Billie Holiday
Billie Holiday; drawing by David Levine


In the spring of 1947, Jimmy Fletcher heard from his bosses at the Federal Bureau of Narcotics that it might be a convenient time to visit Billie Holiday at home. Her manager, a former fight-fixer, whoremonger, and running dog in Al Capone’s pack, had offered up the celebrated Negro “torchchanteuse” and notorious dope fiend as grist for Harry Anslinger’s publicity mill.

Anslinger, the bureau’s first and only commissioner, was the public face of America’s war on drugs, and he hustled as hard, if not as well, as his envied rival J. Edgar Hoover. Splashy arrests kept the congressional purse holders mindful of who stood between America’s schoolchildren and the ravening scourge of narcotics. For doers of the commissioner’s bidding, Billie Holiday was “an attractive customer,” a reliable source of repeat business.

Fletcher was a veteran black undercover operative who knew Holiday from long years of going around. It fell to him, and a colleague named Cohen, to bring her in. They rousted Billie out of bed in a Harlem residence hotel, and found nothing they were looking for, either in her rooms or among her belongings. Agent Cohen suggested then that a policewoman be brought in to inspect their suspect’s body cavities. They could look for themselves, Billie allowed, if they’d agree to leave without her if she proved “clean.” Ignoring their demurrals, she stripped bare, straddled the toilet bowl, and urinated. Cohen tried to close the bathroom door. Choosing shamelessness over complicity in her own humiliation, she pushed it back open, “forcing both of them to see her nakedness and her defiance.” She never averted her stony eyes from the faces of her onlookers.

Fletcher knew then that he was in the presence of a thoroughbred—a true-to-the-game “mud-kicker” in the parlance of the streets she came from—who could take life’s worst without a snivel. “She sealed herself closer to me that morning,” he remembered. “She sealed our friendship.”

But fondness couldn’t trump his calling. Within a couple of weeks, Fletcher had managed her arrest in New York, on a flimsy drug charge that cost her a year in a West Virginia prison. But at least he felt badly about it, more than could be said of other men she knew better and who used her as currency to exchange with Fletcher and his like for favors, or their freedom.

The very qualities Jimmy Fletcher saw in her and admired on that occasion were regularly disclosed in the performances that won for Billie Holiday the audiences she turned into cult followers during more than a quarter-century of playing the high-class joints, the low-class joints, and even some of the honky-tonks in America’s cities and bigger towns. In the four and a half decades since her death, “Lady Day,” though venerated in a smaller church, has become almost as much of a cultural icon as Marilyn Monroe, and nearly as written about.

The latest addition, With Billie, authored by the British writer Julia Blackburn, has been assembled from a cache of recorded interviews and documentary scraps left behind by Linda Kuehl, a devotee with a book contract, who spent most of a decade talking to anyone she could find who’d known the singer at any point in her life. Twenty-six years ago, Kuehl plunged out of the window of a Washington hotel room, leaving behind a suicide note and two shoe boxes of “carefully named and numbered” audiotapes, partially transcribed.

These passed through her family’s custody into the hands of a private collector. Lately, they have been culled, “untangled,” rethreaded, and worked by Blackburn into a tapestry of tales told by persons who worked, hung out, and grew up with Billie Holiday. Blackburn does her best to sort out people’s versions of truth with a biographer’s sense of duty to the facts, while drawing inferences with a novelist’s license. Now and then, she may take a step too far into speculating on states of mind, but Blackburn’s way of working her raw material into a narrative gives an impressionistic portrait of her subject which conveys about as much that was true of Billie Holiday as can be had on a printed page.

All accounts of Holiday’s life—including her own—are mostly just stories like these that have gotten themselves certified as history: apart from government records and newspaper reports, goods of casual provenance. Even at the source. “Billie had always invented huge chapters of her life,” Blackburn writes, “telling stories that made emotional sense, even if they bore no relationship to the facts.”

More of the truth of her story was revealed when she sang other people’s songs. “She had a very small voice,” said Bobby Tucker, a pianist who accompanied Holiday during several years of her late prime, “but she could tell a story, that’s what she could do, and she had a thing about how she felt.” He guessed that “thing” he was trying to describe “might be her pain.”


Blackburn casts light on the origins of that pain in Holiday’s shambled childhood. Born in Philadelphia in 1915, raised in Baltimore, her mother’s hometown, the girl Eleanor, of variable surname, lived her first eight years mostly in the care of an uncle-in-law’s mother. Adjudged a chronic truant and unsupervised child, she spent her ninth year in a reformatory.

