Chicago Shakespeare Theater Debuted Jazz Musical PLAY ON!

The theater opened its 40th anniversary season with a production set in Harlem featuring the music of Duke Ellington.

Updated on Oct. 9, 2026 in Cultural

Screen-print poster illustration showing a brass saxophone on a velvet theater seat, evoking the jazz-infused spirit of the theater production.
Chicago Shakespeare Theater launched its 40th anniversary season with the debut of 'PLAY ON!', a jazz musical adaptation of 'Twelfth Night' set in Harlem. AI Illustration. Upload story photo >

Chicago Shakespeare Theater has launched its 40th anniversary season with a staging of the jazz musical PLAY ON!. This production adapts the plot of Shakespeare's Twelfth Night and utilizes the music of Duke Ellington to tell its story in Harlem.

Why it matters

The production represents a significant milestone for the institution as it commemorates four decades of performance in Chicago. It brings together classical narrative themes and jazz history through the creative direction of Sheldon Epps.

The show marks the 40th anniversary season for the Chicago Shakespeare Theater. The production's musical score is drawn entirely from the catalog of Duke Ellington.

The players

Alan H. Green

He is a performer who portrays the character Rev in this production and previously participated in the 1997 Broadway run of the musical.

Sheldon Epps

He is the director responsible for the choreography and staging of this musical adaptation.

Cheryl L. West

She is the writer who authored the book for this jazz musical adaptation.

Duke Ellington

He was a legendary American composer and pianist whose music serves as the foundation for the musical score.

Chicago Shakespeare Theater

It is a prominent cultural institution in Chicago currently celebrating its 40th anniversary season.

The details

Director Sheldon Epps helms the production, which uses the book written by Cheryl L. West to reimagine Twelfth Night. Actor Alan H. Green, who previously served as an ensemble member and understudy in the 1997 Broadway run, now stars in the role of Rev.

Timeline

  1. The original Broadway run of the musical took place in 1997.

  2. The production opened the theater's 40th anniversary season in 2026.

Industry Dynamics

The production marks a return to the stage for a musical that first debuted during the 1997 Broadway run of PLAY ON!. This revival highlights how regional theaters are increasingly re-examining established works to anchor major season celebrations.

Local audiences can attend the production as part of the theater's 40th anniversary season programming. The show provides a unique opportunity to hear Duke Ellington's music integrated into a theatrical narrative set in Harlem.

The takeaway

This production offers a bridge between classical Shakespearean narratives and the rich history of American jazz music. Attendees can see how professional theater institutions continue to preserve and reinterpret Broadway works for contemporary local audiences.

Further reading

For more on the performing arts in the city, visit the Chicago Cultural section.

Source note: This article includes information reported by Broadway World.