Music Credits: “Memory Song” performed by Larry Owens, “Periodically,” performed by John-Andrew Morrison; “Intermission Song,” performed by Larry Owens and cast...all songs written by Michael R. Jackson, from the play A Strange Loop. Used courtesy of Michael R. Jackson. 

“NY” composed and performed by Kosta T from the cd Soul Sand, used courtesy of the Free Music Archive.

Michael R. Jackson: It just felt very exciting to see this story and like emotional, both for me having gone through the whole arc of things in order to write it, but also just actually seeing the story of like a black, fat, gay man go from like hating himself to loving himself or like accepting himself, at least I wrote this show also because I never had seen it.

Jo Reed: That was Michael R. Jackson talking about his play “A Strange Loop” and this is Art Works, the weekly podcast produced by the National Endowment for the Arts. I’m Josephine Reed. June is both pride month and black music appreciation month—and so it seemed like the perfect time to revisit last year’s interview with playwright, composer, and lyricist Michael R. Jackson whose musical “A Strange Loop” won the 2020 Pulitzer Prize for drama. Michael is the first African American to win a Pulitzer for a musical and the first playwright to win for a musical that hasn’t appeared on Broadway. The Pulitzer is one of the many prizes won by Michael R. Jackson since “A Strange Loop” first hit the stage. Begun as a monologue in 2001, “A Strange Loop” had its world premiere in 2019 at Playwrights Horizons, a production funded in part by the National Endowment for the Arts and, it has played to sold-out audiences. The reviewers praised it for its bouncy Broadway beat, its witty lyrics, and its provocative subject. “A Strange Loop” is a rarity. It’s a play as challenging as it is entertaining and at its center is a black, fat, queer artist trying to create a musical while coping with the often punishing thoughts circling inside his own head.  The Pulitzer jury proclaimed in rather lofty language, “A metaphysical musical that tracks the creative process of an artist, transforming issues of identity, race, and sexuality.” However you want to dice it linguistically, “A Strange Loop” is boisterous, joyous, disturbing, heartbreaking, and innovative.  And the music is fabulous—so sit back and enjoy my conversation with Michael R. Jackson.

Jo Reed: You know, Michael, honestly, if you were going to write a memoir starting now, I would suggest a title being “Awards in the Time of COVID.” You got another one since I asked you if you would be available for an interview. You got the Lambda Literary Award for Drama. Congratulations.

Michael R. Jackson: Thank you very much.

Jo Reed: So, the New York Drama Critics Circle Award and the Pulitzer for Drama, talk about “A Strange Loop.” How are you processing all of this?

Michael R. Jackson: I mean, it’s certainly like bizarre, but it’s also been like a huge pick-me-up during this sort of tumultuous, crazy time in the world. So, I’m grateful for it.

Jo Reed: Can you give me a quick rundown of the show “A Strange Loop?”

Michael R. Jackson: Sure. “A Strange Loop” is about a black queer musical theater writer who works as an usher at a Broadway show who is writing a musical about a black queer musical theater writer who works as an usher at a Broadway show who’s writing a musical about a black queer musical theater writer who works as an usher at a Broadway show and sort of cycling through his own self-hatred.

Jo Reed: And where did you come up with this concept of this Russian doll plot?

Michael R. Jackson: Yeah. It came sort of accidentally/organically because I had written this sort of thinly veiled personal monologue when I was in my last semester, I think, of college at NYU studying playwrighting. At that time, it was a monologue called “Why I Can’t Get Work” because I was like worried about graduating with a playwrighting degree and not knowing what I was going to do. So, just started writing this thinly veiled personal monologue about a black gay man who is just wandering around New York wondering why life is so terrible and from there, I went to NYU for grad school to study musical theater writing specifically and I went in as a lyricist, but then toward the end of the first year, I learned how to write lyrics and a teacher gave us an assignment saying that if you’re a lyricist who’s never written music or a composer who’s never written lyrics, go for it. So, I ended up taking my musical abilities, which I’ve had since I was a child and I wrote a song called “Memory Song,” which at the time was just a standalone song, but it ended up being sort of the penultimate song in “A Strange Loop.” <musical selection plays> I was encouraged to continue writing my own music and just over time, I just began writing more music and the songs I was writing seemed to speak fanatically to the monologue and so, I started trying to put them into there and then just long story short, it just evolved very organically over time into a musical called “A Strange Loop.”

