Metro Weekly

‘A Strange Loop’ creator Michael R. Jackson uses art to “make sense out of the craziness of life”

Michael R. Jackson on making history with A Strange Loop, the impact of Liz Phair, and why the show targets Tyler Perry

Michael R. Jackson, a strange loop
Michael R. Jackson — Photo: Beowulf Sheehan

They say to never meet your heroes, but rubbing shoulders with idols has worked out well so far for Michael R. Jackson. The playwright, composer, and lyricist, whose musical A Strange Loop earned him the 2020 Pulitzer Prize for Drama, drew from a wealth of influences to create his self-referential stage hit — from the gospel he grew up with, to the alt-girl rock that helped him through high school while struggling with his sexuality.

First and foremost, Jackson drew from his life and experiences coming into his own as a Black gay man in America. Though the Detroit native makes a point to say A Strange Loop — playing through January 9 at Woolly Mammoth before heading to Broadway for a planned run this Spring — isn’t autobiographical, it is a show about a Black gay 25-year old named Usher, who works as an usher at The Lion King while also writing his own musical about a Black gay twentysomething usher writing a musical, which describes Jackson at that age, working as an usher at The Lion King, while studying at NYU’s Graduate Musical Theater Writing Program and writing his own musical.

Like Usher, twentysomething Jackson was trying to figure himself out as a man and artist, and finding strength and insight in the lyrics and music of female alt-rockers like Liz Phair. “That’s part of the inspiration for the show,” says Jackson, noting A Strange Loop‘s cheeky, soul-baring tune, “Inner White Girl.”

“In a lot of my white girl music that I used to listen to, when I was in high school and into my 20s and young adulthood, and to this day, a lot of those ladies, they just let it all hang out, because nobody was going to tell them they couldn’t do it,” he says. That audacity encouraged Jackson to be just as fearless in putting his whole self into A Strange Loop. “Especially if I’m suffering and unhappy. And I’m an artist and I have a canvas, why not just let it all hang out?”

Jackson, and Usher in the show, single out Phair for her singular inspiration, both in creating the song that lends the show its title, and for embodying a spirit of artistic freedom. For years, Jackson recalls, he was circling the singer-songwriter, “because there used to be a version of the show where Usher was trying to get permission from Liz Phair to use her actual songs in the show.” But Jackson’s attempts to reach Phair proved futile.

“I was much younger then,” he says. “I had a very naïve idea of how easy or hard that would be. Eventually, after many years of doing it, I ended up making contact with her through the person who is her archivist kind of guy. He contacted her. She responded to him with an email saying, ‘No. You can’t use my music. I’m honored that you were inspired by me, but you need to write your own songs.’ Which was really fantastic advice, because it forced me to go back into the piece and figure out how to just make my songs be the songs that were driving the story forward.”

As the years went by, A Strange Loop went up Off-Broadway at Playwrights Horizons and started getting written about. Eventually, Phair got wind of the show. “And then she started following me on Twitter. And I DMed her and said, ‘Thanks.’ It was very brief.” But the paths of Jackson and his muse still grew nearer.

“After the show closed, she had a concert in New Jersey. And it just so happened that I had a friend whose husband went to high school with her, who was also at the concert. And they had VIP passes to go backstage.” Here is where one would expect good fortune to kindle a dream fulfilled.

“But they wouldn’t let me go back. I was like, ‘Oh well.’ Then the concert ended, and me and my friend James, who is one of the cast members in the show, we just decided to hang around. And she happened to come out on the stage to get her guitar or something. And something just told me to just go walk back in and just wave or something.

“When I waved at her, she recognized me because of the press that had been around, and because we follow each other on Twitter. And she invited me to come backstage. And me and James went backstage, we chatted for a bit. And she was very, very nice….

“It was a really ideal meeting, because it didn’t feel like it did when I was first trying to get her permission, where I felt like this stalker-ish kind of fanboy. It felt like fellow artists getting to meet. And she was very kind and generous with her time. I really appreciated that meeting, especially after all of those years of working on the show, but also just being inspired by what she does in her music and it helping me continue on to work on the show.”

