It is a clear, fresh New York night in March 1939. You're on a date and you've decided to investigate a new club in a former speakeasy on West 4th Street: Cafe Society, which calls itself "The Wrong Place for the Right People". Even if you don't get the gag on the way in – the doormen wear tattered clothes – then the penny drops when you enter the L-shaped, 200-capacity basem*nt and see the satirical murals spoofing Manhattan's high-society swells. Unusually for a New York nightclub, black patrons are not just welcomed but privileged with the best seats in the house.
You've heard the buzz about the resident singer, a 23-year-old black woman called Billie Holiday who made her name up in Harlem with Count Basie's band. She has golden-brown, almost Polynesian skin, a ripe figure and a single gardenia in her hair. She has a way of owning the room, but she's not flashy. Her voice is plump and pleasure-seeking, prodding and caressing a song until it yields more delights than its author had intended, bringing a spark of vivacity and a measure of cool to even the hokier material.
And then it happens. The house lights go down, leaving Holiday illuminated by the hard, white beam of a single spotlight.
She begins her final number.
"Southern trees bear a strange fruit." This, you think, isn't your usual lovey-dovey stuff. "Blood on the leaves and blood at the root." What is this? "Black bodies swinging in the Southern breeze." Lynching? It's a song about lynching? The chatter from the tables dries up. Every eye in the room is on the singer, every ear on the song. After the last word – a long, abruptly severed cry of "crop" – the whole room snaps to black. When the house lights go up, she's gone.
Do you applaud, awed by the courage and intensity of the performance, stunned by the grisly poetry of the lyrics, sensing history moving through the room? Or do you shift awkwardly in your seat, shudder at the strange vibrations in the air, and think to yourself: call this entertainment?
This is the question that will throb at the heart of the vexed relationship between politics and pop for decades to come, and this is the first time it has demanded to be asked.
Written by a Jewish communist called Abel Meeropol, Strange Fruit was not by any means the first protest song, but it was the first to shoulder an explicit political message into the arena of entertainment. Unlike the robust workers' anthems of the union movement, it did not stir the blood; it chilled it. "That is about the ugliest song I have ever heard," Nina Simone would later marvel. "Ugly in the sense that it is violent and tears at the guts of what white people have done to my people in this country." For all these reasons, it was something entirely new. Up to this point, protest songs functioned as propaganda, but Strange Fruit proved they could be art.
It is a song so good that dozens of singers have since tried to put their stamp on it, and Holiday's performance is so strong that none of them have come close to outclassing her – in 1999, Time magazine named her first studio version the "song of the century".
Although lynching was already on the decline by the time of Strange Fruit – the grotesque photograph of a double hanging which moved Meeropol to pick up his pen had been taken in Indiana in 1930 – it remained the most vivid symbol of American racism, a stand-in for all the more subtle forms of discrimination affecting the black population. Perhaps only the visceral horror that lynching inspired gave Meeropol the necessary conviction to write a song with no precedent, one that required a new songwriting vocabulary.
Meeropol, who taught at a high school in the Bronx and churned out reams of topical songs, poems and plays under the gentle alias Lewis Allan, published a poem under the title Bitter Fruit in the union-run New York Teacher magazine in 1937. The later name change was inspired. "Bitter" is too baldly judgmental. "Strange", however, evokes a haunting sense of something out of joint. It puts the listener in the shoes of a curious observer spying the hanging shapes from afar and moving closer towards a sickening realisation.
Meeropol worked out a tune and Strange Fruit quickly became a fixture at leftwing gatherings during 1938, sung by his wife and various friends. It even made it to Madison Square Garden, via black singer Laura Duncan. In the crowd was one Robert Gordon, who had recently taken on a job at Cafe Society, directing the headlining show by Billie Holiday. The club was the brainchild of New Jersey shoe salesman Barney Josephson: a pithy antidote to the snooty, often racist elitism of other New York nightspots. Opening the night before New Year's Eve 1938, it owed much of its instant success to Holiday.
In her 23 years, Holiday had already seen plenty, although her notoriously unreliable autobiography Lady Sings the Blues obscures as much as it reveals. Born in Philadelphia, she spent some time running errands in a Baltimore whor*house, "just about the only place where black and white folks could meet in any natural way", where she first discovered jazz. After she accused a neighbour of attempting to rape her, the 10-year-old Holiday, an incorrigible truant, was sent to a Catholic reform school until her mother secured her release. Moving with her mother to New York, she worked in another brothel, this time doing more than errands, and was jailed for solicitation. Upon her release she began singing in Harlem jazz clubs, where she caught the eye of producer John Hammond, who made her one of the swing era's hottest stars.
Meeropol played Josephson his song and asked if he could bring it to Holiday. The singer later insisted she fell in love with it right away. Meeropol remembered it differently, believing that she performed it only as a favour to Josephson and Gordon: "To be perfectly frank, I don't think she felt comfortable with the song."
Arthur Herzog, one of Holiday's regular songwriters, claimed that arranger Danny Mendelsohn rewrote Meeropol's tune, which he uncharitably dubbed "something or other alleged to be music", which might have made the difference to Holiday.
Either way, Holiday road-tested the song at a party in Harlem and received what would become a familiar response: shocked silence followed by a roar of approval. Meeropol was there the night she debuted it at Cafe Society. "She gave a startling, most dramatic and effective interpretation which could jolt an audience out of its complacency anywhere," he marvelled. "This was exactly what I wanted the song to do and why I wrote it."
