Tim O’Brien is a modern master of illustration, and one of the pre-eminent magazine cover illustrators of our time. He modestly describes himself as a “traditional oil painter,” which doesn’t begin to highlight the full range of his talents. As the most dominant Time magazine cover illustrator of this century, Tim has been the go-to artist for moments of historical import. From the overthrow of Saddam Hussein to the death of Osama bin Laden to the U.S. Presidential election, Tim’s covers have helped to define the public conversation and historical record. In the tradition of the classic Time covers artists of the 1940s-60s—Boris Artzybasheff, Ernest Hamlin Baker, and Boris Chaliapin—Tim has not only created compelling and engaging cover imagery, but has been part of the visual identity of the magazine (although he has a long way to go before he matches Chaliapin’s 413 Time covers!). But of course Tim’s body of work extends far beyond what he has created at Time, including editorial illustrations for countless magazines, stamps, posters, advertising imagery, and numerous book covers (my kids were excited to learn that he did the covers for the Hunger Games series!). Recently he has been creating a brilliant new legacy of cover illustrations with art director Maria Keehan at Smithsonian magazine.

When I was the design director of Entertainment Weekly, Tim created a series of memorable portraits for the magazine, many of them with smart, conceptual themes. Tim’s assignments were always an event: His then-rep would deliver the paintings late on deadline night, carrying them in a specially-constructed box to protect the image surface. The paintings would still be wet, and as the box was opened the smell of fresh oil paint would waft through the office, attracting a crowd of designers, who would marvel at the brilliant detailed brushstrokes and the luminous quality of the artwork. Equally impressive was the knowledge that Tim had created and delivered such a complex and detailed painting on Entertainment Weekly’s short turnaround deadline!

Tim’s deep visual wisdom and powerful wit are most evident on his conceptual illustrations. Some of my favorites include a Mitt Romney Halloween mask done for GQ magazine before the 2012 election, a sad and creepy portrait of Charlie Brown, a 2003 Time cover of a man whitewashing the face of Saddam Hussein, and a rabbit-duck done for Nautilus magazine. Looking at all of these you get a sense of Tim’s impressive range of styles and ever-evolving technical approaches (as well as his always spot-on graphic sensibilities). There is a lot of drama and power in each of his illustrations, oftentimes created with subtle changes of light and shadow.

Tim has a smart social media presence, especially on his Drawger blog, which features a lot of great behind-the-scenes explanations of image creation. As the current president of the Society of Illustrators, he is also using his voice (and talents) to help create a vibrant community for illustrators and illustration.

MY LIFE:
I was born in New Haven, Connecticut. As a child, I was aware that I could do something that others could not: I could draw exactly what I saw and could remember how to draw things not in front of me. This was a fun hobby as a child and it allowed me to really shine in most classes as “the artist.”

I have a blue-collar background. My grandparents came from Ireland, and my maternal grandparents from Quebec and an industrial town in Connecticut. Everyone worked hard in service jobs, and my mother, two brothers and I share that work ethic.

As a teen, I painted houses, worked in a meat market and cut lawns — typical suburban teen industry stuff. When I graduated from art school I didn’t have to take any supplementary jobs—finding illustration work right away—so I’ve been working as an illustrator since 1986. I augmented that work with teaching. I’m an adjunct professor at Pratt Institute and a distinguished adjunct professor at the University of the Arts.

I live in “Ditmas Park” Brooklyn, or “Flatbush,” or “Beverley Square West,” depending on whom you talk to. Cab drivers like Flatbush, real estate agents like Beverley Square West. I go for Ditmas Park. I’ve been married to Elizabeth Parisi, a creative director at Scholastic, for more than 20 years. We have a wonderful 15-year-old son, Cassius.

MY WORKSPACE:
I do my work at home, in my studio on the third floor of our Victorian house. It is often messy, but I know where everything is and I am quite productive in it. When I visit other artists’ studios I’m often amazed how neat their spaces are. I also feel I could really get some work done in those spaces, but I know in one week I’d destroy them and they would end up looking like mine. I’m at peace with my chaos.

HOW I MAKE MY ILLUSTRATIONS:
I am a traditional oil painter mostly, with some digital pre-production. The computer helps me arrive at unexpected solutions. My sketches are digital but I paint in the end in gouache, acrylic airbrush, then oil paint.

MY FIRST BIG BREAK:
My big break was a Time cover in 1989. It was not much work, a painting of a tear drop placed on a Gilbert Stewart portrait of George Washington. This early break in my career made editorial illustration seem like a REALLY attractive avenue of this business. I was a book cover artist at the beginning of my career, and this assignment created a lot of attention, and I liked that. With that cover experience, I made more of an effort to appeal to editorial art directors and that changed my career.

MY INFLUENCES:
Influences change over time but many have “on ramp” artists that help them find a clue to image making, that clarify how to tell a story or some reason to connect ideas into art, helping them onto “the highway.”  In high school I “found” a copy of Norman Rockwell: Illustrator. It was a generous book in that it helped me figure out how one makes a piece of art or a painting. I was also aesthetically drawn to boxing photography and the walls of my bedroom were covered with stark photos of boxers in action. The fluid movement, the lighting and dynamic poses had a real impact on how I thought visually. Finally, in college and onward, I learned about all kinds of artists: from Gottfried Helnwein, George Tooker, Mark Tansey; to Guy Billout, David Suter, and so many others. I have artists I like for their ideas and artists I like for their techniques. I tend to not follow the work of artists who work in my style. That can be dangerous.