A Strange Loop -- Photo: Marc J. Franklin
A Strange Loop — Photo: Marc J. Franklin

METRO WEEKLY: First, congratulations on winning a Pulitzer Prize. You’ve earned other great honors for this show, but that one is, I think, especially historically significant. How did you learn that you had won?

JACKSON: I was on the phone with my friend, playwright Branden Jacobs-Jenkins. And he, unbeknownst to me, was watching the awards. And I was talking to him about Real Housewives of Atlanta, which he does not watch, but I do — or, I used to. He wanted to know, why did I watch it? I was just talking to him about that. And then he interrupted me to tell me that I had won.

MW: Were you not aware that the ceremony was happening and that you were a finalist?

JACKSON: I knew that it was happening. You don’t know if you are a finalist or not. You find out when it’s announced. It had been suggested to me that I might be shortlisted for it by someone who was speculating. But it just was not on my radar at all, because I did not assume — it just was not something I was thinking about.

MW: Was it because this had not happened before for a musical that was yet to reach Broadway? And it had not happened before that a Black author who wrote a musical won the Pulitzer Prize for Drama.

JACKSON: And also it’s the pandemic. We were right in the middle of the very beginnings of it. My brain was disconnected from thinking about a big award. Not in a negative way, but I just was like, “Oh yeah, sure, whatever.” I was in just a different headspace. That’s why when I got it, it was like a thunderbolt, because I was suddenly like, “Wow, that’s amazing.”

MW: The Pulitzer announcement was May 2020. That year in general, a lot happened while you were experiencing this validation as a Black gay artist. Did events of 2020, and the racial reckoning of that summer, cause you to reflect any differently upon how A Strange Loop is being received?

JACKSON: That’s really complicated because, I mean, the short answer is no, not really. The truth of it is that I just feel like my theater career — both my life as an artist and someone who cares about art — is not something that I would conflate with the events of 2020. And something that I actually have found very disturbing is the ways in which people will try to make one thing be another.

I actually think that it does a great disservice to the events of 2020, because I guess I’ve seen so many people — I’m just going to be very real with you — so many people profiting off of George Floyd as a way of boosting their own careers and career goals and their own grievances and their own money, come ups and that sort of thing. And I just find that to be really tasteless and disgusting.

At the same time, I’m proud of the art that I make and the career that I’ve tried to build over many, many years. Those two things are very separate to me. There are other people who feel differently about that. But I don’t think it’s right. I don’t feel right about trying to say the so-called racial reckoning is related to my theater career. I mean, I can certainly talk about my theater career in terms of racialization, for sure. But that, to me, is a very specific conversation that requires nuance.

MW: It’s really cool that you once received the Jonathan Larson Grant, because I see a relationship between A Strange Loop and tick, tick…BOOM! in the outline of the stories. What relationship, if any, do you see between the two works?

JACKSON: It’s so funny that you bring this up, because I just watched tick, tick…BOOM! last night. I saw the original production in 2000, when I was still in college. And I guess there are overlaps in terms of, literally, they are both about musical theater writers who are working on shows.

I think one key difference is that in A Strange Loop, the protagonist Usher, the writing of his musical is also about the living of his life. And it’s actually kind of more about the living of his life than about a musical that he has to achieve something with.

In tick, tick…BOOM!, Jonathan Larson has a specific goal with the workshop that he is working on. And maybe he will make it or maybe he won’t. Whereas in A Strange Loop, it’s his life. He’s dealing with a lot of different areas of his life. I think that that makes them very different. Albeit, they are both musical theater writers. And also, Larson is white and Usher is Black. And Usher has a lot of Black issues and gay issues. And Jonathan Larson is straight and he has a girlfriend. There are so many things that are different about it. Although, and also weirdly, they both have AIDS in them, but they have a different relationship to AIDS.

A Strange Loop -- Photo: Marc J. Franklin
A Strange Loop — Photo: Marc J. Franklin

MW: Those characters, Usher and Jonathan, do have very different experiences fitting into the theater world. But the show reflects certain facts about your own life. How much does Usher reflect your character?

