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illie Holiday is, after Louis Armstrong and Duke Ellington, the most admired artist in the history of jazz. Largely unschooled (comic books were her leisure-time reading of choice) and musically illiterate, she nonetheless made so deep an impression on her contemporaries that Frank Sinatra, writing in Ebony shortly before her death in 1958, described her as “the most important influence on American popular singing in the last 20 years.”

Billie Holiday: The Musician and the Myth



By John Szwed

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But Holiday is no longer as influential as she was in her lifetime. Her deceptively simple-sounding style bears little resemblance to the elaborate improvisational techniques used by 21st-century vocalists, who are inclined as a group to emulate the more explicitly jazzy Ella Fitzgerald. Nor is the literature on Holiday comparable in quality to the music that it celebrates. Indeed, much of it is an unsavory blend of speculation and gush.

The truth about Holiday needs no embellishment to be compelling. She grew up in the ghettoes of Baltimore and New York, dropping out of school at 11 to work as a prostitute. Like Louis Armstrong, whose singing inspired her to become a jazz musician, she used her innate talent to pull herself out of the gutter—but lacked the self-discipline to stay out of it. Holiday started using heroin in 1941, around the same time that she began to be known to the public at large. Over time drugs and alcohol shattered her voice and laid waste to her health, and she died in a New York hospital room at the age of 44, under arrest yet again for possession of narcotics.

It is this cautionary tale that Holiday herself told in her ghostwritten memoir, Lady Sings the Blues (1956, written with William Duffy), and that is writ still larger in the slick, heavily fictionalized film version of Holiday’s story in which Diana Ross, of all people, played her on screen. The book itself was hugely controversial in 1956, discussing as it did matters of sex and drugs that many of the singer’s Eisenhower-era readers found unimaginable and preferred not to believe; they assumed she had exaggerated in order to sell more copies. In fact, the stories that she told were mostly true, as John Szwed explains in Billie Holiday: The Musician and the Myth, a monograph that is, in his words, “not . . . a biography in the strictest sense, but rather a meditation on [Holiday’s] art and its relation to her life.”

Szwed does not quite succeed in answering a critical question: Why does Holiday remain to this day as central to American culture as any popular singer other than Sinatra himself?

A former academic and jazz musician, Szwed succeeds in cutting through the thick haze of gossip that continues to surround his subject. Among other things, he establishes the essential factuality of Lady Sings the Blues, in the process filling in certain of the gaps on which Holiday’s cautious publishers insisted. But Szwed’s main purpose is to move the spotlight away from her life and direct it toward her art, which he does with admirable efficiency. Still, he does not quite succeed in answering a question that is central to understanding her: Why does Holiday remain to this day as central to American culture as any popular singer other than Sinatra himself? Is it because of the sheer sordidness of her story, which is vastly more dramatic than the comparatively uneventful life of a less interesting personality like Fitzgerald? Or does Holiday’s singing constitute in and of itself a sufficient claim on the attention of posterity?

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orn Eleanora Fagan in 1915, Holiday was the illegitimate daughter of a jazz guitarist who neither lived with nor supported her mother, a maid and part-time prostitute. Predictably enough, she grew up to be a strong-willed woman crippled by a chronic sense of inadequacy. Not only did she follow in her mother’s footsteps by becoming a prostitute, but in later life she was irresistibly drawn to flashy, violent men who, like the pimps she had known in her childhood, lived off her earnings. Her sense of self-esteem was so poor that she actually doubted the quality of her singing, assuring musicians that her voice was a “mess.”

Holiday started singing in public soon after she moved to Harlem in 1929. John Hammond, jazz’s first important record producer, saw her perform in a club in 1933 and was staggered: “She was not a blues singer, but sang popular songs in a manner that made them completely her own.” He claimed that she “sings as well as anybody I ever heard” in a column for Melody Maker, the British jazz magazine. Seven months later, Hammond cut two 78 sides in which she sang with a combo led by Benny Goodman, then signed her to a recording contract in 1935.

Holiday initially recorded not as a soloist but as a “sideman” on a series of combo recordings led by Teddy Wilson, one of the top jazz pianists of the ’30s.1 Nevertheless, she had already become a fully formed artist. Her small, slightly raspy voice sounded at once disillusioned and hopeful, with a touch of vulnerability that was remarked on by all who heard her. “There was something about her—not just the torchy quality of her voice—that made you want to try to help her,” the lyricist (and singer) Johnny Mercer recalled. She could make even the most trivial Tin Pan Alley ditties seem meaningful, and when she performed the work of such first-class songwriters as Irving Berlin and the Gershwins, she brought their immaculately crafted lyrics to vivid life without falling victim to the temptation to over-dramatize them.

Yet for all the distinctiveness of her performing persona, Holiday’s appeal was rooted no less deeply in her natural musicality. Unlike Louis Armstrong, she shunned the “scat” singing that would be adopted by such later jazz vocalists as Fitzgerald and Mel Tormé. In most other ways, though, she followed his example faithfully. She phrased with extreme rhythmic freedom, lagging far behind the beat in a way that occasionally disoriented her accompanists, and decorated the melodies of the songs that she sang with (in Szwed’s words) “small but unforgettable turns, up-and-down movements, fades, and drop-offs” that were all the more effective for their subtlety.

In addition to ornamenting melodies, Holiday paraphrased them in an improvisational manner directly modeled on that of Armstrong. To hear her sing such now-familiar ballads as Kern’s “Can’t Help Lovin’ Dat Man” or the Gershwins’ “They Can’t Take That Away from Me” is to grasp at once the nature of her method: She freely altered the songs she sang, often to accommodate the limitations of her untrained voice, whose effective range was barely more than an octave. Sometimes she stuck fairly close to the tune, but just as often she was more venturesome, at times radically so.

