The Show Must Go On: On Billie Holiday’s Last Live Performance (2024)

May 1959

She had come so far in her life. From hardscrabble beginnings, she had done whatever she had to do to forge a career that over time had taken her to such heights she was sometimes now referred to as a living legend. Yet there was so much more she wanted to accomplish—albums to record, shows to perform, movies to make. Fighting through the anxiety that often seized her before she went onstage, she glanced around her modest dressing room. She had been in better, to be sure, but she had also been in worse.

Rows of empty glasses were lined up on the dressing table where she sat; staring into the mirror, she had just applied the final touches to her makeup. For tonight’s show, she had chosen to wear a turquoise evening dress; nearby stood a rack on which hung additional stage attire. Relaxing in a chair close by was Mal Waldron, a handsomely attired bearded man in his mid-thirties who had served as her piano accompanist for the past two years.

Classically trained since childhood and a graduate of Queens College with a degree in music composition whose song “Soul Eyes” was made popular by John Coltrane, he was influenced in his style by the minimalism of Thelonious Monk. An accomplished chess player, Waldron was such a chain-smoker he always seemed to be holding between two fingers his trademark thin brown cigarette. She had worked with other pianists—Carl Drinkard, Bobby Tucker, Teddy Wilson—but she felt a special connection with Waldron. When he backed her, he knew exactly how to “fill the space” between lyrics without stepping on a line. No singer interpreted a song the way she did, and Waldron complemented her while never interfering with her pacing or, equally as important, her phrasing, which included her tendency to “bend the note,” as she called it.

Beyond appreciating his musical acumen, she considered Waldron a friend; they were good together, on and off the stage. She had not enjoyed this kind of symbiosis with a musician since the years she worked with Lester Young, the tenor saxophonist with whom she had shared a profound bond; his death two months ago had left her heartbroken and bereft.

Taking a sip from her scotch-and-water, she could hear the voice of Norm Crosby coming from the main room, where he was performing his stand-up comedy set. She could not count the number of warm-up acts she had sat through over the years. Judging from the laughter and applause Crosby was receiving tonight, it sounded like the audience was capacity-sized and lively. For that, she was grateful. She had endured more than her share of half-filled rooms and dead audiences.

It was her longing to move on to whatever was to come—a show, a recording session, a television appearance—that allowed her to cling to her unwavering sense of hope.

It was May 1959, and Billie Holiday had been performing in nightclubs since the late 1920s, when she broke into the music business by singing in dive bars in Brooklyn and Queens and then in clubs in Harlem like the Hot Cha and Pod’s and Jerry’s. She had appeared in some of the most venerable venues in the world, from La Scala in Milan to the Savoy Ballroom in Chicago to the Hollywood Bowl in Los Angeles.

She was the first African-American woman to headline an all-white orchestra. She was the first African-American woman to sing on the stage of the Metropolitan Opera House. But for more than a decade now, because of a past conviction for narcotics possession, she had been unable to convince authorities in New York City to issue her a Cabaret Identification Card, which a performer was required to have to work in a venue that sold liquor. As a result, she could not gain employment in most of the nightlife establishments in the city where she lived.

So her manager, Joe Glaser, was forced to book her out of town in clubs like the one in which she was headlining this week—the Flamingo Lounge, on upper Merrimack Street in Lowell, Massachusetts, a midsized city twenty-six miles northwest of Boston that years ago was a vital industrial center but today was mostly known for being the home of Jack Kerouac, a founder of the Beat Generation whose novel On the Road had been published two years ago.

A manufacturing hub for decades, Lowell took an economic hit during the Great Depression, when a number of its mills and factories relocated to the South. Billie had played Lowell during that time when she was an “added attraction” with Artie Shaw and His Orchestra at the Commodore Ballroom in April 1938. Now the city fought to remain relevant. Among its vibrant neighborhoods was an entertainment district downtown that was home to clubs like the Flamingo Lounge, which featured a house band that included a trombone player named “Birdcage” and a talented pianist, known only as Madeline, who, according to one regular patron, “always wore a long black cape like she came out of a horror movie.”

Despite the house band’s musicality, the club, to quote a local observer, was “[not] exactly El Morocco. It was a small club, and it booked matching talent. Sometimes, though, it was big talent, big talent on the skids.” Whether or not Billie was “on the skids”—she certainly did not think so—she was pleased to have the gig. An audience, after all, was an audience.

Actually, she should not even have been here, since her doctor warned her she was too sick to appear in nightclubs. For a year or more now, she had been deteriorating physically, mostly because she was suffering from—and not adequately treating—cirrhosis of the liver, the result of years of heavy drinking. She had lost weight, perhaps as much as fifty pounds, a good portion of it in recent months. The disquieting weight loss was affecting her general health, a decline that had been publicly documented.

