As an aspiring singer, Holiday suffered sexual abuse, struggled with a drug habit and encountered racism everywhere. But the late Lady Day—one of the first African American women to sing with an all-white orchestra—translated all of that pain into some of the most achingly personal songs ever recorded. (Download “Strange Fruit,” which she sang at her 1948 Carnegie Hall concert, and listen for yourself.)

“You can imagine that women at home hearing her songs on the radio felt her vocalizing their emotions and their struggles.”—Paula Patton, 33, of the upcoming drama Push, wearing Holiday’s trademark gardenia in her hair….