
A musical, but it’s just the voices in your head. Sounds just crazy enough to win the 2020 Pulitzer for Drama. “A Strange Loop” by Michael R. Jackson finally makes its Chicago premiere at Raven Theatre in a co-production with About Face Theatre. Mikael Burke directs a fantastic production with a knock-out cast.
Not many musicals are awarded a Pulitzer for Drama. Only 10 in fact. So, when one is selected (before it plays Broadway), there’s a lot of curiosity. “A Strange Loop” is the best kind of new musical—in that it’s hard to explain. In the era of an abundance of movie-turned-musical adaptations, it’s refreshing to see something entirely unique.
In this seven-person, one-man show, Usher (Jordan Harris) is working as an usher at a Broadway theater while writing a musical about an usher who works at a Broadway theater. In a series of songs spurned on by his intrusive thoughts, (played by a delightful cast of six) Usher’s creative process is laid bare, and we see the playwright struggling with his identity as a black gay man.
Ever at odds with his “Internal white girl”, Usher spends his life stuck ruminating on his relationship with his parents, his sexuality, his gender, his race and his place in the world. In cleverly written, but firmly R-rated songs, we learn about his troubled relationship with his unintentionally cruel parents and his discomfort in his own skin.

John-Payne, Michael Turrentine, Eddie Weaver, Mattheus Barbee and Christopher Wayland. Photo by Joe Mazza / Brave Lux.
Jordan Harris’ voice and sheer vulnerability as a performer make this 95 minute show a highly concentrated emotional experience. Usher’s internal monologue is brought to life by a wildly talented ensemble of six with character names like “Thought 1” and “Though 2” played by Micah Mixon, Matheus Barbee, Christopher Wayland, Michael Turrentine, John-Payne and Naphtali Curry.
“A Strange Loop” is a show that plays against the norms of traditional musical theatre in almost every aspect, yet it borrows so effortlessly from a lot of what likely inspired Michael R. Johnson. Instead of being driven by plot, Johnson goes full meta with a concept musical like “Company” meets “for colored girls who have considered suicide / when the rainbow is enuf” but with the playfulness of “Rent”. Each song is an exploration of a life that files down to a heartbreaking raw nerve.
This show never wallows in sadness though. As is often the case, comedians mask a great deal of pain. Johnson plays up the surreal absurdity of Usher’s life. In one song alone the audience is clapping along to a church choir beautifully belting “AIDS is God’s punishment!” all the while Usher is grappling with the trauma of being raised in a strict religion that his parents still belong to. This show is dark comedy about a man finding acceptance with himself, which is highly relatable for those who chronically overthink.
There’s something really special happening in this production. This cast fills the theater to the rafters with soaring vocals and brings the house down with roaring laughter. Michael Turrentine plays Usher’s mother in a way that anybody with a mother can chuckle at. His performance taps into a near constant sense of energy that make “A Strange Loop” highly satisfying to watch and listen to. You’ll be singing some of the unsettling lyrics right out the door.
Now through November 22 at Raven Theatre. 6157 N. Clark Street. 773-338-2177.
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