Sometimes there are moments when you’ve heard a famous name over and over again but never put a name to the face. By the time I had gotten to college (back in the prehistoric age before the internet), I had heard the name Billie Holiday, a good amount of her songs, and more than a few pale impressions of her done by game show contestants in their getting-to-know-you segments.
One day when I was visiting my best friend at the new house she was renting with four roommates at her college, I saw she had three posters on her wall: Bjork (#Bi2), a very young and hot-looking Bob Dylan (whom we had bopped to together because our friend group was hippie-adjacent and loved Simon and Garfunkel and other folk musicians); and a portrait of Holiday. She stared at her mic, her hair pulled back in a sleek ‘do, and donning a chic black outfit and was clearly singing her heart out. The poster’s caption: “Southern trees bearing strange fruit”.
To this day, whenever I think of the gorgeous and tragic life of Holiday, the first image I think of is that poster.
Before I get into the sordid details of Holiday’s life, I should note that there will be mentions of sexual assault, child sex work, drug and alcohol abuse, as well as racial injustice. I should also note that this article should only serve as a taster on the life of the famed musician — Holiday’s life has inspired dozens of biographies, books, and films, which are also worth perusing to get a fuller picture of the trajectory of her life and legacy.
Born on April 7, 1915, Eleanora Fagan (who later took on the stage name most know her as) was born in Philadelphia, Pennsylvania, to teenage parents. Her father, Clarence Holiday, was a jazz musician who eventually abandoned his small family. Her mother, Sadie Fagan, was kicked out of her family for becoming pregnant and often worked on passenger railroads, leaving Eleanora in the care of her mother-in-law as she grew up in Baltimore under her abusive care. Around this young age, she was raped but fought back against her aggressor, who was arrested, but sent to a reformatory school for allegedly seducing her attacker. In the following years, she and her mother moved to New York, and Eleanora got jobs running errands for a madam of a brothel and engaging in survival sex work. During these days, Eleanora found solace in music in the jazz records the madam would play for her on the Victrola, particularly finding herself drawn to the scat sections of the works of Louis Armstrong and Bessie Smith (#Bi2).
In the early 1930s, despite having no formal training and never learning how to read music, she began to get work singing in Harlem nightclubs, quickly learning to improvise the same song at each table to infuse variety into the same tune to get extra pay. It was during this time that she created her stage name Billie Holiday — the surname from her father, the first name after the silent film star Billie Dove, whom she adored.
One night at one of the jazz nightclubs, at the age of 18, Holiday was discovered by music producer John Hammond, who was immediately impressed with her phrasing and improvisational skills. Soon Hammond got touring with big names and big bands like Benny Goodman and in films with Duke Ellington, which got her into cutting records and shooting her into musical superstardom. She was quickly hailed for her poignant, often heartbreaking take on standards as well as her own compositions, pulling together the styles of many who came before her to make her unique sound.
As for her bisexuality, Holiday had three husbands and other male lovers over the course of her life — often passionate affairs, but also tragic and abusive ones, as these men would often physically abuse her as well as introduce and deal drugs to her. She was also known to have had relationships with and made lovers of Orson Welles, Charles Laughton, socialite and philanthropist Louise Crane, and a long-standing relationship with bi actress Tallulah Bankhead.
Holiday performed and toured in an America still kept in a chokehold by Jim Crow, and her celebrity did not bring her immunity from racist treatment. The performer strived to perform in integrated cabarets, but due to segregation on tours, she was often asked to enter performance halls and the hotels she stayed at through service elevators instead of the front doors like her white patrons or co-workers. As a black woman, Holiday was also acutely aware of the racial injustice around her and refused to perform in a political vacuum. When the poem “Strange Fruit” was made into a song, Holiday began to add it to her song list and perform it at cabarets. It is now considered the first protest song of the civil rights era.
While "Strange Fruit” is now hailed as a masterpiece and her recording has been selected for preservation in the Library of Congress, the song — and Billie’s singing it to white cabaret audiences — was extremely controversial. Her record label at the time wouldn’t allow her to record it, so she took it to an independent record label, where it grew to be a lightning rod record across the country. She recorded it again later for Verve records as well.
At the time, a government agency called the Federal Bureau of Narcotics (an early predecessor of the Drug Enforcement Agency, or DEA) was headed by known racist Henry Aslinger, who made it his mission to take down Holiday under the tenuous connection of the singer’s known drug addiction to her singing challenging the status quo of white supremacy. The bureau warned her against singing the song, and Anslinger assigned agent Jimmy Fletcher to immerse himself in Holiday’s circles. He worked with her husband, Louis McKay, and got her set up and arrested for drug possession. Holiday was put on trial and sent to prison for a year — during her time, she never sang a single note.
When Holiday emerged from prison in 1947, her license to perform at cabarets had been revoked, but that didn’t stop her from singing. Instead, the chanteuse toured and sold out Carnegie Hall almost two dozen times, the whole time continuing to perform “Strange Fruit”.
Unfortunately, neither Anslinger nor her drug addictions gave up on her. In 1959, Holiday collapsed and was diagnosed with cirrhosis. During treatment, she was going through heroin withdrawal, which is dangerous to do cold turkey, so she was being administered methadone. Ten days after her hopsital admission, Anslinger had had her arrested, handcuffed to her bed, and the methadone cut off. She passed on July 17th, 1959, at the age of 44, with $0.70 left in her bank account due to her swindling husband McKay.
Despite her struggles and the grievous injustices she endured, Holiday’s courage and musical genius are recognized and lauded to this day, over ninety years after the start of her career. She is still considered one of the greatest singers of all time, in jazz, blues, or any other genre, and still has multiple records in print. Her life story has been the subject of two heralded films — Lady Sings the Blues with Diana Ross in an Oscar-nominated eponymous performance, and 2021’s The United States vs. Billie Holiday, starring Audra Day in a Golden Globe-winning performance as Holiday. Holiday is also the central figure in the Broadway play Lady Day at Emerson’s Bar and Grill, which has been revived many times — most recently with Audra MacDonald in the role and receiving a Tony for her efforts. In 1958, shortly before her death, Frank Sinatra was quoted in Ebony magazine for saying:
With few exceptions, every major pop singer in the US during her generation has been touched in some way by her genius. It is Billie Holiday who was, and still remains, the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last twenty years.
Billie Holiday was unquestionably a game changer — not only for her impact on jazz, blues, and the American musical landscape but also for her immense courage in singing truth to power, despite the consequences. And she was unflappably, unquestionably bi.
Again, there is far too much to Holiday’s story to distill into one column. If you’d like to learn more about this incredible artist that I didn’t get into here (like how the song “Angel of Harlem” by U2 is about her), you can find out more about her from accredited sources online, as well as lots of biographies in your local library, or check out our Media Entry on her 2021 biopic.
But I do really recommend streaming a collection of her greatest works, sitting back, and letting her artistry wash over you like a heartbreaking rain, ideally while staring at a poster of her on your best friend’s wall.
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