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Chicago Shakespeare Theater (CST) announces the cast and creative team for Play On!, which opens the Theater's 40th Anniversary Season. This jazz musical tells Shakespeare's beloved comedy Twelfth Night through the timeless tunes of quintessential American composer Duke Ellington. Play On! was originally conceived by director Sheldon Epps, who returns to the three-time Tony-nominated musical with a newly updated book by Cheryl L. West for the first time in 20 years to stage Shakespeare's story for a new generation. Broadway veterans Hailee Kaleem Wright, Krystal Joy Brown, Alan H Green, James Harkness, and Edred Utomi lead a cast that also features Uria Bennett, Kaylah Janssen, James Earl Jones II, Marquez Linder, Alanna Lovely, Selena Robinson, Dylan C. Smith, Joey Stone, Shelbi Voss, and Danny Dwaine Wells II. The production runs September 11–October 18 in The Yard.

Aspiring songwriter Vy takes the A-Train to Harlem in the swinging 1930s with big dreams of a career in showbiz, only to find that it's a man's world. She disguises herself to reach the inner circle of renowned band leader, The Duke—but plans backfire when she catches the eye of Lady Liv, the star singer of the Cotton Club, and mistaken identities make way for romance. Music is indeed the food of love with big band pizzazz and Ellington's hit songs "It Don't Mean a Thing," "Don't Get Around Much Anymore," "I'm Beginning to the See the Light," and many more.

"Over the last couple of years, Cheryl and I took a deep dive back into the book of the show," shared Epps. "Our credo in all of this has been to enhance and heighten the celebration of Black Excellence, Black Brilliance, and Black JOY. The Excellence being the celebration of the artists who inspired these characters and the actual cast onstage; the Brilliance is that of Mr. Shakespeare and the Duke of Ellington; and the Joy is consistently the experience of the audience that we hope to achieve with each performance. In simple but very effective ways, we have and will continue to focus on the fact that the show is all about the search for LOVE, and removing the masks that we often wear that keep that hoped-for goal from entering our lives fully."

"Play On! couldn't be a better production with which to begin our 40th Anniversary Season," added CST Artistic Director Edward Hall. "It perfectly reimagines Shakespeare's story with the indelible music of Duke Ellington, two geniuses of their craft whose work transcends time to speak directly to us today. This show promises virtuosic performances and infectious joy, and we look forward to sharing it with our audiences this fall."

Playing the role of Vy is Hailee Kaleem Wright, who recently ended a run as Satine in Broadway's Moulin Rouge!, and whose other Broadway credits include Catherine of Aragon in SIX and the original cast of Paradise Square, including the pre-Broadway run in Chicago. In the role of Lady Liv is Krystal Joy Brown, who played Gussie Carnegie in the Tony Award-winning 2023 revival of Merrily We Roll Along, and whose other Broadway credits include Hamilton, Big Fish, and Motown the Musical. Alan H Green plays Rev, returning to Play On! nearly 30 years after appearing in the original Broadway cast. His other Broadway credits include Charlie and the Chocolate Factory, School of Rock, and Sister Act, and he was most recently seen as Count Carl-Magnus Malcolm in Marriott Theatre's production of A Little Night Music. James Harkness, who plays Jester, was in the original Broadway cast of Ain't Too Proud: The Life and Times of The Temptations, Beautiful: The Carole King Musical, and The Color Purple, among many other credits. In the role of The Duke is Edred Utomi who recently ended a run as Alexander Hamilton in Hamilton on Broadway, after touring the US with the production for many years.

In the role of Sweets, three-time Jeff Award nominee James Earl Jones II returns to CST after playing Cogsworth in Beauty and the Beast and Donkey in Shrek the Musical. His other credits include the national tours of Company, Come From Away, and Porgy and Bess, and recent Chicago credits include Theater of the Mind at Goodman Theatre, and Catch Me If You Can and Titanic at Marriott Theatre. Alanna Lovely plays Miss Mary, with Chicago credits including Big White Fog at Court Theatre and Beautiful: The Carole King Musical, The Little Mermaid, Ain't Misbehavin', Guys and Dolls, and Rodgers & Hammerstein's Cinderella at Drury Lane Theatre. In the role of CC is Kaylah Janssen, who recently graduated with an MFA in Acting from the Theatre School at DePaul, where she appeared in Ride the Cyclone and The Lieutenant's Dream.

