How the government caught Billie Holiday

The federal agents who followed Billie Holiday

After the success of "Strange Fruit," the Federal Bureau of Narcotics began surveilling Holiday on suspicion that she was using heroin. Jimmy Fletcher, an agent tasked with following her to clubs and parties, later said that they became quite close. "She was the type who would make anyone sympathetic because she was the loving type," he was reported as saying.

There's no proof that the government pursued Holiday because of 'Strange Fruit'

Music writer Lewis Porter disputes the events of "The United States vs. Billie Holiday," a 2022 film that dramatized the Federal Bureau of Narcotics' pursuit of the jazz legend. Porter notes that the FBN did indeed target Holiday, but believes it's important to note that it wasn't necessarily for the release of the protest song.

Understanding how Billie Holiday's traumatic childhood led her to drugs

At 10 years old, the jazz singer was raped and then returned to House of the Good Shepard under protective custody. Her rapist was eventually convicted, but the court still sent her to an all-girls Catholic reform school. Jake Brennan, the host of the Disgraceland podcast, believes those early events led Holiday to the transcendent world of performing, but that it also led her to the escape of drugs.

After her arrest, a technicality made it harder for Holiday to perform

The Cabaret Identification Card was required for all performers in New York nightclubs that served liquor. After her arrest and yearlong imprisonment, the New York Police Department revoked Billie Holiday's card, making it extremely difficult for her to earn money. The video features contemporary jazz musician Christian McBride breaking down the history of cabaret cards and how the ban affected Holiday.

As a girl, Billie Holiday fell in love with music while scrubbing the floors of a brothel

Record players were rarities in the 1920s, but Holiday had access to one at Alice Dean's, the brothel in Baltimore where she scrubbed floors. It was there that she listened to her heroes, Louis Armstrong and Bessie Smith.

Days after her release from prison, Billie Holiday sold out Carnegie Hall

The jazz icon was released early from federal prison on good behavior. Following her arrest, she was effectively prohibited from performing in New York's nightclubs, but she realized she could still perform, so long as it was in a venue that hadn't been deemed a "cabaret." The solution? The famous Carnegie Hall. The show sold out within a week, and the venue became a regular stop for Holiday, who performed there 22 times.

The story of Billie Holiday's final performance

In her final days, Holiday was still performing—often at clubs outside of New York—though she was struggling with cirrhosis, an effect of her alcoholism. This excerpt from Paul Anderson's "Bitter Crop: the Heartache and Triumph of Billie Holiday's Final Year" details her final show in Lowell, Massachusetts, offering a tragic portrait of the singer running out of steam.

Watch Billie Holiday's only feature film appearance in 'New Orleans'

The 1947 film wasn't known for its sophisticated plot, which mainly centers on a white opera singer who learns about the beauty of blues and jazz. It's more notable for featuring some of those genre's biggest stars, including Holiday, who played a singing maid and the love interest of Louis Armstrong. You can see her first scene around the 11-minute mark.

Watch Billie Holiday's screen debut in 1935's 'Symphony in Black'

The singer appeared alongside Duke Ellington in Paramount's "Symphony in Black," a musical short released by Paramount Pictures in September 1935, when Holiday was just 20 years old.

Analyzing Billie Holiday's impact on American poetry

Although Holiday is sometimes associated with the Harlem Renaissance, the Black cultural movement of the 1920s and '30s, scholar Whit Frazier Peterson argues that her real impact in poetry was on the Black Arts Movement, the more radical Black literary movement of the '60s and '70s that featured writers like Amiri Baraka, Sonia Sanchez, and Nikki Giovanni.

Watch Billie Holiday perform in 'The Sound of Jazz'

The 1957 CBS special, part of its series "The Seven Lively Arts," was a landmark broadcast that brought some of jazz's biggest names—including Holiday, Thelonious Monk, and Count Basie—to a national audience. Watch Holiday offer a stirring rendition of "Fine and Mellow" below.