Jo Reed: I’d like to hear your origin story. So, you were musical when you were a kid. Did you study an instrument? Did you sing? How did it manifest itself?

Michael R. Jackson: So, yeah. I started taking piano lessons when I was about eight years old and I did that all the way through my senior year of high school. I sang in choir at church. I played piano at church for a couple choirs. I sang in an all-city sort of classical chorus when I was from middle school through high school. So, I was always very musically inclined and I learned how to play the piano by ear first and then I took a couple of years of classical piano, but like my real chops came from playing at church and just sort of improvising, which is where a lot of my later composition skills sort of developed out of that.

Jo Reed: Interesting. Were you interested in musicals when you were a kid?

Michael R. Jackson: My parents were like those kind of parents that were like “We have to keep him involved in something positive so he doesn’t get involved in a gang or drugs,” and so...

Jo Reed: Oh, so, they must have known my mother.

Michael R. Jackson: Right. So, I was always in like a dance class or like choir or something or Little League or whatever. So, what I gravitated toward when I was much younger was theater. So, I did child acting for a brief period, like where I was doing like little children’s musicals and I had like an agent for a while. I was in like a commercial like locally, things like that, and then I sort of decided when I was 13 that I was like too ugly to be a movie star. So, I left the business.

Jo Reed: Oh, God. I’m sorry.

Michael R. Jackson: Angsty teenager, what can you do?

Jo Reed: Yeah. God. I think honestly, 13 is the worst age ever.

Michael R. Jackson: It is. It’s horrible. I would not trade it for anything in the world.

Jo Reed: No, I wouldn’t either. Uh-uh. I wouldn’t go back there for anything.

Michael R. Jackson: Right.

Jo Reed: Anyway, so, you transitioned out of performing and began writing?

Michael R. Jackson: Yeah. Although, to be honest with you, I kind of was writing at the same time too. It’s just that like I sort of started keeping a journal. Like, I was always keeping a journal because I always felt like I couldn’t express myself very well and writing was like the only place where I felt like I could fully just say whatever I wanted and no one would judge me or make fun of me. So, I was always journaling and that sort of naturally transitioned into like poetry and into short stories because I was also one of those kid writers who like I intimidated whatever it was I was reading at the time.

Jo Reed: Oh, yeah.

Michael R. Jackson: So, I started off as like a ten-year old reading like Jackie Collins novels that my cousin gave me and so, a lot of the early short stories I wrote were me trying to write like Jackie Collins novels, which is really hilarious to think of like a ten-year old doing that and so, then I just graduated from Jackie Collins to Stephen King and then like Dean Koontz and so, then my short stories started turning into me imitating like horror and science fiction and then I like went to high school and I took creative writing and over time, I just developed and changed.

Jo Reed: So, did you have an a-ha moment when it came to musical theater, like “Okay, this is it.”

Michael R. Jackson: Oh, I think I also forgot to mention that like as a kid, my mother used to take me to see a lot of musicals. That was like our thing that we would do together. So, I remember going to see-- she let me skip school one Friday and then she and my grandmother and I went to Toronto to see the national tour of “Show Boat” that was running in 1994, the Hal Prince one and we saw that and we saw “Phantom of the Opera” in the same weekend and I remember seeing “Show Boat” and like just being utterly transported by it because there was like a black character in it who was like suffering and it seemed like I felt empathy for her and the show was just like about history and stuff and I didn’t have like a deep reading of the show that I would have later, but at the time, the music and the scope and the size of it just like totally impressed me and then we went and saw “Phantom of the Opera” and I was like “I don’t understand this show at all.” Like, I liked the music of it and so, I made my mom buy me the cast album to it and I enjoyed listening to it, but like the story of “Show Boat” I just found to be utterly captivating and so, it really set me on a path of loving what musicals could do and then like not that far after that, my family went to go see the musical adaptation of “A Raisin in the Sun” called “Raisin.”

Jo Reed: Oh, yeah.

Michael R. Jackson: Yes, which to this day, is in my top five of musicals. It’s such a beautiful show and I hate that not as many people know it, but like the songwriting craft is like top drawer and like the singing is just interesting. I bring that up just to say that like the early musicals that I was exposed to were musicals that were dealing with some sort of social issue or things that weren’t just like escapist. So, I grew very much up thinking that musicals could have-- they could really be about something.

