“Amy with Lipstick” was never meant to happen
The photo was taken in July 2003. Amy and I were due to shoot a series of images for the inlay of the artwork that would accompany her debut album Frank. We had already shot the cover in London, and the original concept for this next set was to create something relaxed and intimate at her home in Camden. There were scheduling conflicts. We ended up with 24 hours in New York.
I was 21 years old, and this was my first photo assignment. We were about to get started when a very long and immense thunderstorm washed away all of our original plans. On the night we were scheduled to shoot, we were stuck in a hotel room, and mild panic was setting in.
We woke up the following morning with only a few hours before Amy had to fly to Miami. It was time to improvise. I took Amy to my cousin’s apartment, where she sat on the floor and pulled several outfits out of her suitcase. Before I knew it, she was putting her hair up into a beehive.
The photo of her putting on lipstick was taken just as she finished getting ready. She had bought the lightning earrings the day before from Patricia Fields’s store in Soho, and the dress was one she’d brought from London.
I was trying to be as cinematic as I could with the image; photographing Amy in profile and giving the audience as much of a narrative as possible within a single frame. This was Amy Winehouse in Manhattan, maybe a ‘60s version of the city, getting ready to go downtown and perform in a club, or to meet friends over a whisky sour. I love this shot – I see it as a testament to how great things can come out of complicated circumstances.