Arts

Michael R. Jackson tells Tim Teeman about how feeling trapped in his own “strange loop”—around race, sex, sexuality, writing, indeed every part of his life—became a hit musical.

If you saw the musical A Strange Loop, which ended its much-acclaimed run in New York over the weekend, you might wonder—as I did—about what first to say when meeting its creator, Michael R. Jackson. The instinct to ask, “Are you OK?” or simply give him a big hug felt overwhelming.

This excellent musical is “a meditation on a perception of oneself,” as Jackson put it, and we see a black musical composer called Usher (Larry Owens) agonize, through words and music, about himself in relation to race, sex, sexuality, career, artistic creation, family, and faith—everything in his life—with raw honesty.

“I drew from personal experience to write the character of Usher, but I wouldn’t call it autobiographical,” said Jackson. He started writing A Strange Loop when he was 21. He is 38 now, and a fast, engaging talker. It was once about not being able to get work, Jackson said. He performed it as a one-man version before deciding he did not want it to be “a memoir cabaret act,” but rather a “proper musical, even though it’s an unconventional one.”

Critically acclaimed, Jackson’s play has been attracting not just full houses, but starry ones, with attendees, Jackson said, including Lin-Manuel Miranda, Helen Hunt, Dana Delaney (twice), James Franco, the Rev. Al Sharpton, Billy Porter, Alicia Silverstone, and Lawrence O’Donnell. When we met one recent afternoon in the musical’s final week at the off-Broadway Playwrights Horizons, Jackson was anticipating the rumored presence of Wendy Williams.

As the musical goes on, we are aware that Usher feels eternally, grindingly trapped. The “strange loop” of the title, as Jackson explains in his program note, was created by cognitive scientist Douglas Hofstadter to “theorize the self as merely a collection of meaningless symbols mirroring back on their own essences in repetition until death. He further theorized that a human being is the organism with the greatest capacity to perceive itself perceiving itself, ad infinitum.”

“Strange Loop” is also the title of a song by Liz Phair (whose music Jackson has long loved, particularly the 1993 album Exile in Guyville), and for a time—when the musical was first called Fast Food Town—Jackson had been trying to get permission to use her songs in the play. Then he read about Hofstadter’s theory, “which was weird. I hadn’t realized I had been writing about the theory the whole time. I changed the title.”

Usher thinks he’s too fat to be desirable. He wants to write a musical truthful about his experience as a black queer man, not meet the cultural expectation that such a work be about slavery, or police brutality, or intersectionality.

His parents do not accept his homosexuality. He does not want to write the musical that Broadway and off-Broadway producers want him to write. He is having bad sex for bad reasons, objectifying white men as they objectify him. He is haunted by demons that tell him he is worthless. Usher’s experience and life are harsh, and his tendency to self-denigrate is painful to watch.

Jackson, who lives in Washington Heights, also invokes W.E.B. Du Bois’ idea of “double consciousness” to describe the uniquely African-American experience of “always looking at one’s self through the eyes of others, of measuring one’s soul by the tape of a world that looks on in amused contempt or pity.”

The musical is both self-conscious Rubik’s cube, in conversation with itself, and the moving tale of a person trying to find his way in the world and escape repeating harmful personal dynamics. A Strange Loop—Jackson wrote the book, music, and lyrics—is as witty as it is moving, and sharp as it is intelligent and densely argued.

Six actors join Owens-as-Usher on stage as an energetic, mischievous, sometimes very shady Greek chorus, playing voices in his head, family members, sex partners, and critics both inner and outer.

On a small stage, it was beautifully designed (Arnulfo Maldonado), with one astonishing visual surprise, choreographed (Raja Feather Kelly), and directed (Stephen Brackett). Brackett suggested a cast made up of black and queer people, and over time it became the production made by Playwrights Horizons and Page 73.

Jackson emphasized he is not the Usher we see on stage, at least not now. “This piece has always been about a young twentysomething black gay man trying to understand himself, and so to the extent to which it drew on my own experience, this was me at 21, 25, 27, 29. It got to a certain point where I was far enough away from the misery of that time that I could have a perspective on what my experience was, and what the young, black, gay protagonist was actually dealing with.”

Jackson went to therapy, “stopped hating myself,” and both grew beyond and came to understand the self-loathing he endured when he couldn’t “wait to crawl out of my skin.”

Usher’s parents reject him and make clear their disgust about his homosexuality; his father even asks him if he’s attracted to him.

