Review: PLAY ON! at Chicago Shakespeare Theater

Play On! is a lively retelling of Shakespeare’s Twelfth Night. Conceived by Sheldon Epps (who also directs) and with a book by Cheryl L. West, Play On! transports Shakespeare’s story to Harlem, New York. West’s book skillfully weaves Duke Ellington’s songs into the narrative. 

It’s handy that Ellington wrote so many ditties about yearning and unrequited love. Aspiring songwriter Vy (Hailee Kaleem Wright) arrives in Harlem and wants to make it big. But of course her uncle Jester (James Harkness) warns her that women couldn’t possibly be songwriters (groan!) They hatch a scheme in which Vy will disguise herself as her late twin brother Bass and present her songs to Duke (Edred Utomi). Duke has writer’s block and can’t stop pining after Lady Liv (Krystal Joy Brown). 

Vy comes onto the scene rechristened as Vy-Man, and she just might have the songs to save the day. But once Vy gets to know Duke, she falls in love with him. In classic Shakespearean fashion, Duke suspects he might also have feelings for Vy...except for the fact that he thinks she’s a man.

In the B-plot, Jester and his pals Sweets (James Earl Jones II) and Miss Mary (Alanna Lovely) conspire to teach the nerdy and earnest Rev (Alan H. Green) to woo Lady Liv, expecting the mission will fail. It’s a great device for the trio to perform “It Don’t Mean A Thing” as their lesson to encourage Rev to find his “swing.” But perhaps Jester and Sweets aren’t the best at giving dating advice, after all. Both men suffer from a major case of commitphobia to their respective partners CC (Kaylah Janssen) and Miss Mary. Because this is a Shakespearean comedy, you can guess how it all turns out. 

The cast that bring West’s book and Ellington’s songs to life are definitely the reason to see this show. Wright is a winsome and appealing heroine. She plays Vy/Vy-Man with the right combination of earnestness, energy, and a little awkwardness. Wright has a spectacular, full-bodied singing voice. 

Brown is another undisputed star of this production. She dusts off performing chops that echo her turn as Gussie in the most recent Broadway revival of Merrily We Roll Along. Brown knows how to play a diva, and she delivers each of her numbers with delectable vocal power.

Green seems closest to one of Shakespeare’s clowns as Rev, and he doesn’t shy away from making a fool of himself on stage. Green’s commitment is necessary to making the bit work, and commit he does.

I’m always delighted to see James Earl Jones II on a musical theater stage, and the supporting role of Sweets is a great fit for him. Jones and Harkness duet spectacularly on the second act number “Rocks In My Bed.”

Also I need to mention that An-lin Dauber’s costumes are particularly glorious. She uses a fantastic and visually striking array of colors and fabrics — and ALL of the sequins for Lady Liv’s fabulous outfits.

West ensures that Ellington’s songs fit neatly into the Twelfth Night story, and the songs flow naturally out of the narrative. Still, because we all know how this ends, I think the show could easily trim off 15 to 20 minutes (though the show debuted in 1996, so that’s unlikely to happen at this point).

If you’re looking to see Shakespeare reimagined through the song catalog of another iconic artist and if you want to see Duke Ellington songs sung well, Play On! Supplies that food of love (music) in spades. 

Play On! runs in the Yard at Chicago Shakespeare Theater on Navy Pier, 800 East Grand Avenue, through October 18, 2026. 

Reader Reviews

To post a comment, you must register and login.

Chicago News

Get the latest news, discounts & more