A beginner's guide to the music of Billie Holiday

This primer from NPR breaks down some of the best entry points for newcomers to the jazz legend. From iconic tracks like "Strange Fruit" to deeper but essential late-era songs, the list offers a blueprint for appreciating Holiday before jumping into the deep end of her sprawling discography.

Billie Holiday ensured performances of 'Strange Fruit' had the right context

In the song's earliest performances at Cafe Society in New York, one of a few truly integrated nightclubs in the society, the song was always performed last, after bar service had stopped, with a single spotlight on Holiday so audiences would pay close attention to the lyrics. Later, Holiday included her ability to perform the song in her concert contracts, allowing her to sing it even if venue owners were nervous about its protest message.

Billie Holiday's distinctive vocal technique was aided by new microphone technology, which allowed for quieter singing.

Billie Holiday's influence on Amy Winehouse

Winehouse, who became popular in the 2000s, was known for her jazz style, which was indebted to the vocal technique Holiday had innovated decades earlier. In 2003, Winehouse paid homage to Holiday by covering "(There Is) No Greater Love," a standard that Holiday had recorded in 1947.

Watch Diana Ross posthumously induct Billie Holiday into the Rock and Roll Hall of Fame

Holiday was posthumously inducted into the Hall in 2000 for her influence on the generations that followed her. Fittingly, Diana Ross, who played Holiday in a 1972 biopic, did the honors. She took the opportunity to sing an acapella verse of "Strange Fruit" and then offer some honorific poetry: "In this, a lesson: Artist, handle with care. Don't lose yourself in the music, beware stardom's glare."

Diana Ross starred in a Motown-produced biopic about Billie Holiday

The 1972 film "Lady Sings the Blues" was loosely based on Holiday's autobiography and starred Ross, then pursuing her post-Supremes solo career. The Motown production had big names (including Billy Dee Williams and Richard Pryor) and was nominated for five Academy Awards, including one for Ross' performance. You can watch the film below.

Billie Holiday's label refused to release 'Strange Fruit,' a protest song about lynching, because of fears of negative reactions from southern retailers.

Why Frank Sinatra called Billie Holiday his 'greatest single influence'

In a 1958 essay for Ebony magazine, Sinatra wrote about the impact that Black music had on him, writing that "it is Billie Holiday, whom I first heard in 52nd Street clubs in the early 1930s, who was and still remains the greatest single musical influence on me. It has been a warm and wonderful influence, and I am very proud to acknowledge it."

How tax laws helped the federal government catch mob bosses during Prohibition

The IRS arrested top mob bosses during Prohibition after the Supreme Court ruled illegally-made income could be taxed. The IRS's biggest catch was Al Capone, who was charged with tax evasion and sentenced to 11 years in prison. But Capone wasn't the only bootlegger the IRS nabbed for tax evasion during this era.

The poem behind 'Strange Fruit'

"Bitter Fruit" was written by Abel Meeropol, a teacher, under the pseudonym Lewis Allen, after seeing a photograph of a lynching. Eventually, he set the words to music, and the song was then performed by his wife and other singers. In 1938, he played it for Holiday, who began performing it at the New York's Cafe Society. (Some users may experience a paywall.)

How a Cleveland woman who slammed the door on police changed the Fourth Amendment

In 1957, a bomb exploded under the front porch of boxing promoter Don King in Cleveland. When police received a tip to search Dollree Mapp's home, she refused to let them in. Her case went to the Supreme Court, resulting in a ruling that barred illegally obtained evidence from state criminal trials.

The FBI surveilled Roosevelt for decades, suspicious of her civil rights and political work

J. Edgar Hoover's FBI maintained a large file on Eleanor Roosevelt, monitoring her involvement with civil rights groups, connections to progressive causes, and vocal opposition to McCarthyism. Although a formal investigation was never initiated, Hoover regarded her as a person of interest for most of her adult life.

