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All the Drama: A Strange Loop, 2020 Winner, Pulitzer Prize for Drama
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All The Drama is hosted by Jan Simpson. It is a series of deep dives into the plays that have won The Pulitzer Prize for Drama. The Pulitzer Prize for Drama: “A Strange Loop“2020 Pulitzer winner “A Strange Loop”, by Michael R.
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Jan Simpson
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Michael R. Jackson
App for free or go to Amazon.com ADFreePodcasts that's Amazon.com ADFreeP Podcasts to catch.
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Jan Simpson
Up on the latest episodes without the ads.
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Michael R. Jackson
The year is 2020. The United Kingdom formally withdraws from the European Union. The World Health Organization declares the outbreak of the COVID 19 virus to be a global pandemic. In the US high profile acts of excessive police violence against African Americans continue to rise, culminating in the callous murder of George Floyd, who dies after an officer kneels on Floyd's neck for almost 10 minutes. And Pete Buttigieg, the first openly gay candidate to make a serious bid to become the presidential nominee for a major party, wins the Iowa caucuses for the Democrats and places second in their New Hampshire primary before bowing out of the race when he comes in fourth in South Carolina, where he endorses Joe Biden, who will go on to defeat Donald Trump. And in that year of 2020, the Pulitzer Prize for Drama went to Michael R. Jackson's A Strange Loop, a musical about a young black gay man trying to write a musical about a young black gay man who's trying to write a musical. A Strange Loop was only the 10th musical to win a Pulitzer Prize and the first by a black composer. My name is Jan Simpson. Welcome to all the Drama, a podcast about the plays and musicals that have won American theatre's highest accolade the Pulitzer Prize for Drama. This episode is a little different for me because first off, 2020 is just five years ago, and so many of you are already familiar with the story of A Strange Loop and its author. But it's also different because, as some of you may also know, I've had the privilege of serving as a Pulitzer juror three times, including in 2020. So I know what the discussions about that year's choices were like. But out of respect for the rules protecting the privacy of those deliberations, I can't share much about that. However, I can say that when the prize was announced, lots of people congratulated me for making such a great choice, even though I obviously wasn't the only one who'd been involved in making that choice. But I wasn't surprised by that response, because A Strange Loop seems to hit people viscerally very personally. And I suspect that's because although the musical isn't Strictly autobiographical. People can feel that in creating it, Jackson dug deep into his passions, his dreams and his fears. The musical's central character is a black gay musical theater writer named Usher, who's trying to figure out whether he can create a work that reflects his own interests and respects his artistic integrity while still appealing to a broad audience, or whether he should just write the kinds of shows that Tyler Perry does, even if Usher believes that they trade in stereotypes and pander to audiences. As this debate plays out, Usher is heckled by a Greek chorus of his innermost thoughts, who include the very loud and persistent daily self loathing. Jackson had worked on the show for nearly 20 years before playwrights Horizons gave it a shot, but he knew from a young age that he wanted to be a storyteller. He was born In Detroit in 1981, the second son of Henry Jackson, a police officer who eventually rose to the rank of lieutenant, and Mary Jackson, who worked in the accounting departments of local car companies like General Motors. When Michael was a kid, his grandaunt used to babysit for him, and during their times together, she introduced her young nephew to the afternoon soap operas she regularly watched. And he became devoted to them, too. He was a smart kid. And so Michael got into Cass Technical High School, a magnet school that had an ambitious academic program and a reputation for getting its graduates into top colleges. He began writing his own stories while at Cass Tech, modeling them after his favorite authors at the time, Jackie Collins and Stephen King. And after those soap operas he continued to watch and love. During that time, he also began to grapple with his sexuality, eventually coming out to his parents in a painful session in which he said all three of them cried. His mother told him that God hated homosexuality, and his father asked if being gay meant that Michael was attracted to him. They've all since made peace with his sexual identity, but during that time, Jackson found solace in a local program for young writers. There, his stories became more personal, particularly as he worked with the novelists Peter Marcus, who he says encouraged him to figure out what your obsessions are and write about them over and over and over again. Jackson took that advice with him when he went to NYU's Tisch School of the Arts to study playwriting with the hope that one day he would get a job on the writing staff for one of his beloved soap operas. His first full length effort at NYU was worthy of a soap opera. It was a play called DL, a title and premise he says he borrowed from an episode of Oprah Winfrey's