You may not know his name, but you’ve probably seen the work of the illustrator Risko. If you’ve ever read an issue of Vanity Fair, for example, you’re familiar with his work because it’s on the last page of the magazine. He does the celebrity portraits which accompany the Proust Questionnaire. So when V magazine sought out the most important illustrators for its May issue, Risko was an obvious inspiration. I met Risko in New York, and we dished on how he got started (Warhol, of course) and what makes an easily illustrated face. Read my interview and see four of his works inspired by four of the most important faces of fashion — Giorgio Armani, Donatella Versace, Ralph Lauren and Karl Lagerfeld Lagerfeld — below. But first, Risko’s portrait of me, which hangs proudly in the loo of my New York City apartment. (I wanted to hang it somewhere I was sure everyone would see it.)

Many artists have idolized Andy Warhol, but few have had the guts to walk up to him at a signing and ask for a job. Such was the all-or-nothing approach of illustrator and artist Robert Risko, then 22, now known only by his last name. “I was pretty ballsy back then,” says the world’s most celebrated caricaturist, 56, who like the King of Pop Art grew up in Western Pennsylvania. “Of course Warhol was the hero of Pittsburgh. He was my role model. I mean, my God! When I saw his Marilyn Monroe, I thought…I get it.”

Risko’s talent for composition emerged when he was five years old in profiles he drew of his sister and again a few years later in sketches of his teacher, Sister Monica, at his Catholic middle school. At Kent College in Ohio, he thought he’d be a fine art painter and was influenced by Van Gogh and the Cubists. Yet friends always asked for his caricatures, and he found himself earning pocket money by drawing funny faces for passersby on the boardwalks of the Jersey Shore and Provincetown, Rhode Island. “But I wasn’t happy drawing caricatures for people on the street for $5 when I knew I had talent as a painter. So when I moved to New York, in 1976, I said, I’m going to fuse these things together. I’m going to take my love for Cubism and combine it with the ability to do likenesses and raise the level of taste of the average man.” The result was a style influenced by Picasso, the Bauhaus movement, and 1930s Vanity Fair caricaturists Miguel Covarrubias and Paolo Garretto.

Which brings us to Warhol. “I met him while I was out for the day on Fire Island and he was signing copies of Interview with Halston,” Risko says. He waited in line with his copy, and when it was his turn to get Warhol’s signature, he showed him his portrait of Diana Ross. “And he said, ‘It looks exactly like her. That’s great.’ And I said, ‘Well, I think I should work for your magazine.’ That was that.” It was 1978 and he started doing caricatures for Interview, including an infamous cover of Dolly Parton. In the early 1980s, Risko was working part-time as a retoucher at Vanity Fair when the magazine poached him from Warhol’s Interview, much like they poached Annie Leibovitz from Rolling Stone. In the past four decades at VF, he has drawn politicians, actors, artists, divas, and anyone else of note; since 2002 his work has appeared on the back page of the magazine, with its Proust Questionnaire. His work has also appeared in The New Yorker, Rolling Stone, Playboy, and Esquire. Next up is a series of specially commissioned pieces for the Macy’s flagship in New York, which is currently undergoing a $40 million refurbishment. His portraits of Macy’s pioneers, like Madonna and her daughter, Lourdes, Florence Henderson, Al Roker, and Martha Stewart, will be hung in the top tier eatery, Stella 34 Trattoria.

What makes someone easy to draw? Clearly defined and contrasting facial features. Risko says he looks at the architecture of the face, which goes beyond decoration and makeup. “I think that’s what makes my work stand out, it’s anatomically focused,” he says, adding that sometimes subjects don’t recognize themselves at first. “Without all of the superficial icing, some people don’t know who they are.” Certain blondes, like Goldie Hawn and Jennifer Aniston, can be tough, because their public images rely so much on makeup (can you imagine Goldie without her false lashes?) or they have very soft features. But, he says, someone like Bill Cosby or Meryl Streep is fun to do.

One perk of being drawn by Risko is that his medium naturally flatters. “I’m the best skin doctor a person could ever have,” he laughs, likening his work to Egyptian hieroglyphs. “I’m convinced that Queen Nefertiti was a squat, four-foot-tall, short-necked woman who told whoever was drawing her picture, ‘Give me a longer neck. Longer!’ Sometimes I think I’m in the same business.”