The Musical Stage Company, Soulpepper Theatre, Crow’s Theatre, and new co-production partner, TO Live, are thrilled to announce the cast and creative team for the highly anticipated Canadian premiere of the Pulitzer Prize-winning musical A Strange Loop.

Created by Michael R. Jackson, A Strange Loop is a sharp, hilarious, and profoundly moving exploration of identity, self-doubt, and creativity. Following the journey of Usher, a young Black queer writer working as an usher at The Lion King, this provocative, groundbreaking musical brilliantly blends humour and heart as Usher battles the swirling voices in his head—personified as “Thoughts”—while writing a musical about his own life.

“Furiously entertaining” (Variety) and “a dazzling ride” (The New York Times), A Strange Loop masterfully tackles themes of race, sexuality, familial expectations, and personal authenticity with unmatched wit and honesty. With its bold storytelling and unforgettable music, this production is a must-see event for anyone who has ever wrestled with who they are and who they want to be.

Malachi McCaskill will star as Usher, a Black, queer writer writing a musical about a Black, queer writer writing a musical about a Black, queer writer…Malachi McCaskill starred in the west coast premiere of A Strange Loop in San Francisco (A.C.T.) and Los Angeles (Ahmanson Theatre) earlier this year.

“After two rounds of cross-Canada casting, and a search that extended into the U.K. and the U.S., I am thrilled to welcome Malachi as our Usher,” said director Ray Hogg. “He is an exciting star on the rise whose spot-on blend of tell-it-like-it-is humour and gravitas capture the essence of Usher that allows us into the nakedly honest telling of the Black gay experience.”

Hogg continues, “Malachi has the perfect synthesis of emotional access, technical prowess, and a stunning depth of artistry. This play is entirely about having a plus-size, Black, queer identity and it was critical to find someone who not only has this lived experience, but also has the technical and emotional strength to carry the many facets of this extraordinarily complex character. Malachi will take you on a life-changing journey, bringing you closer to understanding the Black queer people in your life.”

Joining Malachi McCaskill in A Strange Loop as the six Thoughts are: Sierra Holder (Peter's Final Flight, Crow’s Theatre/Ross Petty Productions; choreographer of Guildwood, Next Stage Festival); Nathanael Judah (Sousatzka world premiere, Shaw Festival company member); Marcus Nance (Natasha, Pierre & the Great Comet of 1812, Crow’s Theatre/Musical Stage Company; Stratford Festival company member); Davis Okey-Azunnah (Beautiful - Carole King Musical, Royal MTC; Joseph and the Amazing Technicolor Dreamcoat, Drayton Festival); David Andrew Reid (A Few Good Men, Drayton Festival; Hairspray, Theatre Aquarius); Amaka Umeh (history-making lead in Hamlet, Stratford Festival; Three Sisters, Soulpepper); plus David Lopez (Charlie and the Chocolate Factory, Mary Poppins, YPT); and Travae Williams (Rent, Stratford Festival; Jersey Boys, Drayton Festival) as cast swings.

“I’m also really excited to work with our ensemble of ‘Thoughts,’” adds Hogg. “What I love about this group is their excitement and willingness to come together and work playfully and collaboratively to tell Usher’s story. I consider this cast of Black artists to be musical theatre royalty. Some are long-time collaborators of mine, and some are brand-new partners. In all instances I feel absolutely privileged that they chose A Strange Loop to fill their busy dance cards this season!”

The creative team includes writer Michael R. Jackson (book, music, and lyrics), director Ray Hogg, music director Chris Tsujiuchi, choreographer Rodney Diverlus, scenic designer Brian Dudkiewicz, costume designer Ming Wong, lighting designer Michelle Ramsay, sound designer Brian Kenny, and intimacy director Lisa Karen Cox. The stage management team consists of Sarah Miller, Farnoosh Talebpour and Evan Reid.

The Musical Stage Company, Soulpepper Theatre, and Crow’s Theatre, three of Toronto’s theatrical powerhouses, will now be joined by TO Live, one of Canada’s largest national multi-arts institutions, to co-present the internationally renowned musical A Strange Loop in Toronto.

“TO Live is proud to be a dedicated partner, helping organizations turn their most ambitious dreams into reality,” said Clyde Wagner, President & CEO of TO Live. “A Strange Loop is the perfect embodiment of this collaboration. We are beyond excited to support three remarkable organizations in bringing this extraordinary Toronto production to life.”

The Musical Stage Company, Soulpepper Theatre, Crow’s Theatre, and TO Live present

A Strange Loop

April 22 - June 1, 2025, at Soulpepper Theatre

Opening night: Wednesday April 30, 2025

Tickets, starting at $65, are now on sale and are available online at www.soulpepper.ca, by phone at 416-866-8666 and 1-888-898-1188, and by email at boxoffice@youngcentre.ca. For in-person sales, the Box Office, located in the Young Centre for the Performing Arts, 50 Tank House Lane, is open Tuesday to Saturday 1-5 pm.

Performance schedule: Tues-Sat @ 7:30 pm, Wed, Sat, Sun @1:30 pm

*The first Wednesday (April 23) is a one-show day

*Sunday, April 27 performance is at 7:30 pm

Running time: 1 hour and 40 minutes with no intermission

Young Centre for the Performing Arts, The Marilyn and Charles Baillie Theatre

50 Tank House Lane,

Distillery Historic District, Toronto

ABOUT THE MUSICAL STAGE COMPANY

Where music and storytelling collide.

The Musical Stage Company is Canada's largest not-for-profit professional theatre company dedicated to the development of new musical theatre. Established in 2004, we drive the evolution of musical theatre locally, nationally, and internationally by telling our most important stories with music.

We are inspired by music’s unique ability to affect people viscerally. We are committed to cultivating experiences—onstage and off—that transform lives, build empathy, create community through musical theatre writers, and build national and international partnerships. Our musical productions—including award-winning contemporary musicals, world premieres, and concerts—are seen live by 30,000 people over the 80-plus nights that we are onstage annually in venues both traditional and surprising. Our work has been recognized with 135 Dora Award nominations, 28 Dora Awards, and 23 Toronto Theatre Critics’ Awards.

Beyond the stage, we build and enrich communities through musical storytelling. Our robust education programs develop the artists and audiences of tomorrow, offering musical theatre training that boosts self-confidence and self-expression for over 500 people each year without cost to the participants. We also curate innovative musical programs in partnership with diverse organizations, maximizing the resonance of our work across disciplines and communities.