PicksInSix Review: Play On! - Chicago Shakespeare Theater
‘Play On!’ Has Got That Swing!
PicksInSix® Review | Guest Contributor | Perse Grammer
“Play On!” at Chicago Shakespeare Theater doesn’t give anything away until the curtain rises. A dynamic opening number informs us that this Shakespearean comedy is taking place in 1940s Swing-era Harlem. Beowulf Boritt’s set design and Adam Honoré’s lighting design meld to create electric, dramatically leaning streets and buildings, the most important of which is the Cotton Club.
In this version of “Twelfth Night,” Vy has gone to Harlem to pursue her and her late brother’s dream of being a songwriter. Her uncle Jester decides the only way for her to succeed is as a man, and thus, Vy is disguised as Vy-Man. Jester gives her an in with Duke, a top-notch band leader languishing over his unreturned love for the great singer and diva, Lady Liv. As Vy delivers songs to Lady Liv, Lady Liv quickly falls for her—but Vy is developing feelings for Duke. Meanwhile, Miss Mary and Sweets, Cotton Club workers and bickering couple, have caught onto their boss Rev’s feelings for Lady Liv. Jester leads a charge to humiliate Rev by making him “cool enough” to impress his crush. Meanwhile, Vy and Duke grow closer, hindered by Duke’s confusion over feeling romantically toward a man. Finally, Vy reveals herself as a woman, Miss Mary and Sweets resolve their arguments, and Lady Liv falls for Rev as his true, stoic self. Cue the triple wedding!
There is no such thing as a weak link in this cast. Hailee Kaleem Wright bursts with passion and endearing awkwardness in her performance of Vy. James Harkness (Jester) is a smooth mover and talker, James Earl Jones II (Sweets) is a deft comedian, and Alanna Lovely (Miss Mary) more than earns her round of applause for scatting. Krystal Joy Brown (Lady Liv) is just as magical as her initial grand entrance, and the rich, strong voice of Edred Utomi (Duke) immediately pulled me in. My biggest cast-related critique is that the sensational ensemble was criminally underutilized. Every member is an incredibly strong singer and dancer. Kaylah Janssen as the cheeky CC is especially a delight to watch as she embodies energetic effortlessness onstage.
Director Sheldon Epps has woven together a very coherent show. Physical comedy is well utilized—most notably in “Ain’t Got That Swing,” though the biggest laugh of the night came from a bartending ensemble member leaning in to hear a conversation he never spoke in once. Playwright Cheryl L. West’s dialogue is fast and funny. Admittedly, from a writer’s perspective, the written comedy and wordplay is slightly predictable, but nonetheless effective. An-Lin Dauber’s costumes walk a fine line of vibrant and unique without being over the top. This means the outfits meant to be the most stunning—or the most comical—have the desired effect. The music throughout the show is, of course, phenomenal. Everyone does Duke Ellington’s discography justice, with the harmonies of “Solitude” closing Act I being a particular standout.
In such a music-centric show, it was a pity the audience didn’t get to see the actual band more. They got a nice moment of recognition at the top of Act II, but they spent much of the show shut behind a partition. While every number was wonderful, I found myself more drawn toward the solos and duets as compared to the group numbers. This is likely because they had more emotion and connection to the story than the group numbers, which were quite a spectacle. The duet rendition of “I Got It Bad And That Ain’t Good” was compelling, though three back-to-back romantic duets before the finale was a bit much.
“Play On!” addresses some deeper themes but doesn’t go much further beyond the surface. Vy starts out focused on her ambition and fulfilling her and her late brother’s dream, but that motivation gets dropped as her relationship with Duke gains more focus. Granted, theirs is a love story born of creative collaboration, but it felt a bit short and disjointed. Replacing a few scenes about Miss Mary and Sweets, who have much less of a relationship arc, with Vy and Duke, could help flesh out their relationship more. A conflict between the two that never really gets resolved is Duke’s misogyny. While Vy is dressed as a man, Duke tells her about how he doesn’t believe women have the emotional depth to be songwriters. Vy pushes back, but there isn’t much follow through on this. Which leads me to wonder—when Duke learns his beloved collaborator is a woman, does that change his perception of all women, or does he just see Vy as the exception? As much as I’d like to dig into the darkness and discomfort, that’s not what this show is about. “Play On!” is lighthearted and rousing, guaranteeing you walk out of the theater happier than when you walked in. The influence of Shakespearean comedy is strong, but you don’t need to know much about “Twelfth Night” to understand and enjoy the show. Because indeed, enjoyment is the most important factor of “Play On!” and this musical knocks it out of the park!
GUEST CONTRIBUTOR | PERSE GRAMMER is a multidisciplinary writer and theatre artist based in Chicago. Grammer is currently developing their latest play through a mentorship with Sandy Shinner at Shattered Globe Theatre. They hold a BFA in Playwriting from The Theatre School at DePaul University. www.persegrammer.com
PHOTO|Kyle Flubacker
Chicago Shakespeare Theater
presents
PLAY ON!
The Yard
Navy Pier
through October 18, 2026
WEBSITE
PROGRAM
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