It’s always troubling whenever a young person dies. And now, Amy Winehouse joins the dreaded “27 club,” walking amongst legends like Jimi Hendrix and Kurt Cobain–music stars who passed away prior to their 28th birthday.

But with Amy, her death is all the more disappointing. Having released just two studio albums, the latter of which (“Back to Black”) channeled the retro stylings of the 1960s, Winehouse and those who aided her music career were just beginning to tap into the depth of her talent.

Still, her biggest hit in America, “Rehab,” showed us that her demons might be an unshakeable force.

And then there’s Michael Jackson, a man who fought so many demons (some attributed to his father and upbringing, some simply due to growing up in the limelight), that the King of Pop became a total recluse.

With an ever-changing face, two high profile trials, and a relentless media that perpetuated rumors in order to sell newspapers and magazine subscriptions, you knew–deep down–that it wasn’t going to end well for Michael Jackson. That this wasn’t going to be an artist who would be receiving a Lifetime Achievement Award at the 2035 Grammys.