Wide Angle

From Monologue to Pulitzer-Winning Musical

The evolution of Michael R. Jackson’s A Strange Loop.

A smiling young black man wearing a bright pink shirt.
Michael R. Jackson Joey Stocks

On this week’s episode of Working, Isaac Butler spoke with playwright Michael R. Jackson, whose musical A Strange Loop won the 2020 Pulitzer Prize for drama. This partial transcript of their conversation has been edited and condensed for clarity.

Isaac Butler: For people who are unfamiliar with it, what is A Strange Loop?

Michael R. Jackson: A Strange Loop is a self-referential, as opposed to autobiographical, musical about a young Black, gay musical-theater writer who works as an usher at a Broadway show, who’s writing a musical about a young Black, gay musical-theater writer who works as an usher in a Broadway show, who’s writing a musical about a young Black, gay musical-theater writer who works as an usher at a Broadway show, ad infinitum, and sorting through his own perceptions of himself and his own self-hatred.

You mentioned that the musical is self-referential rather than autobiographical, which is really fascinating. What do you see as the difference between those two things? Because obviously the temptation as a listener or viewer of the show is to treat it as autobiography.

And some people do, even after I tell them that! I think of autobiography as being a linear, one-to-one ratio of life events to fictional events. I drew from my own personal experiences, but I definitely fictionalized quite a lot of A Strange Loop—everything isn’t a dramatization of something that happened in my life. There are some things that happened, but there are other things that I made up. If anything, it’s emotionally autobiographical. I have felt everything that the protagonist, Usher, has felt, but it’s not a documentary.

Let’s talk about the original version of A Strange Loop.

At the very beginning, it was only a monologue. I had no thoughts of it being a musical, I had not written any music. It was just a straight-up monologue that I wrote during my last year as a playwriting student at NYU. I was 20, 21 years old and about to graduate with a playwriting degree. I didn’t know what I was going to do with my life, so I wrote this thinly veiled, personal monologue called “Why I Can’t Get Work.” That was about this young Black, gay man walking around New York, wondering why life was so terrible. And it just was that. And then in grad school, I went in as a book writer who was learning how to write lyrics, because I had never written lyrics before. I was a very musical person. Having grown up in Detroit, I took piano lessons from age 8. I was in an all-city classical choir. I played piano for church. And I had lots of musical ideas, but I didn’t know how to write lyrics.

So once I went to grad school and learned how to write lyrics, I had an idea of what song form was. So taking what I learned about song form, I decided to take my musical impulses and try to write my own song. And the song that came out of that was “Memory Song,” which is the penultimate song on A Strange Loop.

At that time, it was a stand-alone personal song. A lot of the lyrics were different, but it was liked well enough by my classmates and my teachers that I was encouraged to continue writing my own music, even though for my thesis project, I was going to be paired with the composer Rachel Peters, and we were working on our musical, Only Children. I kept writing music on the side, just for myself. And then I ended up working with this director who had read the monologue, heard some of the songs, and they seemed to thematically overlap with what the monologue was, so we started trying to figure out how to put them together. That turned into a one-man show called Fast Food Town, which is another version of the monologue, but with music in it.

I performed it one night at Ars Nova, in 2006 or 2007. Twenty people came, two people walked out, and I came from that experience having learned something about the piece, but knowing that I didn’t want it to be a one-man show, I didn’t want it to be a cabaret act. I wanted it to be a proper musical, albeit a probably unconventional one. That’s when me and the director ended up partnering with the Playwright’s Realm to crack what the book of it was. That’s when it turned into A Strange Loop, though it was still very different from what people would come to see later on at Playwrights Horizons.

But I assume there’s a lot that you need to learn to be able to take this and make it your first show that you’re writing the book and the lyrics and the music for.

I had to learn what the story was. I’m a very story-driven writer, and it was drawn from my personal experience, but it needed to have a beginning, middle, and end, and there was no beginning, middle, and end to my life. It was almost like the piece was a mirror to me, and whenever I moved, it would move. I was living my life and trying to go, “What’s my struggle, and therefore what’s Usher’s struggle?”

It wasn’t until I started going to therapy that I realized the problem was, “Oh, you think something’s wrong with you. And there is nothing wrong with you.” Once I captured that that was Usher’s problem, something’s wrong with him, he’s got to fix it. And once it was married to this strange loop structure, I knew what I was chasing.

It’s almost that once you moved a bit beyond where Usher is in his life, you had exactly enough distance to shape it.

I had perspective that I hadn’t before. Then I was able to start fictionalizing things. I knew how to move story points around, how to shape the characters.

To listen to the full interview with Michael R. Jackson, subscribe to Working on Apple Podcasts or Spotify, or listen below.