There are few moments more perfect than walking into a dimly lit old bar late at night and hearing a Billie Holiday song, either on the jukebox or being covered by the four-piece in the corner. “These Foolish Things” is practically custom made for sliding onto a stool and ordering an Old Fashioned as you prop your elbows up on the bar and think about lost loves and life’s regrets. Her discography is not composed entirely of anthems for the lonely, but few American artists seem to have captured the melancholy of 2am quite like the woman who would become known as Lady Day. And for much of her career, her unique voice could be heard in one of the many clubs that used to line Manhattan’s 52nd Street, a stretch of the city that became known as Swing Street.
Confirmed details about Holiday’s early life are scant. She was born Eleanora Fagan in Philadelphia and raised in Baltimore, but her father left his family and her mother worked such long hours that Holiday was usually left in the care of her mother’s half-sister, Eva Miller, who herself worked so much that she in turn left young Holiday in the care of her own mother-in-law. Records from this era are sketchy, and Holiday’s own autobiography is vague and riddled with inconsistencies (it was, in fact, written by a man named William Dufty, and when questioned about some seeming errors in it, Holiday once famously shrugged and replied “I ain’t never read that book.”)
She was in and out of a reform school called House of the Good Shepherd, first when she was caught skipping school and a second time after a neighbor attempted to rape her and the police needed to keep her somewhere with more protection than her frequently empty home. She worked as an errand girl in a brothel, and it was there that she first heard the music of Louis Armstrong, the artist she credits as having the most profound influence on her eventual drive to become a performer. In 1929, Holiday followed her mother to Harlem, where both of them found work in a brothel. Holiday was thirteen at the time. When the house was raided by police, she found herself imprisoned in the workhouse on Blackwell’s Island, later renamed Roosevelt Island.
When she was released in October of 1929, she decided she had had enough of being Eleanora Fagan. She sought work as a singer, taking the stage name Billie from her favorite actress, Billie Dove, and the last name Holiday from musician Clarence Holiday, the most likely candidate for being her father. She teamed up with neighbor and aspiring saxophonist Kenneth Hollan and began knocking on club doors. It didn’t take long for club owners and talent managers to realize there was something special about this tragic young kid. She soon had a new home, on Swing Street — 133rd Street between Seventh Avenue and Lenox Avenue in Harlem.
Everything I Have Is Yours
By the time Holiday and Hollan were looking for work as musicians, the Harlem Renaissance was in full swing and Swing Street was its artistic heart. An event as momentous as the Renaissance doesn’t have a specific start date — such cultural shifts grow organically, and sometimes it’s only in hindsight that we can see a Movement — but if forced to chose, many people cite 1917, the year in which a white playwright named Ridgely Torrence cast black actors in a series of performances that allowed them to actually be actors — no minstrelry, no blackface. In 1919, poet Claude McKay wrote the angrily political “If We Must Die,” a piece that served as a sort of clarion call to black Americans to stand up and defy the racism and subjugation that had been their lot in American life for so long.
In the final days of the 1910s, Harlem experienced a cultural, artistic, and intellectual awakening — all set to the sound of a new piano music called the Harlem Stride style. As jazz became more acceptable — it had previously been regarded as something a bit low class and “Southern,” not really the stuff for more sophisticated urbanites — clubs began to open to showcase the new sound. With the onset of Prohibition, many of the Harlem jazz clubs — Tillie’s Chicken Shack, Pod’s and Jerry’s, the Rhythm Club, the famous LGBT friendly Harry Hansberry’s Clam House — became some of New York’s most famous speakeasies.
White patrons, fancying themselves adventurous, even began making the trip up to Harlem to see this once in a lifetime community of musicians that included, people like Louis Armstrong, Duke Ellington, Fats Waller, and a guy named Buck Clayton, who eventually moved to Shanghai, where he partnered with a Chinese musician named Li Jinhui, resulting in the birth of “Shanghai Jazz,” an incredible melding of traditional Chinese music with modern American jazz, condemned by the government as pornographic (they branded it “yellow music”) and embraced by the masses to such a degree that, despite the hand-wringing on the part of moral watchdogs, it became the sound of Chinese pop music during the 1930s and 1940s.
Back in Harlem, the influx of white patrons was good and bad. Good because it exposed whites to black culture — not just the music, but also to the social and political defiance that was growing. Good because it resulted in integrated streets. Bad because those streets sometimes integrated at the expense of black locals. Bad because some of the clubs, including Harlem’s famous Cotton Club, opened specifically to showcase black talent for white-only audiences.
It was in this dynamic and tumultuous atmosphere that Holiday found herself performing. Her reputation grew quickly, and in 1933 producer John Hammond heard her sing for the first time. Later that same year, he arranged for her first recording, backed by Benny Goodman and resulting in her first hit, “Riffin’ the Scotch.” Hammond — and most of America — had never heard anyone sing like Holiday. Her voice is still today instantly recognizable. There’s something about it, something to do with smoke and shadow and sex; something that seems melancholy even when the words and melody are happy; something a little slurred, a little muddled, the exact voice you need late at night.
