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by Michael R. Jackson, directed by Roy Hogg

The Musical Stage Company, Soulpepper Theatre Company, Crow’s Theatre & TO Live, Young Centre, Toronto

April 30-June 8, 2025

Usher: “It’s the idea that your ability to conceive of yourself as an ‘I’ is kind of an illusion”

A Strange Loop is also a strange musical. It’s a musical about identity politics that does not believe in identity. It’s a musical about musicals that is also a brutal satire of musicals. It’s a story that has no ending. It’s a musical with a cast of seven but only one character. The audacious musical by Michael R. Jackson, first produced in 2019, was awarded the 2020 Pulitzer Prize for Drama and the 2022 Tony Award for Best Musical. Now four theatre companies in Toronto have banded together to present the work. From the results one can see why such a cerebral piece that deliberately flouts Broadway expectations might have been a critical success, but at only 293 performances it had a run that the New York Times noted was “usually short for a best musical winner”.

The sole character of A Strange Loop is Usher, a 25-year-old queer, fat Black man who works as an usher at The Lion King, the 1997 stage musical that gives audiences a Disneyfied vision of Africa where all animals are apparently vegetarians. Usher is a would-be musical theatre composer who is currently working on a musical called A Strange Loop about a queer, fat Black man who is writing a musical called A Strange Loop about queer, fat Black man who … ad infinitum.

The musical received praise for putting a queer, fat Black man at the centre of its story and highlighting the multiple forms of prejudice he encounters – homophobia, sizeism and anti-Black racism. As a queer Black man who uses dating apps in a vain attempt to find a partner or even a hookup, he finds that the gay White majority of users who favour those who are “straight looking and straight acting” are even more sizeist and racist.

The struggles Usher has in dating and with his family has led many to praise A Strange Loop as an identity play in musical form. Although set in 2019, Usher’s parents believe being gay and living in New York means certain death from AIDS. As for writing plays, they wonder why Usher can’t write a gospel play like Tyler Perry, whom they claim “writes real life”. For those who don’t know, Perry, a successful actor, playwright and filmmaker, presents stories from a “Christian” and frequently homophobic point of view. In the movie Temptation: Confessions of a Marriage Counselor (2013), based on his own play from 2008, Perry promotes the idea that AIDS is a “sinner’s disease”.

Tempting as it is to view A Strange Loop as an identity play, to do so is to ignore the musical’s peculiar title. As Usher explains in the musical, the title comes from the theory of David Hofstadter as articulated in his books I Am a Strange Loop (2007) and Gödel, Escher, Bach (1979) that there is no such thing as “I”. It is an illusion. As Hofstadter says, “In the end, we self-perceiving, self-inventing, locked-in mirages are little miracles of self-reference” or, in other words, “A mirror mirroring a mirror”. Hofstadter says, “The ‘I’ we create for each of us is a quintessential example of such a perceived or invented reality, and it does such a good job of explaining our behavior that it becomes the hub around which the rest of the world seems to rotate. But this ‘I’ notion is just a shorthand for a vast mass of seething and churning of which we are necessarily unaware”.

It should be clear that A Strange Loop cannot actually be about identity politics if Jackson believes like Hofstadter that there are no such things as self or identity. Obviously, such a view of the self is almost too abstract for the average theatre-goer to take in. Yet, this view is exactly what Jackson has used to structure his musical and thus challenge the norms of a traditional musical. The only character in A Strange Loop is Usher. The other six performers are his Thoughts. Usher is plagued or encouraged by the Thoughts and the forms they take but they are still Thoughts and never characters outside of Usher’s mind.

The first clue we have that this is so occurs when all six Thoughts appear dressed as Usher’s mother, exit, then re-appear dressed as Usher’s father. Thus, the Thoughts can take whatever form Usher is thinking about. Our natural inclination is to view the actors who seem to be playing other characters as independent from Usher. But, Jackson disabuses us of this notion quickly and irrefutably. He presents Usher on the subway where Thought 5 begins to flirt with him. Usher falls for the attention until Thought 5 reveals that he is not a Black man but one of Usher’s Thoughts: “I live in your imagination…. I’m white obviously…. And the fact that you would allow yourself even a moment of weakness to fantasize about a dick appointment with … me when you should probably just kill yourself? Well, that’s a testament to the awesome power of the white gaytriarchy.”

Though it is difficult to do, what we have to remember throughout the show is that all of Usher’s arguments with his mother and father and meetings with other characters are events occurring inside Usher’s mind. This includes the sequence when a kind woman, Thought 1, gives Usher encouragement when Usher is supposedly at work. This also includes the scene when Usher has sex with the White Man “Inwood Daddy”, Thought 6, and immediately regrets it.