Billie Eilish broke records at the 2020 Grammys

Alternative pop star Billie Eilish had a fascinating rise to fame. She cemented her album "When We All Fall Asleep, Where Do We Go?" in Grammys history by becoming the first woman and youngest person to win all the Big Four awards in the same night.

Ginsberg's 'Howl' portrayed people outside the American mainstream

The poem’s portraits of people on society's fringes—including vivid descriptions of drug use, psychiatric wards, and homosexuality—led to its seizure by US Customs agents and the arrest of its publisher Ferlinghetti. The American Civil Liberties Union defended both in a landmark trial that ruled the book was not obscene.

In 1985, New York Mets star Keith Hernandez said 40% of his MLB peers used cocaine, highlighting an open secret about drug use in the league.

The Washington Post's Janet Cooke returned her Pulitzer

When Washington Post reporter Janet Cooke published her profile of an 8-year-old heroin addict named Jimmy in 1980, it created an instant uproar. Social workers, police officers, and even the mayor of Washington, DC, all jumped into action to try to get the child help, but no one could find him. Within hours of Cooke receiving a Pulitzer for the piece, everything began to unravel as it was revealed that she had fabricated not just Jimmy's story, but her own as well. She eventually returned the award.

See how DOJ prosecutors took down a pharmaceutical company's executives over the opioid crisis

This FRONTLINE documentary follows federal prosecutors as they used anti-racketeering laws to convict executives at Insys Therapeutics, a pharmaceutical company that bribed doctors to overprescribe a fentanyl painkiller.

Hamilton publicly admitted to an affair to rebut corruption charges

In 1797, Alexander Hamilton published the Reynolds Pamphlet, confessing to an extramarital affair and blackmail payments to disprove accusations of financial corruption—clearing his name legally but ruining his reputation.

How one trial tested the limits of satirical music

The rapper Afroman, who earned jokey hits in the '90s with songs like "Because I Got High," was taken into court by police officers by police officers in Adams County, Ohio, who alleged that he'd defamed them in his songs. The music in question was recorded after those officers raided his house and satirized the situation, often in graphic terms. The rapper beat the case, but not before his satirical songs were analyzed in court.

Jazz provided a soundtrack for the Civil Rights Movement

Songs like Billie Holiday's "Strange Fruit," which portrayed the grim brutality of lynching, and John Coltrane's "Alabama," which was modeled on the rhythm of a speech by Martin Luther King Jr., were the backbeat of the movement.

Musician Gladys Bentley defied gender norms during the Harlem Renaissance and was openly gay, even though homosexuality was still widely considered taboo.

The story of Olympian Ryan Wedding's rise and fall as drug kingpin

After a disappointing finish representing Canada in the slalom at the 2002 Winter Olympics, Wedding turned to growing cannabis and selling cocaine. After serving prison time, he upped his game and came to control major drug routes in North America, finding himself on the FBI's 10 Most Wanted List. He was captured in Mexico City in January 2026.

How a government chemist founded the FDA—by poisoning people

The Poison Squad tells the story of government chemist Dr. Harvey Wiley who, determined to banish these dangerous substances from dinner tables, took on the powerful food manufacturers and their allies.

'The Chinatown Sting': Unraveling an international drug smuggling ring

In the late 1980s, a group of women connected through the mahjong parlors in Manhattan's Chinatown were caught in a massive undercover drug bust. But this bust was just the beginning of an even bigger case.

The long history of Kurt Cobain suicide conspiracy theories

Cobain died by suicide in 1994, but it wasn't long before fans began espousing conspiracy theories alleging that the government or his wife and lead singer of Hole, Courtney Love, had him killed. Seattle police revisited the case in 2014, but determined that it was indeed a suicide.

The FBI ran a covert campaign to discredit Dr. Martin Luther King Jr.