Josephson, a natural showman, knew there was no point slipping Strange Fruit into the body of the set and pretending it was just another song. He drew up some rules: first, Holiday would close all three of her nightly sets with it; second, the waiters would halt all service beforehand; third, the whole room would be in darkness but for a sharp, bright spotlight on Holiday's face; fourth, there would be no encore. "People had to remember Strange Fruit, get their insides burned by it," he explained.
It was not, by any stretch, a song for every occasion. It infected the air in the room, cut conversation stone dead, left drinks untouched, cigarettes unlit. Customers either clapped till their hands were sore, or walked out in disgust. Back then, before her life took a darker turn, Holiday was able to leave the song, and its politics, at the door on the way out. When Frankie Newton would hold forth on Marcus Garvey's black nationalism or Stalin's five-year plan, she would snap, "I don't want to fill my head with any of that sh*t." Holiday's biographer John Chilton suggests that this was not because she wasn't interested but because she felt embarrassed by her lack of education. All that she knew and felt about being black in America, she poured into the song.
Holiday's regular label, Columbia, blanched at the prospect of recording it, so she turned to Commodore Records, a small, leftwing operation based at Milt Gabler's record shop on West 52nd Street. On 20 April 1939, Holiday entered Brunswick's World Broadcasting Studios with Frankie Newton's eight-piece Cafe Society Band and recorded Strange Fruit in one four-hour session. Worried that the song was too short, Gabler asked pianist Sonny White to improvise a suitably stealthy introduction.
On the single, Holiday doesn't open her mouth until 70 seconds in. Like Josephson with his spotlight, the musicians use that time to set the scene, drawing the listener in as if to a ghost story. Newton's muted trumpet line hovers in the air like marsh gas; White's minor piano chords walk the listener towards the fateful spot; then, at last, there's Holiday. Others might have overplayed the irony or punched home the moral judgment too forcefully, but she sings it as though her responsibility is simply to document the song's eerie tableau; to bear witness. Her voice moves softly through the dark, closing in on the swinging bodies like a camera lens coming into focus. In doing so, she perfects the song, narrowing the sarcasm of "gallant South" to a fine point and cooling the temperature of the most overheated image: "the stench of burning flesh". She is charismatic but not ostentatious, curling the words just so. Her gifts to the song are vulnerability, understatement and immediacy: the listener is right there, at the base of the tree. Look, she is saying. Just look.
Released three months later, it became not just a hit but a cause celebre. Campaigners for an anti-lynching law posted copies to congressmen. The New York Post's Samuel Grafton called it "a fantastically perfect work of art, one which reversed the usual relationship between a black entertainer and her white audience: 'I have been entertaining you,' she seems to say, 'now you just listen to me.' If the anger of the exploited ever mounts high enough in the South, it now has its Marseillaise."
Holiday quit Cafe Society in August 1939, but she took Strange Fruit with her and carried it like an unexploded bomb. In Washington DC, a local newspaper wondered whether it might actually provoke a new wave of lynchings. At New York's Birdland, the promoter confiscated customers' cigarettes, lest their firefly glow distract from the spotlight's intensity. When some promoters ordered her not to sing it, Holiday added a clause to her contract guaranteeing her the option. Not that she always exercised that right. "I only do it for people who might understand and appreciate it," she told radio DJ Daddy-O Daylie. "This is not a 'June-Moon-Croon-Tune'."
Yet Holiday could no more detach herself from it than if the lyrics had been tattooed on her skin. Strange Fruit would haunt Holiday for the rest of her life. Some fans, including her former producer John Hammond, blamed it for robbing her of her lightness. Others pointed out that her burgeoning heroin habit did that job.
So did the persistent racism which poisoned her life just as it poisoned the life of every black American. In 1944, a naval officer called her a nigg*r and, her eyes hot with tears, she smashed a beer bottle against a table and lunged at him with the serrated glass. A little while later, a friend spotted her wandering down 52nd Street and called out, "How are you doing, Lady Day?" Her reply was viciously blunt: "Well, you know, I'm still a nigg*r." No wonder she clutched the song tightly to her breast, as a shield and a weapon, too.
Holiday discovered heroin in the early 40s, an addiction that eventually earned her a year-long prison term in 1947. Ten days after her release, she performed a comeback show at New York's Carnegie Hall.
According to Lady Sings the Blues, she accidentally pierced her scalp with a hatpin and sang with blood trickling down her face.
There could be only one contender for the closing number. "By the time I started on Strange Fruit," she wrote, "between the sweat and blood, I was a mess." Time called the performance "throat-tightening".
During the 50s, she performed it less often and, when she did, it could be agonising to watch. Her relationship with it became almost masoch*stic. The worse her mood, the more likely she was to add it to the set, yet it pained her every time, especially when it prompted walkouts by racist audience members.
By the latter half of the decade, her body was wasted, her voice weathered down to a hoarse rasp, and Strange Fruit was the only song that seemed to dignify her suffering, wrapping her own decline in a wider American tragedy. Writing about her final years in his definitive book Strange Fruit: the Biography of a Song, David Margolick says: "she had grown oddly, sadly suited to capture the full grotesqueness of the song. Now, she not only sang of bulging eyes and twisted mouths. She embodied them." It was as if the song, having lived inside her for so long, had finally warped its host.
Extracted from 33 Revolutions Per Minute by Dorian Lynskey, published by Faber & Faber Ltd on 3 March at £17.99. To order a copy for £13.59 with free UK p&p go to guardian.co.uk/bookshop or call 0330 333 6846
