JACKSON: I wrote it when I was in grad school, and that song, like, went over well enough in my class that my teacher encouraged me to continue writing my own music. OWENS: (As Usher, singing) Five-foot-four, high school gym, sneaking a cupcake - these are my memories. SHAPIRO: What was the first song you wrote? And it just sort of took on a life of its own, slowly but surely, after that. And I - so I just wrote this monologue about this young, Black gay man walking around New York wondering why life was so terrible. It was just a monologue called Why I Can't Get Work because I was about to graduate from playwriting school at NYU, and I just wasn't sure what was, like, in store for me. And it was just a personal monologue that I sort of wrote for myself as I was about to graduate from college at that time. SHAPIRO: You began it, like, almost 20 years ago - right? - just after 9/11? You know, and especially with this show in particular, just because the way that it started was such a - like, a personal thing for me, and, like, I'd never expected it to go any of the places that it went when I began it. I mean, it definitely wasn't on my vision board for sure. It's got to be, like, a mind leap to suddenly be embraced by, like, the biggest awards there are, right? SHAPIRO: This show is so much about being an outsider and not being accepted by the mainstream and feeling, like, apart from. JACKSON: I'm into it, but every once in a while I have, like, a moment of I can't believe this. How does it feel to have that attached to your name now, like, forever and ever and ever?
SHAPIRO: Hi, Pulitzer Prize winner Michael R. OWENS: (As Usher, singing) I hate days like today. And so we are bringing you an edited version of that conversation from 2020. Well, two years later, that long postponed opening night has arrived. And he'd also gotten some bad news - the show's Broadway opening was postponed indefinitely because of the pandemic.
SHAPIRO: A couple of years ago, I spoke to Jackson for the Kentucky Author Forum's podcast series "Great Podversations." At the time, Jackson had recently gotten the good news that he'd won the Pulitzer after the show's off-Broadway run. But change comes way too slow, and I am in a hurry. OWENS: (As Usher, singing) I want to break the cycle that's so ingrained in me. Ad infinitum and is sort of cycling through his own perceptions of himself and his own self-hatred.
MICHAEL R JACKSON: So "A Strange Loop" is about a Black, gay musical theater writer who works as an usher at a Broadway show, who's writing a musical about a Black, gay musical theater writer who works as an usher at a Broadway show, who's writing a musical about a Black, gay musical theater writer who works as an usher at a Broadway show. When I asked him to explain what this semi-autobiographical musical is about, he described it this way. SHAPIRO: This big, Black and queer-ass American Broadway show was written by Michael R. UNIDENTIFIED ENSEMBLE #2: (Singing) Big, Black and queer-ass American Broadway show. UNIDENTIFIED ENSEMBLE #1: (Singing) Big, Black and queer-ass American Broadway. LARRY OWENS: (As Usher, singing) Big, Black and queer-ass American Broadway. It's called "A Strange Loop," and here's how the cast describes it in the show's opening number. A musical that opens on Broadway tonight has already won the Pulitzer Prize for drama.