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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.”
“Abigail! Nooooooooo!”
Cartoon by Hartley Lin
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.
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