Island

2006

When Amy Winehouse won Record Of The Year for "Rehab" at the 2008 Grammys, she was visibly stunned. Footage still circulates, her face frozen in pure shock. She had won five awards that night. Her friend Juliette Ashby turned to her and told her she was proud of her. "Jules," Winehouse replied, "this is so boring without drugs."

The singer’s short life was littered with tragedy, but that disillusioned moment encapsulates the darkness she inhabited. She had just achieved international success with her second album, Back To Black , which came out 20 years ago today in her native UK. (It would arrive in the US about five months later.) Recognition couldn’t save Winehouse — in fact, it could only accelerate her plunge as she endured scrutiny and mockery. She was only 23, yet sang soulfully with the skill, cleverness, and pain of someone who’s lived a thousand lives.…