Michael R. Jackson spent almost two decades writing a show about a guy writing a show about a guy writing a show. It sounds like a headache. On paper, A Strange Loop Broadway shouldn't have worked. It’s a "big, Black, and queer-ass American Broadway show" (his words, not mine) that tackles systemic racism, sexual identity, body image, and the crushing weight of artistic ambition. Usually, Broadway wants something safe. It wants The Lion King. It wants a jukebox musical where you already know all the words.
Instead, it got Usher.
Usher is a fat, Black, queer writer working as a front-of-house usher at The Lion King. He’s stuck in a cognitive feedback loop. He is haunted by "Thoughts"—six physical actors representing his daily anxieties, his parents' disapproval, and the historical ghosts of James Baldwin and Zora Neale Hurston. It’s raw. It’s uncomfortable. It’s also one of the few things in recent theater history that feels genuinely dangerous.
The Long, Weird Road to the Lyceum Theatre
Most people think this show was an overnight success because it won the Pulitzer Prize for Drama in 2020 before it even hit the big leagues. Nope. Jackson started working on this as a monologue at NYU back in the early 2000s. It breathed. It morphed. It sat in drawers. By the time it reached Playwrights Horizons off-Broadway in 2019, it had become a cult phenomenon.
When it finally landed at the Lyceum Theatre on Broadway in 2022, the stakes were weirdly high. It wasn't just a musical; it was a litmus test for whether the "post-2020" Broadway actually cared about diverse stories or if it was just posturing.
The show is meta. Like, really meta. The title comes from Douglas Hofstadter’s concept in Gödel, Escher, Bach, which basically argues that the "self" is just an abstract loop of symbols. Jackson takes that dense philosophy and turns it into a catchy, albeit biting, score. You’re tapping your foot to songs about "Inner White Girls" and the trauma of "Exile in Gayville." It’s a jarring contrast that works because the music is so damn good.
Why People Got It Wrong
A lot of critics and casual theatergoers tried to box A Strange Loop Broadway into a "trauma plot" narrative. They thought it was just another "woe is me" story about being marginalized. That’s a massive oversimplification. Honestly, the show is more of a comedy than a tragedy—a dark, cynical, biting comedy that refuses to give the audience a "happily ever after."
Usher isn't always likable. He’s judgmental. He’s stuck. He’s often his own worst enemy. That is what makes it human. Real representation isn't about making characters perfect; it's about letting them be as messy as everyone else.
The Casting Shift
When the show moved to Broadway, Jaquel Spivey took over the lead role of Usher. He was a newcomer. Fresh out of college. No Broadway credits. People wondered if he could carry a 100-minute show where he never leaves the stage. He didn't just carry it; he redefined it. His performance brought a vulnerability that made the audience feel like they were intruding on a private therapy session.
The "Thoughts"—Antwayn Hopper, James Jackson Jr., L Morgan Lee, John-Michael Lyles, John-Andrew Morrison, and Jason Veasey—stayed mostly the same from the off-Broadway run. Their chemistry is what kept the show from spiraling into total abstraction. They are a Greek chorus of insecurities. They are hilarious, terrifying, and deeply familiar to anyone who has ever had a voice in their head telling them they aren't enough.
The Cultural Impact and the Tony Awards
2022 was a wild year for the Tonys. A Strange Loop Broadway went in with 11 nominations. It walked away with Best Musical and Best Book. Jennifer Hudson, who was a producer on the show, achieved EGOT status that night.
But beyond the trophies, the show did something more important. It proved that there is a massive, underserved audience for experimental theater. You don't need a falling chandelier or a helicopter to make an impact. Sometimes you just need a guy in a red vest talking to his own brain.
It’s worth noting that the show didn't run forever. It closed in early 2023 after 301 performances. Some saw this as a failure. It wasn't. For a show this specific, this challenging, and this unapologetic to run for nearly a year on 45th Street is a miracle. It paved the way for shows like Fat Ham and Jaja’s African Hair Braiding to find a home on the Great White Way.
Acknowledging the Critics
Not everyone loved it. Some traditionalists found the language too graphic. Others thought the meta-narrative was too "inside baseball"—a show for theater nerds about theater nerds. There’s some truth to that. If you aren't familiar with the tropes of musical theater or the specific cultural references Jackson pulls from, some of the jokes might fly over your head. But the emotional core—the desire to be seen and the fear of being truly known—is universal.
What You Can Learn from Usher’s Journey
If you’re a creator, or just someone feeling stuck in your own "loop," there are actual takeaways from how this show was built and received.
Don't wait for permission. Michael R. Jackson didn't wait for a producer to tell him his story was "marketable." He wrote it because he had to. He spent 18 years refining it. Quality takes time, and sometimes the world needs a decade or two to catch up to your vision.
Specific is universal. The more specific Jackson got about Usher’s life—his specific church upbringing, his specific body dysmorphia, his specific taste in music—the more people from completely different backgrounds saw themselves in him. Don't file down the edges of your story to make it "accessible."
Embrace the discomfort. The most talked-about scenes in the show are the ones that make people squirm. The "Tyler Perry" sequence is a scathing critique of Black entertainment tropes that many people found offensive or "too much." But that friction is where the art lives.
Actionable Next Steps for Theater Lovers
If you missed the Broadway run, you haven't missed out on the experience. The legacy of the show lives on through its recordings and its influence on new writers.
- Listen to the Original Cast Recording: Start with "Intermission" and "Today." Pay attention to the lyrics. Jackson is a master of the "patter song," and the wordplay is dense. You’ll need a few listens to catch everything.
- Watch the Documentary Clips: There are several "making of" features on YouTube and through the American Theatre Wing that detail the transfer from off-Broadway to the Lyceum. They are masterclasses in production.
- Read the Script: The book of the musical is published. Because the show is so meta, reading the stage directions provides a whole new layer of understanding that you might miss while watching the actors.
- Support Local Independent Theater: A Strange Loop Broadway started at a small non-profit. The next ground-breaking show isn't starting in a 1,500-seat house; it’s starting in a basement or a 99-seat black box. Go find it.
The loop might be strange, but it’s ours. Usher’s struggle to define himself outside of the expectations of his family, his peers, and his "Thoughts" is the definitive struggle of the modern era. We are all just trying to write our way out of our own loops.