***** “Play On!” is the magical transformation of Shakespeare’s play Twelfth Night into a modern musical that rejuvenates the original gender-bending story. The fusion of the Bard’s original romantic comedy with Duke Ellington’s songs and jazz compositions is nothing short of extraordinary! Written and conceived by Sheldon Epps and first produced in 1996 at the Goodman Theatre and later on Broadway in 1997, the three-time Tony-nominated musical has made its return to Chicago, now in its run at the Shakespeare Theater at Navy Pier. This is one of the best shows that you’ll see all year and can rival anything that you might see in New York or London.Several strands of plots and subplots neatly come together in this tale, each of which are easy to follow and largely based on the web of relationships among the characters. The famous opening line from Twelfth Night “If music be the food of love, play on” is paraphrased in the second act, with the medium of music ultimately being the glue that ties people together. All throughout, we see how love triangles, career interests, and other personal and professional connections keep shifting as the story moves forward. We watch how various songs are used to express ambitions, feelings, and circumstances and ultimately reveal the way that everybody finds their most perfect mates.
The entire cast of fifteen makes this show a one-of-a-kind success, featuring high-quality acting with panache and verve. The main cast members have incredibly beautiful singing voices, foremost among them being Hailee Kaleem Wright (whose voice is in the mezzo-soprano range). She plays Vy, a young woman who takes a one-way ticket from her hometown in Mississippi to New York City in the 1930s. Vy’s destination is Harlem, and Billy Strayhorn’s “Take the ‘A’ Train” leads us off music-wise. Vy intends to reconnect with her Uncle Cootie, known to his friends as Jester (James Harkness). She knows in her heart that she is a talented songwriter, and now she wants her uncle to make introductions on her behalf. Specifically, she would like to write for a star like Duke Ellington (Edred Utomi). But Jester says that it’s a man’s world out there, and no woman songwriter could possibly be taken seriously. So guess who decides to dress up as a man and call herself Vy-Man?
Now Jester introduces Vy-Man to Duke, who has entered a fallow period in his songwriting. But he is anxious to hear something that Vy-Man has created in the hopes that it will rekindle the affections of his love interest Lady Liv (Krystal Joy Brown), a famed torch singer at The Cotton Club. And when Vy-Man is tasked with bringing the new song in person to Lady Liv, she notices that there is something very different about this new person, namely, a sensitive side, which she finds to be intriguing. Coincidentally, Vy-Man’s sensitivity is something that Duke notices too.
In addition to Vy being attracted to Duke, the show highlights all sorts of romantic interests among the characters. Jester is fond of a woman named CC (Kaylah Janssen). Miss Mary (Alanna Lovely), who is the dresser for Lady Liv, is attracted to a man called Sweets (James Earl Jones II). And then there is Rev, or the Reverend (Alan H Green), who is extremely fond of Lady Liv, and wants to do whatever he can to attract her romantically. The musical implicitly asks the questions: How do you find your true love? What is your true destiny? And what are your dearest wishes for the way that you want to lead your life?
The plethora of Duke Ellington hits throughout the performance provides the answers. From “It Don’t Mean a Thing” to “I Got It Bad and That Ain’t Good” to “Love You Madly”, the songs have been arranged in the most perfect order to accompany a hefty storyline. Choreography by Edgar Godineaux is sublime and invigorating with its authentic nod to entertainment in Harlem during the 1930s and early 1940s. The show is music directed by Theodis Rodgers Jr., who is also the band’s conductor and its keyboardist. Orchestrations are the province of Luther Henderson Jr. While Sheldon Epps has directed this show for a good number of years (and is listed as director in our playbill), an announcement was made right before the opening night performance that it was being directed by associate music director Nathanael Wilkerson.
An amazingly well-envisioned multipurpose set provides the backdrop for this show, thanks to the fine work of scenic designer Beowulf Boritt. The sliding back and forth of Duke’s piano and his living room is especially well accomplished on stage. Adam Honoré’s lighting design, with all of its red neon, adds flair to the entire presentation but especially to the dance numbers at The Cotton Club. Note that this production uses a proscenium arch that creates a dramatic viewing portal, unlike a traditional Shakespearean play whose thrust stage re-creates the one once used at London’s Globe Theatre. Sound design by Ray Nardelli is great for this space. The performance is bolstered by a huge range of beautifully designed and executed clothing by costume designer An-Lin Dauber. From the glitzy-glamor of Lady Liv’s outfits and those of the dancers to the lavish yellow tuxedo worn by the Rev and the red checked outfit worn by Vy-Man, we see the origins of these outfits in hand-colored drawings, located in the hallway on the second floor between the doors to the theatre. There we can examine poster boards that sketch out the wardrobe for each of the main characters; plus, there are various photographs of the actors wearing the finished apparel. Wig, hair, and make-up design by Kevin S. Foster II could not have been done any better, and I especially like how well Utomi is made up to resemble Duke Ellington.
“Play On!” is running through October 18, 2026, at The Yard at Chicago Shakespeare Theater, on Navy Pier, 800 E. Grand Avenue, in Chicago.
Tickets range from $65 to $150 and vary in price depending on time and date of performance and seat location.
Performance schedule:
Tuesdays – 7:00 p.m.
Wednesdays – 1:00 and 7:00 p.m.
Thursdays and Fridays – 7:00 p.m.
Saturdays – 2:00 and 7:00 p.m.
Sundays – 2:00 p.m.
For more information and to purchase tickets, please visit: https://www.chicagoshakes.com/productions/2627-play-on/.
For general information and to learn about their other offerings, go to: https://www.chicagoshakes.com/.
Note: There is a mistake in the printed program. To see the full digital program, visit https://www.chicagoshakes.com/play-on-digital-program/.
To see what others are saying, visit www.theatreinchicago.com, go to Review Round-Up and click at “Play On!”.
More Stories
“Kowalski”
“The Front Page”
“The Attic: Things I’ve Seen While Lying On My Back”