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Understanding the History and Mystery of Michael R. Jackson


“A Strange Loop” has a lot to say in a one-act show. The metafictional musical is playwright, lyricist and composer Michael R. Jackson’s meditation on self-perception, race, sexuality, art, faith, identity and everything in between. The off-Broadway success of this ambitious work earned Jackson the 2020 Pulitzer Prize for Drama. He breaks down the emotional journey behind “Memory Song” – the first song he ever wrote music and lyrics to and the penultimate song in “A Strange Loop.”

Joe Skinner (VO): Before he became a Pulitzer Prize-winning playwright, composer and lyricist, Michael R. Jackson was 23 years old and a recent graduate from NYU’s undergraduate dramatic writing program. He looks back on this era now as “the lost years.”

Michael R. Jackson: I had moved to this little old lady’s bungalow house in the middle of nowhere in Jamaica, Queens. It was $400 a month. It’s like the last stop on the E train. It’s the last stop on the F train. And then you have to take a bus. And I just was in this house on the top level with my little Compaq Presario laptop, and I just was like, “I don’t know what I’m going to do with my life.” Not sure how I was going to get a job or support myself. Or anything.

Joe Skinner (VO): So Jackson wrote a monologue called “Why I Can’t Get Work,” a piece he is quoted describing as, “a young Black gay man walking around New York, angst-filled and trying to understand his own alienation.”

Michael R. Jackson: So there’s this one section where he ends up talking about coming out and he says, “See I didn’t come out to myself until I was 16 years old and I felt 16 like a prison sentence…”

Joe Skinner (VO): These excerpts from his early work crackle with energy. The dialogue is raw and confessional.

Michael R. Jackson: Even if Shawan did just die from AIDS I just wanted to run like a wolf with them from bar to bar to Palmer park and back, skating on Mondays and Northland roller rink after choir rehearsal.

Joe Skinner (VO): The main character in the piece cycles through anecdotes in an internal conversation with himself.

Michael R. Jackson: So even though in that moment waiting for the 6, I think “maybe he’s just into you,” I think right after that, “he probably just wants to gay bash you.” So that’s where I’m at – a bitter custody battle: thought versus thought and thought wins. When you look at the monologue it’s almost like you’re just looking at raw materials. There are sections within it that essentially allude to what would be the creation of “Memory Song.”

Music: Five foot four, highschool gym, sneaking a cupcake. These are my memories, these are my memories. Shooting hoops off the rim, slow on the uptake. These are my memories, these are my memories. 

Joe Skinner (VO): I’m Joe Skinner, this is American Masters: Creative Spark. In each episode, we bring you the story of how one work of art came to exist, in the artist’s own words. Today’s focus: Michael R. Jackson on the making of “Memory Song.”

Joe Skinner (VO): “Memory Song” is the first song that Jackson ever wrote. It’s a song that would journey with him throughout his career – it took over a decade to write – and ultimately It would go on to become a revelatory scene in his 2020 Pulitzer prize-winning show, “A Strange Loop” – a metafictional musical about, well, a strange loop.

Michael R. Jackson: “A Strange Loop” is about a Black gay man who works as an usher at a Broadway show who is writing a musical about a Black gay man who works as an usher at a Broadway show who is writing a musical about a Black gay man who works as an usher at a Broadway show and sort of cycling through his own self-perception and self-hatred.

Joe Skinner (VO): Thoughts envelop the main character, Usher, around issues of identity, race and sexuality. And those Thoughts? They literally surround him.

Music: Blackness, queerness, fighting back to fill this cis-het, all-white space, With a portrait of a portrait of a portrait of a Black, queer face, And a choir full of Black, queer voices, treble clef (and also bass!) 

Joe Skinner (VO): In “A Strange Loop”, an ensemble cast of six all-Black and queer actors voice Usher’s inner thoughts as physical characters.A Strange Loop” is full of big musical numbers like the one you just heard, titled “Intermission Song.” But in contrast to these larger than life performances is “Memory Song” – it’s quiet and introspective. So how did this song that Jackson wrote 16 years earlier as a standalone tune, find its way into his wildly successful off-Broadway musical?

