1) We pulled a fabulous Benjamin Cho dress for Maggie Gyllenhaal to wear. She loved the dress and someone had the idea of using a fan to blow the dress out a little. The cover shot ended up being an adorable photo with her laughing and her ass completely hanging out.
2) Speaking of the Gyllenhaals... We were shooting Kirsten Dunst when her then-boyfriend Jake Gyllenhaal stopped by the shoot wearing snug-fitting dark indigo Levi's. This wasn't actually in the magazine, but it was magical.
3) Actor Leo Fitzpatrick arrived to the photo shoot for our Beautiful People issue with a black eye and a beaten up face. We later found out he had asked his friend to rough him up just for the shoot.
4) Every shoot with Björk.
5) Every shoot with Chloë Sevigny.
6) Joanna Newsom wearing Rodarte. Somehow this cover just captured the moment.
7) Stylist Timothy Reukauf and Nigel Barker (yes, Nigel Barker from America's Next Top Model) did a story called "You're So Vain" inspired by that season's Versace men's show. The sight of top male models with their hair in giant rollers to achieve the bouffant-y hair look was precious.
8) Kelly Osbourne showed up at her cover shoot wearing a black wig and a gigantic black bow for her head. (Four years later, she showed up at the 25th anniversary cover shoot with her own black Balmain jacket).
9) Our cover shoot with Jimmy Fallon had been scheduled for September 11, 2001. We had to totally rethink the whole issue and decided to photograph him wearing a "New York City" T-shirt. This shot still makes me smile.
10) We shot dreamboat DJ/producer Mark Ronson as a sexy nerd in Jil Sander and Cary Grant glasses.
11) Artist Marilyn Minter was dying to photograph fellow redhead Julianne Moore to showcase her freckles. Julianne agreed, and had extra freckles drawn on, bangs attached and water splashed repeatedly all over her face. SUCH a good sport!
12) Timothy Reukauf also styled a totally over-the-top fashion story at the Russian Tea Room entitled "The New Vulgarity," featuring sexy model Emmanuel at a urinal. Talk about high-low!
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