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Lady Day Sings the Blues (at Emerson’s Bar and Grill)

Alexis J. Roston stars as Billie Holiday in Milwaukee Rep production

Aug. 30, 2016
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Billie Holiday didn’t sing with the intimidating virtuosity of Ella Fitzgerald, but with an intimacy that continues to speak directly to listeners a century after her birth. Singing mostly about romance and sex, Holiday brought heartfelt experience to lyrics that could have sounded trite in the mouths of others. Her posthumous fame is sustained as much by her story as her music, especially the tragedy of the heroin addiction that sapped her strength, and her death in a Harlem hospital, her room raided by police who arrested her after finding a tinfoil packet of heroin. She died in that room in 1959, age 44. 

Little wonder her life and the music that was inseparable from it inspired a popular movie, Lady Sings the Blues, and later a stage play, Lady Day at Emerson’s Bar and Grill. Playwright Lanie Robertson’s Lady Day returns to the Milwaukee Repertory Theater this month with Alexis J. Roston, previously seen in the Rep’s rendition of The Color Purple, in the lead role. Roston comes to the part well prepared after starring in an award-winning production of Lady Day at Chicago’s Porchlight Music Theatre.

For Lady Day’s Milwaukee Rep director, Leda Hoffman, the show is not a musical revue but “a full piece of theater with a full story to tell—the text is interwoven seamlessly into the songs.” Although still best known for directing King Lear at Alchemist Theatre and her work at Shakespeare festivals around the Midwest, Hoffman sought the challenge of helming a play with music and was drawn to Holiday’s recordings. “She was known for telling a story through her songs,” Hoffman says. “The lyrics were real to her—she sang deeply from what was in her heart, connecting what was in the song with the audience. Honesty in performance is important to me as a director.” 

Although Lady Day is a fictionalized recreation of a performance from the final months of Holiday’s life, the play is rooted in reality. Holiday actually sang at Emerson’s, a seen-better-days bar in Philadelphia that becomes a metaphor for a singer in decline following her triumphant Carnegie Hall concert only a few years earlier. “You see a woman whose prime of life is past as her addiction and health problems pile up,” Hoffman says. “She’s aware of the strain on her body. Lady Day includes incredibly hopeful moments, but Billie Holiday is aware of what she’s lost.”

Lady Day’s second character is Holiday’s accompanist, a fictional piano player called Jimmy. “Jimmy is her rock. She knows she needs Jimmy to keep her on track,” Hoffman says. “Jimmy cares deeply about her as an artist. There is a struggle between the two of them as they figure out how they will make it through the performance.” Lady Day’s music director, Abdul Hamid Royal, plays Jimmy.

In between “God Bless the Child,” “What a Little Moonlight Can Do” and other songs associated with Holiday’s career, the singer flashes back into her past. “One of the exciting challenges about the play is figuring out how to dive into Holiday’s stories and memories,” Hoffman says. “Our design team takes it a step further than the songbook of a legendary singer, using light and sound to take us to emotional places different than what would literally be happening at Emerson’s Bar and Grill.”

As for casting the new production of Lady Day, Hoffman skipped the usual audition process and went to Rep veteran Royal (“everyone was talking about what an incredible piano player he was”) and straight to Roston after her buzz-generating turn as Holiday at Chicago’s Porchlight. “I watched videos of her performance and said, ‘This is the person,’” Hoffman explains. “It’s so important to have a great performer at the center of this play. She had put so much work and thought into her performance as Billie Holiday and was excited to look at the material again.” 

The Milwaukee Repertory Theater presents Lady Day at Emerson’s Bar and Grill, Sept. 9-Oct. 30 at the Stackner Cabaret, 108 E. Wells St. For tickets, visit the box office or milwaukeerep.com or call 414-224-9490. 

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