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The soft but declarative quality that Holiday brought to many of her songs was also part of the rhythmic irregularity that is so often noted in discussions of her work. It enabled her to find something valuable in melodies of otherwise weak song lyrics by shifting accents around and eliminating melodic excess. From 1939 on she sometimes sang so slowly and with enough emotional detachment that the rhythmic intentions of the original songs became lost. On the other hand, in “Strange Fruit” the horrors she describes benefit from the sense of shocked immobility that this approach can provide. Critic Margo
Jefferson suggests that this emotional distance allowed her to refashion “all of the ordinary elements [of song], somewhat realigned and reproportioned, but recognizable and perfectly shaped . . . like a cubist painting . . . a musical cubism.”

Billie Holiday and Lester Young: The Romance of Obbligato

In the four years between 1937 and 1941, Holiday and tenor saxophonist Lester Young appeared on a number of recordings together under pianist Teddy Wilson's name. Later, when she was better known, they also performed on recordings under her name. The records were made cheaply, with only sketches of the music to play and no rehearsals, and
were aimed at the newly developed jukeboxes that were beginning to be installed in African American bars and restaurants across the country. Yet many of these three-minute recordings are now acclaimed as among the best that either of them made in their lifetimes. Together they were finding a new way for vocalists and musicians to relate to each other. Margo Jefferson once wryly observed that Holiday and Young had the kind of musical collaboration that Louis Armstrong had with himself as a singer and a trumpet player.

Lester Young was a quiet man with a taste for beauty in music who shunned the strutting instrumental theatrics and rough overstatement of many of his contemporaries on the tenor saxophone. Instead, he played softly, with slight vibrato, much the way Holiday sang, and his long, liquid lines were intended to convey what he insisted was a kind of storytelling. Billie wrote that “
Lester sings with his horn. You listen to him and can almost hear the words.” Telling a story was what Lester Young believed a jazz musician was expected to do. Even if words were not involved in that story, the instrumental solo had to have some sort of narrative line to it, with a coherent flow of sound throughout that was resolved at the end. This was a view widely shared by many horn players of that generation, even if they played in very different styles from Young. Tenor saxophonist Dexter
Gordon sometimes spoke a few lines of a song before he played it, and spoke them with carefully pitched words and a rhythm that suggested where he was going to take his improvisation on the horn.
Holiday and Young each chose to avoid playing the melody of songs as written, and instead sought to create new melodies close enough to the originals to paraphrase and evoke them, but not be bound by them.

Lester and Billie were very different in manner and character, but when it came to music they both found themselves in the same aesthetic zone. Young declared Billie his favorite singer and called her “Lady Day,” a title that acknowledged her dignity. The irony of the name was that at the time no black women could be ladies in the eyes of white people. They could not be addressed in any way that raised their status—not
even be recognized as “Miss” or “Mrs.,” with the more significant consequence that even marriage could not be fully acknowledged. The further irony is that in much of her public behavior Billie was hardly “ladylike.” Her manner was street-hardened, and stories abounded about her temper when wronged, her willingness to be violent when called for. She took no stuff from nobody. But as a singer, as a musician, her stage persona was one of grace in every sense of the word; her poise could freeze a noisy room into shocked silence. She returned Lester Young's compliment by saying there was no musician she'd rather work with, and named him “Prez,” the president of the saxophonists.

Holiday's and Young's shared musical affinity is often understood as evidence of their being soul mates, if not star-crossed lovers. (A 2002 Sony CD compilation of some of these recordings was titled
A Musical Romance
.) A video from the 1957 CBS television special “The Sound of Jazz” features the two of them in their last days, and is often pointed to as proof of a special relationship. The actual circumstances were that both of them were ill—Lester too weak to play with the Count Basie band earlier in the show, and Billie not only in bad health but annoyed that she had bought an expensive dress for the show only to learn that the producer wanted the musicians to dress informally. Then, on the day of the live broadcast, a sponsor attempted to have her removed as undesirable for a family audience. But the producers resisted, and she stayed in the show.

It was decided that one of the last numbers that night would be “Fine and Mellow,” with Holiday accompanied by a small group of musicians including saxophonists Young, Ben Webster, Coleman Hawkins, and Gerry Mulligan along with trumpeter Doc Cheatham and trombonist Vic Dickenson. To everyone's surprise, Billie sang better than she had in years, and Young's brief solo was a brilliant example of blues minimalism. Many who've seen the video of the program speak of the love and affection that is evident between the two of them during the performance, even though they had actually not spoken for several years following an argument of some sort. Billie's smiles and nods
during Lester's brief solo have been read as a sign of their enduring relationship, but for his part Lester shows no acknowledgment of her presence, and she can also be seen nodding in approval at the other soloists.

What in fact made the two of them seem such natural partners were the similarities in their approaches to improvisation on ballads. Lester had a jazz singer's approach to a song: follow the melody, maybe paraphrase it, and create a new one in a horizontal fashion, never constructing one exclusively from the harmonic or vertical structure of a song. And when he and Billie came together they wove mutual melodic lines and in a sense “sang” together. The name for that sort of musical relationship in the Western classical tradition is “obbligato,” where one musical line accompanies another, typically with a secondary melody that is independent but that seems necessary to what is heard as the principal melody. But Holiday and Young are far more creative and daring in their understanding of the different possibilities in this relationship. On both the 1937 master
recording and alternate take of “Me, Myself, and I,” for instance, in the second chorus she improvises lightly but stays close to the melody of the song as written by its composer. Meanwhile, Lester is playing
a fully improvised, freshly created solo alongside her, based on the same tune. Both of them are soloing at the same time; that is to say, they are collectively improvising on a common theme without any harmonic clashes, something that Young would have certainly understood, as it was a basic organizing device in the jazz of New Orleans, the town where he was born. On “Who Wants Love?,” recorded three months later, they perform together, again in the second chorus, but now it is Young who stays closer to the melody as written, while Holiday improvises behind him. On “He Ain't Got Rhythm,” recorded even earlier in 1937, clarinetist Benny Goodman and pianist Teddy Wilson each play different lines as she sings around the melody, again with no clashes, despite there having been no arrangements or rehearsals before they recorded. When the three of them finish, Lester Young comes in on tenor and constructs a different melody.
Billie Holiday once said that “
the only ones who can take a solo while I'm singing and still not interfere with me are Lester Young and Teddy Wilson.”

