April 22 – June 1, 2025 | CANADIAN PREMIERE
Baillie Theatre, 55 Mill St, Toronto
Get ready for a theatrical experience like no other as A Strange Loop, the 2022 Pulitzer Prize-winning and Tony Award-winning musical, makes its Canadian premiere! With Best Musical and Best Book of Musical accolades under its belt, this daring and dynamic production promises to captivate audiences with its bold storytelling, humour, and emotional depth. At the heart of this extraordinary show is a spectacular cast, led by Malachi McCaskill, who brings the iconic role of Usher to life.
The Story
A Strange Loop takes you on a rollercoaster ride through the life of Usher, a Black, queer writer who is writing a musical about a Black, queer writer writing a musical. It’s a story of self-discovery, identity, and the struggle to reconcile personal truth with societal expectations. Usher is at a crossroads in his life, grappling with his self-worth, relationships, and the weight of creative expression. The musical is not just a reflection of his life, but also a deep dive into the messy, magical process of artistic creation and what it means to live authentically.
Malachi McCaskill as Usher
The Canadian premiere of A Strange Loop features Malachi McCaskill as Usher—a role he knows well, having played it during the West Coast premiere in San Francisco (A.C.T.) and Los Angeles (Ahmanson Theatre) earlier this year. McCaskill brings exceptional depth to Usher, capturing the character’s vulnerability, humour, and complexity. His performance has been hailed as both powerful and poignant, earning him critical acclaim as one of the standout talents of the production.
Joining McCaskill as his ‘Thoughts’ are:
- Sierra Holder (Peter’s Final Flight, Crow’s Theatre/Ross Petty Productions)
- Nathanael Judah (Shaw Festival company member)
- Marcus Nance (Natasha, Pierre & the Great Comet of 1812, Crow’s Theatre/Musical Stage Company)
- Davis Okey-Azunnah (Beautiful – Carole King Musical, Royal MTC)
- David Andrew Reid (Hairspray, Theatre Aquarius)
- Amaka Umeh (history-making lead in Hamlet, Stratford Festival)
- Plus David Lopez (Charlie and the Chocolate Factory, YPT) and Travae Williams (Rent, Stratford Festival) as cast swings.
A Strange Loop – Meet the Cast
About the Musical
Written by Michael R. Jackson, A Strange Loop is a fearless exploration of race, sexuality, and the artistic journey. The musical weaves together elements of comedy and drama, offering a visceral, yet deeply relatable experience. The show’s innovative structure allows the audience to experience Usher’s thoughts and emotions in real time, making it a truly immersive theatrical experience.
With a cast that brings such a layered and compelling story to life, A Strange Loop is sure to be an unforgettable and transformative theatrical event. This is one show you won’t want to miss—prepare for a performance that is as strange as it is extraordinary!