JACKSON: I always try to be very precise with people by saying that A Strange Loop is not autobiographical. I call it self-referential, because even though I drew from a lot of personal experience to write it, it’s not an apples-to-apples relationship of events in my life to things that happened in Usher’s life. There is a true mix of fact and fiction in the piece.

For example, I did have an “Inwood Daddy” experience, actually more than one. But that experience, it’s an amalgamation of a couple of experiences. And it’s also about the perception that maybe my 25-year old self had on those experiences. Do you see what I’m saying? I fictionalized what I needed to fictionalize just to tell the story of that, of what it felt like. If I had to describe it as autobiographical, I would describe it as emotionally autobiographical. I felt everything that Usher has felt. The events, they may bear some resemblance to things in my life, but they are also very different. I did put craft into it. I didn’t just open up a vein and bleed on the pages. It was work to tell a story.

MW: What was your process of deciding what of yourself to include and expose versus what really didn’t need to be in there?

JACKSON: Well, it took me 16 years from the start to our first production. That’s a lot of drafts. I had to produce quite a lot of content on the page. So I pretty much poured out everything. I could go back and share so many versions of the show that had so many different elements to it. And it just was a process of working on the show, working with my collaborator, my director, Stephen [Brackett], working with the actors, many of whom had been developing the show for many years prior to it going to Playwrights Horizons. Hearing it out loud a bunch of times.

And also, I always just tell people that I started writing the soup of what A Strange Loop was when I was about 22 or 23 years old. The piece has always been about a young man trying to write about a young man. But I, Michael R. Jackson, was getting older and getting more distance from being the 22- or 23-year-old, who was ultimately still kind of a 17-year-old at heart with his experiences. I had to get a certain distance to even figure out what the show was about, really, because otherwise it just would have been this totally, totally self-indulgent, solipsistic thing that didn’t have any structure to it or any perspective on the experience of being a miserable twentysomething who was dealing with a lot of self-loathing. And also trying to move toward a place of not self-loathing.

MW: Given that distance, do you look at the show now — especially after that much work and many drafts — and feel removed from that personal piece of yourself that is in Usher? Or do you still feel exposed by that?

JACKSON: I don’t say I feel exposed. I would say I feel like the thing I always wanted to do with the piece was just to share something vulnerable and honest about Black queer life, what it felt like to me, because I never felt represented. And you hear this from so many Black artists about representation. But for me, I never felt it even when I would see other Black queer representations and stories in media and so forth.

What that meant was that I had to be willing to get as specific as possible about what it was to walk in that skin through my eyes. Maybe I’m a little bit of an exhibitionist. I don’t know. But I don’t feel exposed. It just feels like this is the truth. And the truth will set you free. And I, for many years, felt not free. The only way to get free is to tell the truth, even if it’s not always convenient, or if it paints me in a certain light. I wanted to just really go there.

MW: That gets me to religion, which you deal with in the show. Did you grow up in the church?

JACKSON: I grew up Baptist.

MW: One song in particular I wanted to ask you about is “Precious Little Dream/AIDS Is God’s Punishment.” That song just gets into the idea of the Black church being a place where gays thrive and are really part of the community, but also risk being ostracized for being themselves. What’s the story for you behind that song?

JACKSON: It’s a very complex story. Basically, what happened was I wrote this song called “Memory Song.” And it was a song that I started writing when I was in grad school. Well, first what happened was I went to NYU’s Graduate Musical Theater Writing Program as a book writer and aspiring lyricist. I was not writing music at that time. I mean, I grew up playing piano in church and I was very musical, but I didn’t think of myself as a composer. I wasn’t trying to be a composer. But by the end of the first year, I had figured out lyric writing. It ended up being a really good container for a lot of the writing I was going to do. One of our teachers gave us an assignment that said if you are a lyricist who has never written music, or a composer who has never written lyrics and you want to try it, go for it. I decided to try putting my own music to a lyric.