Nowhere is Holiday’s musical approach more successful than in “I Must Have That Man,” a little-known 1928 show tune by Jimmy McHugh and Dorothy Fields that she recorded when she was 21. Accompanied by a Wilson-led all-star band whose other members include Benny Goodman and Lester Young, Count Basie’s incomparable tenor saxophone soloist and Holiday’s favorite musical partner, she sings just one chorus of the cunningly rhymed song (“I need that person / Much worse’n just bad / I’m half alive and it’s drivin’ me mad”). On paper the lyric is little more than clever, but Holiday’s plaintive voice transforms it into an unforgettably intimate confession of unrequited love.


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f Holiday had died in 1937, the year in which she recorded “I Must Have That Man,” she would still be remembered as a great singer. But she went on performing for two more decades, and in 1939 she embarked on a long-term residency at Café Society, a New York cabaret, in the course of which she changed her style deliberately and dramatically.

It was at Café Society that Holiday started adding songs to her repertoire that were different in character from the show tunes and movie songs that she, Wilson, and Hammond had previously favored. The first and best known of them, “Strange Fruit,” is a minor-key setting of a poem about a lynching. Sung at a paralytically slow tempo, it is full of melodramatic couplets whose sincerity cannot disguise their staginess: “Pastoral scene of the gallant South, / The bulging eyes and the twisted mouth.” But Holiday embraced the song, recording it for Commodore in 1939 when Columbia, her regular label, refused to do so.

“Strange Fruit” would be followed by equally doleful songs such as “Gloomy Sunday,” “God Bless the Child,” and the quasi-
autobiographical “My Man” (“He isn’t true / He beats me, too / What can I do?”), all sung at the languorous, heroin-throttled crawl that Holiday increasingly preferred. Many were recorded with studio orchestras augmented by string sections, an innovation that dismayed jazz purists. Pop-music fans found her new style more accessible, though, and in 1947 she co-starred with Louis Armstrong in New Orleans, a Hollywood film about the history of jazz that might well have put her on the path to pop-culture celebrity. But she was arrested on a narcotics charge that same year, the first in a series of brushes with the law that instead turned her into a figure of scandal.

In 1952 Holiday started working with the record producer Norman Granz, who teamed her with jazz combos similar to the ones with which she had worked in the ’30s. While her voice had been coarsened by years of drug and alcohol abuse, the best of these performances are quite listenable, and it is only upon direct comparison with her prewar 78s (in particular her original recordings of songs like “I Wished on the Moon” and “What a Little Moonlight Can Do” that she later remade for Granz) that the decay is immediately apparent.

By the end of the ’50s, though, Holiday’s vocal decline was impossible to ignore. Witness Lady in Satin, a 1958 album of ballads on which she is backed by a large studio orchestra. While her versions of such pitch-black torch songs as “I’m a Fool to Want You” still have considerable emotional impact, the youthful saltiness of her timbre has turned to grit and gravel. The results are harrowing, a kind of sandpaper for the soul.


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oliday’s later recordings have always been controversial. Some believe them to be more impressive than the performances of her youth. Asked in 1958 if she was in decline, Miles Davis replied, “I’d rather hear her now. She’s become much more mature.” But many other listeners believe that she was never the same after 1939—and not merely because of the steady deterioration of her voice.
John Hammond was one of them. He regarded her post-1939 singing as “mannered,” and his explanation of what happened to her is worthy of closer examination:

She was still marvelously musical, but she had gotten self-conscious. I felt that the beginning of the end for Billie was “Strange Fruit” when she had become the darling of the left-wing intellectuals. I think she began taking herself very seriously and thinking of herself as very important.

Hammond, himself a lifelong left-winger but one who steered clear of Stalinism, here puts his finger on an important aspect of Holiday’s later critical réclame: Café Society, where she reinvented herself as a politically conscious torch singer, was a magnet for leftists, many of them of the hardest possible kind. Abel Meeropol, who wrote “Strange Fruit” under the pseudonym “Lewis Allan,” was a Communist who is best known by his own name for having adopted the children of Ethel and Julius Rosenberg after their parents were executed for espionage and treason in 1953.

It was because of “Strange Fruit” that Holiday was embraced by other Communists and fellow travelers more interested in her utility as a political symbol than in her artistry. But Hammond was right to suggest that her artistry was also compromised by the song’s success. From 1939 on, she resorted with fast-growing frequency to a lugubrious self-dramatization and exaggeration that are nowhere to be found in her earlier work, and once her voice disintegrated, she became a pure mannerist, reduced to the hollow shell of a style.

Even at the end of her life, Holiday was still capable of singing with moving expressivity. But those who believe her later work to be superior to the recordings of her youth make the mistake of assuming that the unselfconscious simplicity of “I Must Have That Man” was somehow less “mature” than the inflated pseudo-profundity of “Strange Fruit.” They are also, I suspect, confusing Holiday’s life with her art, treating her as a martyr figure instead of seeing her for what she was: a greatly gifted artist who lacked the strength of character that kept Louis Armstrong, who came from a similar background, from succumbing to a similar fate. To romanticize self-destructive behavior is always a mistake, even when it is the behavior of a great artist—and it is an even bigger mistake to take such behavior as a sign of greatness.


1 Digitally remastered versions of the issued takes of these recordings are collected on Lady Day: The Master Takes and Singles (Sony, four CDs). Billie Holiday: The Ultimate Collection (Hip-O, two CDs + one DVD) is a well-chosen selection of Holiday’s later recordings, accompanied by a bonus DVD containing most of her film and TV appearances.

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