My year with Amy Winehouse: What I learned watching her through paparazzi lenses

As a photo editor at Rolling Stone, I became obsessed with the singer as she broke out and fell apart in public

By Rachel Hulin

Published January 17, 2017 12:00AM (EST)

Amy Winehouse   (Getty/Bryan Bedder)
Amy Winehouse (Getty/Bryan Bedder)

In 2006 I was a photo editor at Rolling Stone. This was a title that impressed my grandmother, and signaled to her an enormous improvement in my career after the previous few years I’d spent working at an online sex magazine. “But there are think pieces!” I’d told her. Still, I was happy for the change of subject — at 28 I hoped I was finally on my way.

At my new post, I soon learned that I wasn't the good kind of photo editor — the kind who assigns portraits of celebrities to a carefully chosen photographer and creates a feature or cover shoot. I was the other kind of photo editor (the now nearly ubiquitous kind) who spends most of their time scouring an image portal and then posts the properly cropped and cleverly captioned spoils on the Internet. At Rolling Stone we had access to thousands of images, which were constantly being loaded into the system — many were hard news pictures, but there was also a trove of paparazzi footage, which appeared in front of me almost in real-time.

My new job was an endless, intoxicating, visual buffet of the moment-to-moment reality of other (famous) people’s lives, and I was instantly addicted.  These lives became my daily stories, and 2006 was a good year for it.

There was a lot going on with Pete Wentz and Fall Out Boy, various Kevin Federline dramas, Gnarls Barkley, the requisite overdoses and breakups, and of course Christina Aguilera — but no one affected me the way Amy Winehouse did. Perhaps it was because her meteoric rise almost exactly coincided with my arrival at my new post, or that she was so quickly out of control in a way that I recognized, but it was undeniable that she had a magnetic, tragic air coupled with a shocking level of talent.

At first I couldn’t figure out exactly who or what Amy was — she just appeared one day in the photo editing system — her hair in the bouffant that was so particular and peculiar, her eye makeup aggressively accentuated. She was simultaneously tiny and huge. There were just a few pictures of her early that fall, and then “Back to Black” came out, and it was a torrent. Thousands a week. Many of them were stage shots, but I also saw the others. Amy quiet in the back seat of cars. Amy without eye makeup, Amy walking sullenly with her father, Amy running in alleys. The images, which were uploaded in a hurry, often included shots of other photographers’ cars, running photographers and fans, blinding flashes, crowds, and speeding Escalades carrying Amy away with her hand over her face.

Amy had these shoes she would wear — lovely pink ballet slippers that had been dragged through London gutters. It was sort of ridiculous that she’d chosen these shoes to wear every day — they were so easily marred. They quickly became gray and torn and then almost grotesque. “Get some boots, Amy!” I wanted to tell her. “Get her a box of fresh ballet shoes!” I wanted to tell her boyfriend Blake. I knew a lot about Blake too. I could search for him in the keywords. The metadata was very detailed. Eventually I could go on the grid and look for “Amy” and “vomit” and get 33 results.

I’d listen to Amy on the subway ride home, trudging the mile from my stop to the home I shared with a delightful person I had no future with. I’d stop at the bar and bemoan my lack of a washer and dryer and a savings account and then feel disgusted with myself for not enjoying my incredible good fortune in life. Sometimes Amy would be playing on the bar radio. Sometimes I’d dream of her.

I wondered how I had gotten so wrapped up in looking at someone whom I would never know. In college I had been an art history major because I was too intimidated to take the writing classes; as a freshman I already felt helplessly behind and unprepared. As finals neared, hundreds of us would gather at slide light tables outside the lecture hall to memorize the pictures we’d be tested on. I learned about world history through the images that mirrored it. Now I was watching other women unravel. I’d never meant to be just the observer.

“Back to Black” played on repeat in the office for months. Even the jaded career music journalists were smitten with Amy’s spectacular gifts. She got under everyone's skin.

Each morning I came into the office, I’d check on Amy first thing. I tried to choose good pictures when I’d post about her, not the ones of her falling off the stage. Something accurate, but not humiliating. That place in the middle. I never thought of myself as complicit in Amy’s haunting because I loved her. I wanted her to succeed. I was angry at the paparazzi who hounded her, not really thinking that I myself was — through transitive property — one of the people demanding the images.

I watched Britney too, that year — in a bald rage with a baseball bat after an apparent domestic issue. I was quite proud of her for shaving her head and expressing her anger. Maybe it was a psychotic episode, or perhaps just a reasonable reaction to her situation; either way it translated as brave to me. I had a strange headache that particular day, the kind with sparkly dots in my vision field, after combining a lot of Pinot Grigio with Klonopin, which seemed at the time like a normal thing to do on a Tuesday night. I was feeling uncomfortable, like I’d lost the thread of something. That sex magazine was actually a great job; I’d written a brave essay about my own body there just before I left, but now I wasn’t writing at all.

One day, Courtney Love came to the office. It happened periodically that a big star would come visit, but I was rarely able to meet them, being so low on the totem pole. This time everyone was included. We all crammed into a conference room, sitting cross-legged against the wall, tight against each other and sneaking bits of the catering. Courtney sang us a few songs a cappella with such gravitational power that I put down my hard-won chocolate-covered strawberry out of respect. I remember the bloody smear it made as I folded it in my napkin. Courtney was buzzy and electric and poised. She was alive in her own self, in that moment fully comfortable in her skin.

Amy never righted the ship. When I heard about her death a few years later it was clear that she would leave a legacy of greatness. That was a comfort.

By then I’d been at three more publications, freelancing, writing a bit about photography, about other people’s work and ways of seeing. Then I started a secret blog just for myself called Harry and Matilda. Matilda would confess her fears and shame to Harry, and Harry — in his own way — would absolve her. Matilda drinks an enormous amount. She’s in love with the wrong person. She’s just full of shame and joy and fearlessness and she very often does the wrong thing. It became an Instagram account, and eventually a book.

Another writer I know has a post-it note stuck to her computer for motivation that says: “You’re going to die anyway.”

You may as well do it. I guess Amy taught me that.

Rachel Hulin

Rachel Hulin is a writer and photographer. Her debut novel, "Hey Harry, Hey Matilda," publishes from Doubleday on January 17. Her personal essays and writing about photography have appeared in Rolling Stone, Nerve, Radar Magazine, Huffington Post and The Daily Beast. Hulin has a BA from Brown University and an MA from NYU. She lives with her husband and two children in Providence, Rhode Island. More info can be found at and you can follow Rachel Hulin

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Amy Winehouse Celebrity Life Stories Music Paparazzi Rolling Stone