July 24th, 2011
12:02 PM ET
It was March 19, 2007. Amy Winehouse's album, "Back to Black," had just dropped in the U.S., and this was our first up-close and personal look at the talented, but obviously troubled star we'd heard so much about.
As the music from her borrowed band, the Dap-Kings, filled The Roxy in West Hollywood, she somewhat demurely stepped out onto the tiny stage. She was petite - sporting a teal strapless dress, exaggerated cat-eye make-up and an impressive beehive that looked like it could easily house a whole family of crows.
At 23, Winehouse was endearingly awkward, like a newborn colt - all bony elbows and unsure movements. But the girl could sing.
We watched her from underneath the Crow's Nest - where the soundboard is, and where they stash celebrities who don't want to be seen. The music was infectious, an appealing throwback to '60s girl groups like The Shangri-Las, The Ronettes and The Shirelles. As the show progressed, Winehouse's behavior became more erratic. She left the stage several times and started stumbling around, leading to a couple of wardrobe malfunctions involving her ample tattooed bosom.
Her single, "Rehab," was gaining traction on American radio, and when she finally launched into it, a tall blonde woman in front of us said to a man standing next to her, "It was genius for her to do a song called 'Rehab.'"
"Do you think she'll ever go?" asked the man, who had pink hair.
"No, she's not ready yet," replied the woman in a somewhat matter-of-fact tone. Her speaking voice sounded oddly familiar.
I looked up. The woman was Courtney Love, and her companion was Perez Hilton, who was an early Winehouse champion in the States.
The next year, Winehouse won five trophies at "The 50th Annual Grammy Awards" - including "Best New Artist," "Song of the Year" and "Record of the Year." But the days leading up to the live telecast were a cliffhanger of sorts: Would Amy Winehouse be in good enough shape to attend?
"You use the word 'excitement,' but I remember a tremendous amount of drama, uncertainty and anxiety," Recording Academy CEO Neil Portnow told CNN's Kareen Wynter Saturday afternoon.
The first step was getting her from London to Los Angeles for the ceremony, and it involved teams of lawyers on both sides of the Atlantic.
"She didn't have a visa. It was denied," Portnow recalls. "It became a 'Will She or Won't She' scenario. But how long could we hold out? Two days before the show, 'Okay, we have a visa' - but it was too late to get to L.A., rehearse, etc. We ended up having to find a studio in London."
Surrounded by family and friends at Pinewood Studios in London, Winehouse performed two songs on the Golden Anniversary of the Grammys. The first tune was "You Know I'm No Good." The second was "Rehab" - but this time, it was more of a joyful sing-along than a defiant gesture about addiction.
Immediately after her performance, "Rehab" was named "Record of the Year." Winehouse had beat out Beyonce, Foo Fighters, Rihanna and Justin Timberlake for the trophy. She was stunned. Mouth agape, she fell into the arms of her backup singers. Her father, Mitch, piled on. The crowd in London chanted, "Amy! Amy!"
With her arm around her mother, Janis Winehouse managed a few emotional words of thanks - even giving a shout-out to her husband at the time, "my Blake incarcerated." Even at her most triumphant, Amy Winehouse was woefully inarticulate. But as a singer, she was something else. Unfortunately for Amy, she was a human being, as well.
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