The Infuriating True Story Behind The United States vs. Billie Holiday

Legendary jazz singer Billie Holiday was a survivor—of racism, of misogyny, of sexual assault, of a government witch hunt—but in the end she could only survive so much.

By Natalie Finn Apr 23, 2021 1:00 PMTags
Billie HolidayMichael Ochs Archives/Getty Images

"I spent the rest of the war on 52nd Street and a few other streets. I had the white gowns and the white shoes. And every night they'd bring me the white gardenias and the white junk."

So Billie Holiday relayed in her 1956 memoir Lady Sings the Blues, the book itself a subject of admiration and scrutiny due to the liberties she took in telling her own story and what some critics saw at the time as a missed opportunity to do more than further link the art of jazz to a certain seedy lifestyle that a lot of white people just assumed was part of the Black experience.

Maybe it fed a stereotype, but abject poverty, sexual violence, prostitution and drug use were part of Holiday's story, and she didn't shy away from the hard truths of either her past or her present. She even made them harder in some instances, such as opening her book with the revelation that, when she was born in Baltimore on April 7, 1915, her mother was 13 and her father 16, and they married when their daughter was 3 years old.

In reality, her mother, Sadie Fagan, gave birth to her at 19, her father, Clarence Halliday, was 17, and they never married. But in all versions of her story, Clarence took off when Billie—born Eleanor Fagan in Philadelphia—was little. She would later borrow her first name from her favorite movie star when she was a kid, Billie Dove, and her surname from her guitar-playing dad's stage moniker.

"Much of what we think we know about Holiday, however, is questionable, and over time accounts of her life have been bent to serve some other purpose than telling her story," John Szwed wrote in his 2015 book Billie Holiday: The Musician and the Myth.

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At least a half a dozen biographies have set about separating the fact from fiction (even her FBI file was thin, Szwed noted), leading later authors to wonder why more pages weren't devoted to her songs. Pretty much all studiers of Holiday have agreed that her musicianship, as revered as she remains as a singer and entertainer, was woefully underrated in her day and for decades afterward.


But however unreliable a narrator Holiday may have been, all the later work bloomed from the seed she planted with Lady Sings the Blues, for which she received a $3,500 advance and 65 percent of the proceeds, to her co-author and friend William Dufty's 35 percent. The book later inspired the 1972 film of the same name, starring Diana Ross as the unavoidably tragic chanteuse.

Despite the power of Ross' Oscar-nominated performance, the biopic was criticized for its formulaic treatment of Holiday's woes as she goes from one tragic point in her life to another, men supplying her with drugs and doing her wrong at every turn. This year's The United States vs. Billie Holiday has also received mixed reviews, though singer Andra Day—in her first major acting role—saves the Lee Daniels-directed film from being your average one-dimensional portrait of the artist as a tortured soul.

Day, who won a Golden Globe for her performance and is nominated for a Best Actress Oscar, deftly channels Holiday's voice and musical styling and unsurprisingly wears those glittering gowns and gardenias with ease. More importantly, though, you can see the increasingly weary charisma of an artist who sold out Carnegie Hall but was also unfathomably tired (as well as often under the influence of heroin and alcohol). Holiday was a woman who stuck to her guns but, in that day and age, coupled with her addictions and unsavory enablers, had only so many guns to stick to. 


"It was the most unhealthy thing I've ever done for my physical body, for my voice, for everything, and maybe my mental state too," Day, who uncharacteristically smoked heavily and knocked back gin on the rocks to get her voice just so and her mind in that place, said on Apple Music's The Message. "But it was the healthiest thing I've done spiritually ever. It was actually, probably one of the greatest experiences of my life, and the hardest thing I've ever done."

Despite being a huge admirer of Holiday, Day admittedly had zero inclination to play her, worried that flubbing the part would be a stain on the singer's legacy. (And Daniels initially didn't think she was up to the task, either.)

Her first response, when she learned the movie was being made was, "'Let me know how it goes! I'll watch it in theaters, let it come out,'" Day told E! News. "So I don't think I ever got to a point where I was like, 'I'm the one.' Hello, no, I'm still baffled, to be honest with you."

But after meeting with Daniels and reading the script, "seeing that would be vindicating Billie Holiday's legacy," she said yes.


Because while Lady Sings the Blues was more of an indictment of the ravages of drug use, the system that punished the artist—and countless other people of color—so unfairly is what's on trial in The United States vs. Billie Holiday. The script (which, like Lady Sings the Blues, takes a lot of liberties as to what happened when, conjuring some scenes purely for dramatic effect) by Pulitzer Prize-winning playwright Suzan-Lori Parks is based on the study of Holiday and her legally authorized persecutors in Johann Hari's 2015 book Chasing the Scream: The First and Last Days of the War on Drugs. 

