These days, it sure seems like the word “legend” gets tossed around and attached to names a little bit too often. I’m sorry, but some of the big names in music today are NOT legends. One person who actually does deserve the title, however, is Billie Holiday. When the famous jazz singer was given the accolade, it really meant something. She was definitely one of, if not THE, best jazz singers of all time. I mean, when you think of early Jazz, her name comes up – and that’s because she was a legend.
Billie Holiday, aka Lady Day, could sing, write, and perform brilliantly. But like many other musical (and other) geniuses, Holiday led a troubled life. She was alive at an unforgiving time in a then unforgiving country, which played a major part in her untimely death at the age of 44.
This is the story of how the issues of race, drugs, and misogyny turned a talented young girl into a complicated woman and eventually into a legend.
Billie Holiday was born as Eleanora Fagan on April 7, 1915, in Philadelphia, the daughter of an unmarried teenage couple: Sarah Julia “Sadie” Fagan and Clarence Holiday. Billie’s mother moved to Philadelphia at the age of 19, after being kicked out of her parents’ home in Baltimore, Maryland for getting pregnant.
Without support from her parents, Sadie asked her older, married half-sister, Eva Miller, to take care of her newborn daughter and have her stay with her in Baltimore. Soon after Eleanora was born, Clarence abandoned Sadie to pursue a career in music as a jazz banjo player and guitarist. Billie’s true father is debated. The birth certificate named her father as Frank DeViese, but she always insisted that he was Clarence Holiday, her mother’s childhood sweetheart.
Billie grew up in Baltimore and endured a challenging childhood. Her mother had to take what were then known as “transportation jobs,” where she served on passenger railroads. But Billie wasn’t raised by her mother. Eva Miller’s mother-in-law Martha Miller was the one who took care of her, and Billie suffered from her mother’s absence for the first decade of her life.
Young Billie frequently skipped school, which resulted in her being brought to juvenile court on January 5, 1925, when she was just nine years old. She was then sent to the House of the Good Shepherd, which was a Catholic reform school for troubled African American girls. She was baptized there at the age of 10. It was during her time there that she became a victim of sexual assault.
After nine months of basically serving time in what could be considered a prison, she was “paroled” to her mother. Sadly, the abuse she experienced in the children’s home wasn’t the last. On December 24, 1926, Sadie came home and found their neighbor, Wilbur Rich, trying to assault Billie. She managed to fight him off, and Rich was arrested.
Officials placed Billie back in the House of the Good Shepherd, unfortunately, but this time under protective custody as she was a state witness in the rape case. She got released in February 1927, when she was nearly 12 years old. By 1929, Billie moved to Harlem to live with her mother. That’s when she got introduced to a life that is simply not meant for young girls.
Their landlady in Harlem was a sharply-dressed woman by the name of Florence Williams. Florence happened to run a brothel on 151 West 140th Street. Desperate times call for desperate measures, and so Holiday’s mother became a prostitute. Within a matter of days of moving to New York, a young Billie who wasn’t even 14 years old, fell victim to sex trafficking.
The house was raided by police on May 2, 1929. Sadie was sent to prison. Billie left alone, was charged with vagrancy (begging), and was sent to a workhouse. At that point, the 14-year-old was running errands, scrubbing marble steps and kitchen and bathroom floors in the neighborhood’s homes. Her mother was released in July of that year, and Billie in October.
All the troubles she was facing would make any person seek an escape, a safe haven to avoid the harsh reality of the world. And Billie found hers in music. She had discovered the music of Bessie Smith and Louis Armstrong and particularly loved them. After being released from her duties of serving in a workhouse, Billie soon landed her first paid gig as a performer.
But it wasn’t necessarily the job she had hoped for. She went to a club called the Log Cabin Club, which was run by Jerry Preston. She told him that she was a dancer. She recalled later that night: “He said to dance. I tried it. He said I stunk. I told him I could sing. He said sing … I sang. The customers stopped drinking.”
Preston hired Billie to perform at $18 a week, and this was how she started to develop her voice. She chose to go by the stage name Billie after the film star Billie Dove. And she would try to emulate the singer Bessie Smith, whose music she adored. It didn’t take long for her to become a well-known name around Harlem.
