The two greatest American popular singers of the 20th century, Billie Holiday and Frank Sinatra, were both born in 1915. Billie is up first. This week, on April 7th, she would have turned 100. Of course, she got nowhere near that, dying in 1959, aged 44, her body worn out after a life of hard living, and dying miserably, in police custody for a narcotics arrest. There are so many Billie Holidays; the young singer, all effervescence and charm, plucked from obscurity from an already hard life, who before she was twenty was recording with many of the greatest jazz musicians of her time; the tough but incredibly vulnerable Lady Day, with the gardenia in her hair and her lousy choice in men, her addictions, and multiple run-ins with the law; and the singer in her last years, her voice reduced to whispers and shards, her singing haunted and on the outermost limits of sublimity; the woman who has, in many legends, has become as mythological as Zeus.

Let me explore the Holiday and Sinatra comparison a bit. Holiday and Sinatra are a study in contrasts and similarities. They both greatly admired each other, and influenced one another. They were both jazz singers, of very different sorts, and raised at a time when jazz was part of the mainstream of American popular music, and both came of age in the 1930s in New York City and environs, when New York City was at the center of the jazz world. And both were restless, supremely creative artists, reinventing and rethinking their shared repertoire, what has come to be called the “great American songbook,” rooted in the music of Gershwin, Berlin, Kern, and others.

But of course they led very different lives. One was white and male, the other black and female. One evolved from a cutie-pie high, soaring baritone who projected sweetness and vulnerability to a man who became the personification of macho cool and toughness, a man who could wrestle a song to the ground and knock it out. The other evolved from a mainly up-tempo singer who could convey happiness and excitement like few others, to a singer who preferred things slow and sultry. Sinatra played at being a gangster; Holiday did hard time and spent most almost half her life behind one legal eight ball or another. One lived to a ripe old age, as honored a popular entertainer as America has ever produced. The other lived a life that was that poor, nasty, brutish, and short. Perhaps this has to do with their personalities and their life circumstances. It also, surely, is a commentary of sorts on the differences between white and black lives, and male and female lives, in the middle decades of the 20th century.

This is how Billie Holiday’s life has often been seen, as a tragedy into which some deeper meaning has to be imputed. Like all of us, she was both an individual, by all accounts not a particularly easy individual to get along with, and a reflection of her social and ethnic context, and the time and place of her life. Black people, in the middle decades of the last century, did not have much leeway to screw up; lives were lived without a safety net. Because of her extraordinary talents, Billie Holiday was granted more chances and had more opportunities than most black people. But in the end she was just another black junkie, a black body to incarcerate.

But the reason we care about Billie Holiday is because we think we know her from her singing. She primarily sung of love, in all of its wonders and terrors; wanting to be in love, being happy in love, being unhappy in love, wanting not to be in love, passions requited and unrequited, affairs started and stopped, anticipated and regretted. Her art, like much great art, as much transcends as reflects the circumstances of its creation.

But of course, lots of people, in her time, sang love songs. What makes her special is that she seems to be singing the lyrics and singing about something else, her quest, her unhappy quest for freedom. She freed almost everything she sang from its conventional constraints, reimaging and to some extent recomposing her songs, singing in front of the beat, behind the beat, creating it anew, elevating herself, if only for a few minutes, above her calamities, and when we hear her, we also elevate ourselves, for a few minutes, above ours. She is one of the greatest and most accessible of the great musicians, one of the greatest artists America has produced. The centennial of her birth is as good an occasion as any to stop what we are doing, to pay attention, and listen again.