A Strange Loop, the Pulitzer-Winning Musical About a Gay Theatre Usher

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A Strange Loop, Broadway Production
A Strange Loop, Broadway ProductionPhotography by Marc J Franklin

Following a hugely successful Broadway run, A Strange Loop has now arrived in London. Here, playwright Michael R Jackson talks about the inspirations behind the show

Michael R Jackson knows exactly how to sell A Strange Loop, his award-winning musical that is coming to London following a hugely successful Broadway run.I always describe it as a musical about a young fat Black gay musical theatre writer named Usher who works as an usher on Broadway,” Jackson begins. “And he’s writing a musical about a young fat Black gay musical theatre writer named Usher who works as an usher on Broadway. Who is writing a musical about a young Black gay musical theatre writer named Usher who works as an usher on Broadway …” Deep breath. “Ad infinitum,” Jackson continues with a smile, “as it cycles through his own self-hatred.”

Jackson started writing A Strange Loop nearly 20 years ago when he actually was working as an usher on a Broadway show – namely, Disney’s The Lion King. Because of this, he was convinced that his own show was too audacious, too risqué and, well, too gay for Broadway. After all, A Strange Loop opens with a song that promises “truth-telling and butt-fucking”, and then delivers exactly that. “I’d seen Broadway up close for so long and I was like, ‘There’s no way in hell that this musical is gonna get anywhere near it – period,’” he says. “I had decided the most I could maybe get was a respectable off-Broadway production."

A Strange Loop has since obliterated his expectations. After premiering off-Broadway in 2019, it won the prestigious Pulitzer Prize for Drama. Then, having acquired an astonishing roll call of producers including Billy Porter, RuPaul and Alan Cumming – all “lovely ambassadors” for the show, Jackson says – it transferred to Broadway in 2022 and became the most-nominated show at the Tony Awards. On the night, it won two top prizes: Best Musical and Best Book of a Musical. 

Despite being embraced by the mainstream theatre world, Jackson says he still feels like an outsider. “Because a lot of strides have been made by queer people over the last 20 years, there’s now less of a counterculture, which is where this [show] sort of sprang from,” he says. “And ultimately, I would characterise myself in many ways as a countercultural artist. And so to be recognised by, like, ‘the establishment’, I feel a little bit of a dissonance a lot of the time. But I just have to live with that dissonance.”

When A Strange Loop became a stage sensation, Jackson found himself having to point out that the show isn’t strictly autobiographical. “I refer to the piece as self-referential, which is to say that I did draw from personal experience to write it,” he says. “But it’s not as simple as apples to apples in the way events from my life are [portrayed] in the show.” The song Inwood Daddy, a coruscating take-down of racialised fetishisation by white gay guys, is rooted in truth but not ripped from his diary. “That was drawn from an experience I had in my twenties, where I hooked up with this older white man who turned the situation into a racialised experience that I wasn’t looking for,” Jackson says. “But that’s as far as it goes: the song is not exactly what happened in my personal situation.”

Jackson is under no illusion about why A Strange Loop has sometimes been misconstrued as his life story. “On a basic level, it’s just easier to do that – you don’t have to think as much,” he says. “But I also think there’s another component to it, [which is] that it’s easier to think that Black artists are just sort of suffering on the page or the stage.” He believes this reductive presumption is really a denial of Black creativity. “It’s saying our natural inclination is just to open up a vein and bleed,” he says. “We’re not really making anything; we’re just existing for your consumption.”

A Strange Loop is “much more complex than that”, Jackson says, partly as a result of its lengthy genesis. It started out as a monologue before he decided that Usher could write mash-ups of his own songs with alt-rock bangers by Liz Phair, one of Jackson’s favourite artists. A Strange Loop is named after Strange Loop?, the final track from her seminal 1993 album Exile in Guyville. But when Phair denied him permission to use her compositions, Jackson regrouped and wrote his own. He came up with the idea to have Usher surrounded by a chorus of six ‘Thoughts’ who “contextualise the story” after he saw an older theatre-goer who wanted a booster cushion call out “Usher! Usher!” The Thoughts assume a variety of roles during the show, morphing from “theatre patrons who are bothering Usher” to the character’s coolly critical parents.

In London, Usher will be played by Kyle Ramar Freeman, who understudied the role on Broadway, with six British actors – Sharlene Hector, Nathan Armarkwei-Laryea, Yeukayi Ushe, Tendai Humphrey Sitima, Danny Bailey and Eddie Elliott – as the Thoughts. “I hope people leave the show thinking about themselves, because that’s ultimately what it’s about: someone thinking about themselves,” Jackson says. “I hope that people see Usher’s story, and Usher’s story about Usher’s story, and that gives them a moment to reflect on their own story.”

A Strange Loop is playing at the Barbican Theatre in London until 9 September 2023.