“Usher hates himself, and sees the world through those lenses, and I feel he sees his parents in the same way. That doesn’t mean he doesn’t have real struggles with his parents and them with him, but what you’re seeing ultimately on stage is a perception of reality. It’s up to the viewer to determine how real that is.”

For Jackson’s own parents, the show didn’t feel like an indictment, or emotionally grueling. “But it was like being given a Sardi’s caricature of themselves, an honor. The play is larger than life, and my parents are in some ways. They are also totally and utterly in my corner.” They were very proud to see the fruits of Jackson’s labors, and ask him excitedly about what is coming next.

“My parents are who they are,” Jackson said. “I feel like I had to get to the point where I realized I can’t change my parents and actually don’t want to—and change is just an illusion anyway. The only change I could control was mine.”

Jackson said he wanted to examine with care the complexity and ambiguity of black life; the mother’s journey in the play is not to a cookie-cutter “I love you, my gay son” ending, but one that recognizes an ongoing struggle, with love and acceptance at its base. Jackson is mistrustful of the neat bow put on LGBT and black narratives. A Strange Loop is proudly, meaningfully challenging.

Jackson grew up in Detroit. His father was a police officer for 27 years who later became a security consultant at General Motors. His mother worked in finance for a manufacturing company. He has an older brother.

“My parents are complicated people,” he said. “With my dad being a police officer, I grew up in police stations. He would pick me up in police cars, and the kids at school loved him. He was seen as a hero in the community. For him, police work was about serving the community.”

The death of Freddie Gray, and numerous other incidents, changed Jackson’s view. “Now I think of them as a capitalist terrorist force, here to protect property owners. I recall during the Baltimore uprising they rushed to protect a really nice hotel, as if their message was ‘Tear down and burn anything else, but not this.’”

His famous namesake has throughout his life been deemed worthy of comment—first by school buddies, and always by total strangers, even long after the pop star’s death. Jackson has made it a playful boon as an adult: his Twitter handle is @thelivingmj, his Instagram is @thelivingmichaeljackson, and website thelivingmichaeljackson.com.

“It was happy,” Jackson said of his childhood. “My brother and I never wanted for anything. It was a pretty solidly middle-class life. I was always reading, always writing poems and short stories.” He played piano at the Baptist churches he attended.

Then at 15 or 16, Tori Amos “changed my life.” Even though it is another favorite singer, Phair, whose song title is mirrored in the musical’s, “the real person in my high school days was Tori because her music is so emotional and so angsty and so personal and deals very frankly with the intersection of religion and sexuality, questioning patriarchy. Music really spoke to me in terms of how secret I was keeping my sexuality.”

It was a religious home. Jackson’s dad had “grown up” in the church, his mother had been a church secretary for 25 years. His grandfather was a trustee of the church the family attended, his name on its cornerstone. Jackson went to a vacation Bible school every summer. “There was a consistent message that homosexuality was a sin. Today, I do believe in something, but I don’t deal with organized religion at all.”

He came out to his parents at 17. “It was horrible. My dad confronted me over a conversation he had overheard between me and another guy. My mother came home, and it turned into a big, emotional, intense confrontation about me being gay.”

There were lots of other black gay young men around Jackson at school and in the school choir, “dating, having dramas and intrigue. I wasn’t dating anyone. My parents kept me on a pretty tight leash.”

Jackson said he wanted to describe his parents and religion carefully because of the label of homophobia that he felt had become unfairly attached to black churches after the Proposition 8 vote in California.

In America, Jackson said, it is necessary to look at the history of slavery and white supremacy “and the impact on slave bodies and bodies used in that. If that does turn into something homophobic, it didn’t come out of a vacuum. Homophobia is not a particularly black trait. It’s important to be sensitive when talking about black homophobia.”

But, Jackson said, “you have to acknowledge the existence of it. If you don’t, you can’t do anything about it. My parents really struggled with me being gay. They did it from a place of concern and love—that’s what’s complicated about it. I don’t think any of us knew how to support each other or ask each other what was needed. I certainly didn’t know. When I came out to them I felt mostly I had failed them in some way. I felt a disappointment to them. I didn’t know how to ask for what I needed emotionally. It made me shut down, and I didn’t talk about it for a long time.”

Things didn’t improve when Jackson went to college in New York. He didn’t date anyone because of the shame around his sexuality. The city and its gay environs like Hell’s Kitchen “felt like it was run by white gay men,” which made him feel more shame. At home, his parents didn’t like him being gay.

