
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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Despite the fact that I have never read the Newberry Award-Winning children’s book called Last Stop on Market Street, I chose to see the musical adaptation on a sunny Saturday afternoon. And I have to say, I am impressed with this fun-loving musical at the Young People’s Theatre of Chicago. This show is everything you could ask for with beautiful variations of music, singing, dancing and a playful cast.
The show adapted by Cheryl L. West from Matt de la Peña’s best-selling picture book, begins with a young boy named C.J. arriving at his Nana’s house for a short stay while his parents are on a work trip. C.J. is quickly introduced to his Nana’s neighborhood with a joyous welcome song from the neighbors that is contrasted with C.J. 's wishes to go back home. As time goes on, Nana and C.J. reach a point of contention over C.J. wanting to use his electronics and Nana wanting to spend quality time with her grandson. Nana realizes C.J. has been closed off to the world around him and takes him on an adventure through the city on the bus and to a soup kitchen. These experiences challenge C.J. and open him up to the diversity of humans and life around him. Throughout the story C.J, learns valuable life lessons that we all can benefit from.
The backdrop of the stage is a colorful painting of Nana’s street in the city. The buildings and nature on that street are similar to the illustrations in the Last Stop on Market Street book. The setting has smooth transitions from the vibrant neighborhood street to Nana’s old-fashioned living room, and to the bustling soup kitchen. As the stage transforms throughout the story, the cast keeps you entertained by making their way through the crowd.
The six-member cast is packed with talent. Many of them play multiple characters and have fun on stage acting out each of their roles. I love how magnetic the cast is and feel that each of their characters are relatable to those who live around us in Chicago.
One standout cast member is Aja Singletary who plays the main character, C.J. She brilliantly captures the childlike personality of the young boy. She fully embraces the wild ride of emotions C.J. endures as he has his electronics taken away, meets interesting people on the bus, and asks a million questions about the world around him. Despite being an adult woman, Singletary acts as a convincing child who the children in the crowd seemed to have identified with. She takes on C.J.’s mannerisms, whining, imagination, and laughter with ease on stage.
The wide-range of music is the best feature of this show. The song genres include hip-hop, soul, gospel and Motown funk. I found myself tapping to the beat and bopping my head along with many children dancing along in the crowd. Each song is super catchy and carries a powerful message worth remembering. Last Stop’s wonderful score is by Paris Ray Dozier and his father Lamont Dozier, writer of Motown hits like “How Sweet It Is” and “You Can’t Hurry Love. The lyrics are cleverly written and even left a few of us laughing with interwoven jokes.
Each cast member does a great job singing and dancing along to the music throughout the show. The choreography is on point and complements the music with engaging moves. The cast definitely shows off their talent and even takes their dance moves to the theatre’s aisles among the crowd. Richuan Stewart, who plays as the Tattooed Man and Vernon, shocked me with an impressive vocal range and beautiful singing voice. He captivates the crowd with a few solos and a contagious smile.
If you have an upcoming free Saturday or Sunday, I highly recommend seeing ‘Last Stop on Market Street.’ This musical is an uplifting story filled with diversity and lifelong lessons both children and adults can benefit from. It’s an awesome way to spend some time with your little ones or even on your own. It will leave you feeling joyful and may even give you a new and loving perspective on those who are around you.
Last Stop on Market Street is at the Young People’s Theatre of Chicago located in the Greenhouse Theater Center on 2257 N. Lincoln Ave in Lincoln Park. The show will run May 11th through June 2nd, 2024. Performances run Saturdays at 11:00 a.m. and 1:30 p.m. and on Sundays at 1:30 p.m. This show is best enjoyed by everyone ages 4+, even including adults like me. The show has a quick 60-minute runtime with no breaks. Tickets are $25 for adults and $19 for those under the age of 12. Visit Young People’s Theatre of Chicago’s website at yptchi.org and buy your tickets today!
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