In mid-April, Dorothy Kilgallen announced in her widely read national column “Voice of Broadway”: “Jazz singer Billie Holiday… is suffering from a serious case of cirrhosis of the liver, but is disregarding doctors’ advice and resisting hospitalization.” Another columnist echoed the story in May: “Billie Holiday has been told to give up liquor or else. The doctors say it will be only a matter of time if she starts boozing it up big.”

In fact, Billie had never stopped drinking, as evidenced by the scotch-and-water she was nursing as she waited to go onstage. Not surprisingly, the drinking continued to affect her health, as recently as this week. For the first two nights of the run, when she tried to make it through one of her seven-song sets, she could finish no more than a song or two before she had to leave the stage.

Finally, Jimmy Makris, the club’s managing director, a hard-boiled businessman who nevertheless had an amiable side to him, approached her in her dressing room. “Listen, Billie,” he said, “no hard feelings. I’ll pay you what the contract calls for, and you come back another time, when you’re feeling better.” It was hurtful for him to watch an artist of Billie’s eminence struggle but fail to do what had once come so effortlessly to her. He also had to deal with his audiences, who were crestfallen by her inability to finish a show.

Billie Holiday photographed by Jay Maisel during the last year of her life. Photo by Jay Maisel.

Billie was unnerved by the offer; no, she absolutely did not want to cut short her engagement. She would do whatever it took to carry on. And she did, too, turning in shows that were as good as any of her recent efforts. It was as if she tapped into some force deep within herself—the very drive that had compelled her to step onstage in the first place all those years ago—that allowed her to do whatever she had to do to perform.

She demonstrated that same primal strength tonight when, once Norm Crosby finished his set to resounding applause and Waldron preceded her onstage with the rest of the trio to vamp for her entrance, she took her place in the wings and, hearing her name announced over the house audio system to a sold-out crowd buzzing with anticipation, stepped through the darkness to head toward the spotlight awaiting her at center stage. Her entrance brought a collective hush over the crowd, then gasps, then a thunderous ovation.

A reporter in the room, on hand from the Lowell newspaper, documented what happened: “The fabled Billie Holiday takes slow steps into the spotlight, walking like a dreamer over a carpet of eggshells. Before the microphone, as the celebrated voice lifts and pours, she is alive again, as though all the long, long road leads always and only to this moment in the lights. She stands there, with nothing in her stance of lure and invitation, and immobile as she is, she establishes an instant and private contact.”

One song ended; another began. “[Her] face is still curiously unlined…the forehead high and serene where the hair is pulled tightly back. The oriental lids hood eyes with tears that have welled, but never fall. She wears a dress of shining turquoise silk, cut like a dashing trench coat. The only movement is in the hands that clutch pink Kleenex, that shake slightly down to their black fingernail polish.”

Billie proceeded on to “Lover Come Back to Me.” As she sang, she moved so little the long gold chain and pendant hanging around her neck barely swayed back and forth on her chest. Once she finished, the room exploded with applause, as it did at the conclusion of each song. At last, for the first and only time during her set, she spoke to the audience, before her final number.

“Now,” she said softly, almost offhandedly, “I’d like to do a song I wrote myself.” Then she launched into “Lady Sings the Blues.”

At the end of the song, she turned and, without saying anything by way of conclusion, without addressing the audience in any way, lowered her head and walked slowly away from the microphone toward the dimly lit wings as the deafening applause rained down on her.

Back in her dressing room, she returned to her seat at the vanity. Pouring herself another scotch-and-water and lighting up a cigarette, she was soon joined by Waldron, who sat back down in his chair. But before she could get on with the rest of her night, Billie had an obligation to keep, an interview Jimmy Makris had arranged for her with a reporter from The Lowell Sun. To steel herself for the conversation—she had never taken pleasure in talking to the press even though she was close friends with William Dufty, a reporter for the New York Post, and had particularly enjoyed an interview she once gave to Mike Wallace for his show Night Beat—she slipped over her shoulders a silver mink stole.

*

Tonight, as she sat at her vanity in her dressing room, she felt tired from her show and more than slightly exercised by the prospect of reliving episodes from her past, accurately or not, with her scheduled visitor, whom she greeted warmly when she was shown into the room. Her name was Mary Sampas, and she published a daily column in The Lowell Sun under the nom de plume Pertinax, an homage to the French author André Géraud, who used the same pseudonym.

Women were beginning to break cultural norms—no woman represented this trend more than Billie Holiday—but the public was still unaccustomed to women assuming prominent roles in the newspaper business, which was why Sampas relied on pseudonyms in her career. Previously, she had written a column called “Girl Friday” before moving on to Pertinax. Her husband, Charles, worked at The Sun as the executive news editor.

Sampas was an elegant, nattily coiffed woman who had a penchant for stylish dresses and fur hats. She affected a professional yet congenial manner. She was, as one friend recalls, the kind of woman “you just had to hug.” She sat in a chair across from Billie, who was polite but standoffish in the early part of their exchange, which was defined by non sequiturs and fits and starts—not what Sampas needed to write an engaging column.