“It took many years of struggling through that, and feeling that, going to therapy and getting older and fighting for my own self-worth until I got to a point where I was able to talk to my mom about being gay, and being more resolute about it. She appreciated that. She still does hold the view that homosexuality is wrong, but she also loves me and she would never do anything to denigrate me. Or my life, in fact.”

When marriage equality was passed, the pastor of his parents’ church asked the congregation to vote on whether to disallow gay weddings there. Most voted to do so—except Jackson’s parents and some other relatives.

That was a big surprise, said Jackson, although his mother still believes “man is for woman and woman is for man. But she is also much more open than when I was 17. That complexity is important for people to understand.”

Just like Usher’s father in the musical, Jackson’s father asked him when he came out if he was gay, did that mean he was attracted to him.

“That was very disorienting in a lot of ways. It wasn’t a weird come-on. He was really trying to paint homosexuality as illogical. It came from a place of fear. Now he and I are in a good place.” Jackson talks to his mother more; his father communicates things to her to convey to him. The show allowed both of them the opportunity to see what parts of Jackson’s life had been like. They would also have seen the responses of the audience: the shouts and murmurs of recognition, the sighs of sympathy, the laughter.

Jackson studied for a BFA and MFA in playwriting and musical theater writing at the NYU Tisch School of the Arts.

Being an usher at The Lion King on Broadway (just like Usher in A Strange Loop) was “fairly miserable,” with a horrible uniform, an occasional awful hat, a lot of mess, little kids throwing up, people being generally annoying, and also “being in the belly of the beast,” looking at the musical on stage and thinking, “I don’t do this, and no one will ever make my musical. But I could also see it brought people a lot of joy.”

Next, Jackson managed two people in the finance department of an advertising agency. “I didn’t like them, and they didn’t like me. I hated my racist bosses. It was an utter nightmare. I learned the capitalist system squeezes all it can from you.”

Next, he became an executive assistant at a nonprofit, better in some ways, but “they still wanted to squeeze as much from you for as little as possible.”

Then, in 2017, he was awarded a Jonathan Larson Grant and became one of Lincoln Center’s emerging artists. He was that year’s Williamstown Theatre Festival playwright in residence and won the ASCAP Foundation Harold Adamson Award and a 2016/2017 Dramatist Guild fellowship.

It was great to be liberated to write full time, and a bummer to realize he had to pay taxes on his prize money, Jackson said. (When writing, the words come to him much more easily than the music, he said, but he writes them both together.)

Jackson could, he said, “write a bunch of sequels” for Usher based on his own life, such as when, while at the advertising agency, lost 80 pounds in nine months on a Weight Watchers (now rebranded WW) diet.

Jackson said he had felt as thin and trim as he possibly could, but still did not qualify as a member of what he calls “the fine ass n—a finishing school. I didn’t have abs or a big dick, or any of those things to fit into the ‘gaytriarchy.’”

Then, when he left the job, and the gym and Weight Watchers membership expired, he gained 90 pounds. Today, he would like to lose weight for health reasons, as there is a history of diabetes in his family. “I love myself now. I feel like I have character, integrity, and more wisdom than I did 20 years ago, or even two years ago.”

Now Jackson doesn’t feel subject to the judgment of others, and notes that the white men who he was once jealous of have aged. “It’s not shady. You forget that time is happening to all of us. With my self-hatred glasses on, I had thought they were put on earth to torture me. It’s not how life is.”

He rewrote one scene “900 times,” when Usher wonders out loud why interracial gay couples are so highly prized. Why can’t black gay men couple up with each other, Usher asks. What are the aspirational and cultural pressures to find a white partner?

“I had to say it out loud. I feel that because of the anti-blackness in our world, the ideal of two black men being together seems limiting, strange, or outright disgusting to some people. Some black gay men believe that and gravitate to interracial relationships to show they have achieved some social status. White partners are trophies to them. I think that can be OK, but I get bothered when it’s put under the rubric of ‘Love is Love.’ That feels like false neo-liberalism to me.”

Usher’s sex with white gay men is because he doesn’t feel able to be with black gay men. Likewise, Jackson “scrambled” after white men in his twenties “who were not worth my time. I was desperate. I needed to be keeping up with my peer group. When you’re young and gay, you have to get all the notches in the belt you can.”

Jackson never felt satisfied with this sex, always felt ashamed afterward, and wondered why he was doing it, he said. “I always felt no one would love me. I always felt undesirable.” Then sex apps happened, and new levels of snap judgment were brought right into his phone. This for Jackson was another “nightmare within a nightmare,” with free-flowing racism and judgment about dick size now available at the click of a button.

