If I had to pick my favorite female singer, without a doubt it would be Billie Holiday. Once you hear voice, you automatically know it’s her. Prior to Billie Holiday, jazz singers did not personalize the songs that they sang. As a result of being forced to sing standards and Tin Pan Alley songs, she would often sing around the beat and improvise.
Holiday was often quoted as saying that she tried to sing like a horn – and if you listen to her recordings it makes sense. It’s soothing and she she works around the song, and is not bound by it like many of her contemporaries.
Probably her most famous recording is “Strange Fruit”. Holiday didn’t write the song – although it’s associated most with her. “Strange Fruit” is protest music before Guthrie, Dylan, and Lennon. Abel Meeropol’s poem about Southern lynching already cuts to the core, but under Billie Holiday’s voice it becomes a tearjerker.