"Portrait of Billie Holiday and Mister, Downbeat, New York, N.Y., ca. Feb. 1947" by William P. Gottlieb. PD

Few major musical artists faced the obstacles Billie Holiday had to face, but then few can match her musical legacy. She sang, she said, the way Louis Armstrong played his horn, and she sang the only way she knew—with her heart and soul. PKM’s Sharon Hannon chronicles the career of ‘Lady Day’; her fruitful collaborations with Lester “Prez” Young, Teddy Wilson, Count Basie and Artie Shaw; her terrible declines and amazing comebacks–including now, with two new films about her life in heavy rotation. On this, Billie Holiday’s birthday (April 7), we honor a great and lasting artist.

Café Society nightclub, New York City, 1939. The set that night ended with the house lights off, the singer standing center stage behind her mic, lit by a lone spotlight. The club’s waiters had stopped serving and had retreated to the back as the pianist began the slow mournful song from the shadows. After the intro, the 23-year-old singer opened her mouth and began:

“Southern trees bear a strange fruit

Blood on the leaves, and blood at the root

Black bodies swinging in the Southern breeze

Strange fruit hanging from the poplar trees.”

By the time she finished the song, some in the integrated audience had walked out. Of those who stayed, some clapped, while others sat in silent shock. Billie Holiday, one of the most important, and arguably the greatest, jazz singer ever, turned and walked off the stage. As planned, there would be no encore after “Strange Fruit” — people needed to be left thinking about what the words meant.

Whether they liked it or not, “Strange Fruit” would demand the rapt attention of audiences for the remainder of Holiday’s life. But the song, which Time magazine called the “song of the century” 60 years later, and its singer, also attracted the attention of federal agents.

“Strange Fruit”-Billie Holiday, 1939:

Billie Holiday packed a lot of living into her 44 years, not the easy livin’ she sang about so beautifully, but her kind of living — days and nights full of sublime music, friends and lovers of all races and classes, and relentless inner battles against self-defeating life choices. She lived life on her own terms, for better or worse, and never saw herself as a victim. She was a self-taught singer with an innate understanding of music who worked hard to develop her unique improvisational style. Her friends say she was intelligent, generous, funny, could tell a good story, and drank and swore prolifically. She also developed a horrific addiction to heroin, and later alcohol, that haunted her for the last half of her career.

For a quarter of a century, Billie Holiday used her voice to share the thoughts and feelings of a woman born poor and black in early 20th century America. Today we can still listen to her voice and hear it and understand it, although her unique gift remains incredibly difficult to describe.

Holiday at the Downbeat Jazz Club in New York City, 1947 by William P. Gottlieb, Public domain, via Wikimedia Commons

Holiday was born Elenora Fagan Gough on April 7, 1915, in Philadelphia, the child of two unmarried teenagers, Sadie Harris and Clarence Holiday. She was brought up hard in Baltimore where she lived off and on with extended family members, neighbors or her mother, who came and went when she found work elsewhere. Her father, mostly absent from her life, later became a professional guitarist and played in Fletcher Henderson’s Orchestra.

At age nine, Holiday did a one-year stint in reform school, the House of Good Shepherd. She was later raped and molested and dropped out of school in the fifth grade. For a time she had a job running errands in a brothel where she first heard, and studied, records by Bessie Smith and Louis Armstrong — musicians who would influence her profoundly. In 1929, she joined her mother in New York City, where they lived together and worked in a brothel. A few months later when the house was raided, the two women were arrested for prostitution, and Holiday was sent to New York’s Welfare Island, where she spent time in the hospital and the workhouse. She was 15 years old when she got out.

1930s: A Jazz Musician

After her release from the workhouse, to pay the rent, Holiday began going table-to-table in Harlem nightclubs and at house parties singing for tips.

“One day, we were so hungry we could barely breathe,” she told Downbeat magazine in 1939. “I started out the door. It was cold as all hell and I walked from 145th to 133rd down Seventh Avenue, going in every joint trying to find work. Finally, I got so desperate I stopped in the Log Cabin Club, run by Jerry Preston. I told him I wanted a drink. I didn’t have a dime. But I ordered gin (it was my first drink — I didn’t know gin from wine) and gulped it down. I asked Preston for a job … told him I was a dancer. He said to dance. I tried it. He said I stunk. I told him I could sing. He said sing. Over in the corner was an old guy playing a piano. He struck “Travelin’” and I sang. The customers stopped drinking. They turned around and watched. The pianist, Dick Wilson, swung into “Body and Soul.” Jeez, you should have seen those people — all of them started crying. Preston came over, shook his head and said, ‘Kid, you win.’ That’s how I got my start.”

