Amy Winehouse: I Knew She Was No Good

Credit: Gil Kaufman

Photo by Gil Kaufman/MTV News

I've been to 50 shows, maybe 100, where I was assured I was seeing the next big thing. And most of the time, sadly, I was seeing something, but it wasn't big and it was hardly a thing.

But this one felt different.

There was something off about Amy Winehouse when I first laid eyes on her in March of 2007. Here was this latest British next big thing, a truly buzzed-about artist with a larger-than-life persona who shuffled out on stage and looked like a hyper-realized version of 1,000 other hipster chicks at that year's South by Southwest music festival in Austin.

From the big, retro gold doorknocker earrings, to the towering 1950s beehive with the blonde streak up front, the gold anchor necklace pendant, pin-up girl bicep tats and cat-eye mascara, Winehouse made an impression, sure.

But she was intensely shy, even awkward, on stage. That is, when she finally got to the stage.

She, of course, showed up horribly late, an almost unforgivable sin at SXSW, where showcases are run like clockwork. Her voice was as promised, a massive instrument, deep and rich, well-lived in for a woman in her early twenties. Too well lived-in, if I'm being honest. But that's what made her stand out. The whole wise-beyond-her-years effect. Though, looking back (and the thought might have occurred to me even then), I'm not sure it was wisdom that had rung those miles up.

Amy Winehouse

It was a day party for the British music industry. The tent was set up on a lot just outside the convention center on what I remember as an oppressively hot Austin day. The line was typical, a giant snake that ran down one block and around the corner, filled with too-cool-for-schoolers obsessively checking their phones, trying to figure out where they'd go next if this was a bust and there was a cooler place to be.

There was no way to get in.

The two curt publicists at the front of the line told me that in no uncertain terms, just like they told everyone else. "Capacity, we can't, the fire marshal is already here," said one without making eye contact. I nodded, looked down the line and realized nobody was leaving, they were all going to get in somehow. They had to. It was their duty to check this one off their list.

Nobody was getting in. But I got in. Perhaps not my finest moment, but sometimes you gotta do what you gotta do.

I grabbed some truly awful Mexican food and stale tortilla chips and wolfed them down, before pushing my way to the front of the small, low stage in the tent. And I waited, and waited. Winehouse was 45 minutes late, at least.

When she strolled out the crowd erupted, but I was a bit surprised at what I saw. Here was this already mythical figure in filthy, ratty ballet slippers with what looked like dried blood on them, body hugging skinny jeans that hadn't been washed in ages, a food-stained white sleeveless T-shirt, a little silver stud above her lip and the already mythical cascading mane of black hair, offset by that very heavy eyeliner.

Her arms, often held out over her head in a kind of surrender pose or hidden behind her back, were cross-hatched with scratches (maybe cuts), another ominous sign that this girl was troubled, or danger, or some scary combination of both. She sounded boozy, looked a little woozy, but never lost a note. She didn't seem drunk, or high, just enveloped in a kind of thick, mellow fog that made her seem ultra cool, even in the harsh light of day.

I was so close I could hear her breathing between notes during the four-song acoustic set that included her future hits "Rehab" and "You Know I'm No Good."

She was great. Impossible to take your eyes off of and obviously a superstar in the making. But she was also hard to watch. Twitchy, uncomfortable in her own skin, Winehouse clearly loved performing, but seemed unsure what to do with herself.

She mumbled thank yous and avoided eye contact.

And okay, maybe great isn't the right word. She was really, really good, but also a bit too laid back. At times you felt like this – what I believe was one of her first major U.S. shows in front of a tastemaker audience – really didn't mean that much to her. Not just the pose of not meaning much. When you're that new, you're supposed to act like you want it a bit more and she just didn't. I guess that's what made her seem even cooler.

I had dozens of bands on my list that night to check out, but I decided to ditch them all to try and squeeze into a full, plugged-in Winehouse set. She was, of course, late. Not just late, but epically late. Like, two hours, which is a cardinal sin in Austin. And the show was practically impossible to get into, but again, I found a way.

While I whiled away the hours, I snuck upstairs into her dressing room (I used to do a lot of this kind of thing) and I ran into Flaming Lips singer Wayne Coyne. We started chatting and I noticed he was staring out over my shoulder, which is not unusual at industry gatherings, but was a bit odd for Wayne, who usually maintained good eye contact during our chats. He was lasered in on Winehouse, who was sequestered in another room, surrounded by bodyguards and various label folk.

Coyne was a well-established star in his own right, but you could tell he was entranced by the expanding Cult of Winehouse. He said he was supposed to interview her later that night, but it got called off and I could tell he was disappointed. Just standing there a few feet from Amy, you could feel this electricity around her, even if she seemed numb to it.

Amy Winehouse 2

The set, when it did come off, was worth the wait. Winehouse was energetic, playful and her backing band, the peerless Dap-Kings, were in full swing, providing sassy, brassy backup and full support to Winehouse's thrilling vocals. That night she delivered on the promise and while her too-cool pose was still in effect, she earned it by making that swagger fill the room.

I only saw her those two times, but the images of Winehouse from those shows stuck with me over the years. Admittedly, I often joined in the macabre parlor games that professional journalists engage in when their beat includes a star whose rap sheet and rehab tally exceeds their recorded output.

But every time I had to write yet another sad story about her latest trip to rehab, punch up at a local pub, bloody fight with a boyfriend/husband, gig canceled due to her inability to shake her demons and, sadly, her death at age 27 on Saturday, I thought of that first day in the tent in 2007.

I thought of how great it would be if she could prove us all wrong, get right and put out another world-beating album that lived up to her brightest moment, if only to shut up cynical bastards like me. I wanted to be wrong about her, to be wrong about someone like her, just this one time.

I thought of how great she was if you closed your eyes and let her soul-stirring vocals into your heart and shut out all the other offstage noise and nonsense. And how when you opened them up again you saw that fragile lost soul who could never find a path out of that midnight black pain she was singing about.

I guess now I'll just have to listen with my eyes shut if I want to remember that feeling.