Michael R. Jackson: To talk about the history of “Memory Song,” I kind of have to give the context of how I came to write musical theater in the first place. I’m from Detroit Michigan originally. I started playing piano when I was eight years old and at that point, maybe you have taste or maybe you don’t. I grew up listening to you know whatever my parents were listening to, my earliest music was like whatever was at church and then Motown, soul, that kind of thing. I started playing piano and I don’t think I liked it very much in the very beginning. A lot of what I was doing was just like songs that I would have sung at church.

Suddenly they started letting me play for the kids choir at church. A lot of improvisations, where I’m playing “No Not One” or “What A Friend We Have in Jesus,” but like the Black way, which was influenced by the soul music and blues and all that stuff that I was growing up with.

But then Something very important happened. I’m beginning to develop my own taste. My cousin Zanita brought me back all of this white girl music. She gave me this album called “Under the Pink” by Tori Amos when I was like 15 years old. So I had a Walkman and one night I turn off the lights and I put it on and my life was changed forever.

The first words I heard go, “Tears on the sleeve of a man, don’t want to be a boy today…” And the moment I heard that it was like a door opened. Questions about queerness and about religion because then the next song is, “God sometimes you just don’t come through…” I would make my dad take me to the music store and buy her piano books. What happened was that the more I listened to her music the more I began to try to imitate it. A lot of my compositional style of improvisation that I developed listening to her piano bass music has followed me through the years.

Joe Skinner: So do you think that piano-based music would – years later – inspire your work on “Memory Song?”

Michael R. Jackson: Absolutely. So it’s actually really quite explicit. It’s a totally different sound and everything but the gesture is the same. The way Tori Amos’  song “Pretty Good Year” starts – it starts like this:

“Tear’s on the sleeve of a man, don’t want to be a boy today.” So then years later when I sat down to write “Memory Song” I wanted to write a song that made me feel the way it felt when I heard that song, and what came out was:

“Five foot four, high school gym, sneaking a cupcake, these are my memories, these are my memories. Shooting hoops off the rim, slow on the uptake, these are my memories, these are my memories.

That’s the Tori in me. I was obsessed with the way that music made me feel because it gave me chills. And so I want to make people feel the chills that I felt – but from my perspective.

Joe Skinner (VO): Almost a decade had gone by since the Tori Amos-inspired musical revelation from Michael R. Jackson’s childhood. He was now 23, living in Queens, trying to figure things out. He still had never formally written a song. But a teacher saw his potential, and recommended he apply to NYU’s MFA program in musical theater writing. He got in.

Michael R. Jackson: For this one particular class that was toward the end of our first year a teacher said if you’re a composer who’s never written lyrics, you can try it for this one assignment. And so I decided to try writing my own song even though I was not a composer in the program. I never studied composition. I just grew up playing piano and loving music.

Joe Skinner (VO): The seed for Jackon’s first song came from one sentence, drawn from a meaningful connection.

Michael R. Jackson: I was in a class, and one of my classmates, a friend of mine, was another Black gay man who wrote a song about a one night stand and feeling deep religious guilt about it and other feelings that I recognized because I grew up Black and gay around a lot of other Black gay boys.

And it just struck me. And I wrote in my notebook, “All those Black gay boys I know who chose to go on back to the Lord.” So then fast forward a couple of months and I get this assignment at the point where I’m like, “Oh I’m going to try writing my own music now to my own lyrics.” So I went to my little notebook, and I fell upon, “All these Black gay boys I knew who chose to go on back to the Lord.” And so I just was noodling around and playing around and trying to figure out how to set this lyric, which I had never had done before. And so I just sat down and I like finally figured out:

Music: These are my memories, these are my memories. Of one lone, Black, gay boy I knew, Who chose to turn his back on the Lord.

Michael R. Jackson: And I just really liked it. I thought it sounded kind of haunting and a little funny, and that became the touchstone for which the rest of the song would spring from. I then started to slowly figure out the verses that would earn that chorus.