It was in a Harlem nightclub that a 22-year-old jazz enthusiast and future record producer named John Hammond first heard Holiday sing. Hammond was so taken with the young singer, he returned several times to see her. “I heard a singer who was an improvising horn player,” he later said. “That’s how she sounded.”

Holiday concurred: “When I was a little girl, there was a lady on the corner that had a record machine and I could hear Bessie Smith and Louie Armstrong and I always wanted to sing like Louie Armstrong played, I always wanted to sing like an instrument.” By then Elenora Fagen had become “Billie Holiday,” in part to honor her favorite actress, Billie Dove.

Hammond arranged for Holiday to record two tracks backed up by the not-yet-famous Benny Goodman and a group of white musicians. One of those recordings, “Riffin’ the Scotch,” a bit of a novelty song, hit No. 6 on the charts in 1934.

“Riffin’ the Scotch”-Billie Holiday, Benny Goodman & His Orchestra:


She was young, not yet 20, but her talent and potential were undeniable. She began appearing regularly at the Apollo Theater in Harlem and soon appeared in a nine-minute Duke Ellington film, Symphony in Black: A Rhapsody of Negro Life, singing “Saddest Tale.” Hammond signed her to the Brunswick label and that began her fruitful collaboration with pianist/arranger Teddy Wilson and his orchestra that lasted until 1941. Throughout the 1930s, while recording a number of her early classics with Wilson, including “These Foolish Things” and “I Cried For You”, she also recorded for the Columbia/Vocalion labels with an orchestra assembled for her that featured future jazz legends Ben Webster and Lester Young on sax.

Symphony in Black, “Saddest Tale”-Duke Ellington (Billie Holiday appears at 4:40):

On “He’s Funny That Way” and “I’ve Got My Love to Keep Me Warm” from this period, her style was already maturing. Her voice floats around each song’s melody, which she adapted to fit her barely one-octave range, while she moved both behind and ahead of the beat, using subtle inflection to express the emotion behind the lyrics.

“He’s Funny That Way”-Billie Holiday, 1937:

Her 1939 version of “Night and Day,” when compared to Fred Astaire’s 1934 original, illustrates how profoundly she would change the melody and tempo to match her voice. As she admitted later, “When I did “Night and Day” I had never seen that song before in my life. I don’t read music, either. I just walked in, Teddy Wilson played it for me, and I did it.” That Holiday couldn’t read music made her an outlier among the musicians on her sessions. But, as John Szwed, author of Billie Holiday: The Musician and the Myth, told PKM in a recent interview, “It didn’t matter. She was going to improvise anyway. You can see it as a handicap that she didn’t read music, but in her case it was the springboard.”

Of all the musicians she worked with, Young’s smooth melodic lines on the sax were the perfect match for Holiday’s laid back, improvisational style. His playing elevated her performance, and some of her best early recordings, like “Easy Livin’” and “The Man I Love,” all essential parts of the jazz canon, were recorded in the late ’30s with Young. Why did it work so well? “I don’t think I’m singing,” she said. “I feel like I am playing a horn. I try to improvise like Les Young, like Louis Armstrong, or someone else I admire. What comes out is what I feel. I hate straight singing. I have to change a tune to my own way of doing it. That’s all I know.”

“The Man I Love”-Billie Holiday, 1937:

Over time, Holiday and Young developed what trumpeter Wynton Marsalis has called “a true musical kinship.” They became partners in music, friends, soul mates, but never lovers. It was Young, who called everyone, men and women, “lady,” who named her “Lady Day.” She called him “Prez,” as in president, because she thought he was the best. “For my money,” she said. “Lester was the greatest.” He would eventually play tenor sax or clarinet on several dozen sessions with Holiday; only Teddy Wilson played on more.

