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Dee Dee & Billie (Bridgewater & Holiday): Two Of A Kind

Russ Davis of MOJA Radio on Bridgewater appearing as Lady Day on Broadway

Dee Dee Bridgewater in "Lady Day" on Broadway
Dee Dee Bridgewater in "Lady Day" on Broadway
Dee Dee Bridgewater and Russ Davis
Poster of Lady Day play

After living in New York City for 25 years now I’ve learned to avoid going to Times Square. There are too many people clogging the sidewalks and not much to lure me there, as I don’t require anything from souvenir shops and franchise restaurants. I was drawn there recently though by the chance to spend some time with one of the most talented and charming figures in jazz, the award-winning vocalist, actress, producer and broadcaster Dee Dee Bridgewater, who plays Billie Holiday in the newest incarnation of the musical Lady Day at the Little Shubert Theatre on West 42nd Street. I met with Dee Dee in the Eugenia Room above the legendary restaurant Sardi’s for a delightful 30 minutes of conversation about this new project that is in essence a continuation of her relationship with the late Eleanor Fagan, AKA Billie Holiday, that began years ago.

Having spent some time with Dee Dee in various settings over the years, and knowing her to be one of the most engaging and personable spirits in jazz, we seemed able to pick up where we had left off over a few years ago. My first thought was that the mysterious Billie Holiday, who certainly possessed some pretty obvious demons that were known to all, was a deep and talented person. Anyone who would attempt to play such a person in any form of depiction be it a musical performance, play or recording would have to possess similar depth and talent. Dee Dee Bridgewater is exactly that person. She’s an international star of the highest order with multiple Grammy Awards, A Tony Award for her previous work on the Broadway musical The Wiz, and a nomination for London’s Olivier Award for her work in an earlier incarnation of Lady Day that was also presented in Paris, both in the late 1980’s.

After having paid homage to Billie Holiday on stage in those European productions decades ago, Dee Dee created a true masterwork with the Grammy-winning recording in 2010, Eleanor Fagan (1915-1959) To Billie With Love From Dee Dee Bridgewater. The title itself indicates a depth of understanding of and reverence for the real person Billie Holiday. The performances on the album, created with the stellar cast of long-time associate, pianist Edsel Gomez, along with bassist Christian McBride, saxophonist James Carter and master drummer Lewis Nash, exhibit the depth and range of Holiday material and, of course, the incredible scope of Dee Dee Bridgewater’s talent as well. There are all the swinging standards and many shades of blues all presented with Dee Dee’s own stamp in honor of Billie Holiday’s ground breaking and distinctive style.

But the song on the album that seems to set the stage for what Dee Dee will bring to the theatre performance is her deeply personal and heart felt delivery of “Strange Fruit,” the famous protest song from 1939 that pointed out the horrors of lynching and the terrible injustice that seemed to be tolerated by a country about to go through a social change that would mark one of the most turbulent times in history. In Dee Dee’s voice you hear real pain. True heartache. You hear a deep understanding of the essence of the soul of Billie Holiday that few of us could ever understand. Dee Dee Bridgewater certainly seems to understand. She may not have been a street urchin, rape victim or abandoned child like Billie Holiday. She may not have suffered the taunts from racist audiences or daily disrespect from the racist society in which she was one of the greatest artists of the day, but Dee Dee Bridgewater knows, truly KNOWS, these things in her soul. With the talent and personal power that she possesses Dee Dee will surely bring these truths to the stage in her performance in Lady Day.


The musical Lady Day, previews began on September 19th with the opening on October 3rd, is not a complete survey of the life and times of Eleanora Fagan. One assumes that most people in the audience will have a basic idea of what Billie’s life was like leading up to the point in time that the play covers. The performance takes us backstage as Billie, in the later stages of her life and career, is attempting a final comeback. The first act sets the stage and tells the story of Billie’s struggle to recapture another moment of public greatness while battling all her inner trials and torments. The second act features the live performance of over twenty-five Billie Holiday standards. It promises to be another moment of Broadway magic that will truly make an historical figure come to life. She told me that she considers Billie Holiday the most important jazz singer of all time, above Ella, Sarah, etc. This is serious business for Dee Dee and she seems dedicated to “getting this right” for all time.

When I asked her what she wanted the audience to take away from the show, Dee Dee was quick to say that she would be disappointed if they remembered it as “Dee Dee Bridgewater in a great performance as Billie Holiday.” Instead she wants the audience to leave “knowing the real Billie Holiday,” with all her faults and triumphs, the elegant fighter. Dee Dee’s own, personal note from the Eleanor Fagan CD insert explains perfectly her intention to teach a lesson with this performance. It reads…”Young people take note of this woman’s life, this woman’s bravery, so you too can learn to stand up, and not be afraid to speak in your own voice. Children, stand tall and dare to be a Billie Holiday.”

As I was walking through Times Square on my way to speak to Dee Dee Bridgewater I had the thought that if someone were to attempt to portray Dee Dee Bridgewater they’d need to have great beauty and charm, immense musical talent, great intelligence and strength of spirit and character. Only someone with all of these qualities can effectively and completely portray Billie Holiday and truly bring this woman back to life. Dee Dee Bridgewater is exactly that person.


Russ Davis produces and presents the only jazz program – “Jazz America” – for the U.S. Government Service, Voice of America. He also programs and presents the online modern jazz channel MOJA Radio, a subscription service. You can hear a number of free programs, including the latest Jazz America show by visiting MOJA Radio’s website.

Originally Published