About a month after her release, she stopped going to school altogether. Raped by a neighbor at eleven, she used to get drunk on corn whiskey and accost men in the street, then run away, taunting and cussing them until one could be provoked into chasing, catching, and beating her. At fourteen, she joined her mother in New York, where they lived in a Harlem brothel. Within several weeks of Eleanor’s arrival, she and her mother were picked up in a police raid.

Facing a judge “notorious for giving harsh sentences [to]…what she called ‘wayward minors,'” too-grown-too-fast Eleanor was found guilty of being a “vagrant and dissipated adult.” She served six months, chiefly among convicted prostitutes, in the city’s workhouse on Welfare Island. When she got out, she “did a little prostitution,” waited tables, and sang for money thrown on barroom floors.

At sixteen, she was “a fat thing with big titties,” who’d worked her way up to singing in a Harlem saloon for two dollars and tips “in the same [common] dress every night.” Around that time, she changed her name to “Billie Holiday,” after the actress Billie Dove and her father, Clarence, a guitarist with Fletcher Henderson’s band.

As soon as she started working in bars, she’d kept the steady company of musicians, drinking, coupling, and smoking weed. “Lady was always part of the band,” the tap dancer and comic James “Stump” Cross later observed. She graduated from the noisome chaos of the street into the irregular rhythms of life as a working musician without any mediating institution but jail in between. She was an unruly ghetto child, a “tackhead” with a transcendent gift.

A dancer who knew her then attested that even as a fleshy kid “in tacky dresses,” Billie “already had something in her voice that struck the public like lightning.” Before she turned twenty, she’d acquired a following among cognoscenti and show people drawn uptown to see her at the Hot Cha Club. Holiday was barely twenty-two when she vaulted out of Clark Monroe’s “downstairs place on 134th Street and Seventh Avenue” onto the road with Count Basie. A year later, she bore the brunt of integrating Artie Shaw’s band on its Southern tour.

At twenty-four, during a nine-week engagement at Café Society, Holiday stirred New York’s left-leaning intellectuals and claimed the notice of a wider world when she introduced “Strange Fruit,” an anti-lynching song thought subversive by official America’s Red-scared, especially Hoover. When it came out in the spring of 1939, her recording of “Strange Fruit” was a fair-sized hit, and eventually sold close to a million copies.

Once she became a star in the early Forties, Blackburn notes, Holiday “gave [money] away as fast as she earnt it.” In her autobiography Billie described the Harlem apartment she shared with her mother as a “combination YMCA, boardinghouse for broke musicians, soup kitchen for anyone with a hard-luck story, community center, and after-hours joint where a couple of bucks would get you a shot of whiskey and the most fabulous fried chicken breakfast, lunch or dinner anywhere in town.”

Among its clientele was Babs Gonzales, an avant-garde scat singer who never did much business. “Any musician could go there and eat and get money for the subway or to go to the movies,” he recalled, “and if she was out of town she would leave money with mother.” “[Billie] always respected musicians,” one of her bass players told Linda Kuehl. “She was always trying to keep a hard front… [but] she was generous to a fault.”

“She romanced everybody in the band, so far as friendship was concerned,” fellow Basieite Harry “Sweets” Edison remembered. “Because she was your friend.” Billie was ever one of the boys, even when she could afford to wrap herself in $17,000 worth of blue mink. “No matter how much of a star she was,” a childhood friend reminisced, she never had an entourage, preferring the fellowship of players and the caterers of her bad habits. “She’d go down in the slums, in the bars, and she’d have her mink… and she’d just throw it on the chair and sit down with a little booze and buy for everyone else. And say ‘bitch’ and ‘motherfucker’…and…tell jokes in different voices….”


And always, “behind the pimps and the parasites,” “Stump” Cross remarked, “were these virtuoso piano players that loved her secretly.” She had an affinity for piano players, and a knack for picking them. One said he loved to play for her because “you could go anywhere and she’d be there….” “[Billie] could find a groove wherever you put it. Wherever it was, she could float on top of it.” In 1939, she’d told an interviewer, “I don’t think I’m singing…I feel like I’m playing a horn.”

Holiday once advised an awestruck, twenty-year-old pianist who was playing with her for the first time, “You don’t have to worry about my music. If you can play ‘The Man I Love,’ you can play for me….” Her accompanists enjoyed their working conditions, because even though she “didn’t know one note of music,” Billie was every bit the musician they were.

