A “strange loop” could refer to the concept of a self-referential, cyclical journey through levels of a hierarchy, where one ends up back where they started. It’s also a Liz Phair song.
Michael R. Jackson’s Pulitzer Prize-winning A Strange Loop, making its Canadian premiere in the Distillery District via a Soulpepper Theatre/Crow’s Theatre/TO Live/Musical Stage Company collaboration, shows us one gay Black man’s desire to understand his own place within the hierarchical cycles of his identity — while also wishing he could just sing some Phair. The show contrasts deeply personal reflection with audacious spectacle, challenging the conventions of large-scale musical theatre while carving its radical place in the Broadway canon.
Usher (Malachi McCaskill), navigating the world in his “fat, Black, queer body,” and working as an usher at The Lion King on Broadway, is trying to write a musical about… a fat, Black, queer usher working at The Lion King on Broadway. The piece’s opening number (the most showtune-like in the pop-steeped score) drops us into the middle of Usher’s (and Jackson’s own) meta-narrative struggle to artistically represent his intersecting identities.
Plagued by his own Thoughts (Sierra Holder, Nathanael Judah, Marcus Nance, Matt Nethersole, David Andrew Reid, and Amaka Umeh), Usher grapples with mainstream culture’s expectations for Black queer representation; his struggles to satisfy his desires, despite being deemed undesirable by Grindr standards; and his parents, who want him to write a Tyler Perry-style gospel play, thinking it might save him from those same desires, which they perceive as a sin.
Eschewing linear narrative, this daringly candid show, dripping in references to pop culture (including to that Disney show he works for), follows Usher’s struggle through collisions of race, art, and sex. Particularly refreshing is how openly and explicitly Jackson speaks to internal dynamics of queer intimacy, recontextualizing vulgarity as an honest representation of a person’s reality, and asking why labels like “vulgar” are placed on that kind of reality in the first place.
While the script doesn’t signpost which moments of Usher’s experience are real versus part of his script-in-progress, the ambiguity feels intentional — an outward explosion of internalized cycles of racism, homophobia, and religious/artistic expectations, as well as the self-loathing they imprint. Director Ray Hogg leans into this chaos. The frantically paced first half of the intermission-less show often has Usher cowering among his Thoughts’ embodiment of Rodney Diverlus’ punchy, stage-swarming choreo, or evading Brian Dudkiewicz’s set of wheeled mirrored flats that literally reflect his multitude of self-perceived shortcomings.
After this initial mayhem, the show circles inward to a more grounded but no less intense second half, pivoting from madcap humour to durational discomfort. A song such as “Exile in Gayville,” making light of Usher’s hookup struggles early in the show, directly contrasts the later “Inwood Daddy,” where a white man violently fetishizes Usher in the midst of intimacy — shifts that make us reflect on how hurt can often simmer under laughter. When Usher finally gives his parents a Tyler Perry play, the ensuing stylistic shock of commercialized, wire-rigged neon and choral testifying may at first have you swaying along, until the reality of Usher’s pained rage against cultural homophobia overtakes the spectacle of “God’s punishment” his family would have him buried in fear of.
McCaskill, decked in a bellhop uniform designed by Ming Wong, reservedly carries this pain, next to a cheeky wit he keeps in sight but achingly out-of-reach behind Usher’s self-consciousness — a restraint that had me cheering for the moments of release the character achieves. Usher leads most of the show’s songs, which range from emo rock to impassioned gospel to power ballads, with music director Chris Tsujiuchi conducting him and the five-person pit band through this aural journey. While at the opening night performance, McCaskill’s voice seemed to strain in the score’s higher register, these imperfections feel like part of his characterization, given the metatheatricality at play.
Usher’s ensemble of Thoughts run a marathon, stepping in and out of the many voices his psyche conjures, and all six performers win gold. Even in moments of choral unison, each finds unique physicalities and personalities, always seeming like they could belong to sections of the same brain. Particularly memorable is Umeh’s physically elastic and exaggerated take on Harriet Tubman, who derides Usher’s artistic race-betrayal in the melodically sinister “Tyler Perry Writes Real Life.” I also appreciated Reid as Usher’s mother in “Periodically,” a chilling journey from proclaiming love for her son to viciously judging how he loves.
A Strange Loop transforms an intimately individual musical perspective on identity into an expansively resonant and entertaining experience. While Usher may not ultimately close his loop, there’s catharsis in seeing “one lone gay Black boy” find contentment, if not total clarity, in embracing the messy paradoxes of being. I’m excited to loop back and see it again ASAP.
A Strange Loop runs at the Young Centre for the Performing Arts until June 1. Tickets are available here.
Intermission reviews are independent and unrelated to Intermission’s partnered content. Learn more about Intermission’s partnership model here.
WRITTEN BY
jonnie lombard
jonnie is a trans theatre artist / thing from the woods stumbling through sidequests of sentience. They were a participant in the 2024 New Young Reviewers Program, and will always say yes if you ask them to go dancing.
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