Prior to that, there had been an assignment in one of my classes where one of my classmates who was another Black gay man, he wrote a song that was about feeling religious shame and guilt or whatever after having had a homosexual experience. And he sang the song in the class. It was a character, but it was clearly drawn from personal experience. And I was so affected by it, because he reminded me of a lot of boys that I had grown up in high school with. And when I was in high school, it was like Black gay boys everywhere. It was this whole soap opera in the mid to late ’90s at my high school that I just was on the periphery of.

Many of them were religious boys who would have sex with each other. And then they would go repent at church and stuff. I remembered that, and that’s what that song reminded me of. I took my notebook out of my bag while he was singing the song. And I wrote in my notebook, “all those Black gay boys I knew who chose to go on back to the Lord.” Those words just came up. I didn’t know what I was going to do with it, just because I used to keep a lyric notebook. Then cut to when the teacher said, “If you are a lyricist who wants to write a song, go for it.” Then when I went to go sit down to figure out what song I would write, I flipped through my notebooks, I fell on those words, and I decided to try to set them to music. Then I wrote the song, presented it in my class. It went over really well. I was encouraged to continue writing music, even though I was going to be paired with a composer for my second year of grad school.

Long story, a little bit longer, so I write the show, this, that and the other. I then go to see Tyler Perry’s Temptation: Confessions of a Marriage Counselor. Me and my friend Chris got drunk and decided to go see this Tyler Perry movie. We are sitting in Temptation, and in this movie Jurnee Smollett and Brandy both end up getting AIDS from the same evil Black man, because Tyler has to always do some shit like that. And then literally, in front of me, there is this woman who goes, “Um-hm, that’s what she get.” They both live, but they both just end up walking slowly with a cane, with AIDS. It was just so upsetting to me. And I just was so mad about it because I was like, “Why is he doing this when AIDS has had such a terrible impact on Black folks?”

And also it’s treated like sex is bad. It just brought up a lot of feelings just from memories of church and stuff. And that he was a Black man doing this. And also clearly doing it from a place of just ignorance. And when I say ignorance, I mean I think that probably, if he really thought about it, he would be like, “I shouldn’t be doing this.” But it was something he did for a plotline.

MW: What impact did that have on Strange Loop?

JACKSON: Because Strange Loop was already working up to something with “Precious Little Dream,” I ended up deciding to expand it into this gospel play thing that uses “AIDS Is God’s Punishment.” And originally, it was meant to be just a satirical take, because the Tyler Perry thread was already in the piece.

But then, as we got closer to the show, the friend who had inspired the song “Memory Song,” he was also a collaborator of mine. And he was supposed to be originally the orchestrator of the show. And unbeknownst to me, he was ill. And he had been ill for a decade. And he had not told anyone. And he also had not taken any medication. And then I found out he was ill in January, and he was dead by February. Suddenly, that had a big impact on me and the show. That song already existed in the show, but it suddenly took on a deeper meaning, because it was right at my door in a way that it never had been before. Because I grew up in the ’90s as antiretroviral medicines were reaching a lot of people, particularly white gay men who could afford it.

In terms of HIV/AIDS, it was something I was both afraid it would happen to me, because that was what I was raised to feel like you are going to get it, it’s going to kill you, all this stuff. But at the same time, I wasn’t really having sex. It was the duality of that. AIDS was very removed from my life while at the same time being very present. And then suddenly it was right at the door with the death of friends. It turned that one-in-two statistic into this crazy thing where my friend was one and I was two.

It just felt really important to me that in the midst of this whole satirizing of everything, that there was a real bite to it. That we don’t forget that it’s still with us. And there are people who, for a host of complex reasons that have to do with homophobia and religion and colonialism and the history of all those things, it still can kill. That was really why I ended up including it, or continuing to include it and broaden the meaning of it.

A Strange Loop -- Photo: Teresa Castracane
A Strange Loop — Photo: Teresa Castracane

MW: I think it’s good gospel and good satire. I’m glad you continue to use it.

