If Shakespeare had known Duke Ellington, Twelfth Night might have come with a horn section. Chicago Shakespeare Theater’s Play On! finally makes the introduction, and the party is in full swing.
Set in 1930s Harlem, Sheldon Epps’s Tony-nominated musical reimagining of Shakespeare’s Twelfth Night takes on gender swapping, romantic intrigue, and the heartbreaks behind the blues, scored with Ellington’s biggest hits and Epps back at the helm.
Complete with tap-dancing, feathers, sequin-heavy costumes, and production numbers that go big, it’s a shock that the original 1997 Broadway production only lasted 61 performances. Chicago Shakes’ 40th anniversary season opener is a delightful throwback, daring its audience not to dance out of the theater.
It wants better content.
A songwriter in disguise—what could go wrong?
Mississippi transplant Vy (Hailee Kaleem Wright) wants to pen great tunes under the mentorship of legendary bandleader The Duke (Edred Utomi). If she has to “pull back [her] fat and strap down [her] rack” to be taken seriously, so be it. The Duke believes in “Vy Man,” but he’s in a slump over the rejection of golden-voiced Lady Liv (Krystal Joy Brown).
The Duke will help Vy if she woos Lady Liv on his behalf. But when Lady Liv falls for “Vy Man,” and Vy falls for the Duke, the disguised songwriter must dig deep for her perfect melody.
Epps and book writer Cheryl L. West bring the Bard to Harlem by interweaving Ellington’s songs in Shakespearean moments: soliloquies of unrequited love, moments of connection between strangers, and drunken duets. A hilarious subplot recalls the original play as costumer Miss Mary (Alanna Lovely), her man Sweets (James Earl Jones II), and Vy’s uncle (James Harkness) goad Liv’s devoted, buttoned-up assistant (Alan H. Green) into an ill-fated makeover.
Standout performances include Harkness, who recalls Twelfth Night’s Feste with quippy wordplay and a commitment to keep the party going, and Wright, whose soulful Vy comes into her own as a songwriter and a woman in love. As Lady Liv, Brown is a revelation, capturing a performer tired of her pedestal with brilliant comic timing and stripped-down, shattering vocals.
Does Play On! stand the test of time? Thanks to Epps’s sure hand, a swinging score, a stellar ensemble delivering smart comedic beats and flawless high notes, and Edgar Godineaux’s high-energy choreography, the answer is a resounding Oh yeah!
Is ‘Play On!’ worth seeing?
Chicago Shakespeare Theater kicks off its 40th anniversary season with a must-see: a jazzy, joyful tribute to the Bard that will have your toes tapping from beginning to end.
- Chicago Shakespeare Theater on Navy Pier, 800 E. Grand Ave., Chicago
- Notable performers: Krystal Joy Brown, Hailee Kaleem Wright, James Harkness
- Running time: Approximately 2 hours 20 minutes with one intermission
- Performances through October 18, 2026
Have another minute?
Washington, DC – In ‘The Score,’ Brian Cox plays a composer who tests how much truth a king can take
Off-Broadway – The world has a group chat about America, and Sarah Jones brings the whole family to respond
Hudson Valley – Hudson Valley Shakespeare built a theater and cast the landscape in the lead
