How 'A Strange Loop' went from post-college project to Broadway hit

Creator Michael R. Jackson developed the musical over 20 years.


A Strange Loop by Michael R. Jackson is now the most Tony-nominated show of the season, with 11 nominations. That’s not too shabby for a show that began as a monologue Jackson wrote in his apartment in Jamaica, Queens. A Strange Loop is a musical about a young, gay Black man who works as an usher at The Lion King and is writing a musical about a young gay Black man who works as an usher called A Strange Loop (hence the loop). 

However, when Jackson started writing A Strange Loop, he had no idea it would go on to become a Broadway baby and critical darling. Below is a chronology of A Strange Loop’s 20-year journey to Broadway.

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2002: A strange monologue

The seeds of A Strange Loop began in an apartment in Jamaica, Queens. In 2002, a 23-year-old Jackson had just graduated with a degree in playwriting from New York University. He wrote a monologue in his apartment called “Why I Can’t Get Work.”

As Jackson wrote for the Yale Review, it was “about a young Black gay man walking around New York wondering why life was so terrible — why he was so terrible… It was a dark and uncertain time in my life. The United States was two months away from invading Iraq. I had graduated a semester early and still had no clear sense of how to tell a story featuring characters who wanted something.

“I still had no sense of my own character and what I wanted… And no one was watching me with any interest except perhaps my parents, who wanted to know what I was going to do with my life, my BFA, and my six-figure student-loan debt.”

That seed of an idea still exists in A Strange Loop, as Usher struggles with his own identity as a person and an artist.

2003: “Memory Song”

Jackson decided to go back to school, this time to NYU’s Musical Theatre Writing Program. There, Jackson wrote his first song. It was inspired by a classmate at NYU, a Black and gay student like Jackson, who had expressed feelings of deep guilt after a one-night stand. Jackson, who used to sing in his hometown church choir (he’s from Detroit) identified with his classmate. He wrote one phrase that would become the seed for “Memory Song”: “All those Black gay boys I knew who chose to go back to the Lord.” “Memory Song” became the first song written for A Strange Loop.

Growing up, Jackson had loved the deeply personal and poetic songs of female singer/songwriters such as Tori Amos, Liz Phair, and Joni Mitchell. He also had musical talent; Jackson played the piano for his church’s choir. At NYU, Jackson began to write songs deeply inspired by the feelings he was going through at the time, such as getting his heart broken. “The heartbreak triggered a loop within a loop of self-hatred and criticism about my value as a gay man. I went into a quasi-depression. Even though I was in the program as a lyricist and book writer, I started writing music to work through the pain,” Jackson wrote in The Yale Review.

“Strange Loop” is also the title of a Liz Phair song, from her album “Exile in Guyville.” (In A Strange Loop the musical, there’s a song about dating as a gay man called “Exile in Gayville.”) At one point, Jackson wanted to use Phair’s songs in A Strange Loop, but he couldn’t get permission. That turned out for the best, as Jackson told The Cut: “It forced me to actually go and write songs.” 

2006: Fast Food Town

Jackson performed a one-night-only version of A Strange Loop in 2006 at Ars Nova, then called Fast Food Town. It was a combination of “Why I Can’t Get Work” and the songs he had written at NYU. Jackson recalled on PBS’s American Masters Creative Spark Podcast, “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.” 

2007-2016: “Usher, Usher!”

For a decade, Jackson continued to chip away at A Strange Loop in various workshop settings, such as with the Playwrights Realm, the Lark, the Musical Theater Factory, 54 Below, and at Playwrights Horizons. Along the way, crucial collaborators came onboard: director Stephen Brackett in 2012 and producer Barbara Whitman in 2016 (who is the lead producer on A Strange Loop).

Brackett came up with the idea for the entire cast to be Black, queer people, Jackson then turned the chorus of the show into Usher’s Thoughts, with names like “daily self-loathing” and “sexual ambivalence.”

