Michael Jackson Q and A: “A Strange Loop” and A Strange Time

“Michael Jackson” is not just “the King of Pop” anymore, but also “the Pulitzer winning playwright.” After decades working in obscurity, Michael R. Jackson – or as he puts it, the living Michael Jackson – has gotten one accolade after another in the last few weeks for “A Strange Loop,” a musical that marked the Off-Broadway debut in 2019 of this talented composer, playwright, lyricist and vocal arranger. He began writing “A Strange Loop,”  as he points out in the Q and A interview with me below, shortly after 9/11, and it was not produced until the Trump era — 18 years later!

Jackson had moved from Detroit to New York to become a soap opera writer, but somehow got sidetracked into theater, getting a BFA in Playwriting and an MFA in Musical Theatre Writing from NYU Tisch School of the Arts. “A Strange Loop” is inspired by his own life, but closer to what he calls an “emotional autobiography” than an actual one. It focuses on a character named Usher, a heavyset, queer, black man who works as an usher for “The Lion King,” while struggling to create a musical about a heavyset, queer, black man who is struggling to write a musical about….. This dizzying set-up features six performers who portray Usher’s Inner Thoughts, as well as all the characters in his life, including parents who don’t get him. When I saw it at Playwrights Horizons, I found the musical rich with 18 tuneful songs, skit-like episodes,  witticisms, mini-parodies (most notably of a Tyler Perry play), complex layers of erudition, and knowing allusions, much of it to musical theater.

On May 4th, ten months after the end of its Off-Broadway run, Jackson won the Pulitzer Prize in Drama for the musical,  the first time the prize for drama had been given to a black writer for a musical, and the first time in Pulitzer history that a musical had won without having been on Broadway.  Indeed, producers planned to take it to Broadway, stopping first at Woolly Mammoth Theater this September. Thanks to the pandemic, the D.C. theater has rescheduled for the summer of 2021, with Broadway plans uncertain.

“I don’t know when you’ll be able to see it, as COVID-19 has everybody guessing when we’ll be able to be together,” he told me.

Meanwhile, during the shut down,  Jackson has also been given the New York Drama Critics Circle Award, the Off Broadway Alliance Award , The Dramatist Guild’s Hull-Warriner Award – and most recently, at the beginning of LGBTQ Pride Month,  the Lambda Literary Award for LGBTQ Drama.

He is working on a new musical called “White Girl In Danger” with the Vineyard Theatre, which he has described as “a dark musical comedy about Keesha Gibbs, an African-American teen who lives in the ‘blackground’ of an all white world of a 90s era melodrama and seeks to prove she’s just as much of a protagonist/heroine as Meagan, Maegan, and Megan, the white girls who battle issues such as drugs, alcohol, abusive boyfriends, eating disorders, and finally a serial killer who has been murdering the town’s white girls one by one.”

Jackson also has been busy giving acceptance speeches, participating in panel discussions, and agreeing to interviews, including with me. It seemed like a good time for a Q and A (very slightly edited.)

These feel like surreal times — pandemic, Depression, high-profile race-based killings, worldwide demonstrations, Trump teargassing peaceful protesters to hold a Bible aloft as a prop….. How are you processing it all?

I am processing it all by focusing on my self-preservation and adhering to social distancing and wearing a mask when out of doors in light of COVID-19.

 How do you feel “A Strange Loop” speaks to these times in specific ways?

“A Strange Loop” was begun in the first Bush term not that long after September 11th 2001 and continued to develop over the next Bush term and two Obama terms until it was produced in the Trump era. It’s about what it means to be a self in general and what it means to be a black queer self in particular so its message of self-love and self-acceptance and yet also self-disavowal both speaks to these times specifically and not at all.

When you talk about “these times,” do you mean the Trump era, or do you mean the days since the death of George Floyd?  And can you elaborate on how it speaks to these times specifically?

When I say “these days” I just mean the present. The musical speaks to these days specifically because the character is about someone who is at war with who he is which is shaped by his experiences as a black, queer man/artist. His Thoughts threaten to overwhelm him with feelings of doubt and self-loathing. He comes out of the other side of that realizing that nothing is actually wrong with him. From my perspective, that is a message for our time.

I suppose we need to clarify here: The musical is obviously inspired by your own life. How much do you as the creator intend us to see Usher as an Everyman reflective of the era?

I intend for you to meet Usher wherever you are and to think about your self and your perception of yourself and a black, queer man perceiving himself. He’s both an Everyman and he is himself.

At the risk of sounding like the parents in the show, I am curious as to why you think it took you 18 years to finish “A Strange Loop”

Because I needed to figure out nothing was wrong with me in order to know what the show was actually about. The world is constantly feeding us negative ideas about ourselves and it just took me a while to figure that out.

In a recent interview, you said “we need to have a national conversation about taste and discernment.” What do you mean by this?

I meant that there’s a lot of shitty partisan art out there that is more interested in its appearance of speaking to social justice than doing what art actually does well, which is entertain and provoke thought, emotion and/or empathy, particularly in the theater but not only in the theater. Art is about being particular and having a point of view that you are trying to communicate. Your taste and discernment are key at communicating a point of view. I feel that being lost and I would like to fight to preserve and deepen it.

 Do you feel there is a specific racism connected to the theater world that’s distinct from the world at large? Same question vis a vis homophobia?

Theater sits within capitalism. Capitalism is racist therefore theater is not immune to racism. Homophobia exists within capitalism too therefore theater is not immune however many of the gatekeepers of theater are gay and white and therefore not exempt from being racist in part because they are helping guiding the hands of a capitalist system that is racist. So pick your poison.

If somebody came to you in all sincerity asking for a starter list of ten works of theater to understand where you’re coming from, what would you include?

The Adding Machine by Josh Schmidt

Waiting For Lefty by Clifford Odets

The Bubbly Black Girl Sheds Her Chameleon Skin by Kirsten Childs

Passing Strange by Stew

Bootycandy by Robert O’Hara

In Trousers by William Finn

Hair by Gerome Ragni, James Rado and Galt MacDermott

Blue Window by Craig Lucas

Jackie O by Wayne Koestenbaum and Michael Daugherty

Raisin by Charlotte Zaltzberg, Judd Woldin, Robert Brittan and Robert Nemiroff

It must feel odd to have worked in relative obscurity for almost two decades — and to have felt eclipsed most of your life because of your name — and then, in your moment in the sun, for the world itself to be cast in shadow. What’s the most ironic, the most gratifying, and/or the most amusing thing that has come out of the experience over the last few weeks?

I have not felt eclipsed my whole life. I have a theatrical community that has supported and encouraged me almost the entire time my career has been on its winding path. In some ways the Pulitzer was the most natural evolution of that. The most iconic thing to come out of it was probably having Tyler Perry call me and say that he was going to beat my ass and to congratulate me on the Pulitzer.

Author: New York Theater

Jonathan Mandell is a 3rd generation NYC journalist, who sees shows, reads plays, writes reviews and sometimes talks with people.

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