Today, Jackson revealed, he is happy in a new relationship that started just as the show started. “I’m into it. I’m into him. He’s black and also an adult, which is the best part, not a young person with their head looking over their shoulder looking for something better, so easy in this capitalist city.

“White gay men are fine. I just don’t need them to validate me in any way. Because I love myself I am able to love other black men and see them as potential partners. Whatever white men do or don’t do is immaterial to me. I have met someone who is literally into me for me, and not for a capitalist consumption luxury lifestyle branding thing. It’s the thing I was wanting all along but thought was impossible because I was so ugly and fat.”

Jackson said there had been more and more black gay narratives making it to the stage, but they were full of hot actors who had been to “fine ass n—a finishing school.” He is friends with some of them.

With A Strange Loop, he wanted to convey a message that if you are “ugly and fat,” people may still desire you. Too often such characters on stage get tagged as the clown or best friend.

Gay identity has been commodified; just look at the sexy guys in ads for AIDS and PrEP drugs, Jackson noted. Five months ago, a friend of his died of AIDS. “It was a very shocking death because he had been keeping it secret for over a decade. He hadn’t take any medication. I say he had four viruses: secrecy, silence, shame, and stigma. I think PrEP, Truvada, ‘U equals U’ are all great, but medications are not affordable for everyone. And I think if you think God hates you, or you deserve to die of AIDS, which I believe my friend believed, then you will not take your medication. He had a lot of self-hatred.”

Jackson’s friend also faced a lot of family pressure, although his mother “came around” before he died, and died herself soon afterward. As well as all the current messaging about wellness and images of sexy men, Jackson would also like an emphasis on psychological and spiritual help, and awareness when it comes to talking about HIV and gay sex.

“Broadway Bares raises all this money for HIV and AIDS, but there are so few performers who feel able to be open about their own status,” Jackson said. “A bunch of my friends are HIV positive but because of job opportunities don’t feel able to be open. Stigma is very much alive, and it’s a missing piece in a lot of advocacy. I wish activism around HIV and AIDS was as loud as it was in the ’80s and ’90s, when the plague was at its peak.”

People with HIV on apps also face rejection and judgment if they are open about their status, Jackson said, “which goes doubly for people of color.” The language of sex positivity, Jackson feels, makes bodies seem “disposable.”

“I’m just wondering what, or how, we really change the script about all that stuff, to prevent people isolating themselves in the ways my friend did. People think they don’t have shame, or get angry at those that do. It’s not seen as sexy, it’s not cute. But it would be good if we could talk about all those things and be vulnerable.”

At the end of performances of A Strange Loop, black mothers have thanked Jackson for allowing them to learn something, black queer people have thanked him for helping them feel seen. “It means a lot to see black audiences really responding and living their best lives. Then some little old white man or lady will tell me they loved it: ‘This wasn’t my life but I found it so moving.’

“All those responses mean a lot to me. I believe theater is a great equalizer: We are all gathering together in the dark to learn something about the human condition. I set out to write for multiple people at multiple times to speak to multiple audiences. I wanted everyone to have that disorientating feeling of catching this and not catching something else, and to see people around them responding to that.”

Alongside therapy, writing the show has helped Jackson to personally evolve. It does not mean everything in his life is perfect, Jackson emphasized, but he has made sense out of many of the disabling demons in his own strange loop. He said there had been a time when he thought the show would not get made, then wondered what people would make of it.

One thing Usher does express that Jackson also feels powerfully is a visceral dislike of Tyler Perry and the way Perry portrays black people in his plays and films—for instance the HIV diagnoses given to two female characters who “exercise their free sexuality” in Tyler Perry’s Temptation: Confessions of a Marriage Counselor (2013).

For Jackson, there is a lot of queer-phobia and homophobia in Perry’s works. “The language he traffics in serves a black evangelical Christian audience. Too many black people died from HIV and AIDS, and they hit our communities so hard in ways that are still unacknowledged. I cannot deal with a piece of pop culture that just puts more toxicity out into that atmosphere.”

Jackson, like Usher, acknowledges Perry’s philanthropy and power, and he has heard Perry is “a nice man. This is not personal. I just think his humor is harmful at a time when we don’t need it. In the black community, there’s an expression, ‘When you know better, you do better,’ so maybe he needs to know better to do better.”

Jackson said he was still going to work on A Strange Loop and refine it, having seen people react to things within it not in the way he had intended. He said he hadn’t had to compromise anything when he wrote the play, encouraging him that he won’t have to with future works.

