We particularly value plays that tackle longstanding social injustices, but do so through a decidedly personal story that humanizes the issues and illuminates real-life personal tolls (and triumphs, where applicable). The best of these plays let you get to know multi-faceted protagonists, often with a well-honed sense of humor that provides both entertainment and a humane coping mechanism. Here’s a sampling of our favorite “it’s personal” stories taking on big issues.
(in alphabetical order)
At the Wake of a Dead Drag Queen by Terry Guest, produced by The Story Theatre in 2019: We’d never seen a play by Terry Guest before The Story Theatre’s 2019 premiere of At the Wake, but we went into it with high expectations, having seen the playwright’s incisiveness, wit, and wisdom in personal conversation and in published interviews. Even so, the play and production soared well beyond those expectations. We had no idea that a piece ostensibly about a wake could be so life affirming—and funny—while exploring “Blackness, queerness, and the fine art of drag,” along with a deep dive into personal identity, progressive illness, and much more (in a 90-minute two-hander!). The script was fully realized thanks to exquisite acting by the playwright and Paul Michael Thomson in charismatic performances, breathtaking costume design by Uriel Gomez, sound design by Sam Clapp that was essential to the story, captivating choreography by the cast, Mikael Burke’s sensitive direction, and production values that went way beyond any reasonable expectations for the second full production of a fledgling storefront theatre company. Recommended viewing: The playwright explains what At the Wake is about and its genesis (four minutes).
Dontrell, Who Kissed the Sea by Nathan Alan Davis, produced by First Floor Theater in 2018: We’ve seen hundreds of plays about familial relationships, but none that wove the current generation and their ancestral legacy together so poetically and provocatively. Director Chika Ike enlisted a brilliant and cohesive cast and crew to bring to life the story of 18-year-old Dontrell’s quest to understand his heritage, specifically his nautical search for an ancestor who leapt into the Atlantic during the Middle Passage to escape the bonds of slavery. What made this epic story also personal were Dontrell’s family and friends, all richly written and vividly portrayed. They were caring, funny, complex, quirky, and made us sorry to see this play end. However, our special fondness for First Floor’s production of Dontrell is based not just on the fine performances, design, and direction, but also on getting to know the artists themselves and feeling their compassion and collaboration firsthand. Interesting note: We originally fell in love with this play in 2016 when we saw a student production at the University of Illinois, directed by Tyrone Phillips (like the playwright, a UofI alum). Many of the student cast members were able to experience the First Floor production and interact with their counterparts in the Chicago cast.
Dutch Masters by Greg Keller, produced by Jackalope Theatre in 2019: The relationships and revelations in this play ooze out in small increments, ratcheting up the tension onstage and the audience’s unease during Greg Keller‘s brilliantly written 80-minute play. Experiencing this two-hander would be intense under any circumstances, but director Wardell Julius Clark’s staging and pacing allowed no physical or emotional escape from the truths about racial oppression illuminated on stage by Patrick Agada’s and Sam Boeck’s gut-wrenching acting. The mid-play transformation of the set (part of Ryan Emens’ ingenious scenic design) was an experience in itself, as an entire living room appeared upstage and rolled disconcertingly toward the audience, stopping just short of taking out the front row. Interesting note: Jackalope’s Dutch Masters proved to be a unique and moving experience not only for us, but also for many critics. Kevin Greene’s review in Newcity expertly captured both the mood and import of the production (without giving away the plot). Also of interest: We went back to see the production a second time, and happened to catch a searing understudy performance by Daniel Gadaj, described in our favorite understudies page.
The Light by Loy Webb, produced by New Colony in 2018: Before seeing New Colony’s world premiere of The Light, we had seen more than three thousand shows; but we had never seen anything like this play. Here was a story about two young, intelligent, funny, professional people of color deeply in love—all too rare on any stage, sadly. In its fully engrossing 90 minutes of running time, the play ranged from clever comedy to devastating denouement, grappling with a range of timely, weighty, and interrelated issues with a remarkable level of complexity and clarity, always through a personal and relatable lens. Everything about the issues in this play, the humor, the characters, and the emotions we experienced as audience members was multi-dimensional. The instant the play ended, the audience leapt to their feet en masse, applauding, weeping, and taking a collective deep breath. The play was a masterpiece, the performances by Jeffery Freelon and Tiffany Oglesby were breathtaking, and Toma Langston’s direction was exquisite. Theatre simply doesn’t get any more powerful than this.
The Magnolia Ballet by Terry Guest, produced by About Face Theatre in 2022: It’s no surprise that Terry Guest has multiple shows in our “It’s Personal” favorites list. He has a special gift for telling stories from an authentic and relatable perspective, while capturing the deep and far-reaching consequences of longstanding prejudices and inequities, rarely out of sight or mind for anyone who happened to be born on the wrong side of privilege. The Magnolia Ballet tackles racism, homophobia, and toxic masculinity through the experiences of a Queer Black boy (played by the playwright himself in About Face’s sterling production, directed by Mikael Burke)—illuminating 400 years of American and family history. This play is humorous, poetic, atmospheric, and makes every word and every movement count. Note: The Magnolia Ballet garnered awards for both production and performer in a principal role (Terry Guest) at the 2022 Equity Jeff Awards ceremony.
Ride or Die by Shepsu Aakhu, produced by MPAACT in 2022: Imagine that you’re lucky enough to have an exceedingly wise friend or family member, and you get to sit down with them for 90 minutes and soak up their hard-earned wisdom on personal and societal implications, from the beginning of the pandemic through the January 6 insurrection. You become fully engaged in the encounter, and leave with a perspective that has expanded in depth, scope, complexity, and clarity. That’s the best way we can describe our experience with Ride or Die, only the insights are not those of a character in the play but instead come directly from the playwright himself, by way of his diary entries in 2020 and 2021, augmented by his contemporaneous photos of flowers illustrating both delicacy and resolute resilience. The words are spoken by actors of unassailable honesty—directed by Chuck Smith— conveying the everyday reality of a Black man in America (is he safe photographing flowers in a white neighborhood?), pandemic anxiety (how do you survive the loss of community?), and insurrection (will democracy survive?). Ride or Die is a personal saga embodying urgent questions about our shared world, and a vivid reminder of why we go to theatre. Interesting note: When we saw the show, understudy Kairis Rivera performed on short notice; their moving performance is described on our favorite understudies page.
