Chicago Shakespeare Theater Debuts 'PLAY ON!' Trailer for 40th Anniversary Season

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New footage previews the Duke Ellington score driving this Twelfth Night reimagining.

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Chicago Shakespeare Theater has released an official trailer for PLAY ON!, giving audiences a first extended look at the musical ahead of its run. The clip highlights the production's jazz-infused energy, inviting viewers not to miss what the theater calls the show's 'A-Train.'

PLAY ON! reworks Shakespeare's romantic comedy Twelfth Night using the music of Duke Ellington as its score, blending the play's mistaken identities and tangled romances with a big-band jazz sound. The musical has previously earned three Tony nominations during its stage history.

The production marks the opening of Chicago Shakespeare Theater's 40th Anniversary Season, continuing the company's practice of pairing classic texts with reinterpreted musical frameworks. The show has been in rehearsal in the weeks leading up to its premiere at the theater.

Chicago Shakespeare Theater previously shared behind-the-scenes footage from rehearsals, showing the ensemble working through musical numbers ahead of the opening. That rehearsal video captured performers finding the show's rhythm as they prepared for the run.

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_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/chicago/article/Video-PLAY-ON-Trailer-Released-Ahead-of-Chicago-Shakespeare-Theater-Premiere-20260918)._