Billie was known for her distinct vocal style, something most listeners weren’t even able to describe. She only referenced Bessie Smith and Louis Armstrong when speaking of her influences. She had limited range, and her voice didn’t always project, but her intonation, phrasing, and emotion were unmatched. Her vocal shortcomings were later made all too apparent in her later career when drugs got the best of her…
As a young teen, Holiday found herself singing in nightclubs. In those days, she spelled her last name, “Halliday,” which was her father’s surname at birth, but she later changed it to “Holiday,” which was his performing name. Clarence Holiday had a career in music, playing rhythm guitar and banjo as a member of the Fletcher Henderson Orchestra between 1928 and 1933.
Billie teamed up with her neighbor Kenneth Holland who was a tenor saxophone player. They played together from 1929 to 1931, performing at clubs like Grey Dawn, Pod’s and Jerry’s (on 133rd Street), and the Brooklyn Elks’ Club. Billie was starting to feel like a different person like this is what home feels like. And her talent wasn’t going unnoticed.
Benny Goodman, known as the King of Swing in those days, recalled hearing Billie Holiday at the Bright Spot in 1931. As her reputation was growing, she was booking more and more jazz clubs, including Mexico’s and the Alhambra Bar and Grill. She met Charles Linton, another singer, and even reconnected with her long-lost father. At that point, Clarence Holiday was playing in Fletcher Henderson’s band. I guess the apple doesn’t fall far from the tree.
By late 1932, the 17-year-old replaced singer Monette Moore at Covan’s, which was a club on West 132nd Street. That’s where she met producer John Hammond, who loved to come to Covan’s to hear Moore sing. But he was surprised to see this new young girl who replaced her. A girl with a very interesting voice.
John Hammond fell in love with this new sound he was hearing and knew what he had to do. So he arranged for Holiday to make her first record, at age 18, in November of 1933. She recorded it with Benny Goodman. Her first two songs: “Your Mother’s Son-in-Law” and “Riffin’ the Scotch.” The latter ended up becoming her first hit.
“Son-in-Law” sold only 300 copies, but “Riffin’ the Scotch,” which came out on November 11, 1933, sold 5,000 copies. Hammond was taken aback by Holiday and said: “Her singing almost changed my music tastes and my musical life because she was the first girl singer I’d come across who actually sang like an improvising jazz genius.” He compared her favorably to Louis Armstrong.
It would be about a year before Billie recorded another song. In 1935, Holiday was signed to Brunswick Records to record pop tunes with the famous pianist Teddy Wilson and his orchestra. Teddy was known as the “definitive swing pianist,” so this collaboration was a great move for Billie in establishing a name for herself. They recorded songs in a swing style for the growing jukebox movement.
They were allowed to riff and improvise. Holiday had a way of making her melody fit the emotion of the tune, and it was pretty revolutionary for that time. Over the next year, Billie recorded nearly 100 songs with Teddy, and one of their first collaborations included “What a Little Moonlight Can Do,” which ended up becoming Billie’s “claim to fame.” But the studio didn’t like those recording sessions.
Brunswick Records wasn’t so pleased with that recording session because producers wanted Billie to sound more like Cleo Brown. They didn’t realize what kind of talent they had on their hands until the track “What a Little Moonlight Can Do” became very successful. Then they realized that she could really be a money maker. They started considering Holiday as an artist in her own right.
The Wilson-Holiday recordings from 1935 to 1938 were a big asset to Brunswick. According to Hammond, the company was broke. Wilson, Holiday, Young, and others came into the studio without any contracts, which reduced the recording costs. Brunswick paid Holiday a flat fee instead of royalties, which also saved them money. The song “I Cried for You” sold 15,000 copies, compared to the average of 3,000 to 4,000.
Holiday started recording under her own name a year later for Vocalion Records in 1936. Those studio sessions were still produced by Hammond and also Bernie Hanighen. While she was becoming a solo artist, she still did sessions with Teddy Wilson, with some featuring Lester Young, a tenor saxophonist who had been a resident at her mother’s house years prior. Billie knew and was fond of Lester.