In 1937, the year her song “Carelessly” hit No. 1 on the charts and she had four other top 10 hits, she was still mostly playing nightclubs in New York. So when the opportunity came to join the Count Basie Orchestra on the road, she jumped at it “to make a little money and see the world,” she said.

I always wanted to sing like Louie Armstrong played, I always wanted to sing like an instrument.

Like most traveling black musicians at the time, Basie’s band stayed in the homes of black families on the road since most hotels wouldn’t accept them, and they ate in black establishments when possible because they couldn’t eat in restaurants that served white people. This network of support from black communities across the country could only shield the musicians a small degree from the pervasive racist taunts and threats they faced on the road, particularly in the south, but the indignities weren’t limited to that region. When the band arrived in Detroit, Holiday was asked to darken her face when she sang so no one could mistake her under the spotlight for a white woman singing with a black band to a black audience. “It’s like they say, there’s no damn business like show business,” she said. “You had to smile to keep from throwing up.”

By leaving Basie and joining Artie Shaw’s Orchestra the following year, Holiday became the first black singer to be featured as the star with an all-white band. But Shaw’s decision to tour through the South made what looked to be a difficult situation even worse when he insisted that Holiday sit onstage with the band throughout the concerts and had his tougher band members strong-arm hotel clerks into giving her a room.

“It’s like they say, there’s no damn business like show business,” she said. “You had to smile to keep from throwing up.”

Still, she found the struggle to get hotel rooms or have a meal exhausting. “Most of the cats in the band were wonderful to me,” she wrote later, “but I got tired of scenes in crummy roadside restaurants over getting served. Some places wouldn’t even let me eat in the kitchen. I got tired of having to make a federal case over breakfast, lunch and dinner.” The stress of the situation came to head in New York City, when they played the Blue Room in Hotel Lincoln and the staff told her she couldn’t ride up to the ballroom with the band. She would have to take the freight elevator.

But when one door closes …

Three weeks after leaving Shaw’s band, Holiday was asked by Barney Josephson, a shoe salesman with a deep appreciation for jazz, to open his new club, Café Society, New York’s first integrated nightclub. Josephson’s plan was to introduce jazz artists to black and white audiences alike, and he understood the attention his club would attract. He advertised it as the “Right Place for the Wrong People.” Holiday sang on opening night, December 31, 1938, and performed there for most of the following year.

“Portrait of Billie Holiday and Mister, Downbeat, New York, N.Y., ca. Feb. 1947” by William P. Gottlieb. PD

She performed “Strange Fruit,” which was written by poet, activist, songwriter Abel Meeropol, each night for several months before she recorded the song. Hammond and Columbia had refused to record it, so it was released on the Commodore label with her own composition, “Fine and Mellow,” as the B-side. The record sold 20,000 copies when it was first released and it continues to sell today. It has been covered more than 60 times, most often after 1990.

During her residency at Café Society, Holiday’s musical interests were changing; she told Hammond she wanted a string section on her next record. This more expensive approach to recording had not been used for other jazz singers at that point and Hammond refused. It wasn’t until 1944, when she switched to the Decca label, that producer Milt Gabler recorded her using an orchestra and more sophisticated arrangements. Her new sound didn’t please a lot of jazz aficionados at the time, but it brought her more popular success. Her first record for Decca, “Lover Man,” was one of the biggest hits in her career.

“Lover Man”-Billie Holiday, 1944:

As her style changed throughout her career, Holiday would rerecord some of her older songs in different ways, making it possible to track her musical evolution by comparing the various versions. “God Bless the Child,” a song she wrote in 1939 with Arthur Herzog, Jr. and first recorded in 1941 with a small combo, eventually sold over a million copies and was No. 3 on Billboard’s top songs that year. After moving to Decca, she recorded it again in 1950, slower and with strings and a chorus. Finally, she recorded a third version in 1956 with a small swinging group, featuring Oscar Peterson, Ray Brown, and Barney Kessel. By then her health was extremely poor and her voice weathered, but there’s a depth to her performance that adds a richness to the song. Likewise, she recorded Duke Ellington’s “(In My) Solitude” three times between 1941 and 1952, and the vulnerability and frailty in the final recording, the pathos in her well-traveled voice, feels as if she’s offering a glimpse of her soul.