Hammond paired her with an increasingly impressive array of musicians and bandleaders both black and white, including Teddy Wilson, Artie Shaw, and Count Basie, who was at the time famously in a musical duel with Chick Webb, whose lead vocalist was Ella Fitzgerald. Holiday’s working relationship with Basie and his band was tense. They claimed she was temperamental, unprofessional, and difficult. She claimed they were cheap, and that they demanded of her artistic changes that undermined the very reason so many people were coming to see her. In the end, the differences were irreconcilable, and Billie left the band.
By the end of the 1930s, Swing Street was gone. The Depression, the end of Prohibition, the rise of organized crime, and the brutal suppression of demonstrations that became the Harlem Riot of 1935 kept patrons away. By then, though, Billie Holiday was a star, and Hammond booked her at a new place downtown, in New York’s Bohemian Greenwich Village neighborhood, called Café Society.
There was a night in 1939, at Greenwich Village’s Café Society — the first nightclub in Manhattan to become racially integrated — that Billie was scheduled to perform. The club was started in 1938 by a New Jersey shoe salesman named Barney Josephson, and from the get-go he intended it as a thumb to the nose of high-falutin’ society. The very name was chosen as a joke, a satirical reference to writer and socialite Clare Boothe Luce’s praise of sophisticated “café society.” Josephson referred to his club as “the wrong place for the Right people” — the word “Right” being specifically capitalized as a reference to the conservatives he thought throttled American culture.
Popular nightclubs had a long history of booking black talent but only allowing white clientele. Josephson’s club was integrated though, welcoming black as well as white patrons and treating both equally. The list of performers who worked the stage at Café Society is staggering. Among the club’s star performers was Billie Holiday, who took the stage that night in 1939 and slinked through an otherwise usual set. Until she got to the last song, one she’d not performed before. Audience members were thrown for a loop. All wait service stopped. All the lights but one were shut off, a spotlight on Billie’s face, her eyes closed. In that silent darkness, Lady Day launched into the song, “Strange Fruit.”
The song was written as a poem by a teacher named Abel Meeropol, who was moved to pen it after seeing a photo taken by Lawrence Beitler in 1930 of the lynching of two black men, Thomas Shipp and Abram Smith. Originally published in a teaching trade journal, Meeropol searched unsuccessfully for a partner who could set the poem to music. Eventually, he did it himself, performing “Strange Fruit” with vocalist Laura Duncan. Someone at Café Society, either Josephson himself or show director Robert Gordon, heard it and convinced Holiday to perform it at the club. It is a chilling song, subverting the classic image of trees laden with fruit with the lynching of blacks. Although Holiday was initially nervous about reprisals for such a famous singer performing such a powerful and controversial song, it was so well received that it became a regular part of her shows at Café Society. When it came to recording it, however, producers were wary. After Columbia, the label to which Holiday was signed, refused to let her record the song, she turned to her producer John Hammond, who also balked. In the end, Holiday took the song to Milt Gabler’s avant-garde Commodore label, where she was finally able to record “Strange Fruit.”
Café Society continued challenging the establishment, breaking down barriers, and fostering incredible musical talent until the club came under intense, sustained harassment from the House Un-American Activities Committee (the Congressional mob charged with ferreting out Communist threats, usually at the expense of any sense of free speech or Constitutional rights). After Barney Josephson’s brother Leon was called to testify before the committee and refused, a propaganda campaign was waged against Café Society by an all too compliant press. Customers shied away, and in 1947 Josephson had no alternative but to close it down.
I Got a Right to Sing the Blues
When social upheaval and the end of Prohibition conspired to shutter many of the famous nightclubs on 133rd Street, jazz proved it could adapt and survive. It found a new home in the cafés and nightclubs of Greenwich Village, and it found a new Swing Street on 52nd between Fifth Avenue and Seventh Avenue. New clubs like 3 Deuces, The Onyx, and Club Carousel kept the Harlem musical Renaissance alive, even if it wasn’t in Harlem anymore (the biggest club in Harlem at that time was Minton’s, popular because the owner was more than happy to indulge musicians with free food and drink), and the pioneers of the 1920s slowly turned the new stages over to the next generation of jazz legends: Miles Davis, Charlie Parker, Thelonious Monk. The big band sound gave way to bebop. But Lady day remained. In 1939, a young Italian-American crooner named Frank Sinatra — born the same year as Holiday — saw her perform at the Uptown House. He was entranced (and maybe a bit smitten). “Standing under a spotlight in a 52nd Street jazz spot, I was dazzled by her soft, breathtaking beauty.”
Sinatra undoubtedly learned lessons from Holiday, things like how to use emotion and how to turn a song into a story. He also became something of an activist, fighting against segregation in nightclubs. Frank’s own home away from home, Jilly’s Saloon, opened on 52nd Street in the waning days of its time as Swing Street. Sinatra later said of Billie Holiday, “Lady Day is unquestionably the most important influence on American popular music in the last 20 years. With a few exceptions, every major pop singer in the United States during her generation has been touched in some way by her genius.” Throughout the 1940s, her popularity continued to rise. Her best known and biggest hits, songs like “God Bless the Child” and “Lover Man,” were from this era. It seemed there was really no stopping her. And then in 1947, it all started to fall apart.