From 1963 to 1968, the FBI surveilled Dr. King with wiretaps, hotel bugs, informants, and anonymous threats, citing concerns about Communist influence—an effort later revealed through declassified files and documented in the film MLK/FBI.

Although payola was made illegal in 1960, it likely continued on the Billboard charts through the '70s

In his book “Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves,” music journalist Chris Dalla Riva argues that payola, the music industry term for undisclosed paid publicity, likely continued into the 1970s with the Billboard chart. Dalla Riva cites chart irregularities and reports about Bill Wardlow, Billboard’s then director of sales, who was a known booster for disco label Casablanca Records.

The wife of Nixon's attorney general was forcibly held to silence her Watergate revelations

While vacationing in June 1972, Martha Mitchell was held captive, sedated, and physically abused by operatives connected to Nixon, intent on keeping her from speaking to reporters.

The story of Marie Nyswander, the woman who co-discovered methadone maintenance

Methadone, an opioid with distinct effects from heroin, revolutionized heroin addiction in the 1960s. Marie Nyswander was a psychoanalyst who helped discover the treatment process which is still in use today. Here's a podcast episode examining her life and role in the field of addiction treatment.

The FBI's most famous cases

From the D.B. Cooper plane hijacking to the kidnapping of Frank Sinatra Jr. to the details about the first FBI agent killed in the line of duty, this FBI archive overviews the agency's most famous cases. Cases are organized by investigative priorities, according to the agency. Clicking any of the linked investigations takes readers to detailed articles about the cases, some of which remain unsolved.

How Audrey Hepburn became a spy during the Nazi occupation

Despite her status as one of Hollywood’s most beloved actresses, Audrey Hepburn experienced a war-torn childhood in Europe that few people know about. During her upbringing in the Netherlands, the Nazi occupation caused Hepburn to quit her life as a ballerina and made her family go hungry. In the face of adversity, Hepburn bravely carried messages for the Dutch resistance. Learn more about the star’s compelling life before finding fame.

Several major artists have embraced manipulating the Billboard charts

Billboard is supposed to be an accurate, objective representation of the country’s listening habits, but artists and their fans have discovered ways to manipulate the magazine’s methodology in order to push tracks to the top of the charts. In 2018, Taylor Swift rewarded fans for purchasing her album multiple times; in 2020, Justin Bieber reposted suggestions that fans repeatedly stream one of his songs while they sleep.

When America's deadliest serial killer went undetected

Samuel Little, who, for years, washed in and out of the justice system on violent charges eroded into lesser offenses, ultimately admitted to killing 93 people, mostly women, over more than 30 years. He tended to target those on the fringes of society—runaways, drug users, sex workers—people whose deaths were more likely to go unnoticed, he remarked, referring to them as fruits to be plucked at will.

The FBI tracked Woody Guthrie's politics for years, amassing an enormous file that was only discovered many years after his death.

Dolly Parton's 'Jolene' was partly based on a real woman who flirted with Parton's husband.

Carole King wrote—and later regretted—the song 'He Hit Me (And It Felt Like a Kiss),' which she now believes excuses domestic violence.

An ESPN documentary alleged that Bobby Riggs threw the 'Battle of the Sexes'

According to a 2013 report, Riggs intentionally lost his 1973 match against Billie Jean King in order to settle a debt to organized crime. The documentary primarily relies on information from a man who claimed to have overheard a conversation about the fraud. King maintains that Riggs played to his full ability but was simply overconfident for his age.

Browse over a century of issues of Billboard, the definitive music industry magazine, to trace nearly every American musical trend of the past century.

Ella Fitzgerald's life in photos

Iconic jazz singer Ella Fitzgerald is known as the "First Lady of Song" for her timeless performances and major contributions to jazz. Decades later, her songs have more than 100 million plays on Spotify. She collaborated with celebrated photographer Yale Joel, who left behind iconic picture galleries and films of the singer.