The title of Michael R. Jackson’s debut off-Broadway musical, A Strange Loop, should make old-school Liz Phair fans sit up. That’s the name of the last song on Phair’s breakthrough 1993 album, Exile in Guyville. It’s no coincidence. Jackson is a serious Phair fanboy, and song and lyric allusions to her work are sprinkled throughout the script. He also sneaks in the philosophical definition of a strange loop, which has to do with the interplay of identity and consciousness.
The show, which runs May 24–July 7 at Playwrights Horizons, is a howlingly funny and honest portrayal of Usher, a young, gay black man who, yes, ushers at a Broadway theater—which Jackson used to do himself at The Lion King. Usher is writing a musical about being a young, gay black man—just as Jackson has done with this musical. A strange loop, indeed!
The score, a mix of pop, gospel, and mock show tunes, savages everything from pretentious Broadway gatekeepers to Tyler Perry to Grindr hookups. The composer-lyricist chatted with us about how his show came together, the evolution of Phair, and how the “white gaytriarchy” ostracizes men who don’t have the perfect bod.
What Should We Do: Tell me about how A Strange Loop traveled from New York University to Playwrights Horizons.
Michael R. Jackson: I studied dramatic writing at NYU. After I graduated, I didn’t know what I was going to do with my life; I was applying for jobs and grad schools. I started writing this monologue called Why I Can’t Get Work. It’s about what it felt like to be a young, black gay man in New York City around 2003. And then I got into grad school for musical theater writing, even though I had never written lyrics before.
WSWD: So this didn’t happen overnight.
Jackson: It takes so long. People ask, “Are you excited? How do you feel going into rehearsal?” And I’m like, “I’m utterly terrified because I’ve been writing this musical on and off since 2003.” Even though I didn’t know it was going to be a musical at first. And in the midst of that, I started ushering at the New Amsterdam Theatre for The Lion King. And that was the first time I was exposed to Broadway up close. Once I saw that, I was like: Oh. No one is ever going to do my musical. This is Broadway, and this cute little musical that I think I’m writing will never be here. So I wrote this musical giving no fucks.
WSWD: And now you’ve got a guy from The Lion King in your show.
Jackson: Yeah, Jason Veasey! He did a national tour of Lion King.
WSWD: The title, A Strange Loop, is the final track on Liz Phair’s Exile in Guyville. And you reference her in the script a few times. What’s the connection?
Jackson: In the period when I was writing the monologue, I was really lost in the world. I didn’t know who Liz Phair was until about 2003, which is when her eponymous album came out. The one that everyone hated and called her a sellout on. And I liked it well enough to be like, Y’know what? This is a pop album, but I’m into it. Let me go back and see other things of hers. And so I bought Exile in Guyville. And I started listening to it and thought, holy shit. I can’t believe that this same woman put out these two wildly different albums and yet I could detect the intelligence as a through-line. The way that she wrote about her experience as a young woman in Chicago dealing with misogyny and relationships. I delved into her as this phenomenon of the early ’90s, when she was this suburban girl with a potty mouth.
I always called Joni Mitchell the mother, Liz Phair the daughter, and Tori Amos the Holy Ghost of my triumvirate of women who really inspired me. I wanted to find my own version of [their fearlessness] in my identity as a black gay boy and man.
WSWD: Which you found relatable?
Jackson: Her humor reminded me of myself in a strange way. Even though I don’t have her background. I’m not white; I’m not a woman. But there was an emotional, aesthetic kinship, and as I started writing A Strange Loop, I wanted to see if I could tap into that—not to copy her or anything, but see if I could write about my own perception of my experience as a young man with the same sort of bite that she did.
WSWD: Something she and your protagonist, Usher, have in common is they are both code switching and navigating the meat market of sex. “Later Liz Phair”—the one you said was called a sellout—is as much a performance as Exile in Guyville Liz Phair.
Jackson: That’s right. Even the register that she sings in. Because she’d been smoking a lot of weed and so her voice was much lower; she was singing like a man. Which was part of the point, that she was singing about sex and relationships and emotions kind of in a man’s voice, but female. There are so many things about Exile in Guyville that I could write a whole dissertation on, artistically and production-wise. It was just so much more than an album.
WSWD: Who are your go-to inspirations for lyric writing?
Jackson: Most of them tend to be singer-songwriter people, Tori Amos being the most notable. I started off attempting to write music in high school by trying to imitate Tori Amos. The depth of emotion that she would reach, the way that she talked about sexuality and religion, was such a part of my childhood. There’s a riddle aspect to her lyric writing. All of that influenced me first, and after her, I fell in love with Joni Mitchell. And then Liz Phair. And so I always called Joni the mother, Liz the daughter, and Tori the Holy Ghost of my triumvirate of women who really inspired me, even though they’re three very different white women. The way they tackled issues in their writing, the fearlessness and the emotionality—I wanted to find my own version of that in my identity as a black gay boy and man.
WSWD: One of your NYU teachers was composer-lyricist Bill Finn, who is known for using autobiography in musicals, like A New Brain. There’s hard-hitting personal stuff in A Strange Loop. Usher has a demeaning hookup with “Inwood Daddy.” How autobiographical is this show?
Jackson: I’m not using the word autobiographical because, to me, it connotes apples-to-apples experiences. And that’s not what A Strange Loop is. For sure, lots of things came from personal experience, but most are fictionalized. And part of how the piece operates is that it’s this person’s perception of events. So while I did have an experience that was similar to Inwood Daddy, it’s not exactly what happened. I’ve been using the term self-referential as opposed to autobiographical, because this is different from I Know Why the Caged Bird Sings. I love Caged Bird. But this is not that kind of piece.
WSWD: In recent seasons, the gay black male experience has been supervisible: plays by Robert O’Hara, Jeremy O. Harris, Donja R. Love. And Tarell Alvin McCraney—whose Choir Boy was just nominated for a Tony. Have they paved the way for yours?
Jackson: I don’t know. I can’t control what connections people make. One difference is that I’m a musical theater writer. But also, part of what I’m hoping to achieve is showing that the black gay male experience is a multiplicity. We don’t all agree on everything; we haven’t all walked the same road. There’s an expression that I came up with a couple of years ago that I use flippantly, but I actually mean it: The Fine-Ass Nigga Finishing School.
Part of what I’m hoping to achieve is showing that the black gay male experience is a multiplicity.
WSWD: What’s that?
Jackson: It’s where you get stories about black gay or black queer people, and the bodies that appear onstage are all Instagram-worthy: thin and muscled and beautiful and abs. In my story, the main character is not that. He’s overweight and he doesn’t have a big dick. He’s not this capitalist object that everyone is oohing and aahing over, whether or not he experiences similar trauma or racism that the Fine-Ass Nigga Finishing School graduates have in those stories. I just think that that’s something that gets lost: Not all gay men get the same access. Class plays into that. I try to represent that in Usher’s story. He doesn’t get to go on Grindr and just be gobbled up. He doesn’t have a rich white man who’s gonna pay for him. He has to struggle to find himself valuable because the world doesn’t have any use for his shape.
WSWD: He’s not a commodity.
Jackson: No. And so he has to rely on his wit and his brain. He can’t take off his shirt and make money. He’s not a graduate of the Fine-Ass Nigga Finishing School. He was kicked out at an early age.