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Billie Holiday: A Complex Woman, A Jazz Legend

An introduction and tribute to one of the greatest jazz singers ever.

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Billie Holiday, Downbeat, New York, N.Y., ca. Feb. 1947 web optimised 1000
Billie Holiday onstage at the Downbeat Club, New York, February 1947. Photo: Library Of Congress

Today, “legends” are ten a penny. When Billie Holiday was accorded the accolade it meant something. Lady Day was a brilliant jazz singer, a great lyrical interpreter, she took chances, lived life hard, she could swing, she could swoon, she moaned low, was elegant and she was a soul singer before anyone had coined the phrase. She was one of the greatest jazz vocalists of all time.

Listen to The Decca Singles Vol. 1: 1945-1949 on Apple Music and Spotify.

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Humble beginnings

We know that Billie was born with the name Eleanora Fagan on April 7, 1915, yet that the facts about her childhood are murky, made no clearer by Lady Sings the Blues, Billie’s autobiography. Billie’s birth certificate named her father as DeViese, whereas she insisted her father was Clarence Holiday – her mother Sadie’s childhood sweetheart, who later played guitar in Fletcher Henderson’s Orchestra.

Whatever the case, Billie’s childhood in Baltimore was rough. She was abused, and spent time in a Catholic children’s home before cleaning and running errands for a brothel madam. By 1928, Billie’s mother moved to Harlem with her daughter and – before long – they were both working in a whorehouse. Fourteen-year-old Billie was subsequently charged with vagrancy and sent to a workhouse.

Upon her release, Billie took up with a saxophonist and the pair began playing Harlem dives. Billie was trying her best, at this point, to emulate Bessie Smith, whose records she loved. In October 1933, John Hammond, a music critic and record producer, heard her singing in a Harlem club and had her record a couple of sides with Benny Goodman. The first, “Your Mother’s Son-in-Law” gives no hint of her promise.

Teddy Wilson, Count Basie, and Artie Shaw

It would be a year or so before Billie recorded again. Hammond coerced Brunswick into a session, and the result was Teddy Wilson and his Orchestra. These four sides, “Miss Brown To You,” “What a Little Moonlight Can Do,” “I Wished Upon the Moon,” and “A Sunbonnet Blue” should be in every jazz enthusiast’s library. Over the next 12 months, Billie recorded a dozen more sides with Teddy before working under her own name, with her own orchestra.

In 1937, Billie sang with Count Basie’s orchestra, and the following year she appeared with Artie Shaw, becoming one of the first Black singers to appear with a white orchestra. It was not an easy engagement, especially during concerts in the South. One notable incident took place in Kentucky. Holiday was called a racial slur, and became so upset that she left the stage. By the end of 1938, a disenchanted Billie quit Shaw’s band after the Hotel Lincoln in New York demanded she use the kitchen entrance rather than the front door.

Joining Café Society

Billie then began appearing at Café Society in Greenwich Village. Her performances amazed everyone, especially her handling of torch songs, including “I Cover The Waterfront.” However, there was one song that became synonymous with Billie during her spell at the club. One night, Lewis Allen, a New York public school teacher spoke with Barney Josephson, Café Society’s owner, asking if Billie would sing a song he’d written – and so began the fascinating tale of “Strange Fruit.”

Allen’s song was about the lynching of a Black man in the Deep South that pulled no punches. The anti-lynching protest poem is incredibly powerful and Columbia, Billie’s label, refused to release it. It came out on the smaller Commodore label, sharply dividing opinion. Audiences were stunned into silence when she sang it live – men, as well as women, wept.

The song would go on to become a standard, covered by everyone from Nina Simone and Jeff Buckley. The power of the song became the basis for the 2021 film The United States vs. Billie Holiday. Based on Johann Hari’s Chasing the Scream: The First and Last Days of the War on Drugs, the movie indicates that Harry Anslinger, the head of the Federal Bureau of Narcotics, targeted Holiday with drug charges as a way to keep her from singing “Strange Fruit.” (Andra Day was nominated for a Golden Globe for her portrayal of Holiday.)

Personal obstacles

Billie wrote one of her most beloved songs along with Arthur Herzog Jr. in 1939. “God Bless The Child” was eventually recorded two years later. It was around this same time that Billie married Jimmy Monroe, best described as a hustler. A year later, Monroe was caught smuggling drugs into California. By 1944, she was using heroin. Even so, one of Billie’s biggest successes came that same year when she signed to Decca Records and released “Lover Man.” Released during World War II, it was a song that resonated with many servicemen overseas and their wives and lovers back home. In February 1945, Billie appeared at her first Jazz At The Philharmonic concert, and the following year she featured in the movie New Orleans alongside Louis Armstrong.

Billie’s drug problems finally caught up with her in May 1947. She was arrested in Philadelphia and charged with possession of heroin and received a one-year sentence. When Billie was released, she had kicked her habit and looked better than she had in years. Almost immediately after she left prison a concert was arranged at New York City’s famed Carnegie Hall in March 1948; it was a sell-out. She sang over 30 songs, despite not having sung for nearly a year, including “All of Me,” “Fine and Mellow,” and, naturally, “Strange Fruit.” As one newspaper put it, “Billie took her homage like a queen. Her voice, a petulant, sex-edged moan, was stronger than ever.”

Jimmy Monroe, the man who a federal prosecutor described as the “worst type of parasite you can imagine,” lost no time in getting Billie back into her bad habits. She got arrested again on a similar charge to her conviction, but this time she was acquitted. Before long a new man entered her life: John Levy was a club owner and about as bad as Monroe. Despite everything, Metronome Magazine named Billie the best female singer in its annual poll in 1949.

All or nothing at all

In 1952 Billie recorded for the Clef label for the first time, away from JATP concerts, backed by Oscar Peterson, Barney Kessell, Flip Phillips, and Charlie Shavers. She would go on to record a number of albums for the imprint, which eventually turned into Verve Records.

During this period, Billie met a new man named Louis McKay. They would eventually marry in 1957. A year earlier, Billie published her autobiography Lady Sings the Blues with journalist William Dufty. Life seemed to be on an upswing for Billie. She even left Verve for Columbia and recorded the beloved Lady in Satin, an album that featured a 40 piece orchestra.

Things between Billie and Louis McKay, however, were unraveling. When Billie found out he had lost much of her money in risky property speculation, things dissolved for good. Billie moved into an apartment in New York with just her dog for company. Her drug habit, fortified by excessive drink, turned her into a pale shadow of herself.

A complex woman

When saxophonist Lester Young, the man who named her Lady Day, died in March 1959, it was a terrible blow. Two months later, Billie was in the hospital due to her drug use. When a nurse found drugs at her beside, she was arrested once again. Just over a month after that Billie Holiday died, on July 17, 1959, still in the hospital, still under arrest.

Billie Holiday was a complex woman. She exasperated her friends. At other times, she was the sweetest-natured woman alive. Before the drugs, the booze, and the lifestyle of an addict ravaged her voice, and her body, there was no singer that came close to matching her intensity or her allure.

Since her death, she’s become an icon. Her music helped soundtrack the Civil Rights movement, her life has become the subject of countless books and movies. (Diana Ross played Billie in a 1972 biopic, while Lee Daniels directed the aforementioned The United States Vs. Billie Holiday). Many of her songs have been inducted posthumously into the Grammy Hall of Fame. It’s a sad indictment that so much of this celebration has taken place after her passing. But it’s inspiring to see new generations finding her work and coming away inspired. It’s essential, timeless music.

Explore our Billie Holiday Artist Page.

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