If she favored piano players as road partners and confidants, she mostly chose lovers from other sections of the band, and husbands of the outlaw caste. The first of these was Jimmy Monroe, “a suave sort of cat…a very fair-complexioned, nice-looking, frail type,” a hustler lately returned to Harlem from several years in Paris. He was married to an actress when Billie met him, and reputedly pimping whores on the side. It’s said he introduced Billie to smoking opium and sniffing cocaine. She broke with her mother over Monroe, which soon became a source of regret, since the marriage lasted less than a year. Monroe left for California with “most of Billie’s money,” which he apparently used to “set himself up with a stable of women there.” In 1942, he was arrested for drug smuggling, and sentenced to a year in prison. She paid for his lawyers, but divorced him as soon as he got out.

By then, Holiday was twenty-eight and the toast of New York, where she was celebrated as the “Queen of 52nd Street.” She’d moved on to a dope-fiend bass player named John Simmons, and had begun to recoil at the approaches of strangers who presumed to think that because they knew something of her they knew who she was. “She got to the point,” Simmons said, “where she thought everyone was trying to use her and so she said ‘Fuck the world!'” She’d decided by then, Blackburn says, “that nothing really changed, no matter how successful she became.”

In 1947, at the height of her career, Billie was “a sometimes addict” being hounded cross-country by federal narcotics police. She was making about $50,000 a year, and keeping next to none of it. At the time, she was living with another “hop head,” the trumpeter Joe Guy. She and Guy eluded an attempt to arrest them in Philadelphia, but a couple of weeks later, in New York, a small amount of his heroin was found by law enforcers outside the window of their room at the Grampion Hotel.

Holiday wasn’t present and wasn’t charged, but was held anyway, as a material witness. Under questioning, she took responsibility for the drugs that had been found in their hastily vacated Philadelphia hotel room, thus sparing Guy. Disdaining a lawyer—on advice of the same manager who’d sold her out to the Bureau of Narcotics—she was in a courtroom within hours to enter a guilty plea, asking only that the judge send her to a hospital for treatment.

In fact, Holiday was never the hope-to-die heroin addict she was made out to be. Cannabis and alcohol were truly her drugs of choice. “Billie’s heroin addiction was never particularly dramatic,” Blackburn suggests. “Few people ever saw her injecting and it seems that whenever she stopped using heroin, …she always managed to avoid the usual traumas of withdrawal….” Nevertheless, she was sentenced to a year and a day in a federal reformatory for women. Joe Guy was tried and acquitted. Her career was never the same, or her state of mind. “A lot of people go to jail,” Bobby Tucker told Linda Kuehl, “but Billie took it personally.”

When she came out of prison in 1948, she felt herself the target of any crimebuster who needed to look busy in public. Once she became a federal parolee, the local authorities revoked her license to work any place in New York City where alcohol was sold. In the center of her commercial universe, she was only allowed to sing in theaters and concert halls and so was forced into full-time itinerancy to make a steady income.


That year, she hooked up with John Levy, an “Italian-looking,” yellow Lincoln Continental–driving, opium-addicted, self-described “half-Negro, half Jew” from Chicago. One of her piano players characterized Levy as a “sadistic pimp,” then added, “and Billie admired pimps.” Levy became her “manager,” and kept her humping, kept her high, and kept her broke, since he was handling all her business and he was the one her employers paid. “If she asked him for fifty dollars,” another of her piano players recalled, “he’d say, ‘Don’t ask for money in public,’ and he’d knock her down literally, with his fist in her face, in the stomach, anywhere.”

Four days into 1949, federal agents broke in on the couple in their San Francisco hotel room, catching Billie in the act of trying to flush away the opium and pipe John Levy had put in her hands. Clad in white silk pajamas, Levy, an inveterate police informer, bargained, while she “sat there… sober and clear-headed…very quiet and passive.” He avoided prosecution and fled California, leaving Holiday in San Francisco to finish her engagement there, and face her trouble alone.

“We could have indicted Levy if we had wanted to,” the district attorney there reportedly told her lawyer, “but Billie Holiday is the name and we want to get some publicity.” She appeared for trial, two months later, with an eye blackened by Levy, and “no trace of drugs…in her system.” Holiday’s lawyer contended that Levy had conspired with a federal agent in her arrest, and produced a photograph of the two men chatting amiably at a table in the local night spot where she was working at the time of the raid. “[Levy] was turning Billie over,” he suggested. “[He] wanted to get rid of her. He had cleaned her out of money….”

In court, she “act[ed] dumb,” Blackburn reports, and “simply said that John Levy was her man and she loved him so.” She beat the case. A month and a half later, when she was back in town, working at the same place, she was arrested again on the charge for which she’d already been acquitted. “The police and other government agents were always at her shows,” Blackburn says, “…heckling, threatening, raiding her dressing room, making embarrassing enquiries at her hotel and spreading rumours at the clubs where she was booked to sing.”