show about black men. Who secretly engage in gay sex, doing it on the down low. As Jackson recalled in an essay he wrote years later, D.L. told the story of a black police lieutenant who had a secretly gay teenage son who was having an affair with one of his father's white officers. But as it turned out, that officer was also having a secret affair with the father. Jackson admits that the play wasn't very good, but he kept working at his craft, and he went on to get an MFA at Tisch. He'd gone back to school to develop skills as a book writer and lyricist for musicals, but he gradually began writing the music as well. He wasn't a complete novice when it came to music. He'd begun taking piano lessons at age 8. He later sang in a citywide choir that specialized in classical music, and he sang and played in church throughout his boyhood. But a real turning point in his relationship to music came when he was around 15 and a cousin gave him an album by the singer songwriter Tori Amos. Jackson instantly identified with Amos intimate songs about sexuality, politics and religion. He'd later say that he recognized her as a soulmate who expressed feelings he hadn't even known he had. He quickly began searching out and listening to other confessional singer songwriters like Joni Mitchell and Liz Phair. But it was an Amos song called Pretty Good Year that inspired the first song he wrote for his MFA class, which also ended up anchoring a significant moment in a strange loop and is my favorite song in the show. It's the haunting tune Memory Song, which chronicles the complex emotions of a young black gay man growing up in the church, knowing that it condemns homosexuality and seeing how that had destroyed other boys like him. Five foot four High school gyms Sneakin a cupcake these are my memories these are my memories Shooting hoops off the.
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Jan Simpson
Rim Slow on the uptake these are.
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Michael R. Jackson
My memories these are my memories After Jim the Locker Room My eyes photographing naked me measures in at four and a half inches. These are my memories these are my memories of one lone black dead boy I knew who chose to turn his back on the Lord. His Tisch classmates liked the song and encouraged him to write more. Eventually, Jackson combined a monologue he'd been working on called why Can't I Get Work with some Music for a one man show that he did at ars Nova in 2006. It didn't attract much attention. Still, over the next dozen or so years, Jackson continued to work on and expand the show, supporting himself with a variety of odd jobs that included interning at Time magazine working as a gopher at the ABC soap All My Children and famously serving as an usher at the Lion King, just as the character Usher does. In A Strange Loop during that time, he found the encouragement to continue on with his musical writing in the growing number of awards he won, including a Sundance Theatre Institute Fellowship, a Drama Guild Fellowship and a Jonathan Larson Grant. In 2017, he was named a winner of the Lincoln Center Emerging Artist Award. Then finally in 2019, his musical, now called A Strange Loop, opened at Playwrights Horizons. The title was in part an homage to scientist Doug Hofstadter's theories about self awareness and in part a tribute to a song with that same title on the singer Liz Phair's debut album. In fact, at one point during the show's development, Jackson had even included a storyline specifically about Fair's music. But the real life Fair was refused to let Jackson use her music in his show and instead encouraged him to go ahead with his own music. It turned out to be good advice. The Off Broadway production of A Strange Lou quickly became one of the hottest tickets in town and it won almost every award it was eligible for the New York Drama Critics Circle Award, the Drama League Award, an OB Citation, five Drama Desk Awards, six Outer Critics Circle Awards, and of course, the Pulitzer. In 2022, when theaters reopened after the pandemic lockdown, the show moved to Broadway's Lyceum Theater where it ran for 293 performances and won that year's Tony. Just a year later, Jackson opened the musical White Girl in Danger at Second Stage Theater. The show, a satire set in a fictional soap opera town, had the sidelined black characters scheming to find a way to move into the main narrative. It drew mixed reviews. Theatermania declared it a musty new musical, but the New York Times's theater critic Jesse Green found it to be overstuffed and at three hours, way too long. The show closed after its scheduled six week run. Undaunted, Jackson was back at Playwrights Horizons the next year with Teeth, a musical Adaptation of a 2007 comedy horror film about a teenage girl who discovers that she has teeth in her vagina and that they will actively attack men who force themselves on her. The show, which Jackson co wrote with Anna K. Jacobs, was scheduled for a month long run at Playwrights, but was extended twice and then moved to New World Stages for a commercial run, although that only lasted 78 performances. A strange Loop continues to be done at some of the more adventurous theater companies around the country, and five of those productions are currently scheduled for this year. And of course, Jackson is still a relatively young guy, and so there's plenty of time for him to make more shows. In the meantime, I'm delighted that he accepted my invitation to talk with me about A Strange Loop. Hello, Michael R. Jackson. Welcome to all the drama.
