Meet Stanley Chow, the Artist Who Draws All The New Yorker’s Contributor Portraits

“The problem with writers is some of them just don’t like having their pictures taken,” said Stanley Chow, who’s been drawing The New Yorker’s contributor portraits since 2012. “They’ll send you a shitty little tiny JPEG, and you have to work from that.” Usually, it takes him between half an hour and an hour to finish each illustration. “I get $400 for a portrait,” he said, “so in terms of hourly wage, I’m doing alright.” But sometimes, he’ll go back and forth on revisions as many as three or four times to fine-tune a portrait so the contributor is happy. “Normally, they’ll say, ‘Can I have my eyebrows further apart or my smile bigger?’ Well, if you can actually show me a photograph where you’re smiling, maybe I can draw you with a smile,” he said. “If they’re going to send me all their pictures of glum expressions, they’re going to have a glum face. I can’t invent a smile if it doesn’t exist.”

Chow was born, raised, and lives in Manchester in the north of England, more than 3,000 miles away from The New Yorker’s offices. “I think I piss off a lot of New York artists,” he said of his work with the magazine, “purely because they can’t even achieve that while being in the city.” He started drawing on wrapping paper in his parent’s combo fish and chip and Chinese takeaway shop, but he didn’t learn about the magazine until art school. “A teacher said to me, ‘If you get in The New Yorker, you’ve made it,’” he recalled. “It was like Time magazine. It was famous. So those two always stuck in my head. I never read them. The cost of reading The New Yorker here is doubled, obviously, because you have to pay import prices.”

He broke into the magazine for the first time in 2008, after a USB stick he designed for the White Stripes won him a Grammy nomination in the “Best Boxed or Special Limited Edition Package” category. But he didn’t start working for The New Yorker regularly until after Wyatt Mitchell joined the magazine as creative director in December 2011. “He’s a big soccer fan, and I’m a big soccer fan,” Chow said. “I spent years just posting soccer illustrations on the internet, and he said, ‘Look, I’ve seen all your soccer pictures all over the internet. I want them in our magazine.’ And that was that, really.” Chow’s work appeared regularly in print until Mitchell moved on to a new job at Apple in 2015. He illustrates articles less frequently now, but his contributor portraits have become a fixture.

“Sometimes, I just don’t think I get enough credit for this job,” Chow said. “I’m the only one that fucking does it.” Despite this uniqueness, he worries about his job security. “I get paid for each one. There’s no contract, so they could just fire me whenever they feel like it. The fact that they keep coming back is always encouraging. They really should put me on a retainer or something,” he said before adding, “I do think they’re going to sack me at some point. It’s a matter of when. I think the thing keeping them from sacking me is it’s going to cost them a lot of money to redo all of them in the same style. So they’re thinking, ‘How many dollars do we pay Stan? That’s a few hundred dollars times a few hundred people. Ah, nah, we’ll just keep him.’”

Almost ten years after he started doing the portraits, the contributors have changed, both in that new people are writing for the magazine and that the old ones have only gotten older. “Some of the early ones, I’ve had to update because either their hair has gone gray or they’re wearing glasses or whatever.” Usually, as Chow understands it, the writer points out that something about their look has changed and asks for the portrait to be updated. “I don’t know what half of them look like now,” he said, “but I have noticed if you go on their Twitter, some of them have literally had theirs for ten years. Emily Nussbaum must have changed now from the image that I gave her ten years ago.”

All these years later, his goals are about getting into the magazine. “For me, the bucket list is actually to get a New Yorker cover,” he said. “I think that’s the holy grail for most artists. It’s a difficult club to break into, but once you’re in, you’re in.”