“God Bless The Child”-Billie Holiday:

1940s: High and Low

Along with increasing success as a performing artist, the 1940s brought the men, violent and manipulative, a fearsome drug addiction, and an ongoing struggle to make money and avoid federal authorities.

Holiday’s upbringing had made her tough. She swore incessantly, drank prodigiously and smoked marijuana (then legal) heavily. Poet Maya Angelou, who knew Holiday in the early 1950s, said, “She used profanity with the deftness of an ice skater doing a figure 8.” If she sensed someone had insulted her, she wouldn’t hesitate to punch them or hit them in the head with a bottle. As one musician who played with her said, “She had strong appetites — for alcohol, for drugs, for sex with men and women. She was abused but she could fight back and got into many brawls with men who she felt disrespected her. She stood up for herself.” Yet, she also had a lifelong attraction to violent, predatory men who beat her and used her to their advantage.

In September 1941, Holiday married her first husband, Jimmy Monroe. Their relationship was short-lived. They cheated repeatedly on each other. Among her many lovers were Orson Welles, wealthy heiress Louise Crane, and actress Talullah Bankhead. Though they didn’t divorce until 1947, Monroe’s lasting contribution to Holiday’s life seems to have been two-fold: He inspired her song “Don’t Explain” and introduced her to opium, the first step in her descent into a brutal addiction.

“It was during this time that I got hooked,” she said. “But … Jimmy was no more the cause of my doing what I did than my mother was. That goes for any man I ever knew. I was as strong, if not stronger, than any of them. And when it’s that way, you can’t blame anybody but yourself.”

“Don’t Explain”-Billie Holiday, 1945:

While married to Monroe, she began a relationship with trumpeter and drug dealer Joe Guy, who introduced her to heroin. She was soon addicted and began showing up late for shows, refusing to come out of her dressing room, or missing shows altogether. During World War II, she worked the clubs on and around 52nd Street in New York. “I had white gowns and white shoes. And every night they’d bring me the white gardenias and the white junk,” she said.

Yet despite her growing addiction, her career was reaching new heights. Every year from 1944 to 1947, for example, she received Esquire magazine’s Gold or Silver Award for Best Leading Female Vocalist.

Among her many lovers were Orson Welles, wealthy heiress Louise Crane, and actress Talullah Bankhead.

To get through the filming of New Orleans, in which she appeared with her idol Armstrong, she had Guy come to Los Angeles to provide heroin for her. Holiday was making about $1,000 a week from club performances and spending most of it on drugs. Finally, her agent, Joe Glaser, banned Guy from the set. Soon after, she attempted to break her addiction by having herself committed to a sanatorium in New York City. Upon her release she noticed she was being followed by men she pegged as agents from the Federal Bureau of Narcotics.

From New Orleans, with Louis Armstrong, 1946:

Holiday had actually come to the attention of the FBI, the Federal Bureau of Narcotics, and the New York police back in 1939, around the time she first performed at Café Society, according to Jimmy Fletcher, a black agent with the Bureau of Narcotics. In the mid-1940s, Fletcher worked undercover in New York, ingratiating himself into the jazz scene to track who was selling drugs, who was buying them, and who could and should be prosecuted.

The world Holiday knew in the nightclubs of the 1940s was full of mobsters, pimps, hustlers, drug dealers, gamblers, and all categories of other crooks. So it’s not surprising that her long-time agent, a man with connections, Joe Glaser, was one of those men whose motives went far beyond enriching the lives of his clients. With the help of Glaser, Holiday and Guy were arrested on May 16, 1947, in their New York hotel room for drug possession. Glaser had told Fletcher he only wanted to help his client get off drugs, but he also saw to it that she had no legal representation when she went before the judge. She was charged with possession of heroin, didn’t fight the charges and asked to be sent to a hospital. Instead, she was sentenced to a year and a day in a women’s prison in West Virginia, where she had to detox cold turkey.

“In My Solitude”-Billie Holiday:

Nine months later, on March 16, 1948, Holiday was released from prison. She had served her time but faced the lingering punishment of losing her New York cabaret card for the felony. Without that “police card,” she would not be allowed to perform in New York nightclubs for the rest of her life.