Though often known of by the people with whom she worked, Holiday’s addiction to heroin became public knowledge when she was arrested in 1947 for possession of narcotics. Many who owed their success to her abandoned Billie in droves. When her own lawyer no-showed the trial, Billie plead guilty. She was sent to Alderson Federal Prison Camp, better known as Camp Cupcake and much later the temporary residence of Martha Stewart. She was released less than a year later and, despite having no new album released in a few years, performed to a sold out house at Carnegie Hall. A similarly successful show on Broadway in 1948 seemed to signal that despite addiction and legal setbacks, Lady Day was still a force to be reckoned with.
But in 1949, she was arrested again on possession charges, this time in San Francisco. Although she recorded another of her most famous songs, “Crazy He Calls Me,” in the wake of this second arrest, her popularity was taking a hit and she began to disappear from American radio. A crippling blow was delivered when New York City used her drug arrests as justification for revoking her Cabaret Card. Implemented in 1940, the New York City Cabaret Card system required artists to be licensed to perform in any establishment that served alcohol. The requirement was finally repealed in 1967, thanks largely to Frank Sinatra’s threat to never perform in New York again. Still today, although the Card was abolished, New York City has a bewildering number of antiquated cabaret laws on the books. But for Holiday at the time, that meant she was effectively banned from just about everywhere in New York that would have otherwise booked her– though she was in good company; Charlie Parker, Chet Baker,Thelonious Monk, and Lenny Bruce all had their cards revoked over the years. Loss of the card forced Billie into smaller and smaller venues, with less and less pay, most of which went to heroin.
Even as the drugs took their toll on her health and her talent, she soldiered on. Her voice was shot critics said, but in the 1950s she toured Europe and began recording for the legendary Verve label — records that proved audiences still wanted her music and that reports of the demise of her voice were exaggerated. In 1956, in support of the release of her (suspect) autobiography, she recorded Lady Sings the Blues, the title that would become synonymous with Billie Holiday. She returned triumphantly to Carnegie Hall that same year. In 1957 she married a guy named Louis McKay, a Mob goon who, liked most of the men Billie ended up with throughout her life, beat her. But he also committed to getting her off heroin, even if it was not for the most altruistic of reasons (he lived better when she was performing, and he planned to franchise her name, opening a chain of Billie Holiday recording studios). By then though, it was just too late. She toured Europe again in 1959 and recorded an album for MGM. It was released posthumously.
As Time Goes By
Sitting in a small Greenwich Village cocktail bar called Orient Express, listening to a playlist compiled by the bartender, who bears an uncanny resemblance to Bennett from the Schwarzenegger film Commando (but with a tweed waistcoat instead of a chainmail one). It’s a mix of Billie Holiday and Tom Waits, and the drink of the evening is called the Mata Hari — bourbon, mezcal, lemon juice, and agave, topped with ginger beer. There’s only a couple of other people in the bar at this hour, and at these times one can drift into the realm of quiet contemplation as one stares at the drink in one’s hands. Dwelling on Billie Holiday’s death in 1959 seems ghoulish, and it seems unfair. We all of us meet the reaper sooner or later, and whatever brought us into his company is ultimately inconsequential when measured against what we did with the life we were granted.
If there’s any testament to Billie Holiday I could deliver myself, it would be there, sitting in a bar late one night not so very far from where Café Society once stood at 1 Sheridan Square. Swing Street is gone, both 133rd and 52nd. The Cotton Club, 3 Deuces, Onyx, all gone. Minton’s remains, reopened recently though not with any legal connection to the original (though they do their best — and their best is pretty good — to honor the spirit of the original, with live jazz and good food). Most of the Greenwich Village clubs that inherited the jazz scene are gone as well. Where Café Society once stood, the first club in New York (one of the first in the whole country), there is now a park, the Sheridan Square Viewing Garden. No plaque commemorates Café Society, though a block away another historic joint, the Stonewall Inn, just got their official designation as a landmark.
Yet despite all the changes, despite the trends that have come and gone, despite the fact that as is its fashion New York City has torn down and rebuilt itself half a dozen times since she first set foot on a Swing Street stage, Billie’s voice remains. It transcends race and era. I’ve heard her songs performed by a regal, aging dame in a Harlem cocktail bar and a twenty-year-old in a rough dive in the mountains along the North Carolina-Tennessee border. You don’t want to wish misfortune and woe on anyone, but when tragedy forges a talent like Billie Holiday, you can tell yourself at least part of it was worth it. Like Sinatra said, she’s one of the most distinctive and important artists modern American music ever produced. “It is Billie Holiday who was, and still remains, the greatest single musical influence on me,” he said. Nothing can tarnish that. Over fifty years later, you can still bow your head at the bar, feel the chills as you let Billie’s voice wash over you, and take one last drink before you bid adieu to the bartender and head out into the night.
This article was originally written in for Alcohol Professor and has been reprinted here with permission.