The ensemble features Uria Bennett (Personality: The Lloyd Price Musical at the Studebaker Theatre), Marquez Linder (Mrs. Doubtfire National Tour, Tootsie National Tour), Selena Robinson (Cats at Paramount Theatre), Dylan C. Smith (I Was There When The Blues Was Red Hot with eta Creative Arts), Joey Stone (Mrs. Doubtfire National Tour and Motown the Musical on Broadway and National Tour), Shelbi Voss (The Color Purple at Goodman Theatre, The 25th Annual Putnam County Spelling Bee at Paramount Theatre), and Danny Dwaine Wells II (Shrek the Musical at Marriott Theatre, Cabaret at Paramount Theatre).

Director Sheldon Epps spent two decades as Artistic Director of the renowned Pasadena Playhouse for two decades, where he first developed Play On!, and still acts as the company's Artistic Director Emeritus. He currently serves as Senior Artistic Advisor at Ford's Theatre in Washington, D.C. Epps has directed numerous plays and musicals at many of the country's major theatres, including the Roundabout, Manhattan Theatre Club, the Guthrie, Playwrights Horizons, Seattle Repertory Theatre, Arena Stage, Ford's Theatre and the Goodman Theatre. He conceived and directed the Broadway productions of both Play On! and Blues In the Night, which both received Tony Award nominations. Blues in the Night also was nominated as Best Musical for the prestigious Olivier Award in London. He co-directed the Tony-nominated production of Baby It's You! Epps has also had a busy career as a television director, helming episodes of shows such as Frasier, Friends, Everybody Loves Raymond, Girlfriends, and many others. His memoir, My Own Directions: A Black Man's Journey in the American Theatre, was published in 2022.

Joining Epps on the creative team are Choreographer Edgar Godineaux (Lucille Lortel, Outer Critics Circle, and Drama Desk nominee for The Harder They Come at the Public Theater), Music Director Theodis Rodgers, Jr. (world premiere of safronia at Lyric Opera), Scenic Designer Beowulf Boritt (Tony Award winner for New York, New York and Act One), Costume Designer An-Lin Dauber (credits at ACT, Oregon Shakespeare Festival, Seattle Rep, and many more), Lighting Designer Adam Honoré (Tony Award nominee for Cats: The Jellicle Ball and Ragtime), Sound Designer Ray Nardelli (Lookingglass Alice at Lookingglass Theatre Company and Off-Broadway, Fault, Shakespeare in Love, Sense and Sensibility, The Tempest and more at CST), and Wig, Hair and Makeup Designer Kevin S. Foster II (credits at Carnegie Hall, Signature Theatre, Drury Lane Theatre, and many more). The production also features the work of The TRC Company - Claire Burke, CSA and Kevin Metzger-Timson, CSA (New York Casting), Bob Mason (Chicago Casting), Christopher Chase Carter (Associate Director), Kaeli Carr (Associate Choreographer), Nathanael Wilkerson (Associate Music Director), Shartoya Jn. Baptiste and Alexis Distler (Associate Scenic Designers), Trey Brazeal (Associate Lighting Designer), Emily Hayman (Associate Sound Designer), Heather Boehm (Musicians Contractor), Rolando Linares (Production Stage Manager), and Katrina Herrmann (Assistant Stage Manager). 

Opening is set for 7:00 p.m. on Friday, September 18.

Special events include: 

• Black Creativity Night – Tuesday, September 22 

Join CST to celebrate the legacy of Black Excellence, Black Brilliance, and Black Joy across music, dance, and art. This lively pre-show event will feature signature cocktails, music, an artistic conversation, and space to gather in community. Special guests and speakers to be announced. 

Chicago Shakespeare strives to make its facility and performances accessible to all patrons. Accessible seating, assistive listening devices, large-print and Braille programs, and sensory tools are available at every performance. Enhanced performances include: 

• Open captioned performances – Thursday, September 17 at 7:00 p.m. & Wednesday, October 7 at 1:00 p.m. & 7:00 p.m. 