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Jan Simpson
Hello. Thank you for having me.
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Michael R. Jackson
I'm going to start right off by asking if you remember how you got the news that A Strange Loop had won the Pulitzer.
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Jan Simpson
It was in the middle of the COVID lockdown in 2020. I was in my old apartment. I was on the phone chatting with my friend, playwright Brandon Jacobs Jenkins, and we were just sort of, you know, just catching up. I think I was vaguely aware that the Pulitzer was going to be announced that day, but I put it completely out of my mind because the pandemic was raging and I sort of thought theater was over. I, like, was not thinking about anything theater related at that time. But sort of unbeknownst to me, Brandon, while he was talking to me, he was watching the Pulitzer announcements, and he was the one who told me that I had won.
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Michael R. Jackson
Wow. Yeah, that's a pretty cool way to find out. What effect did having it announced within Covid have?
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Jan Simpson
It was. It was really odd because it was such a huge honor and an announcement, and yet it was in this really muted environment. And so my phone was just like non stop ringing and text messages coming in and emails and best dealing social media. And yeah, I couldn't do anything about it. Like, the only thing I could do was I went for like a walk and I listened to Chaka Khan. Like, that was, to me was like celebration, you know, that was like the most I could sort of celebrate in that way. And then I came back home and my producers sort of put together an impromptu zoom and they, like, had campaigns sent to my house and we had a little zoom party. So I got to see people that way, and that was, like, really exciting. And. But it was like, again, it was a kind of muted experience because we couldn't gather together in person to celebrate.
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Michael R. Jackson
Right. I'm going to dial back a little bit because as I understand it, you started off as a solely playwright guy. So I'm interested in what got you interested in creating musical theater to the point that you went back to NYU to get an mfa.
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Jan Simpson
So my story is a little loopy, pun intended, I guess, because I started out acting in musical theater as a kid when I was growing up in Detroit and I loved musicals. My mom used to take me to go see shows all through middle school and High school, and I was involved in an all city black classical chorus, and I studied creative writing and I took piano lessons and I played piano at church. And I used to try to write songs when I was in middle school and high school, but I never quite make the music and the lyrics go together because I didn't understand song form. And so I always had sort of an interest, not necessarily in musical theater writing, because I didn't even really understand that people wrote musicals. I thought like all sort of, you know, movies and tv. I thought he just sort of sprang out of the ground like magic. And so when I applied to NYU as an undergrad, it was kind of on a whim because I really wanted to go to Columbia. And then I didn't get into Columbia, and so I went to NYU instead. And at that point, my dream was to be like a soap opera writer because I really loved my, my stories. But I was taking these theater classes, and the more theater that I studied and the more shows I saw on Broadway, off Broadway and so forth, the more interested I became in the form of playwriting. And one of my teachers happened to also teach him the graduate musical theater writing program. And he said if anybody was interested that they could go to the open house. I went to the open house. And then I graduated shortly after that from undergrad, and I was sort of lost and didn't know what I was going to do next with my life. And so I just started applying to grad schools while I was applying for jobs. And I just sort of figured whichever one I get is what I'm going to do. And I got into the NYU Grad Musical Theater writing program, and it just, it changed my life. It was like exactly the right program and, and like, studying musicals just really, really interested me. And it gave me a form to work with that I think I'd been pushing toward all along, even since middle school and high school, particularly with lyric writing, because I didn't go into the program as a composer. I went in only as an aspiring book writer and lyricist.
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Michael R. Jackson
I've read also that you were maybe still are, a fan of Showboat.
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Jan Simpson
Oh, yes, I am a massive, massive fan of that show. I saw the Hal Prince revival tour of it in Toronto when I was 13 or 14, and I know that score like the back of my hand, and I love it. Unironically, problematically, whatever you want to call it, I love it. Those songs Cannot Be Beat, and I had never seen the Moody version, which I recently watched. And I, I think I just appreciate what it, like, was attempting to do. And the breadth and the depth of what it was trying to do really resonated with me in terms of, like, it's the craftsmanship of it. And, you know, I understand, like, sort of the political. How dated it is and. And there's all kinds of problems within it, for sure. But, like, I think I just identified with it from, like, a craft level as a writer trying to write something kind of ambitious, which I think Edna Ferber was trying to do. It's a novel in which I think that it's Rogers and Kern. Yes. No, it's Hammerstein or Hammer. Hammerstein and Kern were trying to do in the musical. And so I just think I've always been excited by the ambition of it.