Music: Guilt and shame, Jesus’ name, church every Sunday. These are my memories, these are my memories. Eat his body, drink his blood, communion buffet. These are my memories, sweet, sour memories. After church we’re driving home to radio crackle, jazz muzak or Motown blues, and skin is a shackle-

Michael R. Jackson: It’s about a young gay Black man remembering images from when he was a teenager in high school.

Music: Dad is drunk and on the couch, while mom eats a porkchop. Daily bread mill, daily treadmill won’t ever stop.

Michael R. Jackson: More religious imagery with the daily bread mill, daily treadmill. The idea of life is sort of in this loop, things are not changing in this sort of Black urban experience. Then this image of being crucified the way Christ would be within his identity.

Music: I am lying on the couch, I dream that I’m flying, flapping both my wings so hard, to keep me from dying, with a crown of godforsaken thorns on my head, like all those Black gay boys I knew who chose to go on back to the Lord.

Michael R. Jackson: I wrote “Memory Song” when I was 23, but the spirit of the song is recalling when I was 15 or 16, which is around the time when I was coming out, which was a very difficult and painful and weird time.

Joe Skinner (VO): Michael R. Jackson turned in an early draft of the music and lyrics of “Memory Song” for his class, and from there, his career turned a corner. Over time, the song found its way into the evolution of his monologue, “Why I Can’t Get Work.” Along with some other songs, this new piece became a one-man show – called “Fast Food Town.”

Michael R. Jackson: I performed one night only at ARS Nova in New York City. 20 people came and two of them walked out in the middle of it. And then from there I was like, I don’t want this to be a one man show, I don’t want this to be a cabaret act, I want it to be a musical, albeit a probably unconventional one, and one that is sort of more in the vein of what they used to call concept musicals in the 70s, like “Company” or “A Chorus Line.”

Joe Skinner (VO): “A Strange Loop” was born. He now had his main character – named Usher for his job as a theater usher; A position Jackson himself held for 4 years for “The Lion King” on Broadway.

Music: I am a Disney usher, I’m barely scraping by, my discontentment comes in many shapes and sizes. When I wake up each morning, I tell myself to try, I tell myself that I will make no compromises.

Michael R. Jackson: Because Usher is a character who is essentially a perception of myself, as I would change Usher would change. Our experiences were very parallel. I had to get to a place of objectivity in my own life to understand what Usher’s problem and story was, and once I got to that point I was able to capture his experience in a bottle.

Joe Skinner (VO): Usher – tirelessly performed in the show’s off-Broadway run by actor Larry Owens – journeys through decades of emotional terrain in one-act: He confronts his parents religious beliefs and homophobia; he balances a soulless commercial ghostwriting gig; he navigates a racist dating community. All of this inside his own head. Many of these elements seem to mirror aspects of Jackson’s own life. But he says “A Strange Loop” is not a work of autobiography.

Michael R. Jackson: The show is a study of the self and of Black queer selfhood in particular and of selfhood in general. And so it’s not a show that you should watch and just feel like you can just look at me and know everything. If I were to call it autobiographical I would call it emotionally autobiographical because I have felt everything that Usher has felt, but the events of that are not necessarily the same.

Joe Skinner (VO): Near the end of “A Strange Loop” – just before “Memory Song” finds its way into the show – Jackson’s main character Usher sings an impassioned and ironic song, titled “Precious Little Dream / AIDS is God’s Punishment.”

Music: AIDS is God’s punishment! Everybody in the building, clap with me on the two and the three, with my altos! AIDS is God’s punishment!

Joe Skinner (VO): This is Jackson’s direct confrontation with the fear mongering and hateful messaging around the HIV and AIDS crisis that he so often heard in his youth.

Michael R. Jackson: He’s just railing against you know the church and against homophobia and against the theater and it turns to a big old megillah of a song, just sort of bringing this idea of Black people wailing away in church and all this stuff, but meanwhile you know someone in his life has died of AIDS, which is this thing that is constantly lobbed at him, like if you keep being gay, you’re going to get AIDS and all this stuff.

