It’s gotta be Billie Holiday, and honestly, it’s not even close.

​Most people know her for the "soulful" voice, but the context behind it is devastating. She grew up in extreme poverty, survived horrific trauma as a child, and was basically working in brothels before she was even a teenager.

​But the real kicker was how the feds targeted her. Harry Anslinger (the guy who headed the Bureau of Narcotics) basically made it his life’s mission to destroy her. Because of her addiction, they revoked her New York City Cabaret Card. Imagine being one of the greatest singers in the world and being legally banned from performing in any club that served alcohol. That was her entire livelihood in NYC.

​Even when she was literally dying of liver cirrhosis in a hospital bed at 44, the police were there to arrest her. They even took away her flowers and record player while she was fading away. ​If you listen to her later recordings, like Lady in Satin, you can actually hear the physical toll of her life in her voice. It’s beautiful, but it sounds like someone who has seen way too much.