“I came out [of jail] expecting to be allowed to go to work and to start with a clean slate,” Holiday told Ebony magazine. “But the police have been particularly vindictive, hounding… and harassing me…. They have allowed me no peace….” According to Bobby Tucker,

Billie’s sense of insecurity was worse than ever. She was amazed that people hadn’t forgotten her, but she was afraid they had only come to see what a woman prisoner looked like.

No matter her states of mind or being, Billie stayed out on the road, grinding away. John Levy once told Carl Drinkard, Holiday’s piano player du jour, “You gotta keep your foot up them bitches…otherwise they get lazy on you….”

“Throughout the 1950s,” Blackburn writes, “Billie was…on the move more or less all the time. Three weeks in San Francisco, one week in Los Angeles, back to New York for a single performance….” She was home for only four months of 1950 and 1951. John Levy had bought with her money a house among those of the other stars of jazz who’d settled in St. Albans, Queens, and held it in his name. He wasn’t there much when she was, since he was busy gambling, tending his night club, juggling “property deals and at least two other women….” They were no longer together when Levy died of a brain hemorrhage late in 1956. Upon hearing of his death, Billie declared it “the best Christmas present I ever got.” By then, she’d moved on to her terminal husband, Louis McKay. He was “the real true man she always dreamed of,” Carl Drinkard believed. “He could knock her unconscious with a single blow….”

“For Billie,” the “other” John Levy—this one a bassist—concluded, “her manager must be her man or her husband.” Louis McKay became her man and manager in 1951. They were married six years later. Some said McKay was a bit better than preceding others, but he was nothing like the helpmeet Billy Dee Williams portrayed in the movie version of Billie’s “autobiography,” Lady Sings the Blues.

Blackburn reproduces “a slightly shortened version” of the transcription of a telephone conversation that was secretly recorded early in 1958. The participants were Louis McKay and Maely Dufty, the wife of Billie’s ghostwriter Bill, and herself a manager of jazz musicians. McKay was just back in town, and looking for his wife. Apparently, she’d misspent some money he gave her. He was ranting, and his interlocutor was goading him on under the guise of calming him down. “You know I got the wire,” he fumed, at one point in their exchange.

I know what this woman done…. Fuck the seven hundred dollars…. I want some of her ass this morning for playing me cheap. If I got a whore, I get some money from her or I don’t have nothing to do with the bitch….

Basing her account on Holiday’s accompanist, Blackburn has Billie wondering ruefully why she’d known

so many men…who were good and kind and gentle…but instead… had been drawn irresistibly to the hustlers and the pimps; she had chosen to be cheated and beaten and humiliated, and shared with other women and discarded when she was no longer useful.

To Carl Drinkard the reason seemed clear enough. “She’d grown up in that pimp-whore environment,” he said, “[and] felt and believed that if a woman was making money, the man should have it….” If she hadn’t been able to sing, Holiday would likely have been whoring, or thieving, or jailing for most of a short life, like thousands of other hard-knocked and tenderhearted females who came from the same places she did, and never got out. However far she got beyond the low places she was bred to, Billie could never view life from any other outlook than the one she’d acquired when higher ground seemed unreachable.

But for all the hard men she submitted herself to, the softer men with whom she engaged in a “little light housekeeping,” and numberless others she merely laid down with, her truest love was never her lover. The most important of Holiday’s relationships was the one she had with Lester Young, a player of the tenor saxophone who was among the twentieth century’s great masters. They met in New York in 1936, where he lodged for a time with Holiday and her mother. They worked and recorded together regularly during the late Thirties.

Young was an eccentric: idiosyncratic and bohemian, down to his dress and bearing. A colleague, the pianist Bobby Scott, described his walk as having “something Asiatic about it, a reticence to barge in. It was in keeping with the side-door quality of his nature.” But, as with the tale-telling about Holiday’s addictions, legends about Young’s peculiarities have ripened into myth, and masked such of his authentic characteristics as discipline, wit, intelligence, and perceptiveness. Fiercely private, inclined to melancholy, his sensibilities, like Billie’s, were easily abraded by contact with the world.

There was no one of whom she ever spoke more highly, or fondly, or to whom she was more loyal, or liked as much. Blackburn characterizes them as being “like a brother and sister who shared many character traits.” Claire Lievenson, a neighborhood pharmacist’s wife who befriended Billie in the mid-Thirties, remembered that “when they saw each other they wouldn’t kiss, but their faces would just light up.” Holiday used to call Lester Young “the greatest motherfucker she ever met.” Blackburn quotes Jimmy Rowles, a pianist who’d played with both Young and Holiday over the years, describing what it had been like between them whenever “they’d bump into each other.”

