updated 07/23/2011 AT 6:45 PM ET
•originally published 07/24/2011 AT 9:40 AM ET
The first time I saw Amy Winehouse was at Joe’s Pub – an intimate, cabaret-style setting in Manhattan’s East Village – in early 2007. Even before the release of her game-changing album Back to Black a couple months later, there was already so much buzz about this soulful, saucy Brit with the beehive. And with celebs like Jay-Z in the house, you could feel something special in the air that night. Winehouse didn’t disappoint, filling the room with a smokiness even when no smoking was allowed.
As she brought life to the bad-girl drama of her songs, it sometimes felt as if she were teetering on the edge. This was no act.
Sadly, the same darkness and demons that made Winehouse’s music so compelling would prove to be her undoing, as the world watched her spiral out of control even as she won international acclaim. Once a sort of joke to some, the rebellious “no, no, no” refrain of her signature hit “Rehab” – which won her three of the five Grammys she took home in 2008 – became all too real. Just as telling was the Etta James-esque “You Know I’m No Good,” on which Winehouse seemed to foreshadow her own downfall: “I cheated myself / Like I knew I would / I told you I was trouble / You know that I’m no good.”