Back to Black: Remembering the Day I Met Amy Winehouse

This article originally ran on Yahoo! Music on July 23, 2011, the day that Amy Winehouse died at age 27. We are re-running it today, two years later, as a tribute.

Back in March 2007, Yahoo! Music went to South By Southwest, the annual Austin music festival where so many up-and-coming artists flock to kickstart their careers in America, and booked a studio where SXSW 2007's buzziest buzz acts came through to perform for the Y! cameras. All sorts of impressive musicians stopped by--Mika, Peter Bjorn & John, Albert Hammond Jr. of the Strokes, Brandi Carlile. But the moment I remember most from that whirlwind weekend is, unsurprisingly, when the infamously rehab-resistant, beehived British bad-girl, Amy Winehouse, sauntered through the door.

Part of what made Amy's appearance at Yahoo!'s SXSW headquarters that hot Austin day so memorable was the fact that she showed up at all. While Amy wasn't quite a superstar yet, she'd already established a reputation for being troubled, flaky, and living up to her apparently autobiographical hit, "Rehab." That year at SXSW she was probably the most hyped act of the entire festival, and she was scheduled to perform at a series of high-profile parties and showcases, but she ended up canceling about half of her appearances. So my fellow Yahoo! staffers and I weren't entirely convinced that our shoot would go on as planned, until we actually saw Amy arrive.

But when Amy finally arrived, oh boy, she arrived in style. The scene was like one of those old '80s commercials for E.F. Hutton. Everything stopped. Everyone fell silent. A star, albeit a somewhat tarnished one, had undeniably entered the room. This was not a normal person.

Dressed in skinny jeans (and I do mean skinny) and a sleeveless tee that showed off her copiously tattooed skinny arms, balancing a bouffant on her lollipop head that looked like it weighed more than she did, and compulsively sucking on an actual lollipop while simultaneously shuffling a deck of cards from one hand to another, Amy looked like T-R-O-U-B-L-E. But I liked her straight away. When she shook my hand, she gave me a little wink that almost made it seem like she was flirting with me--and I enjoyed it. She came across like the leader of some tough-as-acrylic-nails girl gang--like Grease's Rizzo, only British--and man, I wanted to join that gang. Amy was, in a word, cool.

Still, it was obvious she was a bit of a mess, and maybe very fragile behind her misleading tatted-up, tough-girl exterior. She explained that she sucked on her ubiquitous lollipops to ease her cravings as she tried to quit smoking. She explained that fidgeting with that deck of cards eased her nerves after breaking up with her boyfriend the night before. (I believe the boyfriend in question was chef/musician Alex Clare, not her infamous future ex-husband known to the world as "Blake Incarcerated.") She then went outside, sat on the sidewalk, shed her tank top, and kicked back on the concrete to bask in the Texas sun--in her bra. And this was not a bra that could pass for half-shirt or swimsuit top, but a full-on lace-trimmed, hook-and-eye-backed, adjustable-strapped, underwired, hospital-white garment straight out of Marks & Spencer's lingerie section. Sitting there in broad daylight on the highly foot-trafficked street, in her brassiere and winged eyeliner and not much else, Amy seemed oblivious as tourists strolled by and gawked at the beehive-topped spectacle on the grimy pavement. She just didn't care. She was just too cool to care. Or she was too...something.

Her interview was a wreck too, admittedly. While I was not the one conducting the interview, thankfully, I was in the room, and it was downright painful to watch as my well-meaning and well-prepared co-worker asked her question after valid question, yet she answered monosyllabically and almost defensively while he squirmed. There was so much uncomfortable silence between the questions and answers, I could actually hear the electrical hum of the video equipment and studio lights. Nothing about Amy seemed to come easy. She was a complicated woman, to put it mildly.

But then...Amy's acoustic guitarist joined her. And Amy sang. And that is when everything fell into place. Singing was one thing that came easy to Amy.