His next musical after the success of A Strange Loop will be a “kind of sequel,” White Girl in Danger. He has also written the lyrics and book for the musical adaptation of the 2007 horror film Teeth with composer and co-bookwriter Anna K. Jacobs.

White Girl in Danger orbits thematically in the universe of ’90s Lifetime movies and daytime soaps, where black characters exist literally in a sphere called the “blackground,” until one black female character, Keesha, decides she wants to exist in the white foreground occupied by a trio of white female characters called Meagan, Maegan, and Megan, who exercise their emotional choices freely and volubly.

Jackson grew up watching white women emote and have those emotions be placed so centrally. In the play, Keesha faces peril when she tries to attain the same. What follows is an analysis of what cultural diversity, inclusion, and equity really means. The theme also surfaces in A Strange Loop. “I’m not saying Usher wants to be a white girl,” said Jackson, “but I’m interested in the way in which white women get to live in a complex way that Usher wishes as black man he had access to in order to express himself more freely.”

Jackson was a fan of Days of Our Lives, Another World, and One Life to Live (and worked in the production office of All My Children when at college). The death of The Young and the Restless’ Kristoff St. John “devastated” him, as the significance of Genoa City’s lead black family, and St John’s commanding presence on the show as Neil Winters, had been so important to him growing up.

The recent controversy over the casting of black actress and singer Halle Bailey in The Little Mermaid was misplaced, Jackson said. For him, the debates should really be about who’s writing the characters and who’s producing and making money from shows and films—usually, Jackson said, those people are white.

Another future commission for Lincoln Center, Accounts Payable, is loosely drawn from Jackson’s time working at the ad agency, 20 years from now in a post-Democrat, post-Republican world, in an office full of squabbling workers as the world “goes insane” outside.

“I think we’re all going mad now,” Jackson said. “We laugh at Marianne Williamson, or Donald Trump, or Bernie Sanders or Pete Buttigieg or Andrew Yang, at our peril.” Jackson is political but stepped away from social media “for a bit” because of its toxicity. For a time he detached from the news cycle completely.

“I think if Donald Trump had not been elected president, then A Strange Loop would not be at Playwrights Horizons, because my guess is that they would not have seen a need for a musical like A Strange Loop had he not been president.” Jackson paused. “It’s complicated. If that is true, do I say, ‘Thank you, Donald Trump?’

“The Trump presidency is useful creatively in the sense that it makes me look at everyone else. I loathe him, I think he’s one of worst pieces of shit ever, but I’m also critical of left-leaning folks who are elitist and not really concerned about what life is like for regular working people.”

For Jackson, “everything isn’t ‘Democrats good, Republicans bad.’ To a certain extent they are just part of the same elite class. We don’t talk about class a lot in this country, because it’s now so chic and cool to weaponize race and identity, and doing that to distract from the truth of people at the top who are pushing down on regular working class people.

“I wouldn’t go so far as to say I am happy there is a Trump presidency, but his election surprised me. I realized Rachel Maddow and Nate Silver had been doing my thinking for me. It forced me to go find other sources. Some of the Trump policy stuff we don’t like, Obama did the same. I voted for Obama twice and was happy to do so, and would do so again. Now I realize he came with a lot of baggage. Why do we think it’s OK to bomb a country when it’s done under one person’s smile, but not when it’s done with another person’s smile?”

There is an expectation that black and people of color writers are “truth-tellers” in this time of Trump, said Jackson, “who will tell us all about the racism and trauma from history at a time of that racist in the White House. Some of those plays I have liked, some I haven’t. But is that our role to do that? It is important for me that A Strange Loop is a personal account of what it feels like to be in a black queer body right now.

“It’s not necessarily about the history of slavery, and teaching and punishing white people. I want you to see this character’s experience of himself: the joy and pain. Usher is not killed or enslaved by the end. The audience is not asked to weep for the destruction of him. This is someone who went through something and come through the other side, and we’ve been doing that since we were dragged over here.”

Jackson said he hoped that if Kamala Harris, for example, becomes president in 2020 that the appetite for black and people of color writers’ material doesn’t ebb; that the mainly white gatekeepers of theater don’t suddenly think, “We don’t need to be as worried about this stuff as we used to be under Trump. Black writers still need to be commissioned, championed, and be allowed to fail.”

Is Jackson now free from his own “strange loop”?

“No,” he said firmly. “As long as we’re alive, it keeps perpetuating itself.”

The trick, as Usher finds, is making sense of the loop, and making it manageable—or even, as Jackson has shown, making a dazzling triumph from it.