A negative consequence of using Hofstadter’s “strange loop” as a model is that the feedback loops Hofstadter refers to do not change and have no ending. And so it is with the show. Usher concludes in the show’s final song that he is “Someone whose only problem / is with the pronoun ‘I’ / maybe I don’t need changing / maybe I should regroup / ’cause change is just an illusion”. The difficulty is that this realization could have come at any point in the musical. The Thoughts question how Usher plans to end the musical right from the start of the show.

There is no conflict in the story except those between him and his parents which are memories in Usher’s mind from when he was 17. Usher vows each day to change but at the same time believes in a form of cognitive science that denies that change is possible. The same scientific theory denies that anything “ends”. The musical ends with the words “strange … loop”, leading us to think the show will simply repeat (which, of course, it will as long as it is commercially viable).

All this means that the two hours of the performance have used none of the usual components of drama – conflict, change and conclusion – and instead have merely painted the portrait of an unhappy queer, fat Black man. As Thoughts 2 and 3 sing in the first number “You can’t just flout every convention / Then command complete attention. Yet, in this ultra-self-aware, metatheatrical show, Jackson does exactly this anyway. It’s a daring move, but without change or a conclusion, the work no matter how well it fulfils Hofstadter’s theory, is ultimately unsatisfying.

For a musical with such an abstract concept to work it needs a compelling performance from the lead performer. That, unfortunately, is exactly what the current production does not receive. Malachi McCaskill gives an adequate but surprisingly unengaging performance as Usher. McCaskill has a sweet, not especially powerful voice and a very limited range of expression both in singing and acting. This is especially noticeable when McCaskill is surrounded by the Thoughts, all of whom have stronger voices and far more expressive faces and a more diverse gestural language.

McCaskill’s odd listlessness is countered by the extremely hardworking chorus of singing and dancing Thoughts, who after multiple quick changes are on stage in various groupings almost all the time. Sierra Holder presents Thought 1 as an upbeat figure and has a chance to show off her powerful voice in “I like this and I like Wicked”, the longest song given to any of the Thoughts. Amaka Umeh portrays Thought 2, who generally embodies Usher’s self-loathing. Thought 2 visits Usher every morning and Umeh gives the Thought’s remarks a particularly snarky bite. Thought 2 later embodies Harriet Tubman during a sequence in which Usher, who is dedicated to his inner White girl, is considered a “race traitor”. Umeh takes the character way over the top, and director Ray Hogg makes a mistake by letting Umeh linger on stage so long trying to milk laughter from the audience.

Matt Nethersole plays Thought 3, who often appears as Usher’s fictional agent. Nethersole makes the biggest impression as the young, fit-looking guy in the subway scene whom Thought 5 goes off with after rejecting Usher. David Andrew Reid is Thought 4, whose biggest chance to shine is as Usher’s mother in the fourteenth section called “Periodically”. This is the longest sequence in which a Thought embodies a single character, here a hilarious portrait in spoken word and song of Usher’s mother. Reid perfectly captures how a mother can begin a conversation by portraying herself as loving and caring and gradually have her caring side shift into criticism and finally downright antagonism.

As Thought 5, Nathanael Judah is most notable in the subway scene where in the space of a few minutes a man who seems to be flirting with Usher suddenly turns on him for falling for such flattery. As Thought 6, deep-voiced Marcus Nance is formidable as Usher’s father but Nance makes the role of the aggressive, disdainful White “Inwood Daddy” particularly disturbing.

Brian Dudkiewicz seems to have paid close attention to Hofstadter’s descriptions of a “stage loop” in his designs for the set. The set is made up of movable bookcase-sized components that are all mirrored on one side but realistically detailed on the other. While we never see “mirrors mirroring mirrors” in Hofstadter’s phrase, we are aware that all the pieces of Usher’s reality are all mirrors of himself.

Music theatre lovers will not want to miss A Strange Loop since the work so deliberately flouts all the conventions of drama and musicals to create something new. Yet, disregarding conventions so completely does have its consequences, of which Jackson is aware, such as the lack of change or development and a premise that precludes an satisfying ending. But seeing a creator take an unusual idea so far is fascinating in a fatalist sort of way. This is why a les disengaged central performance is necessary to put over a musical that is otherwise so abstract. Still, we have to count ourselves lucky to live in a country where so transgressive a musical can be performed.

Christopher Hoile

Photos: Malachi McCaskill as Usher with his Thoughts; Malachi McCaskill as Usher with Sierra Holder, Amaka Umeh, David Andrew Reid, Marcus Nance, Nathanael Judah and Charlie Clark; Malachi McCaskill as Usher. © 2025 Dahla Katz.

For tickets visit: www.soulpepper.ca.