Michael R. Jackson On Groundbreaking Musical ‘A Strange Loop’ & More

Image via Beowulf Sheehan

When it comes to hard work, patience, and dedication, no one understands better than Michael R. Jackson.

Hailing from Detroit, Michigan, the creator of A Strange Loop never sought out to create a revolutionary piece of theater. What initially started out as a monologue almost 20 years ago organically turned into a critically acclaimed Pulitzer Prize and Tony Award-winning musical.


Thought-provoking and hilarious, the production tells the narrative of a gay Black Broadway usher writing a musical about a gay Black Broadway usher. How apropos since Jackson was inspired by his time working as an usher at The Lion King. A Strange Loop is a brutally honest self-reflection that deals with identity, self-perception, and exposes the heart and soul of a young artist grappling with desires and instincts he both loves and loathes

Starring Jaquel Spivey, L Morgan Lee, James Jackson Jr., John-Michael Lyles, John-Andrew Morrison, Jason Veasey, and Antwayn Hopper, the show is currently playing at the Lyceum Theatre. Its final performance is scheduled for Jan. 15, and the CD version of the cast album from Ghostlight Records will be available Nov. 4.

Jackson took some time to talk more about A Strange Loop’s origins and evolution with Instinct, as well as what needs to happen to ensure new voices are highlighted in theater and details about his new piece White Girl in Danger, coming in early 2023.

Thank you for taking some time to chat with me, Michael! If you could describe your award-winning masterpiece A Strange Loop in three words, what would they be?


Big, Black, and Queer.

Image via Marc J. Franklin

Is it true that you spent 18 years working on this production?

Yes, on and off.


What kept you motivated to keep going and not stop?

Because I initially started it from a place where it was sort of a personal testimony. Then as I started to work on it more and add music to it, it began to take on a life of its own and it became a way for me to kind of figure out some things that were going on in my life. That led me to figuring out some things in art. So, it was almost like a mystery that I needed to solve.

For those who don’t know, how did your journey with A Strange Loop begin?

I studied playwriting at NYU, and after I graduated in 2003, I moved to the middle of nowhere to Jamaica, Queens, and I had no idea what I was going to do with my life. The world was kind of in a crazy place then because we were about to go to war with Iraq, and I was feeling very alone and scared. So, I started writing this monologue called Why I Can’t Get Work, and that monologue just a stream of consciousness from a young Black gay man walking around New York wondering why life is so terrible.


It was just that for a while, and then I went to grad school a few months later. I went to the NYU program for graduate musical theater writing, and I began writing music at the end of my first year. One of the first songs that I wrote was called “Memory Song,” and it went over very well in my class. I was then told I should continue writing music even though I was going to be paired with a composer for my thesis project. I just kept writing music on my own, and all the songs had a personal feel to them.

Image via Zack DeZon

Then I started working with a director to put some of those songs into the monologue. As I did that, it started to take on a life of its own and morph. That’s why I kept at it over the years. I did a bunch of workshops, readings, and things of that nature, and then years later, we got our first production at Playwrights Horizons with Page 73, then we went to Woolly Mammoth in D.C. to do it out of town. Finally, we went to Broadway earlier this year.  

And the show was described as groundbreaking. Were you at all surprised at how well it was immediately received?


We had a lot of acclaim since we ran Off-Broadway, so I wasn’t totally surprised, but you just never know because Broadway is such a different space. We never really stopped working on the show, so I think people saw that we weren’t just resting on our laurels. We knew there were still things to fine tune.

Did I expect it to receive so many Tony nominations? Not really, but it was very heartening because for me, the big thing that I keep telling everybody is about quality, hard work, and keep doing it. I feel like all the validation that we’ve gotten in terms of awards and so forth ultimately came because we kept working.

I cannot imagine what you were feeling when your name was announced at the Tony Awards.

It was such a magical and incredible moment. Both my parents were there, my best friend was there, another close friend was there, it was beautiful. Again, validation from all the years of hard work we put into it. It’s not something I ever sought, but it sort of put wind in my sails for things I would like to do next.


Ultimately, what do you hope audiences take away from A Strange Loop?

Image via Marc J. Franklin

I always hope that audiences walk away thinking about themselves because that’s sort of what the piece is exploring. Albeit through this very specific character, but I want people to see themselves through him.

You like to make art that is challenging as it is entertaining.


That’s exactly right.

Did you have any part in the casting process?

Yes, most of the cast has been helping develop the piece for the last six years. Some longer, but I handpicked everybody who was in it.