Hari writes, "Billie Holiday was born a few months after the Harrison Act, the first law banning cocaine and heroin, and it would become her lifelong twin." The book details how Holiday's life and career became a targeted pawn in what was effectively the U.S. government's war on drugs, a half-century before Richard Nixon formally declared it into existence.


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"When Billie Holiday got busted in the forties, when she went to jail, it was headlines in the papers," jazz singer Betty Carter is quoted in John White's 1987 biography Billie Holiday: Her Life and Times. "You didn't hear so much when Anita O'Day got busted, or how many times. There was no rehabilitation places for black people, only prison."

O'Day, "The Jezebel of Jazz," was a white contemporary of Holiday's, a pioneer of the bebop style who was in the school of West Coast artists like Mel Tormé. She was arrested in 1953 after she was caught smoking marijuana in a car, and later spent time in jail on a heroin possession charge—but once she was released she worked for another 40 years and died at the age of 87.

Holiday died July 17, 1959, at the age of 44 of complications from cirrhosis. She had 70 cents in the bank and $750 strapped to her leg.

And as she lay dying in a bed in the public ward of Metropolitan Hospital in New York, having been turned away from Manhattan's Knickerbocker Hospital for being a known drug user, her room was raided and she was put under arrest for illegal narcotics possession. Cops found less than an eighth of an ounce of heroin in a tinfoil packet hanging from a nail on the wall across from her bed.

She was too ill to be taken into custody, so a police watch was posted outside her door while she went into withdrawal, one final indignity after 20 years of the authorities keeping tabs on her.

But while her drug use was their excuse to stay on her case, it wasn't what put Holiday on their radar in the first place.

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It was at a New York City club—Café Society in Greenwich Village—in 1939 that Holiday first performed "Strange Fruit," an aching lament about the lynching of Black men in the South. It opens with a horn's wail as sharp as any piercing cry.

"Southern trees, there are strange fruit / blood on the leaves, and blood at the root / Black bodies swingin' in the Southern breeze / strange fruit hangin' from the poplar trees," begins the song, which was written by Abel Meeropol under his professional pseudonym Lewis Allan.

Holiday's 1939 recording was inducted into the Grammy Hall of Fame in 1978 and the Library of Congress selected it for preservation in the National Recording Registry in 2002.

But in her day, a protest song objecting to the abuse of Black people, sung two years after Congress refused to pass a bill that would have made lynching a federal crime, just wasn't the sort of art that the United States government could sanction. Holiday was ordered to stop performing the song. She refused, despite being warned (by people inside her own circle, as well as by law enforcement) that it could ruin her.

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"It was extremely brave, when you think about it," Holiday's goddaughter Lorraine Feather told Hari in Chasing the Scream. At a time when most entertainers were warbling love songs (which did make up most of Holiday's repertoire, albeit usually with a heartbroken edge), "you simply did not have a piece of music being performed at some hotel that was about the killing of people—about such a sordid and cruel fact. It was not done. Ever."

And so Holiday joined the Federal Bureau of Narcotics' list of targets. Agents who were no longer busy chasing down bootleggers for the Bureau of Prohibition, which was absorbed into the FBI upon the conclusion of that failed experiment in 1933, were then quixotically tasked with wiping out the drug trade. The first commissioner of the FBN, Harry Anslinger, especially targeted Black people because, Hari wrote, he felt that drug use made them "forget the appropriate racial barriers—and unleashed their lust for white women." 

He especially despised jazz, and he instructed his agents to "prepare all cases in your jurisdiction involving musicians in violation of the marijuana laws. We will have a great national round-up arrest of all such persons on a single day."

His big plan didn't work, because even when he did make an arrest, there was no one in the jazz community willing to give evidence against another musician. Eventually Anslinger was told by his bosses at the Treasury Department to drop that particular crusade.

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But according to Hari, who reviewed Anslinger's letters and other papers he left behind, he remained "obsessed with Billie Holiday."

And he was obviously out to get the troubled star, who by all accounts—including her own—drank and used drugs to mute her pain.

"I got a habit, and I know it's no good," Holiday once told a friend, per Hari, "but it's the one thing that makes me know there's a person called Billie Holiday. I am Billie Holiday."

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After being raped at 10 by a fortysomething-year-old neighbor, Holiday was sent to a Catholic reform school, where one time as punishment for misbehavior she was locked overnight in a room with a dead person. (Her attacker was sentenced to five years in jail.) At 14, she moved into a brothel where her mother was employed.

