Michael R. Jackson’s Pulitzer Prize-winning musical A Strange Loop has made its Chicago premiere at Raven Theatre, running through November 8. Directed by Mikael Burke in a co-production with About Face Theatre, the 100-minute production stars Eddie Weaver as Usher, a Black queer musical-theater aspirant navigating his identity, artistic ambitions, and intrusive inner thoughts.
Production Highlights at Raven Theatre
- The Venue and Scope: Staged as an intimate, relatively low-budget Equity endeavor at Raven Theatre rather than a massive Loop showcase.
- Critical Reception: Awarded four stars by Chicago Tribune critic Chris Jones, who argues that the off-Loop staging serves the material better than its original Broadway run.
- The Creative Team: Directed by Mikael Burke, choreographed by Breon Arzell.
A Chicago Premiere Rooted in Intimacy
With any other title holding the pedigree of a 2020 Pulitzer Prize for Drama and consecutive 2022 Tony Awards for Best Musical and Best Book, industry observers would typically anticipate an immediate national tour or a heavyweight Loop-theater run. Instead, the Chicago premiere of Michael R. Jackson’s deeply personal musical arrived in an off-Loop setting at Raven Theatre. In a review for the Chicago Tribune, critic Chris Jones notes that the delay stems from the show’s uncompromisingly raw content. The script delves into specific sexual fantasies and explores whether the central character’s desires stem from the internal pressures of systemic racism.
BroadwayWorld similarly highlights the inventive narrative structure of the production, noting that Usher is accompanied on stage by a Greek Chorus-like ensemble representing his intrusive thoughts—such as Daily Self-Loathing and Sexual Ambivalence. Both outlets point out that while the first half moves at a fast, comedic pace through encounters with ancestral figures and dating apps, the second half shifts into a somber, fever-dream sequence modeled on a Tyler Perry morality play before concluding with a stark solo number focused on radical self-acceptance.
Review: ‘A Strange Loop’ at Raven Theatre is very off-Loop, and breathtakingly good https://t.co/lXReCQkp5u
| Production Milestone | Year / Detail |
|---|---|
| Off-Broadway Premiere | 2019 |
| Pulitzer Prize for Drama | 2020 |
| Broadway Opening & Tony Wins | 2022 (Best Musical, Best Book) |
| Chicago Premiere Run | Now playing through November 8 |
Stripping Away the Broadway Nomenclature
The primary artistic victory of this regional staging lies in its removal from the high-stakes political machinery of Broadway. Jones argues in the Chicago Tribune that on Broadway, the mere presence of the show functioned as a heavy political statement that occasionally overshadowed its profound personal intimacy. By contrast, designer Sydney Lynne and director Mikael Burke keep the focus tightly anchored on Usher’s internal world. BroadwayWorld echoes this praise, emphasizing that lead actor Eddie Weaver anchors the production with a powerhouse performance, rarely leaving the stage during the demanding 100-minute runtime.
The supporting cast, operating as the voices inside Usher’s head, delivers musical execution that exceeds typical regional standards. Performances run at Raven Theatre through November 8, with tickets priced between $30 and $45.

More on Raven Theatre
Good afternoon, Chicago.Here’s what is happening today.- Questions swirl about Pope Leo’s future after lung cancer diagnosis- Illinois QB Katin Houser out 4-6 weeks after hand surgery- Review: ‘A Strange Loop’ at Raven Theatre https://t.co/gXd16ouBeC
Mikael Burke stages an acclaimed metamusical that others wouldn’t tackle.“A Strange Loop” runs through November 8 at Raven Theatre. Learn how Burke brought the play to Chicago: https://t.co/wqDouTSId1