NUNN'S THEATER HABIT

A Strange Loop strikes a chord at Raven Theatre

Sat. October 17, 2026 12:00 AM
by Jerry Nunn

The Pulitzer Prize and Tony Award-winning musical A Strange Loop winds up in the Edgewater neighborhood of Chicago after phenomenal success in New York City. About Face Theatre has been dedicated to supporting work from the LGBTQ+ community since 1995 and continues that mission in theatrical season number 32. The original run was less than nine months at the Lyceum Theatre, so a revisit at the Raven was sought out to amplify the author's voice.

Michael R. Jackson wrote this semi-autobiographical drama, told through the perspective of Usher, an aspiring writer who works nights as a theater attendant on Broadway.

The plot begins with Usher working at The Lion King's stint on Broadway and battling his personal demons depicted as Thoughts. These inner spirits not only haunt him in the mirror, but morph into people in Usher's life, like his father, mother, doctor and lover.

This evokes a journey to the past and present of the mind, body and soul that will hopefully allow Usher to reclaim his future. Throughout the process, he confronts the fact that he doesn't fit into a typical mold.

His mental health, body image and traumatic mistreatment are explored through razor-sharp commentary. Spectators may be triggered to laugh or cry during the experience. Racism, homophobia, stereotypes, misogyny and ethnic slurs hammer home Usher's point of view throughout this powerful piece.

People should be prepared that parts of Loop may be a bitter pill to swallow and it was designed to highlight dark thoughts that can creep into the brain. It lampoons celebrities and calls out questions that everyone should be asking.

From the gospel according to Tyler Perry to jokes about The Color Purple, no one is spared from Jackson's onslaught of social analysis.

The quick-witted delivery of the text can be exhausting for both the cast and the congregation. An intermission would have allowed a break from the approximate hour-and-40-minute running time. The director, Mikael Burke, doesn't allow the production to drag, though and he pulls some strong performances out of those involved.

Eddie Weaver as the protagonist Usher shows strength by giving the character relatability and heart, which is key for the show to succeed. Weaver sometimes struggles with sustaining longer notes, but his shortness of breath comes from his rapid-fire delivery of lines at times.

The entire cast is a marvel to watch as they weave in and out of the scenes at a frenetic pace.

Much more than mere “Thoughts,” they each take moments to shine on the Johnson Stage.

Micah Mixon slips in some zingers as Thought 1 and Matheus Barbee is a scene stealer as Thought 2. Chicago theater staple Christopher Wayland continues to be magnetic on the stage and John-Payne adds a unique style to the mix.

It took Jackson 18 years to see A Strange Loop come to fruition and he was inspired by his previous real-life job as an usher at The Lion King. His humble beginning led to winning a Pulitzer Prize for Drama in 2020. This was notable because it was the first time a Black musical writer without a prior Broadway run won the award.

In 2022, the show received 11 nominations at the 75th Tony Awards and won for Best Musical and Best Book of a Musical. The cast recording also received a Grammy Award nomination for Best Musical Theater Album in 2023.

The metafictional musical endeavor eventually paid off for Jackson and he earned accolades for bringing his insecurities to light. This version of the show is another chance for ticket holders to view his world, ruminate and relate to A Strange Loop.

A Strange Loop has extended to November 22, 2026, at the Raven Theatre, 6157 North Clark Street. Visit raventheatre.com or call 773-338-2177 for tickets.

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