Duke Ellington called Billie Holiday “the essence of cool,” a reference to her equipoise in performance. The most influential jazz vocalist of all time, Holiday had a controlled emotional power that transformed even trite ballads into romantic short stories. Born Eleonora Harris and partially raised in a New York City brothel, she crafted a cool vocal style by tempering Bessie Smith’s shouting power with Louis Armstrong’s rhythmic nuance, then honed her craft on the road with the Count Basie Orchestra. Lester Young named her “Lady Day,” and in their chamber jazz classics, such as “All of Me,” voice and saxophone curl around each other into smoky swirls of late-night yearning. Late in life, Holiday, a drug addict and survivor of abusive relationships, sang in a cracked, broken voice that remained true to the jazz practice of self-expression.

In this iconic photograph, Holiday emerges as if from black satin, part African mask and part Hollywood diva, dragging her shadow along.