Theatre 2025: Strange Loop @ Soulpepper

A co-production between Crow's Theatre and Soulpepper Theatre, Strange Loop is a daring, complex and thought-provoking musical by Michael R. Jackson who won the Pulitzer Prize for Drama in 2020 and the Tony Award for Best New Musical in 2022.  This is a meta, self-referential show about Usher, a self-proclaimed “queer, fat, black man” in his mid twenties, who ironically works as an usher for a Broadway production of Lion King but aspires to be a successful playwright. The musical that Usher is working on is autobiographical, about a gay black man (himself) writing about a show about a gay black man who is writing a show about a gay black man.  The cyclical nature of his play is just one aspect of several recurring “loops” in his life as he struggles to define his identity.

Throughout the show, Usher deals with insecurities, self-doubt and angst regarding his race, sexuality and body image as he faces societal pressures including racism, homophobia and body shaming. These anxieties are amplified by harsh judgement and condemnation from his ultra-religious parents and are perpetuated and personified by the internal Greek chorus of his inner thoughts, including “Self-Loathing”, “Financial Faggotry” and “Corporate N***atry” and “Sexual Ambivalence”.  In the program, the characters are referred to as Thought #1 to Thought #6.  In the opening number "Intermission Song", the Thoughts repeatedly chant "Usher" and it is unclear whether they are calling his name or generically calling for the usher in the theatre.  This adds to the meta nature of the show.

Usher battles the psychological and emotional loops of his self-doubt as he struggles between conforming to the expectations of others and remaining true to his own identity.  Usher wants to form a meaningful connection in the gay dating scene but is mercilessly rebuffed in the song “Exile in Gayville” where he is deemed “too fat, too black, too ugly and dick too small”.  Out of desperation, he accepts a hookup with a sadistic white man from “Inwood” (a New York suburb) who has a fetish for black boys in an unflinching scene that is very difficult to watch.  This experience just reinforces his feelings of shame and self-deprecation.

Usher also deals with constant guilt trips from his parents.  His mother wants him to write gospel plays like Tyler Perry, who is known for writing melodramatic plays reflecting Christian values, focusing on forgiveness and redemption, faith and family values.  Usher shows distain for Perry’s works, deeming them too simplistic, formulaic, commercialized and lacking authenticity, relying on black stereotypes and reinforcing problematic tropes regarding gender and sexuality.  Combating his reluctance to write a gospel play, Usher’s “Thoughts” pressure and convince him by appearing as legendary black figures including abolitionist Harriet Tubman, civil rights activist James Baldwin, the titular character from the movie “12 Years A Slave” and “Whitney” (Houston).  To appease his mother, Usher writes an over-the-top Tyler Perry-esque parody that exaggerates all the themes, plots and characteristics that he finds objectionable.

I thought it was interesting to learn that at least publicly, Tyler Perry did not take offence to the way his work was depicted in Strange Loop and even phoned Jackson to congratulate him on winning his Pulitzer award.

In addition to Tyler Perry, the songs in Strange Loop make passing references to many names within pop culture that might be missed without more research.  In “Didn’t Want Nothing”, Usher’s father cluelessly mentions Scott Rudin, a successful gay (white) TV and theatre producer that Usher should get to know (since they are both gay!).  When Usher sings about feminism in “Second Wave”, he mentions Betty Friedan (writer of the Feminine Mystic) and “Charlene, Mary-Jo, Julia and Suzanne”, the first names of the characters from the TV show Designing Women.  In the final number “Strange Loop”, Usher refers to Dorothy which probably alludes to the character from The Wizard of Oz but might also be a play on the phrase “Friend of Dorothy”. 

The use of the actors playing the six Thoughts is quite interesting in the musical since they also portray other characters including theatre patrons, Usher’s potential lovers, his doctor, and his parents.  But rather than having just one actor play Usher’s mother, in some scenes all of them come out dressed as the mother and each sing a line of the song.  This was particularly impactful given the different vocal ranges of each of the actors, who were each cast with a specific vocal type to create a more diverse and dynamic chorus.  Thought #1 is a mezzo-soprano, #2 a tenor, #3 a high tenor, #4 a bari-tenor and Thought #5 and #6 each sing bass.

After struggling throughout the show, Usher finally realizes that rather than trying to change himself to get out of his unending loops of self-conflict, he needs to learn to live with and accept himself as he is. He is given some sage advice from a sympathetic patron at The Lion King, who tells him to “Live your life and tell your story… truthfully and without fear.  Find joy inside your life while you’re still here”. 

The term “strange loop” refers to American cognitive and computer scientist Douglas Hofstadter’s theory about cyclical, self-referential structures that loop back to their starting points, which is used by the brain to define one’s sense of self and identity.  Jackson’s intelligent application of this complex concept to represent how the recursive loop of a person’s thoughts, self-perceptions and external experiences influence one’s sense of self is very impressive and a bit mind-boggling.

What makes Strange Loop so groundbreaking is its innovative, no-holds-barred, and heartbreaking depiction of the experiences of being a gay black man, told with such vulnerability by a voice that is not often represented in live theatre.  The show is bold and unapologetic, not shying away from profanity, sexuality and subversive topics.

While I really admired the intent of this musical and particularly enjoyed the smart, insightful lyrics in the self-reflective songs sung by Usher, I found all the yelling and abuse from the parents hard to take.  The actor who played Usher had such a sweet, innocent smile and baby face that I just wanted to wrap my arms around him and shield him from the hurt being hurled at him.  I also did not particularly like the gospel play scenes as I found them depressing as opposed to satirical.  But overall, I thought this was a special show and understand why it deservedly won all the accolades that it did.