At the same time, Jackson lived his life and let his life inform his work. Like Usher, Jackson worked for five years as an usher at The Lion King. One day, a female patron cried out “Usher, usher!” to Jackson because she needed help.

“I just remember clocking that and being like, “That’s crazy! She’s yelling for an usher like a taxi cab!” recalled Jackson. That cry, “usher, usher,” became part of the opening number for A Strange Loop, and Usher became the name of the main character in A Strange Loop. (Usher is also the name of a famous singer, which is similar to how Jackson shares a name with “King of Pop” Michael Jackson.)

Another day, Jackson saw a Craigslist ad with the text: “Inwood Daddy sucking cock all Saturday morning.” That line became part of a song in A Strange Loop called “Inwood Daddy.” 

2014-2015: A personal breakthrough

It wasn’t just little details from Jackson’s own life that influenced A Strange Loop. There was also therapy. Sometime in 2014 or 2015, Jackson made a personal breakthrough in therapy that then became Usher’s character arc.

“Suddenly I knew what the protagonist of A Strange Loop wanted. He wanted to change. He wanted to change the same way I had always wanted to change, because I thought something was wrong with me. Because I thought I was an unlovable fat Black gay boy,” Jackson wrote in The Yale Review.

“I realized that no matter what was going on in the world, it was my own perceptions of reality that would hold me back or propel me forward. It was the way that I met my tangible or perceived obstacles that made me who I was. In my play, Usher’s only real obstacle is himself: he is on a journey to change himself through many loops within loops of negative thoughts. It is only when he realizes there is nothing wrong with him that he changes.” 

On April 26, 2016, Jackson debuted the full score of A Strange Loop at 54 Below. 

2019: Curtains up!

A Strange Loop made its world premiere in 2019 at off Broadway at Playwrights Horizons, starring Larry Owens as Usher. This production also marked Jackson’s New York City debut as a writer. Immediately, A Strange Loop received almost unanimous critical acclaim. The show also picked up a basket of awards, including Obie Awards, Drama Desk Awards, and a Pulitzer Prize. 

After its successful Off-Broadway run, it was announced that A Strange Loop would have another run in Washington, D.C. in 2020 at Woolly Mammoth Theatre Company.

2021: Once more, with feeling!

The D.C. run of A Strange Loop was delayed due to the COVID-19 pandemic and finally opened in late 2021, with newcomer Jaquel Spivey as Usher (the other cast members remain the same as the Off-Broadway production). Usher marked Spivey’s first role out of college.

The show quickly sold out and extended, and soon after, it was announced that A Strange Loop would go to Broadway in 2022.

2022: “​​Big, Black, and Queer-Ass American Broadway Show!”

A Strange Loop opened on Broadway on April 26, 2022 at the Lyceum Theatre. Shortly after, it was nominated for 11 Tony Awards, the most of the season. L Morgan Lee, who plays one of Usher’s Thoughts, made history as the first trans performer to be nominated for a Tony Award for acting.

“My mind isn’t processing that this is real,” Lee said. “This nomination is SO much bigger than me. I hope someone will see this moment and feel like they can go on. No matter what the world, or school, or people tell them they are ‘supposed’ to be, how they are ‘supposed’ to sound, that they will keep striving to love and embrace the fullest version of who they are.”

As for Jackson, the Tony nominations have been a culmination of all the years he’s put into A Strange Loop: “It’s a nice feather in my cap. It feels really validating for all of the years and blood and sweat and tears and time that I put into the piece,” he said.

2022: A Strange Loop wins Best Musical at the Tony Awards

During the 75th Tony Awards ceremony, A Strange Loop won two Tony Awards: Best New Musical, and Best Book of a Musical. After the award wins, Jackson said the musical “spoke to the power of art and theatre to bring people together, to let everybody in on a secret that we’re not alone and that there is more that unites us than divides us.”

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