Title: A Strange Loop
Written by: Michael R. Jackson
Performed by: Malachi McCaskill, Charlie Clark, Sierra Holder, Nathanael Judah, David Lopez, Marcus Nance, Matt Nethersole, David Andrew Reid, Amaka Umeh
Director: Ray Hogg
Company: Musical Stage Company, Soulpepper, Crow’s Theatre, TO Live
Venue: Soulpepper
City: Toronto
Year: Until June 1, 2025
Critic’s Pick
Director Ray Hogg’s ensemble cast breathes new context into the production.Dahlia Katz/Supplied
When A Strange Loop premiered off-Broadway at Playwrights Horizons in 2019, the musical, about a fat Black queer man writing a musical about a fat Black queer man writing a musical about – you get the picture – covered new ground for live theatre. Michael R. Jackson’s work asked dark, squirmy questions about race, sexuality and the mental fortitude required to understand and document one’s never-ending plunge into the self. When protagonist Usher wondered aloud whether anyone cared about a writer struggling to write, the answer — a resounding yes — hadn’t yet been answered with a Pulitzer Prize and two Tony Awards.
Indeed, judging by A Strange Loop‘s glowing reviews on Broadway and its subsequent bevy of awards, quite a few people care about a writer struggling to write – at least when that story is told with Jackson’s trademark rhetorical fizz, manifested in A Strange Loop as profanity-peppered jokes about AIDS, The Lion King and Popeyes chicken, as well as an extended Tyler Perry pastiche as funny as it is bizarre.
Jackson was far from the first to dramatize his experience of making musical theatre – [title of show], which opened on Broadway in 2008, shares a common vocabulary of playful jabs against Stephen Sondheim and frilly playwright retreats. Jonathan Larson’s Tick, Tick… Boom!, too.
Malachi McCaskill stars as Usher.Dahlia Katz/Supplied
But A Strange Loop was singular in how it placed the fairly insular process of writing a musical in dialogue with the more broadly relatable experiences of coming out to a conservative family, navigating a complicated relationship with one’s parents and learning how to set healthy boundaries with friends, colleagues and romantic interests. All of a sudden, the idea of a musical-within-a-musical-within-a-musical had marketable, societal appeal.
A Strange Loop‘s latest twist? Its journey across the northern border to Toronto, where Crow’s Theatre, Soulpepper, the Musical Stage Company and TO Live have produced the show’s Canadian premiere. Jackson’s spiky humour has survived the international transposition; so has his zesty, pop-infused score.
But it’s director Ray Hogg’s ensemble cast that breathes new context into A Strange Loop and creates a production where the most interesting thing about Jackson’s work isn’t the meta-theatrical satisfaction of knowing whether Usher‘s musical – also titled A Strange Loop – will succeed. Usher‘s thoughts, anthropomorphized into a small army of imaginary frenemies, all have memorable moments of stage time, but Amaka Umeh is a standout as Thought #2, who takes the form of everyone from Usher‘s mother to Harriet Tubman. There’s not a scene in the show that’s not improved by Umeh’s presence. The same goes for Marcus Nance, Thought #6, whose performance as a racist Grindr hookup is both deeply frightening and terribly, terribly sad.
American Malachi McCaskill is a solid Usher (so named because the 26-year-old works as an usher for The Lion King in midtown Manhattan), but then again, he ought to be: He’s played the role twice in the United States. On opening night, McCaskill struggled in the show’s first half, with some high notes seeming just out of reach after a long tech week and preview period.
By curtain call, however, McCaskill had made a compelling case for why Hogg might have thrown his casting net beyond Canada’s borders. Even after living with Usher‘s story for so long, the character still feels fresh in McCaskill‘s body, his pain newly etched on McCaskill‘s face. (His later songs were note-perfect, too.) When Usher makes a life-changing confession to his parents late in the show, it’s tough not to rush the stage to give him a big hug.
Despite the excellent cast, Hogg’s production is a touch uneven on the technical side. Ming Wong’s usually excellent costumes feel somewhat random here, with the Thoughts dressed in not-quite-matching tie-dye sweatsuits between their various bit parts. Brian Kenny’s sound design, too, could use some tweaks, especially in the first half. On opening night, the show lost a song’s worth of lyrics because of vocalists being drowned out by Chris Tsujiuchi’s (exceptional) band.
Brian Dudkiewicz‘s set is one of highs and lows. When it works, its clever mirrored panels evoke A Chorus Line, another musical about self-doubt within a crushing industry. But those panels seemed to get stuck on their tracks on opening night, landing in odd spots between scenes. They also make the stage feel crowded at times, leaving inadequate room for Rodney Diverlus‘s occasionally overwrought choreography.
I’m unconvinced, too, by some of Jackson’s writing (sorry, Pulitzer committee). A Strange Loop conjures a protagonist who thinks deeply and writes from the heart, but who doesn’t do much over the course of the musical. Things happen to Usher, rather than Usher effecting change in the world around him. That’s not an immediate deal breaker, but it makes for a first half in which Usher can – and does, in this production – become temporarily upstaged by his Thoughts.
That said, having seen A Strange Loop on Broadway, I’m much more impressed by Jackson’s material in Hogg’s production, thanks in part to its positioning in the cozy Baillie Theatre, which feels much more intimate and less sprawling than the 922-seat Lyceum Theatre in New York. When I saw A Strange Loop in 2022, I left the theatre feeling a bit hollow, unsure whether Usher would be okay. This time, I departed Soulpepper feeling buzzy and alive, Memory Song stuck in my head on a satisfying loop.
There are kinks to work out in Hogg’s production, performances to settle and sound levels to refine. A Strange Loop, which often feels more like an episode of Atlanta than a traditional Broadway musical, is a risky programming choice for patrons whose tastes might better align with a slice-of-life drama such as Life After, or a spectacle-heavy hit such as The Lion King.
But A Strange Loop makes the case for itself when Usher parses out the word “radical,” which is how his mother chooses to describe most of his work. Ten years ago, Hamilton was radical musical theatre – and indeed, Jackson wields a Hamilton barb early on in A Strange Loop.
Now, a decade later, theatre that’s reflective of today’s United States has more work to do, more culture wars to sift through, more socio-religious baggage to unpack. By those metrics, A Strange Loop is radical musical theatre, decisive and raw in how it addresses the realities of growing up as a fat Black queer artist gasping for shreds of affection. Could Hogg’s production be cleaner? Yes. But now’s the time for radical storytelling. Or, in A Strange Loop‘s case, for radical storytelling about radical storytelling about radical storytelling about …
