The Story of Billie Holiday, as Told in 5 Songs

By: Michelle Konstantinovsky  | 

Billie Holiday
Billie Holiday was nicknamed 'Lady Day' by her friend, tenor saxophonist Lester Young. William Gottlieb/Redfern/Getty Images

In February 2021, "The United States vs. Billie Holiday" premiered on Hulu, earning a Golden Globe Best Actress award for Andra Day who portrayed the jazz singer. While many may be familiar with Holiday's bittersweet songs and position as a singing legend, few may know as much about the trauma, heartbreak and tragedy that informed much of her work and prematurely ended her career and life.

Born on April 7, 1915, Holiday survived a difficult childhood and became known as a New York City singing sensation by age 18. She graduated from the Harlem nightclub scene to gain international stardom with songs like "What a Little Moonlight Can Do" and "Riffin' the Scotch'' but, she battled a heroin addiction, and was eventually targeted by the government in an effort to persecute Black people in the war on drugs.

Although Holiday had a vocal range of just one octave and a half, it was her distinctive phrasing and emotional connection to her songs that riveted audiences; many of her best-known tunes offered intimate insights into the pain and sorrow she endured behind her stage persona. Here are five Billie Holiday songs that take you into her world:

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1. 'Strange Fruit'

Time magazine deemed "Strange Fruit" the song of the century in 1999, and no wonder. While Holiday popularized the chilling lyrics, the song was originally a poem penned by a Jewish communist teacher and civil rights activist from the Bronx named Abel Meeropol. Lines like, "Southern trees bear a strange fruit/Blood on the leaves and blood at the root/ Black bodies swinging in the southern breeze/Strange fruit hanging from the poplar trees" were inspired by Meeropol's visceral response to the lynching of Black men in the 1930s. "I wrote 'Strange Fruit' because I hate lynching, and I hate injustice, and I hate the people who perpetuate it," Meeropol said, according to the Guardian.

Meeropol published "Strange Fruit" in a teachers union publication and later composed it into a song, which he passed along to a nightclub owner. That's when Holiday first heard it and felt moved to perform it. "It reminds me of how Pop died," she wrote in her 1956 autobiography, "Lady Sings the Blues," referring to her father who died from a fatal lung disorder at 39 after being turned away from a hospital because he was Black. "But I have to keep singing it, not only because people ask for it, but because 20 years after Pop died, the things that killed him are still happening in the South."

"Strange Fruit" played a significant role in Holiday's life due to the impassioned response it evoked from audiences. While many applauded Holiday's poignant performances of the track, others, like Federal Bureau of Narcotics commissioner (and known racist) Harry Anslinger, resented the song. Anslinger tried to ban Holiday from performing the song, and when she refused, he found a way to seek revenge by setting her up to buy heroin. When she was caught using it, she was imprisoned for a year and a half, and when she was released, federal authorities refused to reissue her cabaret performer's license. Holiday managed to continue performing sold-out concerts at Carnegie Hall, but her health deteriorated, and in 1959, she checked herself into a New York City hospital with heart and lung problems and cirrhosis of the liver. Anslinger arranged for his men to handcuff Holiday to her hospital bed and forbid doctors from providing her further treatment, which resulted in her death.

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2. 'God Bless the Child'

Holiday wrote this 1941 track in collaboration with her frequent songwriting partner, Arthur Herzog. The lyrics were inspired by an argument Holiday had with her mother, Sadie, about finances. Holiday's relationship with her mother was historically complex — Sadie was an unwed teenager when she gave birth to Billie (nee Eleanora Fagan), and although she married the child's father, Clarence Holiday, a few years after her birth, he remained largely absent over the years in pursuit of his own jazz career.

A few years before Holiday penned "God Bless the Child," she'd lent her mother a large sum of money to open a restaurant. But when Holiday was in need of a loan, Sadie refused to help her. As she chronicled in her autobiography, Holiday remembers that during the argument, she yelled the proverb, "God bless the child that got his own," at her mother, which inspired the lines of the song.

Herzog, however, later contended that he was responsible for the vast majority of the lyrics. He says Holiday told him about the argument over dinner and when he asked her to elaborate on the meaning of, "God Bless the Child," he was the one who crafted her response into the song lyrics.

Holiday poses with her dog Mister
Holiday poses with her dog Mister in 1946. She was known for wearing a gardenia in her hair when performing, a fashion statement that began as a way to cover up a hot comb accident that burned off some of the hair by her left ear.
William Gottlieb/Redferns/Getty Images

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3. "Gloomy Sunday"

Also known as the "Hungarian Suicide Song," "Gloomy Sunday" wasn't a Holiday original; it was penned in 1931 by Hungarian pianist and composer Rezső Seress. Published in 1933 as "Vége a Világnak" ("End of the World"), the song gained notoriety in 1935 when a shoemaker in Budhapest died by suicide and quoted the lyrics in his final note. There were other tales of suicide associated with the song as well, with one story claiming that either Jávor or Seress' estranged fiancée quoted the song's title in her suicide note and another alleging that two men also supposedly shot themselves after listening to a band play it.

Urban legends say that numerous suicides were tied to the song throughout the 1930s, but there's no hard evidence to support that. The BBC did, however, ban Holiday's 1941 version of the song from being broadcast because it was considered "detrimental to wartime morale." The ban wasn't lifted until 2002.

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4. "Lover Man"

Holiday didn't pen the song herself, but it was written by one of her old friends, Roger ("Ram") Ramirez, along with Jimmy Davis and James Sherman. The lyrics "The night is cold and I'm so all alone/I'd give my soul just to call you my own," allude to Holiday's troubled romantic relationships.

In 1941, Holiday married a man named James Monroe who allegedly abused her and introduced her to opium. Following her divorce, Holiday had a relationship with a man named Joe Guy, who is said to have introduced her to heroin. As Paste Magazine noted in its 2016 roundup of 10 quintessential Holiday tracks, the singer "recorded the song several times over her career," but the "live version from 1958, only a year before her death, is particularly haunting."

Billie Holiday
Billie Holiday performs on stage, Feb. 14, 1954.
Harry Hammond/V&A Images/Getty Images

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5. "Billie's Blues (I Love My Man)"

Holiday wrote this song in 1936, largely improvising it just before or at its recording session. The song showcases Holiday's sassy side and was considered a declaration of her growing maturity – she was done putting up with losers. "Some men like me 'cause I'm happy/Some 'cause I'm snappy/Some call me honey/Others think I got money...Now if you put that all together/It makes me everything a good man needs."

Holiday's version of the track was inducted into the Grammy Hall of Fame in 1989.

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