The cast of ‘A Strange Loop.’ (Photo: Joan Marcus)
Michael R. Jackson’s A Strange Loop follows Usher, a black, queer writer, working a day job he hates while writing his original musical: a piece about a black, queer writer, working a day job he hates while writing his original musical. Director Stephen Brackett chats with Broadway Blog editor Matthew Wexler about the seven-year creative process of bringing this dynamic new musical to life.
How did you become connected with the project?
I met Michael Jackson through a mutual collaborator, an amazing director named Emma Griffin. She was directing his thesis project for a production at NYU. That was my first exposure to his work. She thought we shared similar sensibilities and there was an artistic match. We really took to each other.
I directed a couple of concerts at Joe’s Pub and got to know Michael through disparate songs. I knew he was working on a project called A Strange Loop and there was a moment when he was looking for a director and brought the piece to me and said, “If you’re interested, I’m doing a really low-key reading at NYU.” The thing that drew me to Michael — his authenticity, his own singular voice, his lack of fear, and his intellect through humor — were all powerfully reflected in A Strange Loop. I signed on fairly immediately and started working with him, and that was in 2012.
After that, there were multiple years of development with Musical Theater Factory through several readings and a staging of an excerpt from the show. Through that relationship, we were introduced to Playwrights Horizons where it is now playing in association with Page 73.
How has A Strange Loop evolved since that first workshop seven years ago?
Musical theater development takes a long time. Opportunities are not plentiful, and it costs a lot of money, so these long gestation periods are not uncommon. I’m grateful to be able to stick with the project. Part of that is about Michael’s loyalty to me and the project.
When I first read the piece, there was a casting concept that had the lead character Usher’s mother played by a queer black actor. I thought it was gorgeous and impactful and cracked into the identity politics of the piece. I talked to him about how moving I thought the concept was, which started the conversation about the other characters in the piece being Usher’s perceptions. I proposed the possibility of running with that concept, casting queer black actors to play all of the roles in the show. It tapped into the psychological portrait of Usher that we wanted to build. Michael, in a beautiful way, took to that idea, and said, “Let’s try it.” We learned pretty early on that there was merit in the concept and helped to unlock the piece. Slowly, Michael started writing toward that concept.
It’s gone through a lot of development. For a long time, we were struggling to find the show’s container. The narrative wasn’t screamingly apparent. Once we started to buy into the idea that the action and flow were about the pressure of Usher to write a gospel play — not only from his agent and the world around him but his family (and specifically his mother), it helped lock in the arc, culminating in that big gesture. Once we arrived at the idea, the piece started to open up.

Stephen Brackett (Photo courtesy of Playwrights Horizons.)
Race permeates through A Strange Loop, along with many other emotionally resonant topics. How have you approached the work through the lens of your own racial identity as a white man working with this exceptionally talented group of black artists?
The first thing I’ll say is that the people who were in that room were chosen because of Michael. I want to put him at the forefront of this conversation because ultimately it’s his piece that we’re all translating to the stage. There was pressure, and there were voices that said, “We want a black director for this piece.” That was feedback that Michael got and still made the choice to collaborate with me, and I am extremely grateful for that.
There are many ways to talk about why the piece resonates with me and why it’s important for me, but it was Michael’s decision. And if the results had been different, it would have been painful for me but something I’d understand because the writer is always at the front of the conversation.
One of the powers of this piece is that through the intense specificity of the central character’s perspective a universality is unearthed. I can’t tell you how many conversations I’ve had with unlikely people who have seen that show about how the show resonated and opened them up. There will always be audience members who want to challenge my involvement in the piece, and I don’t want to negate that. That’s part of their perspective, history and understanding. It’s not my job to solve that question for them. My job is to translate the play in a way that opens it up to as many people as possible.
I have to say, I’m a middle-aged gay white man, and felt that this show sucker-punched me with its relevance and also its ability to draw parallels with which I could identify.
That’s a testament to the writing and Michael’s understanding of his audience. He didn’t write it for one specific audience. There are a lot of ways the story reverberates across communities and cultures. That’s Michael’s belief in what theater can do for diverse audiences.
I first met Michael last summer at the Eugene O’Neill Theater Center where they were workshopping Teeth (to be presented this October at the National Alliance for Musical Theatre’s Festival of New Musicals). We were chatting at the bar one night, and I brought up the subject of diversity in the theater. He became so fired up (in my perception) about the idea that by even talking about diversity, we imply a sense of other or inequality (once again, my words, not his). It left me rattled, and I thought, “Wow, he’s a lot.”
I’ve thought about that conversation for a year and am so grateful it happened. As I see more of Michael’s work, I’m beginning to understand the complexities of the themes he explores in his writing. It must be an intense process to unpack it all from a directorial perspective, right?
Tonally, this piece is a wild ride to take on. Michael is a beautifully complex jumble of heart, intellect and empathy. It was important to balance all of that: the heart, yearning and ache of the piece with the fierce intellectual conversations Michael was having about identity, theater and representation on stage.
One of the great luxuries of the piece is that we’ve assembled a company of actors over the seven years we’ve been working on this piece. They love Michael for every single ounce of his being and felt the responsibility to show every atom of his DNA onstage. That only comes with time, conversation and collaboration. It’s not only their talent but their dedication to the singularity of Michael’s voice.

(l to r) Antwayn Hopper and Larry Owens in ‘A Strange Loop.’ (Photo: Joan Marcus)
It also manages to capture authenticity and truthfulness, which I find pretty amazing, given its vast intersection of different styles from realism to epic to fantastical.
It was a challenge because it’s easy to get caught in the meta-theatrics. We had long conversations about who Usher believed the Thoughts (six actors portraying various people and feelings in Usher’s life) to be. His mother, for example, can represent different reflections. In one moment he can be thinking about her overbearing love, and in another moment recognize the weight of her religion on him.
This is not a piece about the virtuosity of extreme character choices. There is a thread line for each of the actors and all of the characters they play.
You’re represented on Broadway this season with Be More Chill and off to the Berkshires this summer to direct the world premiere of the new musical Fall Springs at Barrington Stage Company. Do directors get “typecast” for certain projects, or are you focusing on particular types of work?
It’s been a big year for musical theater for me and feels like a culmination of the past seven years when I started developing some of these projects. I had always loved musical theater and put a concerted effort toward having conversations with musical theater writers. This is the result of years of taking meetings, having conversations and finding artists that are bringing resonant stories to the stage.
If you make a name for yourself doing a certain kind of project, some might see that as your calling card for other works of a similar ilk. That’s one of the industry challenges of being a freelance director. You have to be careful not to become pigeonholed.
When I moved to New York City and started directing, my world quickly became about new play development. Once I got a handle on that, I was yearning for bigger storytelling that comes along with musical theater. I was bowled over by the broader sense of collaboration and loved working with a team that could include up to three authors (music, lyrics and book), along with choreographer and music director —steering a bigger team felt really exciting. I love the musicality, but more importantly, the larger conversations and group of artists working toward creating a singular vision.
A Strange Loop plays through July 28. Click here for tickets.