JACKSON: And just growing up hearing that. Just in church when I was growing up, the pastor could be talking about anything, and somehow it would turn into “gays are going to hell,” and all this stuff. It was such a part of my childhood experience of being a young gay person becoming an adult, and trying to reconcile that with wanting to have a passionate gay life.

MW: Did you, like Usher, feel this conflict between who you felt you were becoming and what your family expected or wanted you to be?

JACKSON: I mean, I think it’s complex like most things. I did feel that, particularly as a younger person. As I’ve gotten older, I have a lot more appreciation for my upbringing and my family. We went through a lot of stuff together, particularly around me being gay. But I love and appreciate them so much, now more than ever. And I think they feel the same. Our relationship is different than it was when I was just coming out. I think the conflict was there when I was younger, but it’s different. Things are different now.

MW: Have you heard from Tyler Perry or his people?

JACKSON: I have heard from Tyler Perry. He called me on the phone. I had a friend of mine who was working with him on something. And when I got the Pulitzer, he heard about it because of the “historic nature of it.” He reached out to me, because he also knew that his name was in it. I had my name in his mouth. So he called me and he said that he was going to beat my ass, but he also congratulated me on the historic nature of the win. And we had a nice little chat.

He texted me after the phone call to show me that he had purchased a cast album, and that he had listened to the song “Tyler Perry Writes Real Life.” He didn’t say what he thought of it. I don’t know what he makes of it or thinks of it. We did not talk about any of that. But I appreciated that he called me. He didn’t have to do that. Every once in a while, I’ll text him. I’ll probably text him Happy New Year or Merry Christmas. That’s normally what I do. And he always responds, at least thus far.

MW: That would indicate that he’s a good sport.

JACKSON: I mean, until he sees the show. That’s the real gag. If he comes to see the show, I’ll be curious to see how much of a good sport he is. And maybe he will be. Also, he is a billionaire. So what does he care what I have to say?

MW: Right, why should he care? In this day and age, though — and I’ve been called a snob by people who know and love me — is it elitist to be making this distinction between what Tyler Perry does and “higher” forms of art and literature?

JACKSON: I guess I’m interested in this idea of elitism, because how elitist can I be of somebody who is worth a billion dollars? But also I always try to be very clear about what my criticisms of his work are. I don’t have any issue with the audience that he is courting, or the language that he uses to court that audience with. My mom is devoted to Tyler Perry, and most of the people in my family are. I don’t look down on them for that. Literally, I just have issues with the work itself. For me, it’s not about, “Oh, snooty Michael.” And I am a snob, but I’m a snob in the sense that I want things to be good. And when I look at a lot of his work, all I see is shoddy work. I see someone who does not put a lot of time in it. And he has admitted that he doesn’t put a lot of time in it. He will say, “I wrote three screenplays in a weekend,” or whatever. And as somebody who spent 16 years working on one thing, yeah, I’m going to have an opinion about that.

MW: I totally understand.

JACKSON: But it’s still his right. I wouldn’t take away his right to make shows, because the things he makes, a lot of people, particularly Black folks, regular-ass Black folks by the way, they love what he makes. And that’s important. But I also think that it’s important that this work be able to be criticized, because otherwise, it doesn’t matter. If it can’t be criticized, then it doesn’t matter. And like I said, he’s got one billion dollars. I don’t. I’m not going to say he is doing something right, because I don’t need a billion dollars. But we both got what we want.

MW: I don’t disagree with the assessment of the work, especially the shoddiness of some of the production, like wigs and makeup and things like that, that are just–

JACKSON: Or people drinking glasses of water that don’t have water in them. I mean, if you have all this money, why not just do it well? That’s the part I don’t understand. Why do you have to film a movie in five days? And the answer to that is: that’s how you become a billionaire, by cutting corners and keeping your expenses very low and not paying people very much money. That’s how you become a billionaire. That’s how you do it. That’s not unique to Black people. He learned from the best. So many white people do that. Look at America. Look at Jeff Bezos. Not paying these people money, that’s how you become a billionaire, by cutting corners and not paying people what they’re worth.

