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I remember the first time (and last) time I saw Amy Winehouse alive. I was covering Lollapalooza  in 2007, and the main attraction at Chicago’s Grant Park was none other than the British invasion herself. Winehouse had long captivated fans across the pond with her raspy, often pain-stricken voice, but it wasn’t until the release of 2006’s Back to Black that America took notice on  a larger level.

As a music fan, I was excited to see the singer—who was the same age as me—take the stage. Unfortunately, what I witnessed was not the person that I had become a fan of, but a woman clearly on the fast track to destruction. Winehouse  emerged with her signature bouffant, wearing a checkered dress and flats. Although her voice was solid, throughout her set she appeared intoxicated, dangerously thin, and confused; there was even a point where she depended solely on her back-up singers to lead her, and while she tried to play it off, many of us realized that we were witnessing the beginning of her public downfall.

The next four years would bring personal and professional high and lows for Winehouse. Winning the coveted Record of the Year and Song of the Year Grammy’s in 2008, did little to help the songstress combat a losing battle with drug addiction, and the dilapidation of her marriage to Blake Fielder-Civil only made things worse. The aforementioned relationship has been a sore spot for the Winehouse family, who have blamed him for the singer’s foray into drugs. Regardless of who is at fault, at the end of the day, the final choice was hers and hers alone, and while addiction is nothing short of a disease, as a fan I feel a mixture of both anger and sadness that she was not able to make it out on the other side.

Given her great talents, sadly, Winehouse’s music was poised out live her. Like many of the greats who took the music industry by storm, she died at 27, joining the likes of musicians including Janis Joplin, and Jimi Hendrix.

In honor of the first anniversary of Winehouse’s death, we’ve compiled a few memorable photos of the late singer. No one knows what she could have become if she were still alive, but rather than dwell on the silly predictions, it’s important to celebrate the legacy she leaves behind.

Check out a few pictures and Winehouse’s performance of the song “You Know I’m No Good” at Lollapalooza.

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