Music: AIDS is God’s punishment! Please stop this music! AIDS is God’s punishment!

Joe Skinner (VO): At the end of this song, one of Usher’s Inner Thoughts stands by, dressed like his Mother, and asks him: “Is this really what real life is like?” Usher is being challenged for his ironic posturing. And this is where we arrive at maybe the most earnest moment in the show – this is where  “Memory Song” has found its way into Jackson’s musical – and his main character begins to find some clarity.

Michael R. Jackson: It’s a standalone song wherein he takes stock of everything that brought him identity-wise to where he stands today, that’s different from the character at the beginning of the show who starts off feeling like he’s worthless.

Music: These are my memories, sweet sour memories, this is my history, this is my mystery.

Michael R. Jackson: Now the image that we are left with that he repeats over and over again is, “All those Black gay boys he knew who chose to go on back to the Lord.” This idea that there’s this other group of people within his identity who made a different choice, but then at the last one of those changes it back to himself, in contrast to these other Black gay boys who chose to go on back to the Lord and one lone Black gay boy he knew who chose to turn his back on the Lord — instead. And so it’s a small but really significant shift about how the character is thinking about himself in contrast to other people in his identity.

Music: All those Black, gay boys I knew, who chose to go on, back to the Lord! And one lone, Black, gay boy I knew, who chose to turn his back- On the Lord – instead.

Joe Skinner (VO): Jackson’s subtle lyrical shift is really important to understanding “Memory Song.” Ultimately, it’s a song about accepting your own identity – against all the pressures you might face from institutions and people that surround you. He has described it as an anthem, to “all those Black gay boys he knew who chose to go on back to the Lord” and to “all those Black gay boys he knew who chose to turn their backs to the Lord instead.”

Michael R. Jackson: As I mentioned the song was initially inspired by just listening to this friend of mine tell his sort of Black gay story – that inspired me that reminded me of my own past. What happened was, the friend was supposed to be the orchestrator for the show, but unbeknownst to me he was dying from AIDS and I did not know that until far, far into the process of even getting the show ready to go up. And yet his death was this weird… It was one of the loops in just the way the show came into being because if I had never heard his song, I would have never written down, “all those Black gay boys he knew who chose to go on back to the Lord,” and I never would have probably written the show ultimately. It’s like his life and death is sort of for me personally… Very wrapped up in what the show is and um – I’m sorry – but it just – it became a really important element of it and he has you know… His life, it just is in it. And it’s tied to my life because we went into two different directions but we were the same.

Joe Skinner: Do you see “Memory Song” now as a way to honor him?

Michael R. Jackson: I mean, it wasn’t how it started, but it became that. It was this weird thing that leapt from reality into fiction, that was reality. It was a strange loop. It’s not like it’s something I planned, I didn’t reverse engineer it, it just was a sad beautiful terrifying organic thing that just happened.

Joe Skinner: What do you think is the purpose of art?

Michael R. Jackson: I think that art is for the purpose of seeing the world through other people’s eyes and for taking something that is intangible and making it tangible or visible or something you can feel. I think it’s a way of telling the truth about what is in front of us. And that can be you know light fare or that can be really dark, but it always in my view needs to be true.

Joe Skinner (VO): The journey for “Memory Song” and “A Strange Loop” continues to evolve: performances of “A Strange Loop” begin Monday, November 22nd in a 6-week engagement at Woolly Mammoth Theatre Co. in Washington, D.C. — And this limited run is being hyped as Broadway-bound.

Thank you to Michael R. Jackson for his interview, and for inviting us into his creative process. Join us for more episodes weekly, as we continue to look into how artists make their work.

American Masters: Creative Spark is a production of The WNET Group, media made possible by all of you. The show is produced by me, Joe Skinner. Our executive producer is Michael Kantor. Original music is composed by Hannis Brown. Funding for American Masters: Creative Spark was provided by the Anderson Family Charitable Fund and the Corporation for Public Broadcasting.


PBS is a 501(c)(3) not-for-profit organization.