The federal agents who followed Billie Holiday

How the government caught Billie Holiday

Louis McKay—who was Holiday's manager and abusive husband—worked with the Federal Bureau of Narcotics to ensure Holiday was caught with drugs. She was eventually put on trial and sentenced to a year in prison, where she briefly got sober.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.)

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."

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 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.

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

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

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.

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."

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.

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.

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.

Fast, cheap, and deadly: How fentanyl replaced heroin and hooked America

This interactive article details how fentanyl has largely replaced heroin in the drug trade, with fatal results. Fentanyl was first developed in 1959 as an anesthetic for pain relief, but the drug took hold in the US black market in 2014 and has since exploded in the intervening decade.

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

​Why heroin became associated with the grunge world

The drug was popular with several Seattle acts in the early 1990s, with artists like Hole's Courtney Love even publicizing her use in a magazine profile. A 1992 New York Times story on Seattle said the city's principal drugs were "espresso, beer, and heroin."

The FBI was thrilled with 'The Silence of the Lambs' and its portrayal of the agency

The film's ultimate purpose was to terrify, but the FBI made it clear that they appreciated the accurate, professional portrayals of its agents. "It never hurts to see the organization we all care about and know to be good well-depicted on the big screen," special agent Walter B. Stowe, Jr., wrote in a letter to director Jonathan Demme.

Why are drug dealers putting fentanyl in everything?

A few grains of fentanyl, a synthetic opioid far more potent than heroin or morphine, are enough to kill a typical adult human. It's made its way into other, less lethal street drugs, where it may be used to increase the highs experienced by unknowing users, increasing their likelihood of addiction and overdose.

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.

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.

Read a 1984 interview with Dolly Parton, conducted by artist Andy Warhol.

Searching for a hate crime's unknown victim

In 2004, two federal agents heard a rumor: two white men, one under investigation for an unrelated crime, had gotten away with killing a Black man 15 years earlier as a requirement to join a white supremacist group. One of the men confessed to the crime, though he didn't know who was killed. This series dives into the search for the slain man and the justice he deserved.

'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.

Why is fentanyl poisoning street drugs?

A few grains of fentanyl, a synthetic opioid far more potent than heroin or morphine, is enough to kill a typical adult human. It's made its way into other, less lethal street drugs, where it may be used to increase the highs experienced by unknowing users, increasing their likelihood of addiction and overdose. This 39-minute podcast episode is the first half of a two-part series exploring fentanyl's rise.

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.

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 kept tabs on Camus and Sartre

Jean-Paul Sartre worked as an American correspondent for Combat, the newspaper edited by Albert Camus. While he was in the States, J. Edgar Hoover's FBI kept tabs on him, concerned that Combat was publishing unfavorable portrayals of the US.

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 FBI investigated John Steinbeck, believing he might be a communist.

Fentanyl is better at crossing the blood-brain barrier than other opioids

Among opioids, fentanyl is uniquely adept at crossing the blood-brain barrier—the brain's security fence against harmful substances. This enables a lightning-fast high. It ends just as quickly, sometimes within minutes (where a heroin high lasts hours), and still results in the same withdrawal symptoms.

From prescriptions to street drugs: Opioids trajectory across America

Exclusive data obtained by The Washington Post from the Centers for Disease Control and Prevention shows how individual counties moved through three waves of the opioid crisis, each wave paving the way for the next. Between 2011 and 2017, the drug responsible for the majority of overdose deaths shifted from prescription pills to heroin to fentanyl. Together, oxycodone, hydrocodone, heroin, and fentanyl have been major drivers in declining life expectancy in the US.

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.

The surprising and strange sources behind 12 famous songs

Britney Spears's "Toxic" borrowed strings from a 1981 Bollywood film, Billie Eilish sampled The Office, and one duo made an entire album using only the sounds of their Whirlpool washing machine. Explore how sampling can pull from pretty much anywhere.

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

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.

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.

The Texas Ranger turned 'serial killer whisperer'

Texas Ranger James Holland earned a reputation for squeezing confessions from suspected serial killers, including the country's most prolific serial killer, Samuel Little. This reputation led the LA Times to declare him "a serial killer whisperer of sorts." With methods ranging from hypnotism to lies, this award-winning article dives into the question of whether this ranger's legal lasso ever ensnared innocents and diluted witness testimony.

In 1988, Basquiat died from a heroin overdose

Basquiat’s fame took a toll on the young artist. He felt pigeonholed and caricatured as a Black artist. He used heroin to cope with the pressure, but his addiction grew worse after the death of his mentor, Andy Warhol. He overdosed in 1988, after attempts to get clean.

The strange story behind President Jimmy Carter's brother's 'Billy Beer'

During Carter's 1976 presidential campaign, his brother, Billy Carter, became a sideshow attraction as a country bumpkin. The Louisville-based Falls City Brewing Company decided to capitalize on the attention and hired Carter has a brand ambassador to promote his own "Billy Beer." What followed was a strange, suspicious bit of guerilla marketing and hucksterism, all of it documented in this Mental Floss retrospective.