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Michael R. Jackson
Now, as I understand it, a Strange loop started off as a monologue and then songs started coming. How did it change over the time you worked on it? What were some of the significant changes?
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Jan Simpson
Oh, gosh, so many. Well, to start, I mean, or among, you know, many things, there used to be a kind of storyline or a loop within a strange loop where Usher was sort of expressed his deep admiration for the indie alternative rock musician Liz Fair. And he was writing these mashups of. With songs of hers from her, primarily from her album Exile and Guyville. And within the musical, he was trying to get in contact with her to use these mashups. And he was writing these songs that sort of culminate in the end of the show where there's this ultimate mashup to a song he writes called Fanboy and a song that she wrote called Strange Lute. And I in real life was also trying to get her permission to use these songs in the musical. And over many years I was trying to contact her through various cockamamie strategies. And I finally did manage to make contact. And she told me I could not use her songs in the show, but. And he told me that he advised me to use. To write my own songs instead. Totally. And that ended up being like, the greatest advice ever, which forced me back into the piece to kind of figure out what the musical through line and sort of structure was going to be. So that was like one big change. Another one was the characters of the Thoughts. They. That was sort of a late addition. Before we went to Claire's Horizons, right before we. I want to say, a couple of months before we were going due to go into rehearsals, the character, the Thoughts had a different identity altogether. I just sort of characterized them as patrons at the theater who just sort of were a little bit Heightened. And so they didn't have a unifying concept. And, you know, I. Once I found out that the show is being produced, I sort of was getting very anxious about making sure that I got everything about it right, because I felt like, if they're gonna do this crazy musical, I cannot get it wrong. I have to, like, make sure that all of my intentions are really sort of aligned. And so I kept going back and doing rewrites over and over and over again to keep trying to refine it. And as I did that, I was like, these characters, they need an identity that unifies the whole thing. And that's when I realized that they were actually Esther's thoughts. And that as his thoughts, they could morph into real characters, perceptions of characters and so forth, and brought that to my director and choreographer for a little planning session. And that really triggered things for them to. To build the physical production with the thoughts as our kind of engine.
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Michael R. Jackson
Yeah, I think they're really beloved by people who see this show. At least they're beloved by me. I think they're terrific.
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Jan Simpson
No, I would say the thoughts are like my Avengers. They're kind of a superpower of the piece, in my opinion.
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Michael R. Jackson
Now, you worked on this show for a very long time and maybe almost two decades. Is that right?
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Jan Simpson
Yeah, I mean, basically on and off. Basically about 18 years to Broadway. So 16 years to off Broadway. 18 years to Broadway, roughly.
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Michael R. Jackson
What kept you going?
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Jan Simpson
You know, it was a lot of things. One was that I had no plan B. And I. You know, the piece, I. As you may know, I don't refer to it as autobiographical. I refer to it as self referential. And as a result of that, as I live life, there were things I wanted to write about, and as I wrote, there were things that affected my life. And so the piece just sort of became a container for that process. And so the thing that kept me going was that every day, every week, every month, every year, more stuff was happening within my experience that I either didn't understand or felt or had certain feelings, positive or negative, about. And I wanted to find, especially as a black gay man, I wanted to. To bring a specificity to the experience that was unlike so much of what I was seeing reflected in the storytelling and the media and the world around me, both fiction, fictive and real. And I wanted to, like, just see if I could do a kind of self portrait, like in musical theater form that really sort of captured what the experience of being a young black gay man was. Even as I was getting older and older by the year and also sort of maturing beyond the initial impulse that spurred the writing of the piece.
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Michael R. Jackson
I think one of the things. One of the many things that people appreciate about the show is that it is so raw, it's so honest. And I wonder, did you ever have second thoughts, even though it's not autobiographical, about being just so open?
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Jan Simpson
I didn't, because the artists who really inspired me the most were open, honest, and raw. And they. And they were the ones I looked to, who I wanted to in some way emulate, albeit from my own perspective. And, And. And so I felt like the gauntlet was thrown down at an early age for me by really delving into these. These artists work.