MW: In addition to the inspiration from Liz Phair, or her music, the title of the show references, was it Douglas–?

JACKSON: Hofstadter.

MW: Hofstadter. His theory of consciousness, which I was not aware of.

JACKSON: Yeah, I wasn’t either.

MW: I really appreciate it as a way of understanding the self. That the stories that we tell about ourselves become us. So which “Strange Loop” did you find first? Did one lead you to the other? And what is it about Hofstadter that struck you?

JACKSON: Liz’s “Strange Loop” led me to Hofstadter, because for many years, I had really loved the song “Strange Loop,” which is on her debut album Exile in Guyville. But I didn’t know what the title meant because it doesn’t recur in the song ever. One day after many years I was like, “You know what? Let me google this. Maybe it refers to something.” And when I googled “Strange Loop,” Douglas Hofstadter came up, because he had written a book called I Am a Strange Loop. And he had coined this phrase in his book Gödel, Escher, Bach. And then I looked up what a Strange Loop was. And it’s all about self-reference and the consciousness of the self, which was eerily, ironically what A Strange Loop was trying to be about. It just didn’t have a name for it. That was also the thing that gave it the title, because it was about this young Black gay man doing this excavation of the self and trying to figure out who he was. And that helped me put a frame around it, what he was doing, or what the show was about rather.

MW: And you’re also introducing a lot of other people to Hofstadter’s theory of consciousness, which maybe will help them understand your show better too.

JACKSON: And themselves. Because everybody has one.

MW: Here’s just a silly question: Approximately, how many times would you say you’ve seen The Lion King?

JACKSON: Oh, God. Well, I worked there for four years. I mean, hundreds. I don’t know.

MW: Is it now a show that you love, or a show that you love to not love?

JACKSON: It’s funny, if you had asked me this when I was 30 years old or something, I would have said I hated it. Now, it’s something different. Actually, I appreciate what they are trying to do. It’s not my thing, it’s not what I aspire to, but I think also because I’m older, and now that I’ve been through my own professional development, I can appreciate making a piece of art that you then share with an audience. I appreciate it on that level. But it’s both not my thing, and yet without it, I couldn’t have written my own thing, because I learned a lot just standing behind audiences every night in the dark watching them be excited about it. Because the audiences, when they do that opening number, people get excited about it. When I wrote my opening number, I wanted people to get excited about it. I learned certain things about spectacle, even though how I approach the spectacle is different in aims and goals and the content. But the form is there. They put on a big show that people want to watch. And that’s what I want to do as well.

MW: Finally, because you will be the last Metro Weekly cover of 2021: What are you going to remember about this long year? And what are your takeaways from living during this crazy period of time, doing what you are doing in it?

JACKSON: I think my takeaway is that life and time are very, very precious. For that reason, it’s important to me to really value both my and other people’s time and their lives. And art, for me, has always been the life raft that I cling to in order to make sense out of the craziness of life. I really want to just go into this next year making my work and trying to give people something that’s really worth their time, and not bullshitting around and not spending all my time being a relentless hype man or hyping things up, and just trying to sell things to people. I want it to be something that stays with you and that is meaningful. And that’s made with care and with quality.

There is this quote I’m always spouting to people, that I encountered over the last year, that Jane Wyman made at an award show. She was getting a Soap Opera Digest Award. And she goes, “When you are in the entertainment world, there is nothing that can replace quality. And the quality is within you. Never settle for anything less than the best you can do. Never settle, just do your best.” And I find that simple but profound.

This past year, with so much that’s gone on, particularly in the theater world, I’m just like, “You know what? I just want to make really great work.” And that matters to me more than anything else. That’s what I feel like I have learned this year, and that I hope to carry and build upon in the next year.

A Strange Loop runs through January 9 at Woolly Mammoth Theatre, 641 D St. NW. Tickets are $42 to $100, with discounted prices for patrons aged 30 and under. Pay-What-You-Will tickets are also available to certain performances by selecting the PWYW seats and adjusting the ticket price. Visit

Follow Michael R. Jackson on Twitter at @TheLivingMJ.

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