Young said, “I think you can hear that on some of the old records, you know. Sometimes I’d sit down and listen to ’em myself, and it sounds like two of the same voices, or the same mind, or something like that.” it was Young who nicknamed Billie “Lady Day.” Her nickname for him? “Prez.”
In 1937, Billie Holiday sang with Count Basie’s orchestra. When she sang with the band, the traveling conditions of the band were poor. They performed countless one-nighters in clubs, going from city to city. In Louisville, Kentucky, a man heckled her and requested she sing another song. Billie lost her temper and had to be taken off stage. Other than the abuse at a concert, the poor traveling conditions, and the racism she faced, others were complaining about her.
Jimmy Rushing, the band’s male vocalist, called Billie unprofessional. According to All Music Guide, she was fired for being “temperamental and unreliable.” She also was said to have refused to sing requested songs or change her style. By February of 1938, Holiday was fired and no longer sang for Count Basie.
In November of 1938, Holiday was going to perform with the band at the Lincoln Hotel in New York. She was forced to use the service elevator instead of the passenger elevator after the white hotel guests complained. This was likely the straw that broke the camel’s back, because shortly after, Holiday was no longer with the Count Basie band.
Holiday spoke about the Hotel incident weeks later, saying: “I was never allowed to visit the bar or the dining room as did other members of the band, and I was made to leave and enter through the kitchen.” A year later, she started performing with Artie Shaw, which turned her into one of the first black singers to ever appear with a white orchestra.
While she was indeed making history, it was nonetheless another difficult period for Billie as she fell victim to yet more abuse and unfortunate experiences. In situations where there was racial tension, Artie Shaw was known for sticking up for his vocalist. In her autobiography, Holiday described an incident where she was not allowed to sit on the bandstand with the other vocalists because of her skin color. Shaw said to her, “I want you on the bandstand like Helen Forrest, Tony Pastor, and everyone else.”
Unfortunately, there are no surviving live recordings of her performances with Shaw’s band. Holiday was only able to make one record with Shaw, called “Any Old Time.” Also, Holiday didn’t sing as often during Shaw’s shows as she did in Basie’s.
While Billie was performing with Artie Shaw’s band, there were many ups and downs. One of the positive aspects was gaining radio exposure. Shaw and Holiday were broadcast on New York City’s radio station WABC. It was a success, and they were given extra time to broadcast in April, which only increased their exposure.
But then there were the problems Billie faced when Shaw was pressured to hire a white singer, Nita Bradley. Holiday didn’t get along with Bradley, but they had to share a bandstand. But while Shaw admired Holiday and having her sing in his band, her tenure with the group was coming to an end.
Meanwhile, Billie was making some new friends. But only after making some enemies first.
Holiday was becoming a star in an era where there was another popular and extremely talented female black singer. And so Billie found herself in direct competition with Ella Fitzgerald. Back then, Fitzgerald was the singer of the Chick Webb Band, which was competing with the Basie band that Billie was in for that short period.
On January 16, 1938, which was the same day Benny Goodman performed his legendary Carnegie Hall concert, the Basie and Webb bands held a battle at the Savoy Ballroom. Fitzgerald and her band were declared the winners by Metronome magazine, but DownBeat magazine declared Holiday and her band as the winners. They ended up polling the audience, and Fitzgerald won by a three-to-one margin. Billie and Ella eventually became friends.
By the end of the 1930s, Holiday had toured with Count Basie, with Artie Shaw, scored a bunch of radio and retail hits with Teddy Wilson, and established herself as an artist in the recording industry. By then, she had the songs “What a Little Moonlight Can Do” and “Easy Living,” songs which were being covered by singers across America.
But as you can see, Billie was constantly faced with turmoil and situations that took a toll on her. While she loved music and performing on stage, she had to deal with things that got the best of her. Holiday’s romantic relationships were also frequently riddled with abuse and self-destruction that she ended up turning to drugs as a way to escape from a harsh reality and cope with a troubled life.
Holiday had started a promising solo career, regularly performing at New York’s Café Society in Greenwich Village and signing with Columbia Records. But despite her success, Holiday was following a self-destructive path that would prove to be a dead-end. Holiday began using hard drugs in the early 40s.