In her tragic later years, Amy became known for her shambolic performances (and her canceled ones), but that fine SXSW day, she was magic, not tragic. She magnificently belted out "Rehab" and "You Know I'm No Good," nailing each song in one take, and her whiskey-gargled voice was one of the most unique I'd ever heard. Accompanied by nothing but her guitar player and doing nothing but sitting on a stool with her heavily mascara'd eyes half-closed, she exhibited more presence and true star quality than most pop starlets manage with all of their costume changes, backup dancers, and multi-tracked vocal effects. Amy was clearly the real deal, and it was actually BECAUSE she was such a mess that her music connected. It was because tunes like "Rehab" and "You Know I'm No Good" weren't novelty songs, and weren't just recorded for shock value, but were real-messy-life tales pulled from the wine-and-nicotine-stained pages of her own fascinating diary.

I never saw Amy Winehouse perform again after that special day. Most of her SXSW gigs that weekend never happened, and my plans to see her play the following week at the Spaceland club in Los Angeles fell through when she canceled that appearance the day of the show. (I still have the tickets; either I'd over-optimistically hoped that there'd be a makeup date someday, or deep down I knew those tickets would one day have historical value.) Later on I attended the V Festival in England and California's Coachella fest in hopes of seeing her rock a proper large stage, but she pulled out of those events at the last minute too. And now, I'll never have the chance to see her sing again.

But perhaps it is for the best that I only recall Amy in her prime--stripped (both literally and acoustically) and just singing her tattooed heart out, before she became better known for her tabloid marriage, tabloid divorce, bar brawls, drug arrests, court appearances, rehab stints, and failed comeback attempts. Because once she started careening along her seemingly unstoppable downward spiral, she no longer seemed so "cool" anymore. Now, she was just plain sad. I wouldn't have wanted to witness a travesty like her disastrous Serbia concert this past June, when she hit the stage an hour late and was inebriated to the point of being unable to sing an entire chorus. (Witnesses claimed bodyguards pushed her onstage and forced her to perform, despite her condition.) The Serbian press dubbed that concert "the worst in the history of Belgrade," and her European tour was subsequently canceled.

I was, I admit, hoping that her tour's cancelation would give Amy time to rest, recuperate, and yes, go to rehab again...because I'd never given up hope that she would finally get it together and record a follow-up to Back To Black. Amy had been frustratingly missing in action since that album swept the Grammys in early 2008, and during her lengthy hiatus other rebel-divas, like Britain's similarly soulful Duffy, Florence Welch, Jessie J, and especially Adele, and the similarly sassy Lady Gaga, Ke$ha, and Katy Perry, had all come along and stolen her thunder. Snooki from "Jersey Shore" practically even stole her hairstyle. It was starting to seem like Amy's career had gone back to black, for good--yet I still believed she had it in her to record another Grammy-worthy classic and reclaim her old glory. Sadly, as we all know now, that was not meant to be. Mitch Winehouse, Amy's jazz-singing, taxi-driving father, actually put out a new album out before she did.

Amy's final released recording was for Quincy Jones's allstar album Q: Soul Bossa Nostra last year; while that track reunited her with Mark Ronson, the superproducer who helmed Back To Black and made her a star, the product of this reunion, a cover of Lesley Gore's "It's My Party (And I'll Cry If I Want To)," didn't come close to the greatness of anything on Back To Black (or Amy's remake of the Zutons' "Valerie," arguably the best cut on Mark's 2007 covers album, Version). Amy sounded stinking drunk, or just not at all lucid, on the slurry recording, which was widely panned. If there is unreleased Winehouse music in the vaults, it's likely that some opportunist will unearth it and get it out in the marketplace soon enough (we all witnessed what Sony did with Michael Jackson's unfinished recordings), but it might be best to leave such recordings unmastered and unheard, if they sound so incohrent and sloppy. Yes, I always wanted to hear new Amy music...but not like that. Amy should really be remembered for her finest work.

Truly, Amy Winehouse should be remembered the way I choose to remember her, based on my one encounter with her on a Texas sidewalk four years ago: as a very troubled, but very talented, old soul.

And yes, she was cool.

Follow me on Twitter, Instagram, Amazon, Tumblr