When Alexis J. Roston takes the stage as Billie Holiday this month in Mercury Theater Chicago’s production of Lady Day at Emerson’s Bar and Grill, she’ll be marking a rare milestone: Her sixth run in the demanding role comes 10 years almost to the day after her initial outing, for which she received a Jeff Award in 2013.

“That first time out, I was so scared to do it,” Roston says. Rob Lindley, who directed that Porchlight Music Theatre production, had asked her to audition. “ ‘Why?’ was my question, because in my mind I sounded nothing like Lady Day,” says Roston. “It was like a sheer testament of how much a friend trusts your gift — that you don’t even see it, but they thought I could do it.”

The play is set a few months before Holiday’s 1959 death at age 44. Playwright Lanie Robertson imagines the singer performing to a tiny crowd at the Philadelphia nightclub of the title, high on heroin and only intermittently lucid between songs. Holiday has some light interaction with the onstage musicians, but Robertson’s play is essentially a 90-minute monologue interspersed with numbers like “God Bless the Child,” “I Wonder Where Our Love Has Gone,” and “Strange Fruit.”

Roston, who in 2013 went by Alexis J. Rogers (she changed her surname after marrying fellow actor Kelvin Roston Jr., with whom she now lives in Chatham, near where she grew up), earned raves for the Porchlight production. Chris Jones, reviewing for the Tribune, wrote that “not only does Rogers sound like Holiday, she captures her power, discipline, free spirit and aching vulnerability in roughly equal measures, which is a decidedly tricky cocktail to mix.”

Roston in her original 2013 performance at Porchlight
Roston in her original 2013 performance at Porchlight Photograph: Kelsey Jorissen

Roston reprised her role as Holiday in 2016 at Milwaukee Rep, drawing a kind of backhanded praise from some audience members. “There were people who walked up to the house manager like, ‘I can’t believe you let your artists go onstage high like that,’ ” Roston recalls. “Like they really thought that I was high and performing!” She returned to the role for a 2018 Chicago run with Congo Square Theatre, where she’s an ensemble member, and has since performed the play at theaters in St. Louis and Kalamazoo, Michigan.

The latest production, staged in Mercury’s intimate Venus Cabaret space, marks Roston’s first time as codirector, alongside the theater’s artistic director, Christopher Chase Carter. “I have, in my mind, taken notes from all of the productions about things that I would have wanted to do,” Roston says. That includes creating an environment that feels more like a downmarket tavern than a theater. “Emerson’s was not a grand stage. Creating that element of ‘This is what she’s been reduced to’ — that’s important to me.”

With showgoers seated at cabaret tables in a small room, Roston sees an opportunity for more intimate interactions. “I can engage the audience in a way I’ve never been able to; I can freely move about the cabin, as we like to say.”

Performances are scheduled from January 27 to March 26, but Roston says the run could extend. “We’ll play it by ear and see how long people want it.” What’s not in doubt is that she wants it, as her empathy for Holiday has only deepened over the years. “All she ever wanted to do, in my mind, is sing and be loved. I realized once I turned 45 last February, I had surpassed Billie in number of years on this earth. And that gave me an extra push — I was like, Well, I have to do this now. It is my job now to continue Billie’s legacy in the best way I know how.”