AS BILLIE HOLIDAY later told the story, a single gesture by a patron at a New York nightclub called Café Society changed the history of American music that night in early 1939, the night that she first sang "Strange Fruit."

Café Society was New York's only truly integrated nightclub, a place catering to progressive types with open minds. But Holiday was to recall that even there, she was afraid to sing this new song, a song that tackled racial hatred head-on at a time when protest music was all but unknown, and regretted it—at least momentarily—when she first did. "There wasn't even a patter of applause when I finished," she later wrote in her autobiography. "Then a lone person began to clap nervously. Then suddenly everybody was clapping."

David Margolick, senior contributor at Vanity Fair, discusses, with Jay Ackroyd, his book Strange Fruit: The Biography of a Song. He takes us back to 1939 when Billie Holiday first performed, and then recorded, one of the most extraordinary songs of the 20th century. The book reflects wide-ranging interviews, from Lena Horne to Pete Seeger, all of which describe how they were affected by the song. LISTEN