
There are some productions you watch, and then there are productions that make your heart swoon and your toe tap. Sheldon Epps’ Play On! is definitely the latter. Now playing at Chicago Shakespeare Theater, this exuberant musical takes Shakespeare’s Twelfth Night, moves it to 1930s Harlem, adds the extraordinary music of Duke Ellington, and transforms the story into a celebration of love, ambition, identity and music.
The magical kingdom of Illyria becomes Harlem, where aspiring songwriter Vy (Hailee Kaleem Wright) arrives with dreams of making it in show business. To get close to the legendary bandleader known as The Duke (Edred Utomi), Vy disguises herself as a man. Complications quickly follow when Lady Liv (Krystal Joy Brown) becomes attracted to Vy's alter ego. Shakespeare's mistaken identities remain at the heart of the story, but Cheryl L. West's book gives the familiar comedy a distinctly African American cultural identity.
West's script is hot and popping, filled with rhythm, humor and personality. She understands that the language of Shakespeare can be transformed without losing the comic machinery that makes Twelfth Night work. The characters may come from Shakespeare, but they walk, talk and move to the syncopated Harlem beat of the 1930s.
And that Harlem beat is everywhere.

The company of Chicago Shakespeare’s production of Play On! Photo by Kyle Flubacker.
The production's exciting choreography by Edgar Godineaux captures the elegance, sophistication and exuberance of the big-band era. The ensemble - Marquez Linder, Selena Robinson, Dylan C. Smith, Joey Stone, Shelbi Voss and Danny Dwaine Wells II - keeps the stage alive with movement and energy. The choreography doesn't simply accompany the music; it becomes part of the storytelling.
The Duke Ellington score is the production's heartbeat. Under the musical direction of Theodis Rodgers Jr., with beautiful orchestrations by Luther Henderson Jr., the music has both sophistication and swing. Ellington's compositions give the characters another way to express what they sometimes cannot say in words.
For me, the Harlem setting brought back a very personal theatrical memory. Play On! reminded me of the very first show I ever worked on, Bubbling Brown Sugar by Loften Mitchell, from a concept by Rosetta LeNoire (my theatre Godmother), in New York City. That experience introduced me to the power of Black theatre, music and storytelling existing together onstage. Watching Play On! brought some of that same feeling back—the excitement of seeing Black history, Black music and Black theatrical expression become one living theatrical experience.
That connection makes Play On! particularly meaningful. This isn't simply Shakespeare with jazz added to it. It is a conversation between William Shakespeare and Duke Ellington, two artists separated by centuries but connected through their understanding of human behavior, love, comedy and the power of performance.
The cast embraces that world beautifully. James Earl Jones II brings comic energy and warmth to Sweets, while Alanna Lovely gives Miss Mary a strong and engaging presence. James Harkness brings charm and theatricality to Jester. Alan H. Green gives Rev authority and comic flair.
At the center, Wright's Vy captures the vulnerability and determination of a young artist trying to discover who she is and where she belongs. Brown's Lady Liv brings glamour and emotional power, while Utomi's Duke possesses the commanding presence of a bandleader who has created his own musical kingdom.
Epps understands that the success of Play On! depends upon allowing Shakespeare's story and Ellington's music to breathe together. The result is a production that feels celebratory without becoming superficial, and contemporary without abandoning its literary foundation.
Play On! is Shakespeare filtered through the cultural richness of 1930s Harlem, propelled by Duke Ellington's music and driven by a syncopated Harlem beat.
It is a joyous reminder that great stories can travel across centuries - and sometimes, when the right music is added, they can still make us want to dance.
Highly Recommended
When: Through Oct. 18
Where: The Yard at Chicago Shakespeare Theater on Navy Pier, 800 E. Grand Ave.
Running time: 2 hours, 20 mins.
Tickets: $55-150
312-595-5600
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