At this stage in the game, it’s really impossible to know the true nature of Amy Winehouse’s legacy. This kind of thing becomes clear with time and distance.
It might be easy to compare her with other beloved singers that left us too soon, like Billie Holiday or Sam Cooke. And perhaps we’ll position her alongside her cohorts in the 27 Club, like Janis Joplin or Kurt Cobain. To be clear, I’m almost certain Amy will be looked upon with similar admiration and awe; her voice, style and songwriting were unmatched by anyone else of her generation.
But its important to recognize that we experienced Amy in a very different way. There are no youtube videos of Kurt Cobain shooting up heroin. There is very little footage of Jim Morrison’s many disastrous concert meltdowns. Janis Joplin and Jimi Hendrix had more than a few nights out on the town drunk and high. But the paparazzi didn’t follow their every move, and random onlookers weren’t armed with camera phones in the late 60’s. 
Yes, Amy Winehouse’s legacy will be very different from theirs because her many highs and lows were witnessed en masse, in real time, via. youtube, tabloids and blogs. We saw practically every moment of it. For better or for worse. And though it may be difficult to admit, there is just no way this won’t influence the way we perceive her life and work.

When we look back at the lives of tragic, cultural icons like Kurt Cobain or Jim Morrison, nostalgia and selective memory can very easily take hold. We forget that Nirvana’s 3rd album had received a lukewarm commercial reception upon its release less than a year before Cobain’s untimely death. We forget that Jim Morrisson was widely criticized and maligned for his wild, drunken onstage antics, which had been numerous and basically “a part of the show” during his latter days.
Amy’s legacy may not be at the mercy of such a phenomenon, as she was a product of a very different era. It is an era in which tabloids in Britain can get unthinkable scoops by hacking into a missing  child’s cell phone. It is an age where a talentless person with a pretty face and zero shame can reach uber-fame by simply being seen, photographed and blogged about. It’s a time where Charlie Sheen can quit his actual job, and embark on a career that centers solely around the numerous bad decisions he has made (and continues to make) in real life. You don’t just get on stage, do a little song and dance, and retreat to a private life anymore. The lives of celebrities are just as important to their success as whatever trade or talent they’ve mastered.
By late 2008 Amy’s incredible talents seemed to have been overshadowed by her wild behavior, and the celebrity-obsessed media generally began to treat her like some drunken socialite. But true fans always knew better. Amy was not Lindsay Lohan; a spoiled child star that grew up never hearing the word “no.” And she was not Paris Hilton; a upper east side rich girl that preserves her fame by scheduling photo-ops with the paparrazzi and hosting parties at nightclubs. Amy didn’t fashion some public image and narrative for herself that required sightings at VIP clubs or “dates” at the Ivy with (insert famous athlete/actor/rich guy here). Amy Winehouse just wanted to sing. She gave very few interviews, and seemed utterly ambivalent to them when she did, and never held her tongue. Fame happened to her. Not the other way around.
And that’s why Amy Winehouse was so unique, controversial and fascinating. It was impossible to tell where her music ended and her real life began. “Rehab” is not a funny song. It’s a brutally honest portrait of an alcoholic that’s self-aware enough to understand that they are drinking because they feel isolated and depressed, yet hopelessly lacks the willpower to do anything about it. Yet, when Amy would bend down mid-song to take a big ole’ gulp from her drink, audiences cheered wildly.

It wasn’t that anyone wanted Amy to be an alcoholic, or to die. It was just shocking and exciting to witness confirmation that she was the real deal, for better or for worse. Labels may have turned her hard-drinking, hard-loving image into a marketing ploy, but it was always firmly based in reality. Amy Winehouse was not a phony. There was no script. In the words of Erykah Badu, Amy was “an analog girl, livin’ in a digital world,” oblivious to the camera flashes and snarky bloggers that surrounded her. In an era defined by “transparency,” it didn’t get more transparent than Amy Winehouse.
She wrote with brutal honesty. She sang with brutal honesty. And she lived her life exactly the way she wanted to live it, whether we were watching or not.
Her legacy will undoubtedly be founded upon her stunning, once-in-a-generation talent. But her harrowing experience in the spotlight will forever stand as a testament to the damage our voyeuristic culture can do to a naive, free-spirit that refuses to conform to its standards.


 R.I.P. Amy Jade Winehouse

14 September 1983 – 23 July 2011