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

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.

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.

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.

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.

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 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.

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

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.

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.

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.

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.

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'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."

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."

See Minnelli's iconic performance of 'Maybe This Time' that helped earn her an Oscar

In the film "Cabaret," Minnelli performs the show tune as Sally Bowles, a protagonist embarking on a new love affair in 1930s Berlin. Minnelli's emotive performance and belting vocals helped land her the prestigious acting award.

In the 1930s, New York banned buskers as part of an antinoise campaign

Mayor Fiorello LaGuardia was hoping to modernize the city and believed that street performers only crowded the streets and added to an annoying cacophony. Residents wrote to the mayor to protest the decision, arguing that buskers were appreciated by the public.

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

Watch a 1934 short film starring Cab Calloway

Singer and bandleader Cab Calloway was a major figure in the Harlem Renaissance's music scene. He was also one of the biggest names in jazz's swing era and would go on to be the first Black American to have a nationally syndicated radio show and the first to sell a million copies of a record. In this 1934 short film, "Cab Calloway's Hi-De-Ho," he reenacts his upbeat performances at Harlem's Cotton Club.

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.

After actress Ingrid Bergman had a child out of wedlock, a Colorado senator proposed granting the government the ability to ban performers deemed morally objectionable.

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.)

Billboard's early music charts were racially segregated

In 1942, the publication introduced the Harlem Hit Parade chart, listing the top 10 records sold at select record stores in the majority-Black borough of New York. In 1945, it changed the chart’s name to Most Played Juke Box Race Records, using the music industry term (“race record”) that identified recordings by Black artists, even if they played music markedly similar to the white artists on the other charts.

Lenny Bruce's stand-up challenged US law

Bruce came up in burlesque theaters, but began to find success as stand-up comedy developed a more political and subversive bent. His sets often satirized what he believed to be an oppressively conformist society, which led to his arrest on several occasions.

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.

Some critics argue bebop and free jazz led to jazz's decline in popularity

Although jazz was once a popular art form, it has largely been confined to the margins of pop culture, with many of the genre's current bestselling albums from previous decades. Some critics argue that this is because the music betrayed its position as dance music and focused instead on musical proficiency.

Liza Minnelli was a regular at Studio 54, one of the trendiest nightclubs in the world

In the 1970s, some of the world's biggest stars would flock to the New York City club to dance and socialize during the disco era. See photos of Liza Minnelli accompanied by other celebrities like Andy Warhol, Bianca Jagger, Robert De Niro, and James Spader.

Edgier burlesque shows helped define the form

Stand-up came into its own at burlesque shows, thanks to audiences who sought humor that reflected the hectic, urban settings where they lived. According to historian Joseph Boskin, “The tempo of the comedy, like the movement of city streets, was swift and jolting and possessed highly recognizable parameters.”

The betting scandal that rocked college basketball

In the 1940s and '50s, illegal bookmaking in college basketball was rampant at Madison Square Garden. In the 1949-50 season, City College of New York players shaved points during games, though they played honestly in the NIT and NCAA tournaments, winning both. This OddsShark.com article explores how the points-shaving scandal was exposed, who went to jail, and its impact on the NIT and CCNY.

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.

Years before the 1969 Stonewall Uprising, patrons at another New York bar staged a protest against an antigay liquor law.

Fearing the corruption of its youth, Santa Cruz, California, banned rock 'n' roll in 1956.

Roosevelt resigned from a prominent women's organization after it barred a Black singer from performing

When the Daughters of the American Revolution refused to allow Marian Anderson to perform at their Washington hall in 1939 because she was Black, Roosevelt publicly cut ties with the group. She worked to arrange an alternative outdoor concert for Anderson at the Lincoln Memorial, which drew a crowd of 75,000.

Explore a map of the Harlem Renaissance's nightclubs

Many of the Harlem Renaissance's greatest performances happened after hours, in one of the neighborhood's many nightclubs. This 1932 map, illustrated by Elmer Simms Campbell, highlights key hotspots, with insider tips on when to arrive, who to see, and how to fit in.

Tina Turner had to change the lyrics referencing American Express in 'Private Dancer' to comply with British advertising laws

In her 1984 hit, "Private Dancer," Turner sings "American Express Will Do Nicely, Thank You." However, advertising laws in England prohibited mentions of companies, leading Turner to release another version of the song with the lyric "A Few Pounds Sterling Will Do Nicely, Thank You."

The Chitlin Circuit provided Black entertainers a safe network during Jim Crow

Black musicians and comedians regularly toured the Chitlin Circuit, an informal entertainment network that developed performers like Tina Turner and Redd Foxx during the Jim Crow era.

Famous scammer Anna Delvey lied about having a $67M trust fund

Delvey conned New York City’s elite with her lies, saying that she was a German heiress and defrauding the city’s banks, restaurants, and more out of more than $275K in just 10 months. Her story was even turned into a Netflix series while she was in prison.

Early 20th-century ID cards protected transgender people in Germany using hormone therapy.

How musical guests disappeared from late night TV

The late-night landscape has changed dramatically in the past five years, with the most visible difference being a severe lack of music. This writer set out to learn why that is—and what it means for audiences and artists alike.

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

Houdini recalls how he became 'Handcuff King'

Illusionist Harry Houdini rose to fame through his many escapes, like from the handcuffs slapped onto his wrists by Los Angeles police in 1899. In this 1907 Los Angeles Herald article, Houdini recalls some of the many times he's thwarted attempts to...

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.

See an original Diner’s Club charge card

Before credit cards, there were charge cards from companies like Diner’s Club. While credit cards allow cardholders to carry a balance from month to month (potentially accruing interest), charge cards like Diner’s Club cards had to be paid off right away.

Jazz was an integral part of the Harlem Renaissance

The Great Migration transformed New York City's Harlem neighborhood into the epicenter of Black American art, with artists such as Duke Ellington, Louis Armstrong, and Bessie Smith regularly performing. The music not only provided the backbeat to the cultural scene—it often influenced it, with Harlem Renaissance poets, in particular, inspired by jazz's approach to rhythm and improvisation.

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.

Atlantic City was a major vacation destination in the early 20th century

The city’s boardwalk, filled with amusement parks and vendors, became a significant attraction for vacationing families. The town also became a hub for entertainment, with actors often starting there before heading to Broadway.

'Shuffle Along,' a 1921 Broadway musical, brought jazz to American musical theater and helped pave the way for Black culture in the 20th century.