On August 25, 1941, Billie married James “Jimmy” Monroe, a trombonist. Jimmy turned out to be a violent and unstable man. Holiday was already a heavy drinker, but Monroe introduced her to a new habit. Jimmy was an opium user and showed Billie a whole new world of substance abuse. She was never able to stop the habit, and it caused turmoil in their marriage. During their unstable union, Billie became involved with someone else.
Billie was having an affair with trumpeter Joe Guy, who was also her drug dealer. It was with Guy that Holiday started using heroin. It was after her mother Sadie’s death in 1945 that Holiday picked up the pace of her substance abuse. She drank more than ever before and used drugs in greater quantities. She was basically trying to drown in her sorrows.
She ended up divorcing Monroe in 1947 and split up with Guy as well. Her drug use didn’t stop, but she was still focused on her career. She was set out to conquer the jazz world. During her days at Café Society, she was making songs like “God Bless the Child” and “Strange Fruit.” And “Strange Fruit,” which came out in 1939, was nothing short of controversial…
The song “Strange Fruit” touched upon horrible issues for African American people of that time. The song told a story about lynching in the country’s south. At that point, Holiday was recording for Columbia Records, and she was introduced to “Strange Fruit,” a poem about lynching written by Abel Meeropol, who was a Jewish schoolteacher from the Bronx.
Meeropol published his work under the pseudonym “Lewis Allan.” The poem was heard by Barney Josephson, the owner of Café Society, who then introduced it to Holiday. She performed the song at the club in 1939, but she was no doubt worried about what it could cause. She feared the possible retaliation. Billie put her worries aside and decided that the song was too important to not sing it.
The protest poem was about the lynching of a black man in the Deep South. The poem, when set to music, is really powerful, and audiences were stunned into silence when Billie sang it live. Her performance of it at Café Society had waiters and audience members alike watching in silence. During the song’s long introduction, the café’s lights dimmed, and all movement came to a pause.
As Holiday began singing, a small spotlight was illuminated on her face. On her final note, all the lights went out. When they came on, Holiday was gone. And the men and women of the crown simply wept. As you can see, this song and especially her performance struck a chord with the people listening.
Even Holiday herself struggled with it…
In her autobiography, Holiday said that the imagery in the song reminded her of her father’s death, which played a role in her resistance to singing it on stage. She said that her father, Clarence Holiday, was diagnosed with a fatal lung disorder and ultimately denied medical treatment because of racial prejudice.
“Strange Fruit” reminded her of this incident. “It reminds me of how Pop died, but I have to keep singing it, not only because people ask for it, but because twenty years after Pop died, the things that killed him are still happening in the South,” she wrote in her autobiography.
Despite the power of the song, Columbia Records refused to release it. It did, however, come out on a smaller Commodore label.
Holiday’s popularity definitely increased after “Strange Fruit.” Even Time Magazine mentioned her. But Holiday wasn’t getting what she knew she deserved. “I open Café Society as an unknown,” Holiday later said. “I left two years later as a star. I needed the prestige and publicity all right, but you can’t pay rent with it.” She then demanded a raise from her manager, Joe Glaser.
“Strange Fruit” remained in her performance repertoire for 20 years. The controversial song sold well, and Holiday said how “The version I recorded for Commodore became my biggest-selling record.” In the late 30s, “Strange Fruit” was the equivalent of what a top-20 hit would be today.
And through all this growing fame, behind closed doors, Billie was still struggling with her personal life…
Billie’s career was moving in all the right directions, but her personal surely wasn’t. Other than her marriage to Jimmy Monroe and her affair with Joe Guy, she also had a relationship with guitarist Freddie Green. Holiday’s drug problem finally caught up with her in 1947 when she got arrested in Philadelphia for possession of heroin.
She was sentenced to 366 days in prison and was also sent to a rehabilitation facility in West Virginia. Even though she was literally behind bars, Holiday’s popularity kept rising. But that doesn’t mean that things were at all easy for her career-wise. Now that she was an ex-con, she couldn’t get a license to perform in night clubs. But she was still the famous Billie Holiday.
