Desiree Montes plays Billie Holiday in “Lady Day at Emerson’s Bar and Grill,” running June 6-29, 2025 at Stageworks Theatre in Tampa, Forida. Credit: c/o Stageworks Theatre
The late, great Billie Holiday was last in Tampa on the Chitlin Circuit at least 65 years ago. But Stageworks Theatre is bringing her music and spirit back to town in the last show of its 2024-2025 season.

“Lady Day at Emerson’s Bar and Grill” takes audiences to a run down South Philly bar in 1959, where Holiday (played by Desiree Montes) gives one of her final performances.

This is Montes’ sixth time reprising the role, where she’ll do renditions of classics like “God Bless the Child” and “Strange Fruit” while telling Holiday’s true stories of a turbulent life shaped by fame, racism, addiction and resilience.

Musical director William P. Coleman stars as Jimmy Powers.

Audience members can be seated at select cabaret tables for two or four, which come with a bottle of wine or cava per pair, or in regular seating.

Tickets are $25-$45 for “Lady Day at Emerson’s Bar and Grill,” opening Friday, June 6 at 8 p.m. in Tampa. The show runs 8 p.m. Fridays; 3 p.m. and 7:30 p.m. Saturdays; and 3 p.m. Sundays through June 29.

Update 6/3: This story has been updated to clarify that regular seats are available along with cabaret tables.

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This article appears in May 29 – Jun 4, 2025.

Selene San Felice is managing editor of Creative Loafing Tampa Bay. Prior to joining CL in 2025, she started the Axios Tampa Bay newsletter and worked for her hometown paper, The Capital in Annapolis,...