Review: A STRANGE LOOP at Raven Theatre

Michael R. Jackson’s wildly inventive and unique 2020 Pulitzer Prize-winning musical A Strange Loop now makes its Chicago premiere. A Strange Loop is a “big Black and queer-ass American Broadway show,” in the main character Usher’s words, about the lead trying to write a musical called A Strange Loop that accomplishes the same. Usher, so named for his gig as a Broadway usher at The Lion King, has taken the job in the hopes that someday he’ll make it big as a musical theater composer/lyricist. Thus, A Strange Loop is an original and episodic look at the creative process.

It’s also a rich and thought-provoking exploration of the self. As Usher tries to navigate his sense of self as a fat queer Black man, he’s accompanied on stage by his intrusive thoughts. This is an ingenious narrative device: Jackson places Usher (Edide Weaver) on-stage literally alone with his Thoughts (Micah Mixon, Matheus Barbee, Christopher Wayland, Michael Turrentine, John-Payne, and Napthali Curry), who become a Greek Chorus-like ensemble. Naturally, Usher’s thoughts often aren’t kind to him, such as his Daily Self-Loathing or his Sexual Ambivalence. It’s fascinating to watch Usher navigate the voices inside his head. And these Thoughts are entirely present from the opening number — ironically called “Intermission.”  The Thoughts call for Usher in a lively cacophony that recalls the opener of Sondheim’s Company. This gorgeously communicates just how much Usher’s inner voices overwhelm him from the jump.

The first half of A Strange Loop comes fast, furious, and funny. Jackson has also constructed a musical that’s a brilliant portrait of Usher’s navigation of identity. In one scene, Usher’s famous Black ancestors — like James Baldwin, Harriet Tubman, and Whitney Houston — berate him for not sufficiently appreciating the work of Tyler Perry.) In another early scene, Usher tries to channel his “Inner White Girl,” in a hilarious song that pays homage to some of his heroes — Liz Phair and Joni Mitchell.

Other moments ask Usher to confront his queerness, as when he swipes on a dating app and doesn’t find much success. A Strange Loop deals frankly and explicitly with queer dating culture. But Usher isn’t necessarily looking for love at this moment...he’s just looking for a hook-up. And that feels both radical to portray in a musical, yet entirely true to the moment and character. 

Jackson also incorporates myriad musical theater references. I was particularly delighted by a scene in which Usher shops his work in progress around for feedback, including to one individual who says he represents the committee for the Second Coming of Sondheim.

The first half of A Strange Loop feels episodic, showing us scenes when Usher tries to write, interacts with family members, self-reflects, and attempts to flirt. The musical loses some steam in the second half, particularly during a long sequence that becomes a fever dream of a Tyler Perry morality play and overstays its welcome. This latter part is also much more somber and decidedly less humorous, so the tonal shift feels somewhat jarring. 

Given the meta nature of this show, that shift is acknowledged. One of the Thoughts literally asks Usher how he plans to end the show, given that this strange loop has no end. Luckily, Jackson does end the show with a terrific button: A beautiful solo number for Usher that’s a reckoning with the possibility of radical self-acceptance.

Directed by Mikael Burke and choreographed by Breon Arzell, it helps that this production is fully realized and beautifully performed. Weaver is a powerhouse as Usher. This 100-minute musical is also a real marathon for him; he rarely leaves the stage for more than a few seconds. Weaver’s Usher is vulnerable and often sweet, but also sometimes brash and lewd. Weaver gorgeously encapsulates the many facets of Usher’s identity, and he’s a winsome hero. 

The Thoughts harmonize magnificently and also have some great individual moments to shine. Turrentine is particularly winning as Usher’s mother, who both loves her son and remains utterly perplexed by his homosexuality. John-Payne is equally compelling as Usher’s father, who appears on-stage accompanied by a liquor bottle. John-Payne’s deep, resonant bass singing voice is a great match for Usher’s gruff dad. I was also especially charmed by Mixon, who in one scene plays a Lion King theatergoer who interacts with Usher at intermission. When Usher starts explaining his show to her, she naturally launches into a solo number with her own advice for his writing — what a classic musical theater device. 

About Face and Raven Theatre’s production of A Strange Loop presents a unique opportunity for Chicago audiences to see a wholly original new musical. There’s truly no other show like A Strange Loop. Jackson portray’s Usher’s character and Thoughts so richly and specifically, and it’s a contemplative exploration of the notion of self. 

A Strange Loop plays at Raven Theatre, 6157 North Clark, through November 8, 2026. Tickets are $30-$45, with discounts for seniors, military, and theater industry members. 

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