Cartoonist Adrian Tomine reflects on 20 years of New Yorker illustrations

About 20 years ago, cartoonist Adrian Tomine experienced two simultaneous major life events: he moved from California to Brooklyn, where he has lived ever since, and he landed his first New Yorker cover.

His instantly recognizable New Yorker covers, which feature keen observations and romance-tinged glimpses of life in the city, are among his most famous works. And for the first time ever, a collection of his covers and other drawings from inside The New Yorker are being shown at the 92nd Street Y.

Tomine, 48, says he is honored that 40 large-sized prints of his work will be on display at the exhibition inside the Y’s Weill Art Gallery through March 13.

“This was an institution that I knew of before I even moved to New York, this place in the city where you can just go see these incredibly high-caliber artists or writers,” Tomine told Gothamist.

Around the same time he landed his first New Yorker cover, he also started work on the comic that would eventually become his acclaimed graphic novel, "Shortcomings." Tomine recently adapted it into a screenplay, and the film, which was directed by Randall Park, premiered at the Sundance Film Festival in January.

“Having an exhibition of work that really had a starting point around 2004, and to be talking about a movie that's based on material that I was working on at that same time … it makes me feel old,” he said. “As a cartoonist, you gotta be very careful because nostalgia is a trap for all of us, and we're naturally very nostalgic people.“

Landing his first New Yorker cover

Tomine had self-published comics as a teen before comics publisher Drawn & Quarterly began releasing his “Optic Nerve” series in 1995. He was still living in California in 1999 when he started getting work at The New Yorker.

“The No. 1 question that I get asked by aspiring illustrators [is] how I got into The New Yorker, and I have to admit that the answer is probably much too infuriating for me to actually be honest about,” he said.

Tomine, then in his 20s, was on vacation in the city when he decided “on a whim” to look up The New Yorker in the phone book, and drop off some samples of his illustration work at their offices in person. “I was an arrogant, young, ambitious kid,” he said.

There was no security at the building on West 43rd Street when he arrived, he said, so he took the elevator upstairs. “I knocked on their door and asked the receptionist if I could leave this portfolio — it was just a folder of tear sheets — and he nodded and allowed me to do it,” he said. “I remember on the front [of the portfolio] I had written my name and my fax number in a Sharpie because that was the way that illustrators corresponded with their employers at the time.”

Art director Chris Curry got in touch with him a few weeks later, and offered him the chance to draw the band Luscious Jackson in the front calendar section.

“I did a terrible job and I hate the illustration, but I got my foot in the door!” he said. (Luscious Jackson did not hate it.) “I think this is an example of this career that I've built on the opportunities given to me by people who've taken a chance on me before I really deserved it.”

He did a lot of interior work for the magazine’s movie reviews and fiction sections in the following years, and officially moved to New York in 2003, spending much of his time sketching people on the subway as he got familiar with his new home.

“I can go months of just wandering around New York going about my business, but if I take the time to get out my sketchbook and draw, I will always notice something that I wouldn't have noticed otherwise,” he said.

His first New Yorker cover was the Nov. 8, 2004 issue. “Missed Connections” features two people in separate subway cars who spot each other reading the same book as the trains pass. He credits arts editor Francoise Mouly with encouraging him to submit it.

“I was so intimidated by that idea [of submitting for the cover] and I had no idea how to go about doing it,” Tomine said. “I think there's a part of me that tends to shy away from intimidating opportunities, even though they would be good for me. Left to my own devices, I might have just never done a cover, but Francoise was very tenacious.” He has worked with her on every subsequent cover he’s done since then – about 20 in total.

In a collection of his work from 2012, Tomine called “Missed Connections” likely his “best-known drawing.” He acknowledges it’s a piece that still resonates today.

“For a number of years after it was published, I would see it appropriated and people would do parodies of it [or] sell bootleg prints of it on a folded table,” he said. “I remember just feeling like, wow, it's weird to see my work as part of the culture, not necessarily specific to me as an artist.”

He believes the best New Yorker covers capture an experience that people have had at some point in the city, and include lots of small details that pop out at locals, like getting the coloring and feel of the subway exactly right. Or as with “Love Life,” his cover art on the Dec. 7, 2020 issue, it was capturing the messy realism of pandemic-era dating.

While some artists are given specific themes or topics to illustrate, Tomine generally shies away from such timely material.

“There's just so many people who are better and faster at that,” he said. “I think it's good to have a few players like me on the bench so they can accept an image and then they'll squeeze it in when there isn't something more important going on.”

What’s next

In recent years, he’s been consumed with adapting “Shortcomings” into a film, which has pushed him out of his normal work comfort zone.

“For 30 years, I'd been working completely on my own without any kind of collaboration, without any kind of compromise, without any kind of coworkers,” he said. “In movie terms, [I was] the head of all departments, not just the writing or the directing, but costume design and hair and makeup, and I was making every little decision on my own.”

Getting to attend the movie’s premiere at Sundance and seeing people’s real-time reactions to his work was a “top five life experience” as well.

Now that “Shortcomings” is complete, he’s pushing himself to work on more film scripts, and even a stage play. He also has a definitive collection of all his illustration work coming from Drawn & Quarterly. Eventually, he expects to return to his regular cartooning and illustration work.

Tomine currently lives in Park Slope with his wife and two children, and although he’s lived in the city longer than anywhere else in his life, he’s still adapting to some things, like getting over the sight of rats running across the sidewalk or ripped-open garbage bags with dogs peeing on them.

It’s “been a really slow evolution," he said. "Now that I've gone through this process, I don't really trust someone who moves to New York and the following week declares himself a New Yorker. I've been here 20 years, and I still feel like I'm an outsider who is learning to get comfortable and become familiar with the city."