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Artist Profile | Tim O’Brien: Powerful Portraits

New York artist built career on intimate, intricate portraits of iconic figures.

Erica Riveraby Erica Rivera
Artwork: Napoleon by Tim O’Brien for Smithsonian magazine.

In 2002, Tim O’Brien got the call. It was from an art director at Time, asking the New York-based illustrator do a portrait of Osama Bin Laden with an X over his face for the magazine’s cover. Though other news media hadn’t picked up the story yet, it was believed that Bin Laden had been killed in Afghanistan.

O’Brien completed the assignment, but didn’t hear back from Time‘s art director until the end of the week. The story had gone cold. The cover would have to wait. Weeks, months, years—nine years to be exact—passed, until May 2, 2011, when confirmation arrived that Bin Laden had been killed by Special Forces in Pakistan. O’Brien received another call, this time from Time’s former and current art directors. The magazine cover would finally run.

Osama Bin Laden by Tim O Brien for Time Magazine

Artwork: Osama Bin Laden by Tim O’Brien for Time magazine.

“It was a long delay, but I got to see that cover finally come out and it was all over the world in one day. It was a remarkable moment to be a part of,” O’Brien says.

What’s most remarkable about the artist’s depiction of the founder and leader of Al-Qaeda is the expression on his face. It’s not hostile, nor self-satisfied. It’s placid. Almost peaceful.

“The easy way to go is to make him look really devious and evil and put an X on his face, but I make him look neutral, so that for a moment, just a fleeting moment, you see that Bin Laden was a human being,” O’Brien explains. “It’s a more interesting piece. Not that I want anyone to feel empathy for Bin Laden, but that’s where the image becomes more powerful.”

O’Brien replicates this subtle, non-expression technique throughout his vast oeuvre of portraiture that includes the likenesses of Muhammad Ali, Einstein, Fidel Castro, Gandhi, Steve Jobs, and Vladimir Putin, among many others. The lack of easily identifiable emotion allows the viewer to project whatever he feels about the subject onto the work. It also keeps O’Brien’s own politics out of the equation. The artist thinks of President Barack Obama, for example, as a “great human being”, but his portraits wouldn’t give that away. Obama is depicted as stoic and serious, neither instantly likable or unlikable. O’Brien anticipates he’ll bestow the same courtesy on President-elect Donald Trump as well, but admits it will be harder, especially as cartoonish interpretations of Trump are all the rage these days.

Whatever your opinions on O’Brien’s subjects, there’s no debate that his portraits are perfection. Skin and hair are so detailed as to seem tactile. Every wrinkle, every whisker, every bead of sweat is life-like. The subjects engage the viewer with intimate, compelling gazes. O’Brien’s ability to infuse the rich and powerful both with a sense of luxurious timelessness and relatable humanity make his work exceptionally awe-inspiring.

Artwork: Beyoncé by Tim OBrien for Entertainment Weekly.

Artwork: Detail of Beyoncé by Tim O’Brien for Entertainment Weekly.

O’Brien’s depictions of pop culture are “on fleek” as well (if the kids still say that these days). From a heavenly-lit Notorious BIG to a polka dot bow-tied Michael Jackson to the lavishly dressed Queen Bey, the artist makes these larger-than-life figures look, well, more real than they do in real life.

“I don’t wake up and think, ‘I’m going to do a pop culture image today,’” O’Brien says. “They happen organically or it’s an assignment. Beyoncé was an assignment [for Entertainment Weekly]. I love Beyoncé, but I didn’t think to paint her until they called and said, ‘Would you paint her?’”

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Plum gigs like the Bin Laden and Beyoncé assignments aren’t the only reasons O’Brien loves what he does. “On the creative side, there are certain assignments that make you feel like a real artist, a real mind,” he says. One of his favorite working scenarios is when art directors provide him with a problem to solve. For Nautilus, a science magazine, he’s been tasked with esoteric assignments, like illustrating articles about the space between objects or the scale between objects. For the latter, he did a painting of a bird on a bottle (below). Landscapes are present inside and outside the bottle. It’s poetically meta. These kinds of assignments “allow for lots of metaphors. It’s really great turf for that kind of thing,” he says. “It’s a way for me to do a beautiful painting and it still works to solve a problem. In that way, I feel really satisfied.”

Artwork: Tim OBrien for Nautilus magazine.

Artwork: Tim O’Brien for Nautilus magazine.

Granted, the conceptual images aren’t as popular as the pop culture pieces on platforms like social media. “Those don’t go viral as quickly as ‘Black Elvis’, for instance, or a Charlie Brown painting. That kind of image goes viral because everyone has a common understanding of the subject matter. That’s sort of built in.”

But at this point in his 30-year career, O’Brien doesn’t exactly need social media’s help to get noticed. His work has graced the covers of Atlantic Monthly, Harper’s, and Rolling Stone (just to name a few). Esquire, the New York Times, and Playboy have also sought out his expertise. His awards and speaking engagements are numerous.

In addition to portraiture and editorial illustration, O’Brien also does advertising work and book covers. (Perhaps you’ve seen a little series called The Hunger Games?) “That’s really what I like most about being an illustrator: the variety,” he says. As if all that didn’t keep him busy enough, he’s also the president of Society of Illustrators and a professor at the Pratt Institute. “I do learn from my students although I don’t really adapt their style,” he says. “You get an idea of what the zeitgeist of the day is—according to a 21-year-old—through teaching.”

It was in school that O’Brien himself discovered an affinity for illustration. Though he had been out-drawing his contemporaries since preschool, it was during his senior year at Connecticut’s Paier College of Art that he landed an agent and his career began to take off.

“The business has changed, but I keep reinventing myself,” he says. The constant turnover of art directors also pushes him in new directions. “I work with art directors who are in their early 20s, who weren’t born when I started as an illustrator and now they come to me and they don’t always know who I am, they just like some piece I’ve done, so I have to start all over again. They have a whole new perspective on the world and they’ll ask you to do things you haven’t thought of. The collaboration I have with art directors is one of the ways I stay fresh. I really enjoy it.”