Not only did she get more famous, but prison helped Billie kick her drug habit. She left clean and looking so much better. She was by definition an ex-convict, but hell – this is Billie Holiday we’re talking about! After her release from prison, which probably only increased her popularity, Billie managed to sell out concert halls, including the infamous Carnegie Hall.
Almost immediately after getting out of prison, a concert was set for Carnegie Hall in March of 1948. She sang over 30 songs, despite not singing for a year. Some of those songs included ‘All of Me,’ ‘Fine and Mellow,’ and, naturally, ‘Strange Fruit.’ One newspaper put it: “Billie took her homage like a queen. Her voice, a petulant, sex-edged moan, was stronger than ever.”
Jimmy Monroe, who the federal prosecutor described as “the worst type of parasite you can imagine,” took no time getting Billie back to her bad habits. She was arrested again and on a similar charge, but this time she was acquitted. Billie moved on and met a new man, John Levy, a club owner who was about as bad as Monroe was. He was also her manager.
He was very controlling of Billie, and she was proving just how much she was dependent on having a strong (and destructive) man in her life. In 1948, Holiday performed at the Ebony Club, which was actually against the law because she lost her cabaret card. Levy was convinced he could get the card back and let her open without one. “I opened scared,” Holiday later said, “I was expecting the cops to come in any chorus and carry me off. But nothing happened. I was a huge success.”
By the 1950s, Billie’s drug abuse, drinking, and abusive relationships were taking a toll on her health. She left Jimmy Monroe, but on March 28, 1957, she married Louis McKay. He was a Mafia enforcer who just wanted to exploit her name and open a chain of recording studios. Like the other men in her life, McKay was abusive. The plus side, however, was that McKay kept Billie off of drugs.
Holiday continued making records throughout the 50s (nearly a third of her records were during this period), but her voice had noticeably weakened. She sounded a lot rougher, more vulnerable, yet still, with the raw intensity, she was known for. For many of her fans, the fragility in her voice only gave her more emotional resonance.
In 1954, Billie toured Europe and seemed as though she was happier than she had been in years. It could be because McKay kept drugs out of her life. By 1956, Billie published an autobiography called ‘Lady Sings the Blues,’ which received some good reviews. By 1957, fights between Billie and McKay became more common. Then she discovered something that threw her back into the hands of drugs.
Billie found out that her husband had lost much of her money in risky property speculation. Before she knew it, she was back on drugs. The two split up, and Billie moved into an apartment in New York City with her dog as her only company. The drugs and alcohol turned her into a shadow of herself.
Though the last years of Holiday’s life surrounded drugs and alcohol, one rare performance with her old friend Lester Young was a sweet note. The nature of her relationship with Young was somewhat mysterious, even to those close to them. They had a falling out in the late 1930s and hadn’t spoken to for years.
They reunited in 1957 for a televised performance of “Fine and Mellow.” Two years later, Young died alone in a hotel room. He, too, was a victim of chronic alcoholism. When Young, who was likely her one and only true friend in life and the one who called her Lady Day, died in March of 1959, Holiday did not take it lightly. You can pretty much guess as to how she dealt with it.
Shortly after Young’s death, Billie was in the hospital due to drug abuse. She wasn’t allowed into one hospital because of the drugs and even one hospital that allowed her in, didn’t tolerate her drug use while being treated. A nurse found narcotics at her bedside, called the police, and she was arrested.
Holiday’s voice got increasingly worse after all the years of substance abuse. But she was still able to find a great deal of success and make some impressive performances. She toured Europe, co-wrote an autobiography, got married in Mexico, performed on the CBS broadcast “The Sound of Jazz,” and recorded a final album called “Lady in Satin,” in 1958. And on May 25, 1959, Holiday gave her final live performance.
Billie Holiday’s last performance was in New York City. By early 1959, Holiday had been diagnosed with cirrhosis (liver failure). Although she had stopped drinking as per her doctor’s orders, it wasn’t long before she relapsed. A few months later, she had lost 20 pounds. People close to her like her manager at the time, like Joe Glaser, Leonard Feather, Allan Morrison, and her friends all tried to persuade her to go to a hospital.