It was one of the most legendary, and quickest, comebacks in show biz history. A week after Holiday was released from jail, she performed the first of two legendary sold-out solo concerts at Carnegie Hall, a turning point for popular singers. “There were no concerts for singers at that point,” Szwed says. “Even Frank Sinatra would appear at a movie house, but they didn’t set aside a concert hall. But she started appearing at Carnegie Hall or Town Hall, when she had a second appearance and they still turned away a 1,000 people and had people seated on the stage around her.” But her sudden mass popularity “did seem to be collated with the bad press she was getting,” Szwed acknowledged. Holiday suspected as much. While the Carnegie Hall performances appeared to be a triumph that reintroduced her to the public, she believed many in the audience “came to see me fall on my ass.”

The following month she did five nights on Broadway in a successful show called Holiday on Broadway, followed by several months of nightclub appearances outside of New York, six weeks at the Strand Theatre with Count Basie, a week at the Apollo, and appearances on several television shows. Billie Holiday was back.

A week after Holiday was released from jail, she performed the first of two legendary sold-out solo concerts at Carnegie Hall.

Enter John Levy, a brutal and sadistic man. Holiday’s friend and former lover, tap dancer James “Stump” Cross, described him as “a pimp, a hustling man, an evil-doer.” But Levy had connections with the New York City police department that paved the way for Holiday to sing at his Club Ebony, making it the only licensed club in the city where she could sing. Not long after they met, he became her unofficial manager and romantic partner. Pianist Bobby Tucker, another of her friends, saw it this way: “John Levy was a sadistic pimp and Billie admired pimps. He was physically strong and he would holler and scream at people, and she liked that as well. He was a man who took over.”

The couple’s relationship was extremely volatile — when they fought he beat her mercilessly, and she hit him with bottles and whatever else was at hand. Within months, in January 1949, they were arrested in their hotel room at the Mark Twain Hotel in San Francisco for possession of opium. This time she booked herself into an institution and got drug-free before her case was heard in court. Given some of the suspicious circumstances surrounding the arrest, the case was dismissed.

Carl Van Vechten – Van Vechten Collection at Library of Congress

1950s: Not Done Yet

After her contract with Decca ended in the early 1950s, Holiday began a productive 5-year run with the Clef/Verve label, where she reinvented herself as a torch singer and rerecorded many of her old classics with a small jazz combo. Though she continued to record and release new music until her death, over time the sessions became more wrought. She tried using alcohol to wean herself off heroin, but her declining health was not matched by a decline in alcohol intake. She was late to sessions, if she came at all, but when she was on, she turned in some stunning performances. Songs from the period, like “Autumn in New York” and “Come Rain or Come Shine,” reveal a singer who’s still a master at her craft.

“Autumn in New York”-Billie Holiday, 1952:

Holiday had started to reach out to the public more directly after her 1949 arrest — she made her first appearances on television and began giving more interviews to music and African American magazines, in which she talked openly about her drug use, bad business deals, poor choice of men, time in prison, trouble finding work without a cabaret license in New York, and perhaps most important, her life as a Black woman in the United States. In 1953, she appeared on the ABC reality television series, The Comeback Story, and was interviewed for an article in Tan magazine entitled, “Can a Dope Addict Come Back.” She made her first appearance on The Tonight Show, hosted by Steve Allen, in 1955.

Like all performing artists of the time, Holiday never received royalties for recordings she made before 1944, and the royalties from the few songs she wrote never amounted to much. By the mid-‘50s, she owed money to the IRS and her record companies. To survive, she relied mainly on live performances and any radio work she could get. Her reputation for unreliability limited her opportunities to perform and reduced the amount she could be paid, so she spent much of her time on the road, traveling back and forth across the country playing in Miami and Anchorage, from Las Vegas to Baltimore.

“Come Rain or Come Shine”-Billie Holiday, 1955:

She also had a new man in her life. Levy was gone and now Louis McKay, a man most commonly described as “a hustler,” but who some saw as a stabilizing force in Holiday’s life, became her lover and took over as her manager, thereby controlling her money. He encouraged her to tour Europe for the first time, and in January 1954, McKay, Holiday and her entourage landed in Copenhagen, set to do 40 shows in 30 days and appear on French television. The receptive and appreciative audiences and informed journalists she met on tour reconfirmed the stories she had heard from other American jazz artists who had found greater success in Europe than at home. “These European writers dig more music. They were hip; they had ears,” she wrote. “The stuff they wrote about me in Europe made me feel alive.”