What made each actor the perfect fit for their character? What was that certain quality you were looking for?


Because of where the piece began, it wasn’t totally clear. It was a real process of collaboration with Stephen Brackett and the actors to sort of figure out what the tracks were because the thoughts were kind of an idea that took a while to land on. There are these voices instead of these breakout characters, but I hadn’t identified them as a group. It was a real process as we did each of our workshops carving things out.

Image via Joey Stocks

We have been seeing a lot of new voices and more queer and Black representation on stage nowadays. What needs to happen to ensure this keeps moving forward?

It just needs to keep moving forward, and people need to sort of open their eyes to the work that’s out there. Support it and help it actually get to a place where it can flourish. For me, that’s the thing that sometimes gets a little lost in these conversations. I don’t think it’s enough to just go, underrepresented voice! Here, put them on stage. You have to make sure that they’re ready and help them get ready. I had a lot of help over the years.


Even though it was a very long journey for my show, not every show is going to take that long, but I needed every second and I’m grateful for every person who helped me along the way. So, I hope other underrepresented voices can get the resources and the time that they need to develop so that when the opportunities come along, they can succeed and not crumble because they didn’t have the proper incubation time.

What advice can you offer to aspiring playwrights?

The advice I always give is something I stole from actress Jane Wyman, and I kind of alluded to it in my speech. “There’s nothing that can replace quality. Never settle for anything less than the best you know how to do. Never settle, just do your best.” It’s very simple, but also profound. You must have an ability to be introspective about what your work is. You’re not a preacher talking down to the people with your work. Nobody cares about that. They care about you as an artist, really thinking and feeling through your work. Making sure that you are saying what you mean and that you mean what you said.

It was announced last month that your new musical, White Girl in Danger, will make its world premiere Off-Broadway next year. What can you tell us about this production?


White Girl in Danger is a piece I’ve been working on for a couple years. I started it at a point when I felt like A Strange Loop could have a whole lot of development, and I wanted to start something new so I wouldn’t be thought of as a one trick pony. It’s a piece that comes from my childhood love of soap operas, Lifetime movies, and melodrama. When I first came up with the notion, it was just going to be a spoof on Lifetime movies, but I noticed that the connection between all these movies and stories, they’re all about white women or teenagers who are in peril or need to be rescued.

Image via Marc J. Franklin

So, I thought, what if I wrote a show called White Girl in Danger? It was just a funny little idea, but then over the years, these conversations about diversity, inclusion, equity, representation, and all that really started to get quite loud in the entertainment space at large, let alone the theater. I began to think about how I felt about those topics from my perspective as a Black writer. I’ve been writing since I was in middle school, but I’ve always written Black characters because there’s nothing foreign to me about that. However, I grew up watching shows like Days of Our Lives.

Suddenly, these little molecules about inclusion, representation, and soap operas started to float together, thus was born this idea of a soap opera town called Allwhite, where there are two races and classes of people. The Allwhite’s, who have crazy stories as far as the eye can see, and the Blackground’s, who just circle and run around telling slavery and police violence stories over and over again. One of them, this girl named Keesha, decides she’s tired of slavery and police violence and she wants a juicy Allwhite story.


After one of the Allwhite girls gets killed, the writer of the universe decides that Keesha can be a best friend to the three main white girls in Allwhite, Meagan, Maegan, and Megan. He starts to take away their storylines slowly, and then that’s when the writer sends the killer after her because the killer is picking off the Allwhite girls one by one. Then the killer’s identity is revealed, and it’s a big shocker. It’s an epic tale of, whose story is this?

What are some future goals you hope to accomplish with your career and platform?

I have some TV and film projects that I’m working on, and I hope to continue working in those mediums. Also, I love live theater and I want to continue working in theater, but specifically as a Black writer, I want to be able to explore and not be locked into anybody’s expectations of what I’m doing. I want to be able to try different things and work with awesome artists and people who I like and want to be around.

I want to create interesting, boundary pushing, and entertaining pieces of art that can push the form that I love. I love musical theater, and I think it can do so much. I consider myself very much in a tradition of musical theater, and I would love to continue pushing that tradition as far as it can go, and even beyond.


Before we wrap up, are there any other upcoming projects or anything else you would like to mention or plug?


Right now, I’m just deep in the trenches working on getting White Girl in Danger up and working on my TV and film projects!

Stay up-to-date and connect with Jackson by following him on Twitter and Instagram or visit his official website. Click HERE for more information on A Strange Loop and to purchase tickets.


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