Billie Holiday at 100

The astonishment about Billie Holiday in her 100th birthday summer is how differently we hear her. Back in the day — in her music, in her autobiography — Lady Day was the full catalog of suffering in a 20th-century underground: abandonment and child prostitution on the way to drink, drug addiction, and death at 44. “The most hurt and hurting singer in jazz,” said the authoritative Nat Hentoff.


But resurrection in art jumps out of the soundtrack here — starting with her breakthrough film with Duke Ellington in 1934, when she sings, at age 19, “Saddest tale on land or sea, was when my man walked out on me.” Then, when we hear Billie Holiday’s recording of “I’ll Be Seeing You,” from 1944, she has stopped at our table in a small club and started speaking directly to us. There’s no other singer who ever made us cheer and cry at the same time. So Billie Holiday stands less for all that pain than for Hemingway’s dictum that a blues hero “can be destroyed but not defeated.”

In Billie Holiday: The Musician and the Myth, the meta-biographer John Szwed (also of Sun Ra, Miles Davis and Alan Lomax) traces the self-invention of an icon and finds the life and art of Billie Holiday running side-by-side with a truth-telling drive that did not quit. In our conversation, Szwed finds that to the end she was “smarter, tougher, funnier” than all but a few knew.


The Lovers, by Jacob Lawrence (1946). 

Five fine singers — Dee Dee BridgewaterDominique Eade, Marissa Nadler, Janice Pendarvis, and Rebecca Sullivan — are guiding us through their favorite Holiday songs: her vocal tricks and the social, emotional resonances of her music. Re-listening with them, we begin to understand and experience not just the Billie Holiday story, but the atmosphere of Harlem streets, nightclubs, and living rooms. We hear an “unflinching” voice and a “sophisticated” new sound in music.

The greatest jazz singer? The perfect jazz singer? Perhaps the only jazz singer that ever lived.

A Very Brief History of the Microphone

Lady Day not only embraced the use of the microphone, she revolutionized it. By bringing the “Harlem cabaret style” into the studio, she helped introduce a more subtle and restrained style of singing to recorded music. Our guest John Szwed gives us the rundown on how Holiday—along with Bing Crosby, Frank Sinatra, Orson Welles, and Johnnie Ray—helped to permanently change the way artists approached the mic. Read the complete story on Medium.

—Zach Goldhammer

Music From The Show

  • “They Can’t Take That Away From Me” (1937)
  • “Symphony in Black” (1935)
  • “Solitude” (1941)
  • “Fine and Mellow” (1939)
  • “Love For Sale” (1945)
  • “Them There Eyes” (1949)
  • “Strange Fruit” (1939)
  • “What a Little Moonlight Can Do” (1935)
  • “Me, Myself, and I” (1937)
  • “No Regrets” (1936)
  • “I’ll Get By” (1937)
  • “I’ll Be Seeing You” (1944)
  • “God Bless The Child” (1955)
  • “Gloomy Sunday” (1941)
  • “Lover Man” (1945)
  • “I’m a Fool To Want You” (1958)
  • “The End of a Love Affair” (1958)
  • “Fine and Mellow” (1957)

You can listen to an expanded playlist here.

Guest List
John Szwed
Anthropologist of sound, sometime professor of jazz history at Columbia and Yale, biographer (most recently) of Billie Holiday: The Musician and the Myth.
Dee Dee Bridgewater
Grammy Award-winning jazz singer and Tony Award-winning actress. Her latest album is Dee Dee's Feathers.
Dominique Eade
Composer, singer, and educator currently teaching at the New England Conservatory. Her latest CD is Whirlpool.
Marissa Nadler
Acclaimed singer, songwriter, guitarist, and painter. Her latest record, out on Sacred Bones, is called July.
Janice Pendarvis
Songwriter and singer of 20 Feet From Stardom fame. She is presently an associate professor at the Berklee College of Music in Boston.
Rebecca Sullivan
Singer and performer based in New York City. Her latest record is titled This Way, This Time.

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  • Dominique eade

    Thank you for a great show Chris, John, guests and crew. So wonderful to hear Billie’s music with some new rays of light on it. She sure sounds timeless! Look forward to the book. ~ Dominique Eade

  • Cal McCrevan

    What I think was most powerful about Billie was her spectacular musicianship and the foundational contributions that she made to American music. This is especially true in the areas of songwriting and song interpretation. The singer Annie Ross said ‘ Every girl singer should drop down on her knees and thank God there was a Billie Holiday’. What she was saying was that Billie was Miles before Miles was Miles. That is, she was the originator and master of all of the languid pacing and dramatic melancholy that we hear in American ballads. Her ability to transmit the emotions of the singer through lyrics as opposed to through technical ability was and continues to be an unparalleled example for singers. Even in the context of the greatest jazz singers like Sara,Ella,Pops and Nat she maintains this unrivaled supremacy. My favorite Billie album is Lady in Satin. I know people are ambivalent about it but in the same way they are ambivalent about Bird with Strings and the Miles Davis classic Quiet Nights. Yet the critics are shortsighted about these works and thereby miss all of their virtues. This goes double for Lady in Satin. Here is a Link to get you in the mood.