Most of all she appreciated the way European countries treated drug addiction as a medical problem and provided addicts what they needed until they could be safely weaned off drugs. “One day,” she predicted, “America is going to smarten up and do the same thing.”

Frank Sinatra, a singer she greatly admired, told Ebony magazine, “Billie Holiday is the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last 20 years.”

According to her friend William Dufty, the white journalist who coauthored her autobiography, Lady Sings the Blues, it was McKay who came up with the idea in 1955 of selling her autobiography to raise some money. Holiday and Dufty quickly began work on it — she would tell him about her life and he would write it down. After much editing and sanitizing to avoid lawsuits from people Holiday had wanted to mention in the book, Lady Sings the Blues was ready for publication. Then, in February 1956, one month before the book’s release, she was busted again, this time in Philadelphia with McKay, for heroin and cocaine possession. (Two years later, the couple, who had since married, were put on 12-month probation. McKay eventually left her and moved to California.)

Lady Sings the Blues, with a new chapter quickly written by Dufty about her most recent arrest, was released in July 1956 and became an immediate best seller. About the book, Szwed notes, “Her book is pitched in a low key, but it explains how every institution in America had failed her, from public school to the Catholic Church to the music business to jails to hospitals, but she’s not complaining. She’s just saying it. It’s a major condemnation of American society.”

The book was a raw and revealing account of Holiday’s life, although over time a number of people have questioned some details in the book and concluded it can’t be relied upon as the absolute truth. In its defense, Dufty said, “The book merely says what was possible in 1955 for a Black woman with a police record.”

Billie Holiday, on Stars of Jazz, hosted by Bobby Troup, aired August 13, 1956:

Holiday returned to Carnegie Hall for two successful shows in the fall that drew an extremely diverse audience for 1956. “Her audience was much wider than other people’s,” says Szwed. “She drew to her classical people, like Leonard Bernstein, crossed race lines and class lines; there were gay men who were deeply moved by her. She had this enormously broad body of fans that ranged from the daughter of the governor of Massachusetts, a lover who was one of the founders of the Museum of Modern Art, women poets, men singers, actors, some as close friends. It seems to break all the rules of her time and even of our time in some ways. And she got away with it. How bad off could she be if she was moving in that company. That’s the high life.”

The Sound of Jazz, television program, 1957:

In early 1957, she appeared on American TV in a CBS special, The Sound of Jazz, and for one performance she was reunited with Lester Young and teamed with the jazz A-team: Ben Webster, Coleman Hawkins, Gerry Mulligan, Doc Cheatham and Roy Eldridge. Together they performed her composition “Fine and Mellow.” Watching this performance today gives viewers an opportunity to see her interact, non-verbally, with the musicians as they perform. It’s a joy to watch her nod appreciatively, open her eyes wide and smile after each particularly pleasing run of notes.

Holiday returned to Columbia on a one-album deal in 1958 and chose to record with Ray Ellis as arranger — she said she wanted a pretty album, something beautiful. For the album, Lady in Satin, they agreed to only record songs she’d never recorded and to use an orchestra. It was a difficult production, as Szwed describes in Billie Holiday: The Musician and the Myth. She failed to show up for any meetings or rehearsals to go over the songs and arrangements she didn’t know. The recording sessions were scheduled to begin at ten each night, but she never arrived before midnight. Her health was poor and she drank gin from a water pitcher throughout the sessions. She was embarrassed by her singing and didn’t want the musicians to hear the playbacks. When they finished the sessions on the third day, Ellis left in disgust and wanted no part of the remix sessions that followed.

“Somehow, though, she had made it work,” Szwed writes. “She was aging prematurely, she was sick and had to be helped on and off the stage, and she was having trouble reading and remembering the lyrics. There were missed notes, her voice was husky at times, and her vibrato had become much faster. … She counted on the strength of her recitative, the ability to sing out of tempo and not seem lost. Her phrasing was still sensitive to the words, remaking their points of emphasis and shifting the meaning by surprising changes of stress as she sang … her vocal artistry was still there. The musicians were impressed. She was still a star to them.”