Jo Reed: They could have teeth.

Michael R. Jackson: They could have teeth.

Jo Reed: You’re a triple threat.

Michael R. Jackson: I hope I’m not threatening anyone. Womp-womp.

Jo Reed: You write lyrics, book, and music.

Michael R. Jackson: That’s right.

Jo Reed: Well, if you don’t mind, I’d like to talk about a couple of the songs that you wrote, specifically, the opening song, “Intermission Song,” which is a fabulous opening.

Michael R. Jackson: Thank you.

Jo Reed: And I’d just like you to tell me the backstory of that and how you came to it and how it came together.

Michael R. Jackson: So, the show is about a musical theater writer who works as an usher at a Broadway show. His name is Usher and I also just have to say just always as a caveat about people’s understanding of the show, I drew from personal experience to write this show, but I do not think of it as autobiographical. I call it self-referential and I make that distinction just because it’s easy to see the show and just think there’s this one to one ratio of events that happened in my life and what happens to Usher. There’s certainly a relationship, but like the show is about writing about the self, but that’s different from just like my life. That said, I was an usher at a Broadway show. I ushered for “The Lion King” for four years and for “Mary Poppins” and “Intermission Song” came about because I was ushering at the mezzanine at the New Amsterdam Theater and we had just opened the doors of the theater so people could come in and start taking their seats and this old white lady was at the bottom of the mezzanine and she needed something and she yells up to one of the ushers with like her hand up like she’s hailing a cab. She goes “Usher, Usher...” and like I just clocked that because I was like she’s like calling for one of us like she’s getting a cab and I just kept that in my mind and that became the main motif of this song that I didn’t know what it was going to be. I just had “Usher, Usher...” and from there, I think I just started writing a song that was called “Intermission Song” about Usher was in the back of the theater and all the sort of heightened patrons were coming up to him and asking all these questions, judging him and being disrespectful or whatever. That version of the song existed for years, years and years and years and years, and then what ended up happening was that once we found it was going to production at Playwrights Horizons in association with Page 73, I just kept thinking “What is this show about?” This show is about what he’s thinking and his thoughts. I had an epiphany that that had to be the actual frame of the show, not this thing about the usher working in the inner workings of the theater or anything like that. Like, that was just an environment where he worked. But really, the show was in his mind, not in the theater. So, I then did a full-scale rewrite where the only thing that was left was “How many minutes until the end of intermission...” <musical selection plays> It was like him trying to figure out “How do I write this show?” and that sort of shifted the song, which musically did not change except for I wrote a dance break at the request of Raja, the choreographer. But the music all stayed the same, but I did a full-scale lyric rewrite.

Jo Reed: It is a fabulous introduction to the play. It just sets the table beautifully and it draws you in. You’re there.

Michael R. Jackson: The line used to be-- it used to be like a little girl character going “I still can’t find my American Girl Place doll,” and that changed in to “Big, black, and queer ass American Broadway show,” and that like that was what we were making. We were making a big, black, and queer ass American Broadway show.”

Jo Reed: And you said when somebody-- I think it was the director or somebody who had done an earlier reading of the play, Michael, when they suggested casting it exclusively with queer black people, you said something-- something just completely snapped for you. You saw it differently. You could see it clearer.

Michael R. Jackson: Yeah. So, what had happened was I had written a monologue for this black, gay, male protagonist sort of character. That then shifted-- I forgot to mention that once I started putting the music into it, that shifted into a one-man show that I performed one night only in 2006 at Ars Nova in New York and then that shifted into something called “A Strange Loop.” The other principal characters didn’t have like a formal identity at that time as a group and so, they just were just all these different characters and the actors would play multiple characters, like double and triple and quadruple cast and at that time, it was like there were white people in it. There were cis women, just anybody who was just a good actor was in it and I did two readings of that with two different directors and then both those directors got busy and couldn’t work on it anymore. So, I called Stephen up and said “Hey, I want to finally do a reading of this musical with the music,” because up until that point, I had only done the book. So, Stephen, who had directed two concerts of mine-- so, he was very familiar with my music and he thought “Oh, what if we cast this with all black queer people?” and like that just opened up things that were just already naturally in it. So, I just started writing more toward that conceptually, which forced me to have to think about what the identity of the other principal characters were. By the time I got to our reading that we did in 2015, the characters were identified as Usher’s thoughts. There was like Usher’s six black queer thoughts, like those bodies-- that’s what they were. So, I casted very specifically for that.

Jo Reed: The music is vibrant and the lyrics are often quite funny, but it’s also a very serious work that’s deeply personal about a queer black man operating in a straight white world.

Michael R. Jackson: But I think also, it’s not only a straight white world. It’s also a world of his black parents, his conservative black parents. It’s also a world of white supremacist gay world. It’s also a world of the theater as gatekeeper for the culture. This body is traveling through so many different universes. This is also a Tyler Perry black ancestor world. He’s traveling through all of those sort of trying to find himself.

Jo Reed: Yeah. It’s not essentializing.

Michael R. Jackson: Right.

Jo Reed: At all, actually. It’s very, very specific and speaking of specificity, another song in the play is “Periodically,” <musical selection playing>, which completely floored me when that songs makes its turn, which I really did not see coming.

Michael R. Jackson: Yeah. So, “Periodically” is actually one of the earliest songs in the musical. After “Memory Song,” it’s probably like the second song I wrote for the show. I did the one-man show version at Ars Nova, but then after that, Ars Nova invited me back just to do a concert of my music and so, for that concert, I had been like messing around with the idea of this mother character, who just was always calling and leaving voicemails and so, throughout the concert, I would have John-Andrew Morrison, who eventually ended up playing the character of The Mother and winning a Lucille Lortel Award for it, throughout the concert of just random songs I was doing, I would intersperse it with him doing these voicemail and then finally, those voicemails culminated in this like grand poobah of a voicemail song, where Usher’s mother is calling him on his birthday to wish him a happy birthday and then that devolving in this complicated homophobic but also like deeply loving phone call, <musical selection playing>. Part of what I wanted to show in that is that like that’s what it can feel like is that it can be both-- your parents can be like homophobic, but they also can love you so much at the same time and those two things are not just like disentangled from each other and those two things crashing together can make you feel all kinds of things if you’re on the other side of it and I wanted to see if I could create that experience for the audience of that like dissonance of those two things.

Jo Reed: I thought you succeeded incredibly because her love was so clear and that’s why that turn was so shocking but at the same time, that love was still there.

Michael R. Jackson: Right.

Jo Reed: Can you remember the first time you saw the whole play mounted at Playwrights Horizons?

Michael R. Jackson: Yeah. I mean and like, we had been working really hard. I did rewrites all throughout previews. I still was tinkering. We got to do that first preview and we could just tell that it was going to-- that it was like resonating with people and so, it just felt very exciting to see this story and like emotional to like watch both for me having gone through the whole arc of things in order to write it, but also just actually seeing the story of a black, fat, gay man go from like hating himself to loving himself or like accepting himself, at least. That arc for me was like extremely moving with this ensemble of other black queer bodies on stage. I find that very moving to watch. I wrote this show also because I never had seen it. I had seen shows that had black characters in them and then I’d see shows that had gay characters in them who were white, for the most part, and like never shall the twain meet. Then like the movie “Moonlight” comes out and that’s like black and gay characters as well, but it’s like black and gay characters who are, to my understanding, are portrayed by like straight men who have these like incredible bodies by cultural standards, like that’s what gayness is and I wanted to show something that was “No, what if you have to both empathize with a really smart and flawed and vulnerable fat, black gay man who’s going through something? What if that’s your protagonist?” I had never seen that and I wanted to see that.

Jo Reed: Did you think about audiences at all when you were writing this?

Michael R. Jackson: Well, I did in the sense that I just assumed that it would never be produced because I was ushering at “The Lion King” and I saw Broadway up close. I saw the audiences. I was flyering for “Rock of Ages.” I saw the audiences when I was trying to get people to buy tickets to “Rock of Ages” and I was just like “Oh, well, I don’t do this. So, no one will ever see ‘A Strange Loop,’ but I’ll just keep working on it,” and once in a while, I’d get a little opportunity to go to a residency or something and work on it. So, that’s why when Playwrights said that they were going to do it, it was like “Oh my God, really? You all are really going to do this?” and so, it was like “Yeah, we’re really going to do it.” Then it was like “Oh, if they’re really going to do it, this is my only shot. So, I better make it really good,” and so, that-- for me, it was about me and Stephen and Raja and the cast and creative team and the crew and Playwrights Horizon and Page 73 and my commercial producer, Barbara Whitman, who was all about us doubling down on what the show was, on like what made it unique and special and just assuming that because it was so specific, that maybe it might have a universal resonance, which I found to my great pleasure that it seemed to. It did. Like, so many people would come up to me after the shows during their run and say either “Hey, I’m a fat, black gay man and this is the first time I’ve really felt seen anywhere or on stage,” and then I’d have like old white ladies from the Upper West Side be like “I’m not a fat, black gay man, but this was so moving to me and I empathize and I get it.” Different people from different walks of life and that for me made me feel really good because I think that that’s what theater should do anyway. Theater should invite everyone to empathize and to like have a shared experience and to meet the protagonists of these stories where they are and decide for themselves how they feel.

Jo Reed: Don’t you find it extraordinary, the great paradox of art is the more specific you are with your story, the more universal it actually is?

Michael R. Jackson: Yeah. I think that that’s like also the beauty of it. At the end of the day, we’re all humans. I think about like a moment where we’re in now where there’s like more division than ever. What I love about theater is that yes, you can like actually empathize with other people who are not you. That is what empathy is. It doesn’t have to be like “That’s my experience and that’s the only thing I understand.” It’s what it means to be alive. We are all alive people. We all like want to be together. We’re social. If you prick me, do I not bleed? All those things and so, I think that’s why I love theater. It can do that.

Jo Reed: Yeah. No, I agree. Art demands empathy.

Michael R. Jackson: Right.

Jo Reed: I also think it has the ability to take you out of your own life and into another life, but then when you come back to your own life, you’re enriched by that.

Michael R. Jackson: Yeah and also, that’s happening for the person next to you as well while you’re sitting there with them and you both are experiencing this exchange of energy at the same time that’s going to the actors on stage and that’s feeding them and then they can then give it back to you and then you can like give it to each other.

Jo Reed: Another strange loop.

Michael R. Jackson: Exactly and that’s a real thing. I said that during rehearsals, that like I want the show, the experience to be a strange loop of exchange of perceptions because “A Strange Loop” is literally about perceptions of self and both white audience members might go into the show with their arms folded being like “Who’s that black gay on the stage? What has he got to say?” and then they find out “Oh, he actually has something to say,” that resonates with them as human beings and then they have to divest themselves of this idea of a hierarchy or superiority. Theater is a shared experience.

Jo Reed: I was going to ask you what you missed the most about live theater, but I think you might have just answered that.

Michael R. Jackson: I mean, that’s what I miss. It’s like a charging station. It’s like a well. You go to the well and you can drink from the water and sort of quench your thirst and keep going forward. It can empower people to be stronger in like hard times. I wish we could go to the theater so much right now and actually tell stories that are taking risks and are entertaining, for sure, because that was another important thing. My mission statement is to make works that are as challenging as they are entertaining.

Jo Reed: Well, I know this is uncertain time for the performing arts, but tell us what’s next for the play?

Michael R. Jackson: So, we’re scheduled to have our DC premiere.

Jo Reed: At Woolly Mammoth and shout out to Woolly Mammoth, a theater I love.

Michael R. Jackson: Yes, Woolly Mammoth and Maria Goyanes, the Artistic Director, who was my first director of “A Strange Loop.”

Jo Reed: Oh, my gosh.

Michael R. Jackson: Yeah. When she was at the Public, she was who I was working with initially until she got like really...

Jo Reed: Oh, that’s wonderful.

Michael R. Jackson: So, it feels actually really great to come-- strange loop-- so many strange loops in the show and in my life, to be able to come back-- come to the Woolly Mammoth in DC with her as one of the producers or as the producer.

Jo Reed: Well, Michael, I look forward to seeing you and “A Strange Loop” down here in Washington DC when you come.

Michael R. Jackson: Me too. I can’t wait to meet you and see you in person, see everyone in person.

Jo Reed: That’s playwright, lyricist, composer, and Pulitzer Prize winner Michael R. Jackson. And  “A Strange Loop” is slated for Woolly Mammoth’s 2021 season. To keep up with Michael or to find out when “A Strange Loop” will go into production in Washington DC, go to his website, thelivingmichaeljackson.com or woollymammoth.net. You’ve been listening to Art Works, produced at the National Endowment for the Arts. I’m Josephine Reed. Stay safe and thanks for listening.