The Saddest Song

Eleanora Fagan was born on this day in 1915. Eleanora cut school so often she was sent to live at the House of the Good Shepherd, a home for “colored girls” run by the Little Sisters of the Poor. She was returned to her mother after a year, but in 1926, 11 year old Eleanora was raped by a neighbor & sent back to Good Shepherd. But the nuns refused to keep her for long.


At only 11 years old, Eleanora earned money cleaning at a whorehouse. The madam let her listen to the records of Louis Armstrong & Bessie Smith. Eleanora was able to express her feelings with music & she began singing at various storefront churches.


As a young teenager, Eleanora moved to NYC with her mother, to pursue a singing career, instead she found work as a prositute in Harlem.


Billie Holiday was the self creation of young Eleanora Fagen. She began to get small gigs & out of the way clubs, but Holiday was gaining popularity with fellow musicians. After years of touring with Count Basie, Holiday was offered her first steady job at Café Society in 1938, earning $75 a week. She went on to be featured soloist at clubs all over the country, acquiring the nickname “Lady Day.” Her distinctive voice, which she used like a musical instrument, transformed jazz singing. Holiday: “I don’t think I’m singing; I feel like I’m playing a horn.”


Holiday had many affairs with both men & women, but was known as a lesbian among many of her peers in the jazz world, where she aquired the moniker- Mister Holiday, because she was seldom seen in the company of gentlemen. Holiday: “Sure, I’ve been to bed with women… but I was always the man.” Who else can you think of who had an affair with both Orson Welles & Tallulah Bankhead?


Billie Holiday was unlucky in life, unlucky in love & dead from drink & drugs at the age of only 44.

By the late 1930s, Holiday had married small-time drug dealer Jimmy Monroe, who introduced her to opium & heroin. In 1947, she spent a year in prison for possession of drugs. After she was released Holiday had difficulty finding work & she had a string of relationships with maniacal men & a decline into dependence on drugs, a roughening of her voice & a physical decline.

On 10 July 1959, Holiday died in hospital in NYC of cirrhosis of the liver. In a characteristically cruel turn she had been arrested on her deathbed for possession of narcotics, & spent her final days under police guard.


The life & legend of Billie Holiday seems to point to a victim, a problematic, profane & pushy woman. She was after all, a junkie & an alcoholic; she had sex with a great many men & many women.




I like to think that Billie Holiday was a determined woman with a great appetite for life, who lived it on her terms in a man’s world. Holiday was never able to capitalize on her amazing talent to live a life as a music superstar. She couldn’t break the pattern of abuse from others or herself, but that fed her genius. Her brand of self destruction was a plea for the love that ironically her bad behavior pushed away. But that voice, that perfectly imperfect gift, will always be loved & will always break my heart.