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BOOTLEG: AMERICA SINGS 1927 at Asolo Repertory Theatre

Dates: 4/21/2027 - 5/16/2027

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Asolo Repertory Theatre

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BOOTLEG: AMERICA SINGS 1927 invites audiences into a vibrant speakeasy setting reminiscent of the Roaring Twenties. Curated by Cat Brindisi, Terrance Jackson, James Monaghan, and Peter Rothstein, this immersive cabaret celebrates a pivotal year in American culture through the words of literary icons like Langston Hughes and Edna Ferber, paired with timeless music from composers such as Duke Ellington and George Gershwin. The show runs from April 21 to May 16, 2027, at the Cook Theatre.

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About the Theatre

Asolo Repertory Theatre

Asolo Repertory Theatre Frequently Asked QuestionsFAQ

What shows are coming up next at Asolo Repertory Theatre?

Fiddler on the Roof (4/11/26-5/24/26)
Marie and Rosetta (5/6/26-5/31/26)
Lady Disdain (6/6/26-6/27/26)
THE WIZARD OF OZ: YOUTH EDITION (7/8/26-8/2/26)
SHAKESPEARE 45: ROM-COM (9/1/26-12/31/26)
BEANSTALK: THE ADVENTURES OF JACK AND THE GIANT (9/1/26-12/31/26)
SHAKESPEARE45: ROM-COM (9/1/26-12/31/26)
SINGIN’ IN THE RAIN (11/18/26-1/2/27)
IT’S A WONDERFUL LIFE: A LIVE RADIO PLAY (12/2/26-1/3/27)
MA RAINEY’S BLACK BOTTOM (1/13/27-2/4/27)
August Wilson’s MA RAINEY’S BLACK BOTTOM (1/13/27-2/4/27)
THE ROYAL FAMILY (2/10/27-3/4/27)
PROVENANCE (2/24/27-3/21/27)
THE DAY THE CIRCUS CAME TO TOWN (3/21/27-4/24/27)
BASKERVILLE: A SHERLOCK HOLMES MYSTERY (5/5/27-5/30/27)
Ken Ludwig’s BASKERVILLE: A SHERLOCK HOLMES MYSTERY (5/5/27-5/30/27)

What shows have played recently at Asolo Repertory Theatre?

The Unfriend (2/18/26-3/22/26)
The Unfriend (2/18/26-3/22/26)
Agatha Christie’s The Mirror Crack’d (1/21/26-3/14/26)
Agatha Christie's The Mirror Crack'd (1/21/26-3/14/26)
Primary Trust (1/7/26-2/11/26)
Primary Trust (1/7/26-2/11/26)
All is Calm: The Christmas Truce of 1914 (12/3/25-12/19/25)
Come From Away (11/12/25-12/28/25)

What is the history of Asolo Repertory Theatre ?

Asolo Repertory Theatre, Florida’s premier professional theatre, is one of the most important cultural forces in the Southeastern United States. A center for theatrical excellence, Asolo Rep stages up to fifteen productions every season, spanning a diverse repertoire of newly commissioned plays, bold reinterpretations of contemporary and classical works, and provocative new musical theatre experiences.

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