    Billie put singers in the mix with the serious jazz/pop instrumentalists. I really loved this show it was a great work of culture. This sort of radio is so important to american society these days since it connects the past to the present. This type of radio programming is another small opening in the american mind to play with the the thinking of Harold Bloom in his book titled The Closing of the American mind. Also to the interested, there are many modern pop artists who have been directly influenced by Billie. Are you hip to Erykah Badu? If not you should be she is a direct inheritor of the Billie Holiday aesthetic. Here is a video of Erykah Badu.

  • Bruce Teague

    Brilliant, touching, heart rendering show. Thanks. Echoes of George Frazier and Storyville in Boston. Strange Fruit penned by Abel Meeropol lives on in the age of #Black Lives Matter. Blessings to Our Lady of Perpetual Sorry – Billie Holiday aka Eleanora Fagan.

    • Conor

      thanks for listening bruce! heart-rending, -rendering, and -wrenching all 🙂

  • Potter

    About Duke Ellington’s “Black Symphony” 1934 movie you posted (thank you!), it’s pretty amazing from start to finish…very modern,

    I was surprised several years ago when my mother said her favorite singer is (also was always) Billie Holliday. The other day she (now 101 and on her own last legs) said of Billie “she had such a sad life, and she took it”. Playing this music has been an enduring comfort and joy to her especially these last years. For me it’s a “zone” I get into when I listen. It’s personal; you have to take it within. As was said, I think one can feel spiritually good or elevated after feeling this sadness because it’s an acceptance of the truth of the human condition,her condition, the black condition here. So she sang the truth but I think we always heard it, not just now. Here we are analyzing and appreciating from the distance, happily with the recordings she left. The jokes and the joy, the upbeat are part of the blues right?. The sequences in Black Symphony go from sadness to joy.

    What I love here is that you (the guests all, but especially John Szwed) go deeper into Billie’s art. This makes me listen and want to listen again to her voice qualities. The guests try to describe what is difficult to describe but I think I get it. I love the connection or the alignment Szwed makes between this music and modernism, modern art, the use/blending of primitivism, the African influences ( alsomost vivid in the last part of “Black Symphony”).

    Watching. The video of the CBS 1957 reminds me now that I caught it at the time so many years ago; it was scary to watch. Billie looked so depraved, spent. I did not understand that, or why, Yet she was the music, This never left me about her. Even today it’s hard to simply breathe in her songs without feeling sad and sorry- for her. Her art maybe healed her somewhat and heals us in moments and it kept her going but still I can’t help feeling she could have done better and lived longer in today’s world, treated, a less cruel ( somewhat) world. I am left with sadness about her along with all else, her gifts, because I cannot separate the music from her life… the life lived between the notes, as Janis Pendarvis put it.

    Billie Holiday and Lester Young are amazing here

    • Potter

      PS: I just can’t enjoy “Lady in Satin”. It’s so incongruous, the orchestra makes a commercialized Billie- over produced even in it’s attempted tastefulness and choice of musicians. It glazes her and she does not need that.

      About “Strange Fruit”: Although it has been done by others before and since, it must be hers forever. What a song! I did not know it was a poem but I read the lyrics to my mother the other day and thought “this is poetry and it’s chilling”. When Billie sings it, it’s chilling to the bone.

  • SADouglas

    As always, a truly great show about music. So well-produced and such guest/host interaction.

    I especially liked that you played the whole “extremely slow” “I’ll be seeing you.” As it’s one of those songs everyone knows this was like listening to it “as Adam in the morning.”

    There is a wonderful contradiction (and what isn’t truer of the era of Bebop and Jazz) where a technology like the microphone brings a recorded live experience into a listener’s personal hearing though miles and years away. That same relentless technology now moves us into sameness (which, apparently, is what chaos actually is) much like industrial food production requires all salmon be that orange color and all pork be pinkish-gray.

    We do applaud the very real benefit of these capabilities; yet maybe we have to admit that it may not be worth it. It is this replication technology that reduces all of life to reception.

    Billie Holiday is great; as is Mingus, Parker, Coltrane, Miles, and on and on. But what made them great was the milieu–the context of being a living being in a certain time and place in a cultural space of art-life…creating as life. It’s not “performing”–it’s living.