It was after that shows that she ended up in the Metropolitan Hospital in New York. She passed away on July 17, 1959, in the bed that she was arrested in for possession of narcotics a month before. She was beautiful but wasted away to a physically small and sad caricature of herself. She was 44 years old.
On a hot July day in 1959, thousands of people gathered to pay tribute and mourn the death of one of the most influential artists of the 20th century. The police had to redirect traffic as the mourners poured into the nearby streets. The funeral was for an artist whose career was overshadowed by her personal problems. Her funeral was held on July 21, 1959, at the Church of St. Paul the Apostle in Manhattan.
More than 3,000 people came to her funeral, and the jazz world will always admire her emotional voice and thrilling personality. She is forever remembered as one of the best jazz vocalists of all time. She was then buried at Saint Raymond’s Cemetery in the Bronx.
When Billie Holiday died, TIME editors published two sentences to mark her passing: “Died. Billie Holiday, 44, Negro blues singer, whose husky, melancholy voice reflected the tragedy of her own life; in Manhattan. Born of indigent teenagers, schooled in a Baltimore brothel, she stubbornly nursed her resentment, poured it out in songs that reached their height of popularity in the early ’40s; Billie’s Blues, The Man I Love, above all, Strange Fruit, a description of a Negro lynching in the South; succumbed to the dope addiction which dogged her to the end.”
Holiday didn’t have any children, but she had two godchildren: Billie Lorraine Feather (a singer and the daughter of Leonard Feather) and Bevan Dufty (the son of William Dufty). Sadly, she was progressively swindled out of her earnings and died with $0.70 in the bank.
When Billie died, The New York Times published an obituary on page 15 without even a byline. She had an estate of $1,000, and her best recordings from the 1930s were mostly unavailable. Holiday’s public status grew in the years after her death. In 1961, she was inducted into the Down Beat Hall Of Fame, and then Columbia Records reissued close to 100 of her early records.
In 1972, Diana Ross portrayed Holiday in the movie Lady Sings the Blues, which was nominated for an Oscar and even won a Golden Globe. Holiday was nominated for 23 posthumous Grammy awards. That in itself is something amazing. Throughout her life, she received awards, from Esquire Magazine, for example. She was also inducted into the Grammy Hall of Fame, Ertegun Jazz Hall of Fame, Rock and Roll Hall of Fame, and the ASCAP Jazz Wall of Fame.
In 1985, Baltimore, Maryland, put up a statue of Holiday that was only completed in 1993. In as recently as 2019, Chirlane McCray announced that New York City would be building a statue honoring Holiday near Queens Borough Hall. Then on June 25, 2019, The New York Times Magazine listed Holiday as one of the hundreds of artists whose material was destroyed in the 2008 Universal fire.
In the 61 years since her death, Holiday has been analyzed and memorialized. She’s been the subject of essays and poems alike. Biographers try to make sense of her life, and jazz singers even try to take a stab at her work. Others have tried to emulate her by sticking a gardenia in their hair.
Greenwich Entertainment has the rights to make a new documentary by James Erskine to be called “Billie.” The documentary already premiered at the Telluride Film Festival in 2019. A 2020 release date is in the works. “Billie” features unearthed interviews from those who knew her best, like Charles Mingus, Tony Bennett, Sylvia Syms, and Count Basie, to name a few.
There are also going to be performances that have been retouched and made into color. It will help paint the somewhat blurry picture of a breathtaking talent whose song “Strange Fruit” exposed the sad realities of black life in America. The documentary tells her story through one of her biggest fans, Linda Lipnack Kuehl, who aimed to write a biography of her in 1971.
Taking eight years, Linda tracked down and recorded more than 200 hours of interviews with the people that knew Holiday well. Her book was never finished, though, and the tapes were never heard, until now. “Documenting the life of an icon is a daunting task, but James rose to the occasion with a mesmerizing tribute that captures the talent and torment of the most influential jazz singer of all time,” Greenwich Entertainment’s Andy Bohn said.
“Audiences will swoon at the performance footage and be riveted by the intimate revelations in these previously unheard interviews.” Considering that this film will take personal accounts of those who knew her best, this is sure to be an exciting addition to the biography of the legend that is Billie Holiday.