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Michael R. Jackson
Who were some of these artists?
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Jan Simpson
Trying to find my own voice. There's a lot of people, but, like, I go to what I call my triumphant, my holy Trinity. Joni Mitchell, Lizbeth and Tori Amos. I call them the. The mother, the daughter, and the Holy Ghost. And they are just three women whose art really rocks me and really challenged me and really made me think. Think about my own experience in the world. Even. Even if, like, things they were singing about weren't necessarily my experience. The way they. They. They talked about it and the way they use language and music and point of view and humor and. And drama and. And. And everything. Like, I just was so impressed by it. And I wanted to. To sort of find my own similarly open and humorous and musical way of telling the stories that I cared about.
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Michael R. Jackson
Have you been in touch with any of them since the success of A Strange Loop?
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Jan Simpson
I've made contact with two out of the three. I had the opportunity to meet Tori backstage in one of her concerts while Strange Loop was running. She wasn't able to see the show because she was always on tour when it was running. So word got back to her about my admiration for her, and I got to have a really great meeting with her backstage. And then Liz, who I'd been in contact with or chasing for so many years, we connected on social media first when I won the Pulitzer, because I think he read about the show in the Times and saw how much Exile and Guideville had. And her work especially had inspired the piece directly. And so we had communicated that way. And then he wasn't able to see the show on Broadway, but then when it went to Los Angeles last summer. Is that what it was? What it was? I can't remember. The months all blend together for me. He lives in California, and so he was able to come and see one of the final performances of the show. And we had a really beautiful meeting in front of the Amundsen Theater. Me, her, and her son. And he really. And the piece really resonated with her. And he. And I think, in that moment, suddenly realized why I had been pursuing her so doggedly for all those years. And I wasn't just, like, a crazy person or, you know, some stalker fanboy that, like, I actually, artistically was responding to her work in a real and concrete way, which she sort of reflected back to me. And so that was like an ultimate Strange Loop moment, for sure.
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Michael R. Jackson
Absolutely. A lovely.
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Jan Simpson
And Joanie. I went and saw the Hollywood Bowl. I saw her from afar, but it was a beautiful concert. And I was so glad that I got to see her, but I have not met her now.
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Michael R. Jackson
A lot of winners of the Pulitzer Prize, it's been such an awesome. Both recognition and responsibility that some of them. It's affected their ability to do more work. That seems not to have been the case with you. And so I'm just wondering, how has winning the award affected you?
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Jan Simpson
You know, it's. Sometimes it's hard to say. I mean, I think it's affected me in that, like, it's. It will be, like, on my, you know, epitaph, like, we're, like, in my obituary. And. And it's what most people know me for. And there was the. You know, I'm not usually one who's into the historic, quote, unquote, historic nature of things, but there's an historic nature to it in terms of it being, I think, the first black musical to win a Pulitzer.
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Michael R. Jackson
Absolutely. Yeah.
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Jan Simpson
And that sort of thing, which my mother. That excites her, like, more than it does me. But, like, there's. There's that. So that. But how's that affected my life? I mean, I don't know. It's kind of hard for me to say because a lot of that is in the eyes of the beholder.
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Michael R. Jackson
Has it made it easier or harder for you to do your work?
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Jan Simpson
I don't think it's made it harder for me to do my work, per se, because all I care about is the work itself. But I will say that. And this goes beyond just the Pulitzer, you know, I will always be Strange Loop author. I will. I don't. I don't think I'll ever be either white girl in danger author or teeth author necessarily. Like, it's always gonna be Strange Loop will be what I'm known as, which I'm proud of. I don't have a problem with that, but it does mean that when I'm doing other things that are not a strange loop, it creates a certain expectation, or at least that's been my experience of like what, what I will do artistically. And that, I think, just comes with the territory. And I'm fine with it because I'm gonna do my work regardless.
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Michael R. Jackson
Well, we're all happy about that and looking forward to what you do next because you're still in your prime and so looking forward to that and grateful to you for talking to us about a strange loop.
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Jan Simpson
Then thank you for the conversation.
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Michael R. Jackson
And thank you for listening. I hope you'll come back next time. And if you have any comments, questions or suggestions, please send them to me@janbrudwayradio.com.
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Jan Simpson
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Michael R. Jackson
The numbers look good. Brad. You're on mute.
- [34:39]
Jan Simpson
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