Half a century after her death, Billie Holiday's music remains a cornerstone of the American songbook.

“Billie Holiday was, and still remains, the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last 20 years.”

—Frank Sinatra, 1958

Life is ultimately mysterious and indifferent about whom it gives much and from whom it expects a measure equal to its gifts. Those gifts are passed out with the same careless precision as handfuls of chicken feed hurled into a high wind.

Billie Holiday was obviously given much more than most, and her talent revealed itself through her intensity, her phrasing and her control of nuance more so than the conventional strengths of big sound, great range and stunning projection. Her voice was small, and her range was equally small. Standing next to most singers, she would never get you to put your money on her, unless you knew in advance that her emotional force and her ability to summon pathos, joy and melancholy with naked precision would demolish almost anyone intent on making a contest out of a hazardous moment on the bandstand with her. 

There the story of one performance with super virtuoso Sarah Vaughan. Vaughan was so profoundly endowed with a superior instrument that she sometimes could not avoid strutting her stuff to the point of obnoxiousness. But the ax fell. When Vaughan called up “I Cried For You,” Holiday whispered, “You done screwed up now, bitch. That’s my song.”

That sounds like a person who had discovered what she had and  bet her life on it. In the face of virtuoso moves, Holiday was so  far ahead on human feeling as to be invincible. She had learned her craft from Louis Armstrong and Bessie Smith, desiring Armstrong’s sense of time and his brilliant choice of notes as well as Smith’s big sound. She did better with Armstrong than she did with Smith, whom Langston Hughes said one could hear out on the street when she was singing in a theater before microphones had been developed to the point that Armstrong, Holiday and Sinatra could make the most of them.

Neither Armstrong nor Holiday nor Sinatra was a belter or would have been much in the world of opera where size, projection and nuance were taken to levels far beyond what one expected in popular music. Each of them brought popular music to heights of varied expression, emotional complexity and even psychological revelation that were far beyond what had been intended by most popular composers or made functionally limited in their strident pluck by Broadway types like Ethel Merman, who was capable of shivering the timbers.

Holiday was so special because she imbued her performances with a tenderness so charismatic that her example and her unbending musical presence forced instrumentalists to do their best at making up melodies or coming as close to crooners as whatever talent they had made possible. One could not be completely satisfied with a brass or reed instrument unless it took on qualities close to a voice elevated by artistry of the sort that only jazz could bring to its material. This was done by combining the highest level of improvisation, with the skill to fit a context and the absolutely essential ability to express oneself best by meeting the demands of the ensemble, adjusting breath by breath to where one is and what is going on as well as recognizing what to do with reality in motion.

That is the supreme achievement of jazz because empathy and individual expression meld. In that sense, it is the most perfect artistic example of what e pluribus unum means. No one has ever been able to do that better than Billie Holiday could. Whatever the moment demanded, she was as ready and was recognized by her peers and her fans for that order of artistry.

She first appeared on record in the middle 1930s and had become a big influence on fellow singers by the end of the decade. The inarguably great Ella Fitzgerald has never failed to call Holiday the greatest jazz singer of all time. Abbey Lincoln, the only singer since Holiday who has a parallel level of feeling, of vulnerability and pathos so far from self-pity, says the same thing. Miles Davis, whose sense of rhythm and whose tendency to float over the beat was as deeply influenced by her as the growing confidence he brought to lyrical recognition of the interwoven mystery of melancholy, frailty and unbounded but unsentimental joy.

That unsentimental joy has often been misunderstood as some sort of Negro foolishness too far removed from the world of the substantial to be taken seriously. But mindless and empty-headed frivolousness is not the issue at all. Thorough acknowledgment of life’s tragic facts is what makes the art of Armstrong, of Holiday and of many other major jazz musicians so compelling. It is much like singing a fervently happy song in the morgue not because we don’t know what awaits us, but because joy is a protest against all that would take us down. So the will to live becomes more than desperation and ascends to a combatively affirmative morale. No minor accomplishment, this may be the most impressive thing that American Negroes have offered the world at large. There can be no doubt that Billie Holiday knew how to bring it.

For those interested in an eloquent and perfectly clear assessment, the very best writing about Holiday’s artistry is contained in The Jazz Tradition by Martin Williams. Then there are some recordings that make it understandable what inspired all of the talk. The Essential Billie Holiday, a 1956 performance at Carnegie Hall, documents her craft at a penthouse point of perfection in which ballads, blues and extremely hard but floating swing are as good as anything she ever recorded. Songs for Distingué Lovers from 1957, just two years before her death, finds the incomparable Lady Day at the height of her talent and possessed of a mature wisdom that one does not hear in her early work, no matter how good it might be.

Then there is her personal favorite, Lady In Satin, done with strings about 17 months before she died.

There are those who enjoy pitying Billie Holiday for the hard life that she led due to drugs, alcohol and the rough men who were incapable of breaking her spirit.

But we should not be decoyed by those unpleasant truths to the extent that we miss what the great Betty Carter observed about the great Billie Holiday. “I think she was only free when she was singing. Everything else didn’t mean much except that it led up to the moment when she stepped out on that stage and became what we all wanted but only she could give us. She was free then, and everybody knew it. When someone brings that much freedom and makes you believe it, you have to get happy. You can’t help it.”

Stanley Crouch is a New York writer.