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Rock and Roll Book Club

Billie Holiday's classic autobiography brims with life

A well-worn 1984 edition of Billie Holiday's 1956 autobiography.
A well-worn 1984 edition of Billie Holiday's 1956 autobiography.Penguin

by Jay Gabler

February 03, 2022

For many listeners, the name Billie Holiday inspires a cascade of painful associations. Racial violence. Sexual exploitation. Addiction. Incarceration. Heartbreak. A premature death, at the age of just 44. You can hear all of that in her music, of course, but you can also hear joy and wit. That fiery, lively sprit permeates her classic autobiography, an essential read for any music fan.

Lady Sings the Blues has been widely read since its 1956 publication, just three years before Holiday’s death. It became the basis for the 1972 biopic starring Diana Ross, whose performance as the late legend earned an Oscar nomination and jumpstarted an acting career for the Supremes singer.

It’s an essential document of Holiday’s life, and even if it’s not entirely accurate, what’s most crucial is that it’s true to the voice of an artist who didn’t let her financial motives for participating in the project get in the way of speaking her mind frankly. The reader is left a strong sense of the honesty and courage that, coupled with Holiday’s inimitable singing voice, fueled her unique and transformative career.

Holiday starts in Baltimore, where it all began. Her first jobs, as a teenager, were cleaning white women’s homes (“all those b—hes were lazy”) and running errands for a local madam whose Louis Armstrong and Bessie Smith records became formative influences on the young Eleanora Fagan. She adapted her father’s name (Halliday) and her nickname “Bill” (“because I was such a young tomboy”) into a stage name when she became a professional singer.

Holiday’s run-ins with the law started early, but she emphasizes that while she wasn’t innocent of crimes including prostitution and drug possession, her encounters with the criminal justice system were flavored by personal pique and institutional racism. When a man tried to rape her at age 10, she was sent to a cruel Catholic reformatory. When she went to jail for hooking, it was because she refused a client who subsequently turned her in. When she went to prison on drug charges, it was one of American history’s many examples of a racist criminal justice perpetrating the kind of punishment on Blacks that rarely does on whites.

Even her legendary nickname, “Lady Day,” started with mockery from Harlem nightclub coworkers because Holiday would ask customers to put tips in her hand rather than on the table. “Look at her,” they’d say, “she thinks she’s a lady.” Holiday shares a vivid memory of the first time she sang for that club’s clientele. “The whole joint quieted down. If someone had dropped a pin, it would have sounded like a bomb. When I finished, everybody in the joint was crying in their beer, and I picked thirty-eight bucks up off the floor.”

That led to visits from music industry notables, kicking off a star-studded parade of Holiday admirers and collaborators. “I didn’t even know what royalties were” when she went into the studio with Teddy Wilson, Holiday writes. “I was glad to get the thirty bucks.” It was easy to do what she loved, she writes. “If I had to sing ‘Doggie in the Window,’ that would actually be work. But singing songs like ‘The Man I Love’ or ‘Porgy’ is no more work than sitting down and eating Chinese roast duck, and I love roast duck.”

Holiday’s account captures a vertiginous journey: she was one of the greats, and Black and white listeners alike recognized it. She recorded with (and dated) Benny Goodman, she collaborated with Count Basie, she was tight with family friend Lester Young (who coined the name “Lady Day”), she had a defender in Bob Hope, and she had an affair with Orson Welles (the book makes no secret of this, and still apparently downplays the closeness of their connection). In short, she was a star - yet still subject to racial harassment and targeted raids.

Lady Sings the Blues takes the reader inside Holiday’s world, where music united artists and listeners across races but couldn’t heal a corrupt system. Finally, in the late 1930s, she landed at an integrated Greenwich Village establishment called Cafe Society, where she worked a Lewis Allen poem called “Strange Fruit” developed into her “personal protest” against racism. “When I sing it,” she writes, “it affects me so much I get sick. It takes all the strength out of me.”

The book also tracks Holiday’s complicated relationship with her mother (the inspiration for “God Bless the Child”); includes her matter-of-fact acknowledgement of the era’s lesbian culture, tracks her marriage to a faithless husband (“Don’t Explain”); chronicles her encounter with racist casting and an intolerant costar in a movie called New Orleans (“and supposedly about it”); and includes an extended description of the trial recently recreated in the Oscar-nominated film The United States vs. Billie Holiday.

Holiday made a triumphant comeback after being released from prison, but couldn’t get a license to perform in establishments where alcohol was sold. “The right to work everybody screams about doesn’t mean a damn,” she writes. So she branched out and toured Europe among other gigs, all the while working to secure treatment for the persistent narcotic addiction that would ultimately claim her life. Poignantly, she writes about reading a pre-publication advertisement for her own book that explained she was writing about a drug problem she understood to be ongoing. “There isn’t a soul on this earth,” Holiday writes, “who can say for sure that their fight with dope is over until they’re dead.”

Although Holiday doesn’t dig deep on the craft of singing, she offers some thoughts on what gave her performances such inimitable soul.

I’ve been told that nobody sings the word “hunger” like I do. Or the word “love.”

Maybe I remember what those words are about. Maybe I’m proud enough to want to remember Baltimore and Welfare Island, the Catholic institution and the Jefferson Market Court, the sheriff in front of our place in Harlem and the towns from coast to coast where I got my lumps and my scars, Philly and Alderson, Hollywood and San Francisco - every damn bit of it.