10/02/2013 02:34 pm ET Updated Jan 23, 2014

Lady Day Lives

When Dee Dee Bridgewater launched the London run of Lady Day, her 1987 musical drama about Billie Holiday's bid for a late-career comeback, she got an audience reaction both gratifying and surreal: Fans flooded her dressing room with letters addressed to Holiday, one of the greatest jazz vocalists of the 20th century, and their messages ranged from "It's great to share an evening with you," to "I'll never forget how you've changed my life."

Holiday, who gave the world "Strange Fruit" and other classics, had died 18 years earlier, broke and alone in a Manhattan hospital. But it obviously didn't matter to her devotees. And now, as Bridgewater prepares to revive the play in New York on October 3rd, she's prepared for similar reactions. It's easy to understand why, given the creative challenge she faces each night on stage.

A Tony and three-time Grammy winner who has mastered the worlds of jazz, blues and musical theatre, Bridgewater is caught between the power of her own electric persona -- well-honed during a 40-year career -- and a legend's magnetic legacy. Who is she, really, when the lights go down? The actress said she's not trying to impersonate Holiday; only to channel and recreate an unforgettable character. Sometimes, however, the lines get blurred.

"To tell you the truth, it's a very frightening journey that I'm on, and I'm nervous about it," said Bridgewater, pausing for a break in rehearsals, several weeks before opening night. "In creating this performance, I've run to her (Billie) and I've run from her. I spent the first two weeks trying to avoid going into all the emotions needed to do her accurately. I wanted to run away from all the dark places in her life -- and my own life -- that I've comfortably put aside. But I know you can't do that forever. To make this show successful, I've got to be absolutely true to her -- and myself."

That can be a challenge for Bridgewater, even in a simple phone conversation. Without warning, she slides into a spot-on recreation of Holiday's purring, almost musical speaking voice, then abruptly shifts back into her own deep-throated speech. "I've gone in and out of these two different voices," Bridgewater says. "And to tell you the truth, I really don't know what will happen on stage."

The two-act show is built around a fictitious comeback concert that Holiday attempts in 1954, beginning with a rehearsal and ending with scorching, full-throttle performances of the singer's most iconic songs. Produced by Thomas Gentile, and written and directed by Stephen Stahl, Lady Day also features David Ayers, Bill Jolly, James Cammack and Neil Johnson. Stahl has freshened the 1987 script with video and other multi-media touches, giving it a more modern feel. But the core show is basically unchanged.

Then as now, Lady Day has tested Bridgewater as an actress. At one point in the London run, for which she received an Olivier nomination, she became ill during a scene where Holiday shoots heroine. It was almost as if she herself went through withdrawal on stage, fighting off nausea, and the memory still rocks her. But in another sense, Bridgewater was simply being true to character.

Throughout her life, Holiday was plagued by drug addiction, police harassment, sexual abuse and a struggle simply to survive as an artist. She died in 1959 at age 44, a shadow of the dominant performer she once had been. But while Lady Day is faithful to that raw saga, Bridgewater and her team are determined to present a more humane and balanced portrait of the artist whose life has been reduced to stereotypes by movies like "Lady Sings the Blues." Indeed, the show is first and foremost a reclamation effort.

"People have the impression that Billie was this forlorn, melancholy person, but she was a very vibrant person," said Bridgewater. "I've done a lot of research, and we're going to show her great sense of humor. I talked to musicians who worked with her. They said she was flirty, funny and loved to cook. She cursed like a sailor. She was a genuinely warm, loving person."

Holiday was also a victim of her times -- a truth teller about America's brutalization of black people at a time when the nation didn't want to hear it. In one of its most stunning scenes, Lady Day portrays the grief and outrage underpinning Holiday's performance of "Strange Fruit," a haunting song about the lynching of blacks in the south that plunged her into controversy.

"That song was nothing but courage," said Bridgewater. "And after she started performing it she started being harassed by the government and local law officers. America didn't want to know about that song, especially a song coming from a black woman. It changed Billie's life. And we make that very clear in the play."

Many of the songs in Lady Day will be familiar to Bridgewater's fans, because they appeared on "Eleanora Fagan: To Billie with Love from Dee Dee Bridgewater," the 2010 CD that won Bridgewater her third Grammy, for Best Jazz Vocal Album. She has equally high hopes for the newly-launched show, and there's buzz that it might move to a Broadway house. But whether or not that happens, Bridgewater has a more fundamental goal.

A budding jazz singer whose career took off in the 1970s, she won a Tony award playing Glinda the Good Witch in "The Wiz." Much of her work since then has been in recording studios and in concert venues around the world, and she also hosts National Public Radio's "Jazz Set" series. But now as she brings her first dramatic presentation to the New York stage, Bridgewater is hoping to settle into more steady theatrical work -- on stage, TV or movies -- while continuing her recording and musical performances.

"I'd really like to get back into the dramatic aspect of my career," she said. "And I'm hoping this show will help me do just that."

The best indication, she added, is how audiences react when the curtain comes down. "I want people to walk out the theatre amazed and stupefied by the life and career of Billie Holiday," the actress said. "They've got to walk away talking about Billie, not Dee Dee Bridgewater. If they do, that will tell me I've done a good job."

Lady Day opens October 3 at the Little Shubert Theatre, 422 W. 42nd Street, New York, NY.

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