite the ways that racism aims to shame you into accepting its rules, which include staying in your own cultural box, Jackson’s tender work about white girl singers, Black queens, and white soap operas is evidence of his abiding faith in his imagination. One musical he fell in love with was “Falsettos,” by William Finn—James Lapine co-wrote the book—which begins with a song called “Four Jews in a Room Bitching”: “I’m bitching. He’s bitching / They’re bitching. We’re bitching / Bitch, bitch, bitch, bitch.” The song plays with cultural stereotypes using humor and I-told-you-you-didn’t-tell-me forthrightness. “The work had its own personality,” Jackson said. “It wasn’t trying to imitate anyone else.” He admired Sondheim for staying true to his voice as an urban gay man. Sondheim’s mentor, Oscar Hammerstein II, once advised him not to write songs about nature—after all, he wasn’t Hammerstein. Sondheim was, as Jackson put it, “an urbane, witty New Yorker, and a puzzle master. And so he’s going to write lyrics that are elliptical and sort of circle back, and are clever and super smart and dark and ironic and all that stuff. That’s him.”
In college, Jackson wanted to write for the soaps. “I subscribed to Soap Opera Digest,” he recalled. “I interned at ABC Daytime.” When he graduated, he applied for a job at CBS Daytime, and to N.Y.U.’s graduate program in musical-theatre writing. “If I had gotten that job in the soaps, I wouldn’t be writing musicals,” he said. In grad school, a Black gay student performed a song he’d written about a one-night stand—an assignation that made him feel guilty, in the song, and ask the Lord for forgiveness. As Jackson listened, he wrote down a line in his notebook about “All those Black gay boys I knew who chose to go on back to the Lord.” He combined this idea with Tori Amos’s “Pretty Good Year,” which led him to write “Memory Song,” the first tune for what turned out to be “A Strange Loop.”
Jackson was not ambitious to get his work produced, because he didn’t think it stood a chance. But he was artistically ambitious, and, as his compositions grew, so did Jackson. (Therapy helped.) In 2006, the producer Maria Manuela Goyanes invited Jackson to perform a cabaret act at Ars Nova, including some early songs and parts from a monologue he wrote between college and grad school called “Why I Can’t Get Work.” (He called the piece “Fast Food Town.” ) The speaker in the monologue aches to win the acknowledgment of white theatre powerhouses such as Tony Kushner and John Patrick Shanley, and equates gay sex with death even as he longs for it:
But a monologue is not a musical. While developing “Fast Food Town,” Jackson created a new main character, named Usher. The show was going to be a mashup of Jackson’s writing and Liz Phair’s, but, when he reached out, Phair told him that he should write his own songs. His friend the director Stephen Brackett suggested casting Usher’s world entirely with gay Black male actors, no matter the role. In 2015, Jackson learned that the trans actor Shakina Nayfack was starting the Musical Theatre Factory, where artists could develop new work, and she invited him to join. Folks began to get it; Usher’s experiences paralleled their own. The times were catching up with Jackson. Days of our lives, indeed. The young writer won a Dramatists Guild fellowship, a Jonathan Larson Grant, and a Lincoln Center Emerging Artist Award. The Broadway producer Barbara Whitman, who was annoyed that the New York theatre scene wasn’t staging more work like Jackson’s, committed to helping him produce the show. A number of theatres lined up to stage it. The Pulitzer Prize-winning playwright Jackie Sibblies Drury told me in an e-mail that one reason she loved “A Strange Loop” was that it was a “relief to see work that was so self-interested—not in a shady way. . . . It felt to me like a piece that wasn’t strictly autobiographical but was interested in the self . . . in exploring his Blackness, his queerness, his communities—familial, artistic, sexual—and how they see a person like him.” She added that, also, “it is really fucking funny.”
On a recent afternoon, I visited the rehearsal hall above the Second Stage theatre, where the company was finishing up a run-through. After the actors were dismissed, Lileana Blain-Cruz, the show’s director, met me with a head of blond Cuban twists; on top of that, set at a jaunty angle, she wore a bright-pink beanie. Blain-Cruz was relaxed, authoritative, and ready to laugh. On one side of the loft-like space there were images tacked up on the wall: the actress and comedian Jackée Harry on the cover of an old Jet magazine, Ruth Bader Ginsburg wearing black gloves, a young Whitney Houston perched on a car, Diana Ross under a cloud of big-ass hair. These are just a few of the major reference points for “White Girl in Danger,” which has more than its share of diva drama.
The show is more sonically complex than “A Strange Loop”; Jackson makes elaborate use of the chorus. In “A Strange Loop,” he had to invent a form to tell a story that had never been told before. In “White Girl in Danger,” he’s using the conventions of a preëxisting form—the soaps—which allows him to be looser. “The piece is larger than life, but it’s still life,” Blain-Cruz said. Her challenge as a director has been to “keep the life part of it, the truth part of it, the ‘what happens next’—all that sex and drama and passion and feeling—part of it that made those ladies watching their stories in the afternoon feel so alive.” Because of the success of “A Strange Loop,” Jackson could work on “White Girl in Danger” without having to live with roommates or hold down a boring job. After checking on a note with the stage manager, Jackson, who was dressed in a gray shirt and dark trousers, joined me and Blain-Cruz. He began to explain a soap structure, describing a plot in “As the World Turns,” which aired on CBS from 1956 to 2010:
When I visited, “White Girl in Danger” was due to start previews in a couple of weeks. It had been a long process. Watching the run-throughs was like sitting inside a movie time wipe—some of the actors were different from when I first saw the show. I heard, too, how the music had deepened. But the key players remained the same: those characters which, whether they knew it or not, had started to take form subconsciously all those years ago, back in Detroit.
Some people think that O. J. Simpson killed the soaps: having real-life drama, in real time, made the shows feel obsolete. The world was subsumed by Lifetime movies, which borrowed soap plotlines, and reality TV. Jackson will, if asked, guide you through soap history with enthusiasm, and he will also let you know that he’s never given up on the form. He’d like to eventually write a sequel to “White Girl in Danger.” He’s planning a musical adaptation of the 2007 movie “Teeth,” based on a fantasy about vagina dentata, and a television project about how sex can be viewed positively within a Black context. In the rehearsal room above the Second Stage, however, he was focussed on “White Girl in Danger.” Blain-Cruz was excited by the challenge of trying to make soaps matter to a contemporary audience. “I feel what’s so satisfying about the work is that Michael is deeply invested in pop culture, and deeply invested in the history of media,” she said. “So he knows how to take the things that are familiar for us, the things that we’ve in some ways dismissed as not even anything to pay attention to, and he makes us pay attention to them.”
It was the “dismissed as not even anything to pay attention to” that made me recall all those young men and women of color who surrounded Jackson outside the Lyceum. In some way, the musical had given them not just a show but an audience; talking to Jackson, and taking selfies with him, was a way of feeling seen, and less forgotten. This was an aspect of the show that had moved the great star Bette Midler, too. She told me, by e-mail, “I thought it was all the things people always say; ‘Brave, bold, goes where no one has ever gone, blah blah blah’, but actually, in spite of all this, or in addition to all this, it also manages to be hysterically funny, illuminating, revelatory, moving, remarkably musical, heartbreaking and ultimately so human, that it makes you want to weep, not just for Usher, but for all of us. And I did. I still can’t understand how he did it.” Midler went backstage to meet Jackson after the show and offer her congratulations. Afterward, as they walked out onto the street, where a crowd had gathered, Midler noticed that his glasses were splotched, and, expressing Mom concern, took them off and wiped the lenses, using a bit of her dress, like a hankie. ♦
