Holiday first performed the song at Cafe Society in 1939. She said that singing it made her fearful of retaliation but, because its imagery reminded her of her father, she continued to sing the piece, making it a regular part of her live performances. Holiday would close with it; the waiters would stop all service in advance; the room would be in darkness except for a spotlight on Holiday's face; and there would be no encore. During the musical introduction, Holiday stood with her eyes closed, as if she were evoking a prayer.

 

Holiday approached her recording label, Columbia, about the song, but the company feared reaction by record retailers in the South, as well as negative reaction from affiliates of its co-owned radio network, CBS. When Holiday's producer John Hammond also refused to record it, she turned to her friend Milt Gabler, whose Commodore label produced alternative jazz. Holiday sang "Strange Fruit" for him a cappella, and moved him to tears. Columbia allowed Holiday a one-session release from her contract in order to record it.