Billie Holiday on Art Ford’s Jazz Party, TV program, 1958:

Holiday thought it the best album she ever recorded. Her fans were emphatically divided by the record, but some, including Miles Davis, thought it was a significant piece of work. Davis said at the time, “I’d rather hear her now. She’s become much more mature. Sometimes you can sing words every night for five years, and all of a sudden it dawns on you what the song means.”

Even Ellis, who first heard the record on a test pressing, said, “I was despondent because I loved it. It was so sad. It didn’t matter whether she sang the right note or the wrong note, because she sang twenty thousand wrong notes on that thing. But she poured her heart out. What she ended up doing was a recitation to the music, although I hadn’t realized it at the time.”

That year, Frank Sinatra, a singer she greatly admired, told Ebony magazine, “Billie Holiday is the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last 20 years.”

“I’m a Fool to Want You”-Billie Holday, 1958:

Granada television studio, London, February 1959. Twenty years after first singing the song, she stood alone in a television studio again backed only by a pianist. Wearing a sparkly dress that hung on her thin frame, her voice much diminished, she still retained her inimitable phrasing and its transcending power as she sang the song’s final lines:

“Here is a fruit for the crows to pluck
For the rain to gather
For the wind to suck
For the sun to rot
For the tree to drop
Here is a strange and bitter crop.”

“Strange Fruit”-Billie Holiday on Granada TV, 1959:

Holiday had cirrhosis of the liver and had lost a lot of weight when she returned to London to perform on the television show Chelsea at Night. She sang “I Love You, Porgy,” “Please Don’t Talk About Me,” and her final song, “Strange Fruit.” It was her last television appearance.

On May 31, 1959, Holiday collapsed and ended up in Harlem’s Metropolitan Hospital with liver and heart problems. When a nurse spotted a white powder in her room, she was arrested for heroin possession; interrogated by agents from the Bureau of Narcotics; had her books, flowers, radio, and record player confiscated; finger-printed without her consent; and handcuffed by her ankle to the bed frame. Police women were stationed outside her door.

At the time Holiday was a flat broke. While she was hospitalized, Dufty sold the last article written under her name, “I Needed Heroin to Live,” to Confidential magazine, netting her $750, which she strapped to her leg in her hospital bed.

After 47 days in the hospital, Billie Holiday, then 44 years old, died of pulmonary edema and heart failure caused by cirrhosis of the liver on July 17, just four months after the death of her musical soul mate Lester Young. More than 3,000 people attended her funeral at St. Paul the Apostle Roman Catholic Church in New York City.

Although Holiday and McKay had been estranged for some time before her death, they had not divorced. As she had no will, he inherited her estate.

I asked Preston for a job … told him I was a dancer. He said to dance. I tried it. He said I stunk. I told him I could sing. He said sing. … an old guy playing a piano. He struck “Travelin’” and I sang. The customers stopped drinking. They turned around and watched.

As for her impact on music, Szwed says, “At least through the ’60s, musicians always thought the singers were the least musical. But she muddied the line between singer and musician and whether the audiences felt that way or not, it did affect how people thought about music at that time. The main thing is she’s still a name from that period and no one else is. Today she and Sinatra are the only singers still fully alive to us from over 60 years ago, still attracting biographical interest. And he was deeply influenced by her, by his own admission.”

“I never felt inferior to anybody and I couldn’t learn to act as if I did. That was my trouble. I never got past fifth grade in school. If I had, I might have been brainwashed like a lot of brown-skinned kids. When I was thirteen, I just plain decided one day I wasn’t going to do anything or say anything unless I meant it. Not “please, sir.” Not “thank you, ma’am.” Nothing. Unless I meant it. You have to be poor and black to know how many times you get kicked in the head just for trying to do something as simple as that. But I never gave up trying.”  — Billie Holiday

Legacy and Accolades

Grammy Lifetime Achievement Award, 1987

Rock and Roll Hall of Fame, inducted 2000

Nesuhi Ertugan Jazz Hall of Fame, inducted 2004

National Women’s Hall of Fame, inducted 2011

National Rhythm & Blues Hall of Fame, inducted 2017

Posthumous Grammy awards — 4

“Strange Fruit,” named “Song of the Century” by Time magazine, 1999

“Strange Fruit,” National Recording Registry, 2002

The United States vs. Billie Holiday-trailer: