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The Heartbreakingly Beautiful Songs of Jazz Legend Billie Holiday

Posted by on September 27, 2013

Photo of Billie Holiday

Jazz Legend Billie Holiday referred to all of her songs as “the blues.”

She talks about them here and performs her classic “Fine and Mellow.”


One of the saddest stories in music history, Billie Holiday died handcuffed to her hospital bed. Under arrest for drug possession. She was only 44.

In her day she was one of the first civil rights activists, risking her life in 1939 to speak out about lynchings by performing the song “Strange Fruit.”

Some say she was the greatest singer of all time.

Let’s go back to Manhattan 1944. A jazz band simmers and smokes.

Lights come up on a regal, almost-too-calm woman in white. Sitting on a stool as if she’s been there forever, she leans into the microphone as the music swells.

Her eyes smolder, flash and hide. The lyrics are unbearably sad. The melody heartbreakingly beautiful.

It’s like she’s fanning the fire of her crushed past. The embers of broken relationships (starting with her parents), jail time, drugs (heroin, opium, marijuana). Constant financial strain.

In defiance of it all, she sings with fiery elegance.


Billie’s early recording years were her prime vocally. It’s hard to say exactly when her voice changed because it seemed to go in and out. I’d guess between 1957 and 1959.

Top songs are “Fine and Mellow”, “My Man”,  “All of Me”, “What A Little Moonlight Can Do”, “Night and Day” and “Swing Brother Swing.” There are countless more.

“I can’t stand to sing the same song the same way two nights in succession, let alone two years or ten years. If you can, then it ain’t music, it’s close-order drill or exercise or yodeling or something, not music.” – Billie Holiday

Billie Holiday was born in 1915 in Philadelphia and given the name Eleanora Fagan Gough. Some accounts contend that this was a “stage age” and Billie was really born in 1912.

Abused, abandoned by both her parents and turning tricks by age 15, Billie somehow found her way.

At 15 she also got a gig singing in a small club in Brooklyn. And at 18 Billie Holiday was discovered by talent producer John Hammond.

John wrote her up in the paper and caught the attention of band leader Bennie Goodman. Benny Goodman raised some eyebrows by creating a mixed-race band when he asked Billie to perform with him.

This would lead to Billie Holiday playing with other jazz masters of the day: Count Basie, Artie Shaw and Louis Armstrong.

I can’t help but love this song “The Blues Are Brewin'” with Louis Armstrong. Billie looks almost happy here. After all, who can resist the buoyancy of the masterful Louis Armstrong?


For more on Billie Holiday’s pioneering civil rights activism, check out the KEXP Documentary “Strange Fruit” in the series Civil Rights Songs.

Tune in to DJ Michele Myers Friday nights at 9pm on KEXP 90.3FM Seattle, Music historian & producer, Michele’s made over 200 radio stories for KEXP Documentaries.

She’s written scripts, lesson plans & features for The SmithsonianExperience Music Projectthe University of Washington & NPR.

If you’d like Michele Myers to spin at your event anywhere in the world please book through Thumbtack or send your email to

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