"I guess that I'm not the only one who heard their first good jazz in a whorehouse," Holiday matter-of-factly—and maybe a bit jauntily—recalled in Lady Sings the Blues. ("Of course, my mother considered that type of music sinful; she'd whip me in a minute if she caught me listening to it," she said in an interview for Hear Me Talkin' to Ya, a collection of conversations with musicians. "Those days, we were supposed to listen to hymns or something like that.")

But when Sadie couldn't afford to care for her, Holiday was thrown out and ended up as a sex worker herself, which would result in her first trip to jail.

Charles Peterson/Hulton Archive/Getty Images

The instantly identifiable vocalist who would also come to be known as Lady Day, who Frank Sinatra called his greatest single musical influence, started singing professionally almost by accident. Having popped her head into every bar and club in Harlem looking for work as a dancer, she was about to be turned down yet again at a place called Pod's and Jerry's (later The Log Cabin) when she asked if they needed a singer. The owner told her to go ahead and sing for the customers, and she had them in tears after two songs.

The story goes that she was singing at Monette's Supper Club, also in Harlem, when she was discovered at 17 by record producer John Hammond, who arranged for her first recording session, with Benny Goodman's orchestra, in 1933. She toured with Count Basie and became the first non-white singer to appear with Artie Shaw, though she eventually quit that gig after one too many separate trips up the freight elevator and entrances via the back door of an establishment while the rest of the band enjoyed the accommodations for white people.

Her first husband, trombonist Jimmy Monroe, was reportedly the first person to give Holiday opium, the singer having preferred marijuana throughout the 1930s. In Lady Sings the Blues she recalls "a white boy in Dallas called Speck" showing her how to inject heroin.

Trumpet player Joe Guy, one of myriad people (including actress Tallulah Bankhead) whom she was involved with during her marriage, was also a heroin addict and just as much of an enabler. 

Charles Peterson/Hulton Archive/Getty Images

Meanwhile, people in Holiday's inner circle, including Monroe and her agent Joe Glazer, buddied up to the authorities who conveyed the message that the U.S. government would appreciate it if she stopped singing "Strange Fruit."

Anslinger hired a Black agent—which he didn't make a practice of but needed to do in order to get eyes on Holiday behind the scenes—named Jimmy Fletcher. Wearing his serviceman's uniform and posing as a wide-eyed fan, he won Holiday's trust. 

"Billie's greatest talent, after singing, was swearing—if she called you a 'motherf--ker,' it was a great compliment," Hari wrote. "We don't know the first time Billie called Jimmy a motherf--ker, but she soon spotted this man who was hanging around, watching her, and she grew to like him." And he would see her stoned on multiple occasions.

In May 1947, Holiday performed "Strange Fruit" during a show in Philadelphia. Later that night, her room at the Attucks Hotel was raided and she ended up being charged with heroin possession.

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The resulting case, The United States vs. Billie Holiday ("And that's just the way it felt," she later wrote), ended in her being sentenced to 366 days in prison. She had pleaded with the judge to send her to a hospital so she could get clean, but she was sent to the Federal Reformatory for Women in Alderson, W. Va.

(Incidentally, part of Anslinger's mission was also to diminish those in the medical community who were inclined to treat drug addiction as a disease in need of treatment instead of a crime meriting prosecution.)

Ten days before she was sentenced, Holiday told Michael Levin for DownBeat magazine that—while the FBI was busy admitting that they were setting an example with Holiday—she didn't want what was happening to her to be used as some sort of indictment of show business.

"When you're writing," she said, "straighten them out about my people. Tell 'em I made my mistake, but show people aren't all like that. Whatever I did wrong, nobody else but me was to blame."

At the same time, she was hardly blind as to why things were the way they were.

"I'm a Negro. I've got two strikes against me and don't you forget it," she also told Levin. "I'm proud of those two strikes. I'm as good as a lot of people of all kind."

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According to Hari, Fletcher would live to regret his role in taking Holiday down, and his merciless views about addicts having no one to blame but themselves had certainly softened once he got to know her. 

"I had so many close conversations with her, about so many things," he recalled in an interview surfaced by Holiday biographer Julie Blackburn. "She was the type who would make anyone sympathetic because she was the loving type." 

In 1956, Holiday sent Fletcher a signed copy of her book, writing inside, "Most federal agents are nice people. They've got a dirt job to do and they have to do it. Some of the nicer ones have feelings enough to hate themselves sometime for what they have to do... Maybe they would've been kinder to me if they'd been nasty, then I wouldn't have trusted them enough to believe what they told me."

