A Strange Loop—the groundbreaking Tony and Pulitzer Prize-winning musical by Michael R. Jackson—has been extended in Toronto!

              ALL BLACK MUSICAL OPENS WEDNESDAY and runs from April 22 to June 1, 2025 at the Soulpepper Theatre in downtown Toronto's Distillery District.

WOWIE. ZOWIE. and Slap My Fanny—ONE OF BROADWAY’S MOST SUCCESSFUL BLACK MUSICALS HITS TORONTO

Four Theatre Companies Unite to Bring A Strange Loop to Canadian Audiences

By Stephen Weir

The all-Black, all-bold, all-out A Strange Loop has landed in Toronto, and it’s making noise—both on and off the stage. Four of the city’s top theatre companies—Soulpepper Theatre, The Musical Stage Company, Crow’s Theatre, and TO Live—have teamed up to present the Canadian premiere of this Pulitzer Prize and Tony Award-winning musical.

The curtain officially rose last Wednesday at the Soulpepper Theatre in the Distillery District to a full house—standing room only (though to be fair, all that standing happened during the thunderous standing ovation at the end of the two-hour show).

Like the name suggests, A Strange Loop is a loopy, raw, and painfully funny story of a young Black queer writer named Usher (played with emotional fire by American actor Malachi McCaskill). Usher works in New York City as—you guessed it—an usher at The Lion King, dressed in a monkey suit while writing a musical about a young Black queer writer... writing a musical. You get the idea. It's self-aware. It's brilliant.

The musical made waves when it won the Pulitzer Prize for Drama in 2020, making Michael R. Jackson (no relation to that Michael Jackson) the first Black solo writer to win that prestigious award. In 2022, the show moved to Broadway, racking up 11 Tony nominations and winning Best Musical and Best Book of a Musical, solidifying Jackson’s reputation as one of the most fearless and important new voices in American theatre.

As a Black, gay playwright and composer, Jackson tells a story rarely seen on any stage—Broadway included. His voice is raw, honest, and unapologetically personal. And let’s not forget—during its Broadway run, A Strange Loopstopped traffic in Times Square, with lines of fans wrapping around the block.

This provocative production mixes humour and heartbreak as Usher battles the voices in his head—personified by six actors called his “Thoughts”—while struggling to write a story that truly reflects who he is.

Enter Malachi McCaskill, who played Usher on the show's California tour, including sold-out performances in San Francisco and Los Angeles. In person, he’s a mountain of a man—tall, stocky, and blessed with a voice that could shake the rafters. When he sings about his mother, the Mylar set walls tremble under the power of his pitch and presence.

The cast is small—just seven—but mighty. The six actors who play Usher’s “Thoughts” take on multiple roles: family members, inner demons, ex-lovers, cultural critics. Gender-swapping is baked into the performance. Usher’s mother is often portrayed by a bearded male actor, which adds layers of complexity, humour, and theatrical weirdness. It’s not played for camp—it’s played for truth.

Let’s be clear: A Strange Loop is about being gay, and it doesn’t hold back. The language is explicit, the humour is dark, and some lines—like Usher being told to “twist his mother’s titties”—will shock some theatregoers. This isn’t a show for young children or anyone looking for a safe, sanitized night out.

That said, the all-Black cast is exceptionally strong. Many come with classical theatre training—Stratford credits included—and they move seamlessly between song, movement, and fast-paced dialogue. Musically, it stays close to Broadway tradition, though it feels intentionally boxed in—reflecting Usher’s sense of being trapped by expectations. The plot occasionally stretches during scenes about Usher’s home life, but even then, the show never loses its emotional punch.

And who showed up? Well, mostly White theatregoers, at least on opening night. In New York, A Strange Loop was hailed as a cultural and commercial triumph that shook up the American Black theatre world. Will it do the same in Toronto? Will Black audiences make the trip downtown to see what all the cheering’s about?

ALL-BLACK MUSICAL A STRANGE LOOP RUNS APRIL 22 – JUNE 1, 2025

Soulpepper Theatre, Distillery District, Toronto