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Though the 2020s are only halfway over, Michael R. Jackson’s “A Strange Loop” will almost certainly be remembered as the greatest — and most important — American musical of this decade. Billed as a “big, Black and queer-ass American Broadway show,” it’s an unapologetically brash, messy, overstuffed and awe-inspiring achievement.Ìý

“A Strange Loop” won the Pulitzer Prize for Drama in 2020, one of only 10 musicals in history to earn that honour, typically bestowed to straight plays. It opened on Broadway two years later, where it deservedly snagged the Tony Award for best musical.Ìý

I was floored by that original production. And I knew the musical had to be seen by Canadian audiences. But ever since it was announced last year that a new staging of “A Strange Loop” would be coming to Soulpepper — co-produced with the Musical Stage Company, Crow’s Theatre and TO Live — I’ve been saddled with a nagging question: could the show be translated for audiences on this side of the border? 

Jackson’s musical is both culturally and geographically specific. Set in New York City, it follows Usher (Malachi McCaskill), a 25-year-old fat, Black and queer musical theatre writer and Broadway usher who’s stuck in a cycle of self-loathing. All the while, he’s constantly badgered by a sextet of pestering, larger-than-life thoughts in his head (Sierra Holder, Amaka Umeh, Matt Nethersole, David Andrew Reid, Nathanael Judah and Marcus Nance) as he’s trying to complete his autobiographical musical called “A Strange Loop.” (If this plot sounds loopy, just wait until you see the actual show.) 

References to the American filmmaker Tyler Perry abound. So too to “The Color Purple” (both the original novel by Alice Walker and the Broadway musical adaptation). Oh, and there’s a song about shagging the now-disgraced theatre producer Scott Rudin.Ìý

Part of what made the Broadway production special, for me, was experiencing it with an audience who got every one of those references. As much as Jackson was writing “A Strange Loop” for himself (he’s described the show as “emotionally autobiographical” and his “life raft”), it also felt like it was written for many of its New York audiences, who saw themselves reflected in the show and had their experiences validated.Ìý

While I don’t doubt some º£½ÇÉçÇø¹ÙÍøtheatregoers may feel that same personal connection with the material, “A Strange Loop” certainly lands differently here than in the U.S. But watching this Canadian staging on Wednesday, I realized that the question I had coming into this new production was based on a false premise. Can the show be translated for audiences here? It doesn’t need to be.Ìý

It doesn’t matter that many of those references flew over the audience’s heads (just like when I first saw the show). Jackson writes with such specificity that, almost paradoxically, it lends the entire work a refreshing sense of universality.Ìý

You don’t need to be anything like Usher to sympathize with him. You immediately feel his plight as he navigates his complicated relationship with his parents, who disapprove of his homosexuality and want nothing more than for their son to write a “clean, Tyler Perry-like gospel play.” You immediately understand why Usher is so hesitant to engage in a gay scene filled with men who only want to “f—k and run.” You immediately get Usher’s disdain for a world of Black art that’s too focused on profitability rather than integrity.Ìý

What makes “A Strange Loop” a landmark piece of theatre is its subject matter. While almost every other musical focuses on the individual in relation to the community around them, Jackson’s story looks inward, taking place entirely in the mind of its protagonist, whose anthropomorphized thoughts transform into apparitions of the people in Usher’s life.Ìý

“A Strange Loop” is a musical about identity, but it also rejects the notion of “identity play” as a genre. Jackson doesn’t draw Usher as a victim. Instead, he’s a protagonist with complete agency over his trajectory, a character who’s far more complex than the sum of his labels.Ìý

Jackson’s musical takes aim at other targets, too: Grindr culture, Beyoncé, sellout Black artists. “Who knew slavery, police violence and intersectionality could be so lucrative?” Usher remarks at one point, with McCaskill breaking the fourth wall and staring out into the audience, implicating the onlookers.Ìý

I’ll admit that I appreciated the material of “A Strange Loop” even more this time around than when I first saw it on Broadway. It’s a show so dense that it demands multiple viewings. And, if anything, the cultural and geographical distance of watching this show in º£½ÇÉçÇø¹ÙÍøoffers the material some much needed room to breathe.Ìý

A test for any new theatrical work is whether it still holds up in the face of new interpretations. In Ray Hogg’s exuberant production, “A Strange Loop” proves that it can. Not only that, the musical also more than overcomes any weaknesses in this somewhat muddled staging.Ìý

The role of Usher is one of the most challenging male roles in musical theatre, up there with Jean Valjean, Sweeney Todd and Evan Hansen. Onstage for almost the entire musical, it’s a part that requires immense emotional vulnerability and superb vocal stamina. (Usher sings a staggering 13 of the show’s 17 pop-infused songs.)

McCaskill, sharing the role with Charlie Clark (scheduled to perform at Wednesday and Saturday matinees), perfectly taps into Usher’s complexity. Particularly toward the end of the musical, his portrayal is coloured with both strength and pain, confidence and overwhelming insecurity.Ìý

McCaskill’s voice, however, sounded somewhat tentative on opening night, with the score sitting uncomfortably in his range, right on the break — or passaggio — between his head and chest voice.Ìý

His Usher also seems to fade into the background for the first few scenes of the show.ÌýMuch of the issue has to do with Hogg’s ostentatious staging, with too many songs featuring the Thoughts standing at the front of the stage and singing to the audience, instead of clearly establishing that these characters are, in fact, voices in Usher’s head.Ìý

But after Hogg’s production snaps into focus, it forges ahead with clarity and style. Brian Dudkiewicz’s set nimbly transforms into various settings, while Michelle Ramsay’s lighting designs are sharp and appropriately colourful. Rodney Diverlus’s choreography, drawing from a wide variety of styles, is dazzling.Ìý

Each of the actors playing the six Thoughts are incredible, deftly balancing pathos and humour. But special mention must go out to Reid as Thought 4, who’s incarnated as Usher’s God-fearing mother and delivers the show’s most searing song, “Periodically,” with fiery passion, and Umeh as Thought 2, nailing each of the comic roles they’re in.Ìý

By the end of “A Strange Loop,” which runs for two hours without an intermission, you’re left exhausted. But Jackson’s deeply moving, introspective masterpiece will also leave you parsing the infinite loops of your own life. There’s pain in that, as Usher can attest. And healing, too.Ìý