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Upon her release from prison, Holiday performed two sold-out shows at Carnegie Hall on March 27, 1948, but that wasn't a sustainable arrangement to earn a living. A number of magazine articles over the years carried Holiday's byline, including one in Ebony called "How I Blew A Million Dollars" and another in Tan that asked "Can a Dope Addict Come Back?" (Her candor was notable for any era.) 

Her star had shined brightest in New York, but after the drug conviction she had her cabaret card—a license to perform at venues that served alcohol (i.e. all nightclubs)—taken away, severely limiting where she could sing (as did her hard-earned reputation for being an unreliable act to hire).

"How do you best act cruelly?" singer and actress Yolande Bavan told Hari in 2013. "It's to take something that's the dearest thing to that person away from them...You can't do the thing that is a passion and that you made your livelihood at, and that has brought joy to people all over the world."

Holiday was arrested again in January 1949 in San Francisco for opium possession, another one of Anslinger's agents showing up at the Mark Twain Hotel to bust her—and likely planting evidence in the process. Holiday insisted that she was clean, that they should send her to a clinic for monitoring so she could prove she wasn't suffering the usual symptoms of opioid withdrawal.

A jury found her not guilty. But she told Ebony that year that she was tired of the "vindictive, hounding, heckling and harassing" authorities who wouldn't leave her alone. And she admitted to feeling suicidal during that time in Lady Sings the Blues, writing, "The hounding and the pressure drove me to think of trying the final solution, death."


In 1955, her friend and sometimes manager Maely Bartholomew, who was married to journalist William Dufty, invited Holiday to come stay at their apartment to hide out—from the authorities, from reporters, from the toxic men in her life (including her louse of a last husband, Louis McKay). That's when she and Dufty got started on the book.

It was assumed, probably correctly, that, after not playing a show in New York for eight years due to her cabaret license being revoked, Holiday was interested in collaborating on the story of her life because she needed money.

"She was writing for money to support her drug habit, and for publicity to make it appear that she was off the habit and to get her back her cabaret card," wrote journalist Linda Kuehl, whose years' worth of research, including interviews with people who were close to the singer, is the most drawn-upon archive for Holiday biographers aside from Lady Sings the Blues. (An odd case in itself, Kuehl planned to write the definitive book on Holiday herself, but she died in 1978, having jumped—according to police—off a building in Washington, D.C. Family members disputed the conclusion that she took her own life.)

Filmmaker James Erskine acquired Kuehl's archive and used it to make the 2020 documentary Billie, which was released in November. In one taped interview, she's heard asking drummer Jonathan "Jo" Jones what they went through back in the 1940s and 1950s, traveling through the South to perform.

"We was going through hell!" he exclaimed. "Miss Billie Holiday didn't have the privilege of using a toilet in a filling station. The boys at least could go out in the woods. You don't know anything about it because you've never had to subjugate yourself to it. Never!"

Talking to The Guardian when the documentary came out, Erskine said, "We finished the film last year and I didn't see it again until September. I was shocked at how political it felt. When we were making it, we felt that we were presenting truths about things that everybody understood, the white man's power, structural racism. I was setting out to make a film about Billie, and one of the joys of it is that you get to really see her. But I guess it tells us that we haven't really addressed any generational wounds in society."

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In Lady Sings the Blues, Holiday shared, "You can be up to your boobies in white satin, with gardenias in your hair and no sugar cane for miles, but you can still be working on a plantation."

But all the while, she never stopped performing "Strange Fruit" when the mood occurred, rankling her determined oppressors until the end.

"She really believed that no one would ever know her story," Andra Day said on ABC's Inside the Oscars podcast. "She thought she would die in obscurity. Matter of fact, I think, forget the story—I think she'd be shocked to know the world still knew 'Strange Fruit,' and that she grew to be—she was hugely famous when she was alive here on Earth, but that her legacy sustained, that people know her name, now today."

Holiday's funeral was held July 21, 1959, at New York's St. Paul the Apostle Roman Catholic Church. Benny Goodman was an honorary pallbearer and thousands of people showed up, whoever didn't fit into the church congregating outside. 

Recalling his eulogy to Hari, the Reverend Eugene Callender remembered telling the mourners, "We should not be here. This young lady was gifted by her creator with tremendous talent...She should have lived to be at least 80 years old."

The United States vs. Billie Holiday is streaming on Hulu.

(Originally published April 7, 2021, at 3 a.m. PT)