“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.