This approach to obbligato is something more than the call-and-response so common in African American music. It's more akin to what Zora Neale
Hurston heard in preachers' prayers that were embedded within the hymns of the congregants of rural Southern black churches: “The prayer is an obbligato,” she said, “over and above the harmony of the assembly.”
Hurston goes on to say that they are different lines of music, but each is essential and mutual, and together ritually affirm spiritual harmony.

The Four Billies

Most fans and writers agree that in her twenty-six years as a singer on record, Holiday had three distinct stylistic periods. But her last two recorded albums are different enough that they would seem to constitute a fourth. From 1933 to 1942 she recorded for Columbia-affiliated companies, where she was promoted by John Hammond Jr. He took the risky path of casting her as a jazz musician, surrounding her with first-rate players in jam session–like settings, often without arrangements, in which she took her brief vocal solos in line with the instrumental soloists.

When she moved to Commodore Records in 1942, a small jazz company founded by producer Milt Gabler and Jack Crystal (the father of Billy Crystal), she continued her trajectory as a straight jazz singer. But once she agreed to record “Strange Fruit,” the first openly political song sung by an African American singer on a pop recording, she announced herself as something more than an entertainer. After Gabler became a producer for Decca Records and signed Billie with them, she began to record more show tunes, and took on torch songs with greater emotional content and fuller musical settings. Meanwhile, as swing moved beyond black communities and was on its way to becoming a national craze
driven by white teenagers (John Hammond called it “the Children's crusade”), she faced the choice of becoming commercial or remaining on the edges of pop music.

On “Lover Man,” a song written for her, she was accompanied by strings, a more audacious move than it might seem, as very few pop song singers had ever been given such plush surroundings and certainly no jazz singers (or jazz musicians). It helped her expand her pop audience, though some of her jazz fans felt left behind. The cruel joke was that just as she began exploring a new approach to song, she was also drifting into drugs and heavy alcohol use.

In Holiday's third period, the 1950s, jazz itself was very different from when she'd made her earlier records. The conventions of swing were becoming exhausted, and jazz had become self-consciously revolutionary and culturally important in ways never anticipated. Her 1930s records were starting to seem quaint in the wake of bebop singers like Sarah Vaughan, who were threatening to replace her, except that Holiday, older and developing a different character, had begun to replace herself.

In the last decade of her life, her voice beginning to coarsen and her range narrowing, she crossed over to Norman Granz's Clef and, later, Verve Records, the premier sources of mainstream jazz in the 1950s. She and Granz began reexamining her repertoire in a new light that would give her the courage to rerecord them. Unlike older black singers, she had never been completely relegated to “race” records, those intended exclusively for an African American audience. Being marketed to a national audience was an enormous advantage to her, but it also meant that she would have to avoid current pop songs that were sometimes ill-suited to her, and she would not be able to depend on the near-blues songs that were still in favor in the black community. Granz encouraged her to stick with jazz standards and to revisit her best songs. Her work over the next few years was enhanced by the arrival of high-fidelity recording with extended recording limits, and by being surrounded by some of the finest younger jazz musicians. There were few
surprises and no innovations in this period, but her popularity spread to a worldwide audience.

By 1958 her health worsened, and her voice had changed so much that she relied on little more than a bare recitative in which only her phrasing, her timing, and a few of her vocal characteristics remained intact. At her request, Columbia nonetheless agreed to record her with a forty-piece orchestra with arrangements by Ray Ellis, the star of a music style that would soon become known as easy listening. To some listeners, the album
Lady in Satin
, which she recorded that year, was unbearable, the death throes of a once great singer. To others, it was a revelation, Holiday at her purest, a distillation and a highly nuanced presentation of all that her music had been about. It's an argument that still persists today, with all sorts of interpretations attempting to explain what is conveyed on this record. (Novelist Haruki Murakami, for example, recently claimed that what he hears in this late music is forgiveness.)

It might not seem surprising that a singer would change her interpretations over the course of a twenty-six-year career, but the demands of aging fans who expected her to sing the same songs in the same way are often abided by, though sometimes with disastrous results. In Holiday's career, this issue was even more obvious since she rerecorded many of her biggest songs an extraordinary number of times: “Billie's Blues,” twenty-two times; “My Man,” thirteen; “All of Me,” ten; and another nineteen of her other songs were rerecorded at least eight times or more. These multiple versions allow us to see that her approach did change over the years—tempos generally became faster, and the keys changed to allow her to lower her voice. But there was still great continuity in the general features of her style: She continued to improvise on the melody in very consistent ways, if anything taking greater risks with pitch as she grew older. Her timing never abandoned her, and she continued to find her way free from the constraints of her accompaniment. (
Compare the versions of “All of Me” as recorded on January 21, 1941, April 22, 1946, and January 2, 1954; or those of “Yesterdays” recorded April 20, 1939,
July 27, 1952, and November 10, 1956; or of “My Man” recorded November 1, 1937, December 10, 1948, July 27, 1952, and July 6, 1957.) But her voice had been so much a facet of her biography, so emblematic of her life, for so long, that to most listeners the changes in it were just the latest phase of the mise-en-scène of her
suffering.

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