Lester would say, “How are you, Miss Lady Day? Lady Day?” Puffing out his pale cheeks and bobbing up and down in a long dark coat, a milk glass full of old Schenley bond proof whiskey clasped in his hand, and the flat black porkpie hat fixed to his head as if it grew there.

And Billie would say, “Hey, Buppa Baby, you motherfucker!” and they’d be smiling and weaving and touching….

On records, the interplay between her voice and his horn can seem like a private conversation between two halves of a Platonic whole. “Sometimes I would sit down and listen to myself and it would sound like two of the same voices,” Young once said of those recordings. “[He] used to know all the words to all the verses of a song,” Blackburn asserts, “thinking with them as he played.”

Holiday told Bill Dufty, who wrote her autobiography, “Lester sings with his horn. You listen to him, and you can almost hear the words.” She said that when she sang, nobody but Young could “fill up the windows” behind her voice. Their collaboration was a form of intimate congress. In art and life, they moved through each other’s interior spaces with the ease and grace of swans.


With Billie ends with an evocation of Holiday’s three-and-a-half-minute performance of a signature song, “Fine and Mellow,” on a television program called The Sound of Jazz, accompanied by an all-star cast comprised mostly of old friends. Blackburn relies on the accounts of writer Nat Hentoff and a couple of the participants, in setting the scene at rehearsal on the day before the broadcast in early December of 1957. “Even Lester Young had made it,” Blackburn writes, “although he was sitting by himself on a bench and wearing carpet slippers because his feet hurt…looking much older than his forty-eight years.” The trumpeter Doc Cheathem noticed that Young “just kept to himself, sat apart. He was very quiet and sad that day.” By then, he was sick, doing bad, willing himself out of life. He hadn’t used alcohol before he knew Billie; now, a bit more than twenty years later, he was almost finished drinking himself to death.

During the show, when Young’s turn to solo came, the camera moved to his face, and, as Blackburn says, “Lester looks as though he has been crying for weeks, his eyes are so swollen and puffy.” Once, years before, “Stump” Cross had been struck by “the look in his eyes when he played for her…. He’d play his whole soul.” That night, Young’s brief solo was slow and spare, the silences between notes seeming to throb with ache. As he was playing, the camera mostly gazed at Billie gazing at him.

All the meanings her face bespoke can never be known, but it can be said that she bore him a look of unspeakable tenderness. “Sitting in the control room I felt tears,” Nat Hentoff wrote, “and saw tears in the eyes of most of the others there.” Later, when asked about Young by a magazine writer, Billie pledged her allegiance: “Lester’s always been the President to me. He’s my boy.”

Both Lester Young and Billie Holiday died in 1959, within four months of each other. He went first, right on the edge of winter and spring. Back in New York from a last-gasp engagement in Paris, he sat in an armchair by the window of his room at the Alvin Hotel “for half a day and half the night and drank a bottle of vodka and most of a bottle of bourbon. Then he went to bed and died at around 3 a.m….” Billie wanted to sing at his funeral, but his wife “stopped her, saying that she might make a fuss and cause trouble.”

She’d become as famous for her troubles as her singing. “I have no understudy,” she reportedly said, wearied and resigned near the end of her life. “Every time I do a show I’m up against everything that’s ever been written about me.” By then, she’d been three years saddled with what she’d ostensibly written about herself in an “autobiography” that both she and her ghostwriter would later characterize as largely fiction. Laced with titillating revelations, Lady Sings the Blues quickly became a best seller, and has never since been out of print.*

Billie died at forty-four, from the effects of liver cirrhosis. While she was in the hospital for the last time, a nurse who may have been an undercover policewoman reported the discovery of a “suspicious white powder.” Holiday was arrested and denied bail. A police detail was posted day and night to guard at the door of her room. Her deathbed arraignment marked the fourth time since she’d gotten out of prison in 1948 that Billie had been detained on vaporous drug charges. Plans were made to transfer her to a prison ward as soon as she was well enough to move, and a court date was set for which she was never able to appear.

Cardinal Spellman denied a request to hold her funeral mass at St. Patrick’s Cathedral. No matter how high she rose, from the viewpoint of official America, Billie Holiday would always be regarded as a lawbreaker and never a citizen. She left behind most of what there is to know of her authentic self in the grooves impressed into the shellac and vinyl on which her voice was preserved. Her recordings disclose the innate refinement of the street urchin who became an artist famously expressive of tender feeling, and a woman whose “first and last word was always ‘bitch.'”

This Issue

July 14, 2005