As they spoke, however, Billie came to feel that the reporter was there not because she hoped to determine if the long sleeves Billie wore on this unseasonably warm May evening were meant to cover up telltale track marks on her arms but, rather, because she admired her work and respected her as an artist. In time, Billie felt trustful enough to answer her questions. “Do you consider yourself a jazz singer or a blues singer?” Sampas asked.

“No, I’m just a song stylist,” Billie said, taking a puff on her cigarette before sipping her scotch-and-water.

“You know,” Sampas said, “I recently saw New Orleans on television.”

Even though Billie was forced to portray a maid in the motion picture—can you imagine, she plaintively asked friends at the time, Billie Holiday playing a maid?—she harbored fondness for New Orleans because it afforded her the opportunity to appear on-screen with Louis Armstrong, who had exerted a germinal influence on her singing style when she was learning early lessons. “I made that movie thirteen years ago,” Billie said, smiling whimsically, as if she could not fathom where all the years had gone.

“So, what city do you play next?” Sampas inquired.

“Montreal at the first of June,” Billie said, glancing over to confirm the date with Waldron, who nodded affirmatively.

Finally, the two women had spoken long enough that Sampas ventured to ask Billie how she was feeling, not as a pleasantry but as a legitimate line of questioning, since news of Billie’s health was in the press.

“My doctor wants me to give up singing,” Billie said. “He thinks I’m too ill. But what else am I made for?” She let out a brief, impervious laugh. “So as long as I have breath to sing and someone still to listen…”

In the end the incessant planning for the future was all an illusion that obscured what was occurring in the present.

She did not finish the sentence. Instead, she reached for a book on the dressing table. “This is what I’m reading between shows,” Billie said, fixing her gaze on Sampas as she held up the book version of Some Like It Hot—the picture had been released in late March—with a shot of Marilyn Monroe displayed prominently on the cover. “I have to laugh a little.”

After thirty minutes, Sampas wrapped up the interview. And when it was over, when Sampas said good night and departed the dressing room, Billie did what she had done on so many nights in so many other dressing rooms over the years—she got ready for the next show.

In the coming days, when Sampas published the piece in her Pertinax column, Billie knew she was right to trust her. Admiration coursed through the article. Sampas got her. “In the style that made her the toast of two continents,” Sampas wrote about Billie’s stage performance, “she mourns love grown old and cold, and you know a special sorrow. You hear rain fall, and you sense that dark clouds obscure the moon, and you feel a lonely whistle pierce a completer loneliness. All God’s children got troubles, and my Mama was right, there’s blues in the night.”

*

Following the problematic shows on Monday and Tuesday nights, Billie flourished for the rest of her weeklong run, which lasted from May 11 to 17. She even felt well enough on Sunday to perform an advertised “jam session” at two o’clock in the afternoon. Years later, Waldron recalled the Flamingo Lounge engagement as being “a very big, successful week for Billie.” The houses were full; the audiences, enthusiastic. Proof was comments Sampas included in her column that she overheard audience members make after the show she attended—“Unforgettable!” “She breaks my heart!” “I [saw] her ten years ago at the Ebony Club and her voice is as marvelous as ever.”

So as Billie traveled back to New York, she anticipated with excitement the dates Joe Glaser had lined up for her: the gig in Canada in early June but first an appearance, along with the Dave Pell Octet, on the weekend of May 29 at Club Jazz Seville, Harry Schiller’s nitery on Santa Monica Boulevard in Los Angeles. A press report promised a show featuring Billie’s “all-time great renditions of jazz classics, plus some of her sensational new recordings.”

What kept Billie going was the next gig—and the gig after that. It was her longing to move on to whatever was to come—a show, a recording session, a television appearance—that allowed her to cling to her unwavering sense of hope. As one friend put it, “She had a tremendous drive for survival.” Yet in the end the incessant planning for the future was all an illusion that obscured what was occurring in the present. She was in a state of precipitous decline.

Even so, there was no way she could have known that the conversation she had with Mary Sampas would mark the last formal interview she gave to a journalist. There was no way she could have known that, after coming so far in her life from the early years in Fells Point to the most celebrated stages in America and abroad, the last night at the Flamingo Lounge would be her final appearance in a nightclub. There was no way she could have known that, as of mid-May in 1959, she had two months left to live.

Or maybe there was a way. For months, her doctor had warned her that if she did not take better care of herself—and specifically treat her liver condition—she ran the risk of suffering a potentially fatal health crisis. For months, friends and associates implored her to heed her doctor’s advice—to no avail. Her gradual but persistent decline had started a year ago during a time when she was dealing with an amalgam of challenges, from financial problems and romantic complications to struggles with substance abuse and run-ins with authorities, all emblematic of the myriad difficulties that had come to constitute the perennial hardships of her life.

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From Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year by Paul Alexander. Copyright © 2024. Available from Alfred A. Knopf, an imprint of Knopf Doubleday Publishing Group, a division of Penguin Random House, LLC.