A text display of the words and sounds heard during a play, synced live with the action onstage. 

• ASL interpreted performance – Friday, October 9 at 7:00 p.m. 

All dialogue and lyrics are translated into American Sign Language by two certified interpreters 

• Audio-described performance – Sunday, October 11 at 2:00 p.m. 

A program that provides spoken narration of a play's key visual elements for patrons who are blind or have low vision. 

Play On! is presented by special arrangement with MMaxwellMedia, Alyssa Melani, and Willette Klausner.

CST thanks Principal Production Sponsor Bulley & Andrews and Lead Production Sponsor Ropes & Gray for supporting this production. 

Play On!

Inspired by Shakespeare's Twelfth Night

Conceived by Sheldon Epps

Book by Cheryl L. West

Music by Duke Ellington

Directed by Sheldon Epps

September 11–October 18, 2026

The Yard

PERFORMANCE LISTING

• Tuesdays at 7:00 p.m.
• Wednesdays at 1:00 p.m. and 7:00 p.m. (no matinee September 16)
• Thursdays at 7:00 p.m.
• Fridays at 7:00 p.m.
• Saturdays at 2:00 p.m. and 7:00 p.m. (no matinee September 12)
• Sundays at 2:00 p.m.
• Sundays at 2:00 p.m.

CREATIVE TEAM

Sheldon Epps – Director

Edgar Godineaux – Choreographer

Theodis Rodgers, Jr. – Music Director

Beowulf Boritt – Scenic Designer

An-Lin Dauber – Costume Designer

Adam Honoré – Lighting Designer

Ray Nardelli – Sound Designer

Kevin S. Foster II – Wig, Hair and Makeup Designer

The TRC Company – New York Casting

Claire Burke, CSA

Kevin Metzger-Timson, CSA

Bob Mason – Chicago Casting

Christopher Chase Carter – Associate Director

Kaeli Carr – Associate Choreographer

Nathanael Wilkerson – Associate Music Director

Shartoya Jn.Baptiste – Associate Scenic Designer

Alexis Distler – Associate Scenic Designer

Trey Brazeal – Associate Lighting Designer

Emily Hayman – Associate Sound Designer

Rolando Linares – Production Stage Manager

Katrina Herrmann – Assistant Stage Manager

CAST

Krystal Joy Brown – Lady Liv 

Alan H Green – Rev 

James Harkness – Jester 

Kaylah Janssen – CC 

James Earl Jones II – Sweets 

Alanna Lovely – Miss Mary 

Edred Utomi – Duke 

Hailee Kaleem Wright – Vy 

Uria Bennett – Ensemble 

Marquez Linder – Ensemble 

Selena Robinson – Ensemble 

Dylan C. Smith – Ensemble 

Joey Stone – Ensemble 

Shelbi Voss – Ensemble 

Danny Dwaine Wells II – Ensemble 

CHICAGO SHAKESPEARE THEATER (CST)

CST is a leading international theater company and the nation's largest year-round theater dedicated to the works of Shakespeare. Under the visionary leadership of Artistic Director Edward Hall and Executive Director Kimberly Motes, the Regional Tony Award recipient is committed to creating vivid, entertaining theatrical experiences that invigorate and engage people of all ages and identities by illuminating the complexity, ambiguity, and wonder of our world. Each year, nearly a quarter of a million people experience CST's artistry through more than 12 productions. With Shakespeare at the heart of the artistic work, CST also produces compelling, contemporary stories from fresh voices of today. CST brings the world to Chicago and sends Chicago out into the world as Chicago's foremost presenter of international theater, and consistent producer of North American and world premieres. Serving more students and teachers than any theater in the city, CST annually welcomes more than 20,000 students to performances and programs like Chicago Shakespeare SLAM, alongside professional development opportunities for teachers. CST activates its campus with three venues: 700-seat The Yard; the 500-seat Jentes Family Courtyard Theater; and the 200-seat Carl and Marilynn Thoma Upstairs Studio. Shared humanity and unforgettable stories—now THIS is Chicago Shakespeare. www.chicagoshakes.com