We have detected that you are using an adblocking plugin in your browser.

The revenue we earn by the advertisements is used to manage this website. Please whitelist our website in your adblocking plugin.

SCRUTINY | Piercing Honesty Characterizes Michael R. Jackson’s Groundbreaking A Strange Loop

By Paula Citron on May 23, 2025

Malachi McCaskill and cast in Soulpepper Theatre’s A Strange Loop (Photo: Dahlia Katz)
Malachi McCaskill in Soulpepper Theatre’s A Strange Loop (Photo: Dahlia Katz)

The Musical Stage Co., Soulpepper, Crow’s Theatre & TO Live/A Strange Loop, book, music and lyrics by Michael R. Jackson, music direction by Chris Tsujiuchi, choreographed by Rodney Diverlus, directed by Ray Hogg, Baillie Theatre, Young Centre for the Arts, closes June 8. Tickets here.

Some Broadway shows become the stuff of legends.

Only 10 musicals have ever won the Pulitzer Prize for drama, while very few have the book, music and lyrics written by the same person. Such a musical is the semi-autobiographical A Strange Loop by Michael R. Jackson which also won Tony Awards in 2022 for both Best Musical and Best Book.

Needless to say, A Strange Loop is a very special theatrical offering.

The Main Theme

The main character called Usher refers to himself as living in a fat, Black, queer body, and so right from the start we know we have someone who is coping badly with identity, sexuality and body image issues, and who is wracked with self-doubt as he attempts to deal with the anxieties and social pressures that pervade his life.

A Strange Loop is a story about personal struggles and deeply felt hopes as we are taken into Usher’s mind. This musical is deeply introspective.

The Characters

There are seven actors on the stage — Usher, and his six Thoughts who are a Black, queer ensemble of various genders.

These boisterous and unruly Thoughts are a Greek chorus of ideas that inhabit Usher’s inner psyche and cause havoc in his mind because they feed into his self-destructive tendencies. They have names like “Daily Self-Loathing”, “Supervisor of ‘Sexual Ambivalence” and “Inner White Girl”. They also reinforce his self-loathing by piling on self-criticism.

When needed, the Thoughts become other people in Usher’s imagination like his parents, real life celebrities or historical figures, but their characterizations are skewered through the prism of Usher’s jaundice eye.

Malachi McCaskill and cast in Soulpepper Theatre’s A Strange Loop (Photo: Dahlia Katz)
Malachi McCaskill and cast in Soulpepper Theatre’s A Strange Loop (Photo: Dahlia Katz)

The Story Line

Usher’s day job is working at the theatre where The Lion King is playing, but he really aspires to write an original musical about a Black queer man who is writing an original musical about a Black queer man who is writing an original musical about a Black queer man, and so it goes ad infinitum. Hence the title A Strange Loop (although the phrase has other meanings as well).

Usher feels he has to write the musical himself because there are so few opportunities for fat, Black, queer wannabes to have a career in musical theatre.

His religious family, who believe he will burn in hell because of his homosexuality, want Usher to write Gospel plays like the uber successful Tyler Perry, and an opportunity does comes Usher’s way when he is asked to ghost write for Perry, the fallout of which is one of the darkest and most satiric chapters in the play.

The Structure

The structure of the musical follows Usher’s inner journey in no particular order, just as our minds dart about in chaotic fashion, but this is where Johnson’s cleverness comes into play.

What is a very dark throughline is offset by catchy upbeat songs with hummable melodies and deliciously clever lyrics that propel the plot. A lighter side is also generated by laugh-out-loud satire that arises out of bizarre or surprising situations.

The encounters between Usher and the Thoughts also provide much amusement at Usher’s expense, particularly when they comment negatively on his play, or worse, make suggestions.

Thus, Jackson has buried the bleak journey through Usher’s tormented thoughts under a blanket of showbiz razzle dazzle. A Strange Loop is all smoke and mirrors.

Summary

A Strange Loop is both a comedy and a drama about a young man feeling trapped in his life and wanting to change but not knowing how. What stands out is the piercing honesty of the material as Usher’s mind touches on racism, depression, suicidal thoughts, and even domestic abuse and sexual assault.

A Strange Loop is so dense with themes and ideas and concepts and astute observations and probing questions that you need a suitcase to unpack them all.

The Cast

Malachi McCaskill as Usher is outstanding.

His role calls for vulnerability and reaction as his Thoughts assault him from every side. Both states of mind are dark, and hard to portray, but McCaskill is brilliant, a real schlub who can’t catch a break and yet he holds centre stage which is quite a feat — a self-doubting character who is strong in his retreat, an oxymoron if ever there was. McCaskill also has an astonishingly powerful singing voice.

The six Thoughts are a very talented group, and in order of their number are — Sierra Holder, Amaka Umeh, Matt Nethersole, David Andrew Reid, Nathanael Judah, and Marcus Nance.

Each Thought gets one or two big stage moment, although admittedly some Thoughts have bigger roles than others. Umeh as Thought 2 is Usher’s mother and Harriet Tubman, for example, and in fact, among a very gifted group, Umeh is a stand-out.

The Thoughts collectively are a raucous bundle of energy who dance and sing up a storm while executing their many fabulous costume changes courtesy of designer Ming Wong.

The Production

Brian Dudkiewicz’s set is interesting.

In the centre is Usher’s cramped room and his writing desk. Around him are ceiling to stage reflecting panels that can be turned for surprise entrances for the Thoughts. The disorienting reflecting motif mirrors the confusion in Usher’s mind. The little room, however, can be wheeled off when more of the stage is needed, and it is the Thoughts who efficiently handle the set pieces in a smooth-running operation.

Choreographer Rodney Diverlus had made sure that the Thoughts are high energy but at the same time, their movement is sophisticated and chic to go with the witty, clever lyrics. The Thoughts may be a rowdy group, but they are never vulgar.

Director Ray Hogg has ensured that the show clips along at a fast pace as the Thoughts swirl around Usher, but at the same time, he has made certain that in the stage picture at large, Usher always has pride of place.

Final Comment

Perhaps the most wily aspect of Jackson’s concept of a fat, Black, queer writer struggling to write a musical, is that we the audience are watching the very musical Usher is attempting to write.

Are you looking to promote an event? Have a news tip? Need to know the best events happening this weekend? Send us a note.

#LUDWIGVAN

Get the daily arts news straight to your inbox.

Sign up for the Ludwig Van Toronto e-Blast! — local classical music and opera news straight to your inbox HERE.

Paula Citron
Follow me
Share this article
lv_toronto_banner_high_590x300
comments powered by Disqus

FREE ARTS NEWS STRAIGHT TO YOUR INBOX, EVERY MONDAY BY 6 AM

company logo

Part of

Terms of Service & Privacy Policy
© 2025 | Executive Producer Moses Znaimer