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Billie Holiday: The Tragic Life of Lady Day

by Legacy Staff

On a sweltering day in July 1959, thousands of mourners gathered to pay tribute to one of the most influential musical artists of the 20th century. Among the pallbearers were some of the biggest names in the business, and outside policeman had to redirect traffic as the overflow of mourners spilled into the nearby streets. It was a moving show of public mourning for an artist whose career was often overshadowed by personal problems and whose best work had occurred at least a decade in the past.

We’re talking not of Michael Jackson’s funeral, but that of Billie Holiday, whose death in 1959 brought to an end one of the sadder stories in American pop music.

Holiday was born Eleanora Fagan on April 7, 1915, to an unwed teenage mother in Philadelphia. She would later choose her stage name as a tribute to movie star Billie Dove and her father, Clarence Holiday (himself a moderately successful jazz guitarist). When Billie was a toddler, her mother moved her to a poor neighborhood in Baltimore and briefly married Billie’s father, but the union didn’t last. At 10, Billie was raped by one of her neighbors. Soon thereafter, she was sent to the House of the Good Shepherd, a reform school known for meting out harsh punishments for even minor transgressions. “For years I used to dream about it and wake up hollering and screaming,” Holiday wrote of her reform school experiences in her 1956 autobiography, Lady Sings the Blues. “It takes years to get over it.”


Holiday moved to New York with her mother in 1928. At 14, Billie was raped a second time and her attacker sentenced to a mere three months in jail. With little family support, only a fifth grade education and the harsh experiences she’d had growing up, it was little surprise when she turned to prostitution. Holiday supported herself on the streets for three years before she was arrested for solicitation.

After being released from women’s prison, she soon landed her first paid performing gig—even though it wasn’t the job she’d hoped for. “I stopped in the Log Cabin Club run by Jerry Preston,” recalled Holiday. “Told him I was a dancer. He said to dance. I tried it. He said I stunk. I told him I could sing. He said sing … I sang. The customers stopped drinking.”

Preston hired her at $18 a week, and it wasn’t long until she became well-known around Harlem for a distinctive vocal style most were at a loss to describe (the only influences she herself cited were Bessie Smith and Louis Armstrong). Her range was limited and her voice didn’t always project well—shortcomings that would only be amplified later in her career after years of substance abuse—but her intonation, her phrasing and the emotion she delivered were unmatched. Nat Hentoff, critic at esteemed DownBeat magazine called her voice, “steel-edged and yet soft inside; a voice that was almost unbearably wise in disillusion and yet still childlike, again at the centre.” Bandleader Artie Shaw later said that her vocal style “has been copied and imitated by so many singers of popular music that the average listener of today cannot realize how original she actually was.”

After being discovered by John Hammond in 1933, she would meet Lester Young, the horn legend who became a lifelong friend, sometimes collaborator and bestowed upon her the nickname Lady Day. The two toured Europe together with Count Basie’s orchestra, for which Holiday was paid a then career high of $14 a day.

Touring the U.S. in the 1930s meant coming head-on against racial discrimination. While with Basie in Detroit, a theatre manager insisted the light-skinned Holiday blacken her face so the audience would not mistake her for White and get angry she was performing with Black musicians. While touring with Shaw’s mostly White band in the segregationist South, it was difficult just finding a restaurant where the band could eat together.

Such experiences may have informed what was to become the most haunting song in her repertoire, if not one of the most chilling in all of American music. “Strange Fruit” was based on a poem written by Abel Meeropol, a Jewish high school teacher in the Bronx sickened by a recent lynching of two Black men. The song was introduced to Holiday by a Greenwich Village club owner, and she was at first reluctant to sing it. Columbia Records was afraid to record it, but the record she cut for Commodore would eventually become her biggest seller (having the jukebox-friendly “Fine and Mellow” on the flip-side helped). She typically closed her shows with the song but was ambivalent about whether audiences understood the song’s point. “They’ll ask me to ‘sing that sexy song about the people swinging’,” she told a Philadelphia deejay.

Holiday would go on to make great recordings throughout the 1940s, but her personal problems began overshadowing her artistic output. Already a heavy drinker, she was introduced to heroin by her first husband, trombonist Jimmy Monroe, himself an addict. Much of the money she made went to supporting their habits. Her situation deteriorated when her mother Sadie died. Holiday sought treatment for heroin addiction, but was eventually arrested for drug possession in 1947 and ended up serving 10 months in a federal prison.

Her conviction meant her “cabaret card” license in New York state was revoked and she could no longer perform at any club where liquor was sold. It was a worse punishment than jail. She played Carnegie Hall, booked gigs in other major U.S. cities and toured Europe, but her heart was in the nightclubs, a steady source of income and artistic outlet now denied her.

She was arrested again in San Francisco on drug charges in 1949 but was acquitted. Her lifestyle was slowly destroying her physical health and her relationships with abusive men were taking an increasing toll. She left husband Monroe for a trumpet-playing drug dealer, then eventually married a mafia enforcer who wanted to exploit her name to open a chain of recording studios. She continued making records throughout the 1950s—nearly a third of her total output occurred during this period—but her voice had noticeably weakened. It had become rougher, more vulnerable, while still retaining the raw intensity she was known for. For some listeners, the fragility of her voice only gave her world-weary blues more emotional resonance. Though the last years of her life were mostly lost to drugs and alcohol, a rare performance with her old friend Lester Young provided a small grace note. The precise nature of her relationship with Young had been mysterious even to those closest to them, but at some point in the late 1930s they’d had a falling out and hadn’t spoken to each other for years. In 1957 they reunited for a televised rendition of “Fine and Mellow.” Young would die alone in a hotel room two years later, a victim of chronic alcoholism (his death would occasion another great jazz standard, the Charles Mingus tribute “Goodbye, Pork Pie Hat”).

Holiday outlived Young by only a few months. She was admitted to the hospital for liver and heart problems in May 1959. The authorities levied one final insult by arresting her on her death bed on narcotics charges after someone allegedly found heroin in her hospital room. A guard was placed outside the room, and flowers and notes from well-wishers were removed, as was her record player. When Billie Holiday died, she had $750 taped to her leg and another 70 cents in the bank. She was 44.

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