Credit: Joey Stocks photo

“I remember taking her class as a creative writing student, and one day asking her, you know, in between classes, if wanting to pursue writing as a profession was too lofty of a goal for me to have, and she said, no, she very much encouraged me to write professionally. It wasn’t just like a stupid dream, or something that was out of my grasp. And I just always remember that because what she said, morphes me still in my life,” said Michael R. Jackson as he reflected on the moment when his instructor Deborah Thompson, whom he remembers as one of the first adults in his life to speak to him like an adult rather than a teenager, acknowledged his dreams.

Jackson is the mastermind behind the “A Strange Loop,” an off-Broadway musical that secured many awards and brought the audience to standing ovations. Jackson used his unrivaled abilities as a playwright and composer to produce a musical about a young Black man who works as an usher at a Broadway show who is writing a musical about a young Black gay man who works as an usher at a Broadway show who is writing a musical about a young Black gay man working as an usher writing a musical.

Jackson grew up in Detroit, Michigan although most of his family hailed from the south. His father was a police officer until retirement, and his mother worked in finance for General Motors. As a child he was very involved in programs that allowed him to grow as a creative; he was part of the youth Brazeal Dennard Chorale group from middle school to senior year of high school where he sang a lot of choral work from Black composers.

During his time at Cass Technical High School, Peter Markus, his creative writing instructor, introduced a program called Inside Out to his school, which allowed Jackson to flourish as a writer. The program along with his teacher had assisted him in honing the skills he mimics today in his writing. During one of his classes with Markus, he wrote a short story called “Big Girls,” which he was able to read at the Detroit Public Library. He recalls the piece as being mature, and the style he developed in it as being similar to what he creates now.

“He was the first teacher of mine to challenge me to write beyond the boundaries that I felt that I needed to write. In high school he challenged me to go deeper into my work and to push the envelope with what I was writing. I alway like to shout him out because if I didn’t have him in my life as a young person I probably would not have been as bold as I did in my career as a writer without him early on giving me purpose as it were,” said Jackson.

After high school, Jackson had hoped to attend an Ivy League college, and had applied to Columbia University, his dream school, in the hopes of being accepted. However, during a visit to his high school one of his peers from the Inside Out program struck up a conversation about one of his short stories. She commented on how cinematic his story was, and inquired about his interest in screenwriting after reading it. He later decided to apply to NYU’s dramatic writing department as an afterthought following his conversation with her.

Following his rejection from Columbia University, he was granted a spot at NYU, and he accepted. He remained at NYU after finishing his undergraduate studies to earn a master’s degree in musical theater writing, as a book writer and lyricist.

“It ended up being a better place for me to go with, I think if I had gone to Columbia, I would not have had the opportunities to actually write as an undergrad because they didn’t have a specific writing program for undergrads. They only have that for grad students. They are creative writing, but I fell in love with theater. So I think I ultimately wound up in the right place,” Jackson expressed.

Jackson began writing a personal monologue during his time as an undergraduate and graduate student, which was inspired by his thoughts of being terrified and unclear about where his life was heading after graduation. During his undergraduate years, he began writing “Why I Can’t Get Work,” a third-person monologue about a young Black gay man walking around New York and wondering why his life is so bad. When Jackson got to graduate school and began composing music for himself, many of the songs he wrote were akin to the monologue. Later, he continued to experiment and began combining songs with the monologue from his writing. “A Strange Loop,” his most well-known musical, evolved from this piece.

“I was sort of throwing my own personal experience to write some of it, I didn’t have any objectivity in it. So it took me very many years to even just figure out exactly what the story was, because this musical is not really autobiographical, it’s more, I would call it self-referential. So there’s distance that I had developed from the personal aspects of it, and from just telling a story. So that took a long time. The other challenges were just that the musical theater world professionally, was not always super open to what I was doing, necessarily, so just trying to find opportunities to even get the piece produced was next to impossible. And so it took a very long time for anybody in the theater world to really recognize that the show I was writing had any merit,” said Jackson.

“A Strange Loop,” which premiered in 2019, earned a lot of excellent feedback and was nominated for a lot of awards. He earned the Pulitzer Prize for Drama, which gave him a sense that he is finally in the business world of entertainment, and that his work is getting the appreciation it deserves.

His proudest achievement from his work, he said, was the reaction he got from his audience, who would come up to him every night after a show, whether it was a Black gay man or queer person, and they would express to him how the character related to them in some way and made them feel seen. Even if the characters did not have the same experience as them, his white audience was moved by it, and learned or felt something within themselves through watching the show.

Jackson intends to continue writing fascinating stories in the wake of his success. He wants to challenge people’s perceptions of what Black, African American stories are. Especially in musical theater, where he feels that African American experiences are frequently underrepresented. He wants to keep pushing the envelope and not follow the crowd. Jackson is now working on a musical called “White Girl in Danger,” which is inspired by his passion for soap operas.