MY MOST ADMIRED CREATIVE PERSON:
I suppose I would have to say I admire movie directors and the materials they get to work with: actors, cinematographers, etc. I come away from watching the work of say, David O. Russell, and my head is spinning. Ideas fly around and it can be so inspirational. Admire is a weird word. It is very close to envy. Of course I would not be telling the truth if I didn’t say that most of my illustration friends are extremely talented and their work and careers are always inspiring.

THE BIGGEST CHALLENGE OF WORKING ALONE:
Procrastination.

MY FAVORITE ART DIRECTOR:
As far as collaboration goes, I’ve been working with my wife, Elizabeth Parisi, for years. She challenges me, she pushes me, and I often learn something valuable in the process. I have worked with some fantastic art directors up at Time magazine over the years: Arthur Hochstein, Joe Zeff, and now D.W. Pine. They are such pros up there, and have always been so supportive and helpful, and just a breeze to work with. Lately, I’ve loved working with Maria Keehan, at Smithsonian magazine. We seem to work well together and she and I are working on a Napoleon piece right now. I think it will be a good one.

MY CREATIVE INSPIRATION:
I will say that early in my career and in college I pored over books and illustration annuals for clues of how to make professional looking images. Society of Illustrators annuals, Booth’s European Illustration Annuals, CA, AI, all of them were inspiring to me. Something happened several years ago, however—I felt that to be original I had to steer clear of studying styles so much, and focus on ideas and visual solutions instead. I now take in others’ work when I passively see it, mostly online, but don’t actively seek out images. Perhaps that’s a mistake, but for me, I need to wear blinders to stay within my personal space.

A MEMORABLE ASSIGNMENT FROM THE PAST YEAR:
I had an idea one day, did some sketches, and then wrote to Rolling Stone to say I had an illustration of Beck that I’d love to do. They were responsive and I pushed it a little more and the result was a record review for his Grammy Award winning album, Morning Phase. It got into most competitions and knowing that I initiated it all was so satisfying.

DREAM ASSIGNMENT:
I don’t want to brag, but truthfully, I’ve had my share of them already. Still, I’ve never done work for a long list of clients and working with those people would make me happy. Dream assignment? The Beatles and Apple Records decide to release something and need an album cover and want me. I would retire after that. Oh, and a Muhammad Ali postage stamp.

THE CHALLENGES OF CREATING A COVER ILLUSTRATION:
I have done a lot of covers and for that I am lucky. Covers focus many eyes on your work and in some cases make your work known outside of the illustration community. That is the great part of creating them. The challenge is twofold—first there are time constraints in many cases that puts these very public pieces of art under a microscope and thus it becomes a pressured situation. The second is that the nature of most covers is to simplify the image and thus sometimes the final image is simple, clean and concise but perhaps there is actually less to shine with. That visual restriction means that the image has to be perfect, or as perfect as it can be.

I got a real sense of how to build a cover image from years of doing paperback covers. The image and type need to sit together well and of course, as an illustrator, I feel the less type the better. My work in general looks like a series of one-frame movies. The lighting I use for portraits or an object is like stage lighting and I think it’s my willingness to hide visual information in low light or to simplify the image overall that allows for type to cover important areas without looking visually spotty. I must say though, I’ve been trained by some pretty talented art directors who’ve taken my sketches and cropped or picked images that I might not have. I’ve always asked them why that one and the answer adds to my knowledge base of why an image works and why a good sketch is not chosen.

If I could ever pull it together, there would be quite an exhibition of killed covers that even represent an alternative history. I’ve done covers of a potential presidential run announcement from Colin Powell, a guilty OJ Simpson, unused person of the year covers and others where the story changed. What all that taught me is that having the cover run is NOT what I focus on. I love them to run but what I care about is the working relationship and that the creative people and the editors appreciate what I’ve done.

WHEN A COVER GOES VIRAL:
I do think about how an image will play in a viral sense, but with many covers they wish to launch them first so I often have to wait until a cover comes out. Also, I sometimes have to sit on a cover for months, even years, because the cover didn’t run but may in the future. The Time Bin Laden cover was a nine-year wait. What I never hope for is a cover to go viral for the wrong reasons. I just want these covers to be compelling and to make the magazines shine that week or month.

MY FAVORITE COVER ILLUSTRATIONS:
I’ve done so many covers over the years and sometimes a cover is part of a national conversation. Time covers can still cross over to the general public and become memorable. The folks at Time have always been so professional and pleasant to work with and if they’re calling me, the chance is that it’s a big story about someone who will dominate the next news cycle.

The Gaddafi cover for Time where his head is sand blowing away was really a great time from start to finish. It was even up for a SPD cover of the year award. Der Spiegel is also a magazine that has used me for numerous covers over the years and their unique strength is how much help they provide in gathering reference—even suggesting what they want in a final with detailed digital comps. Sketches are really not even necessary.

Rolling Stone has provided me some memorable opportunities to do covers for them and while I’m doing these covers I imagine the subjects seeing these covers, even holding them. My David Bowie/Ziggy Stardust cover was like that and I could imagine Mr. Bowie standing, holding the magazine and looking at the painting.

SOME OF MY FAVORITE ILLUSTRATORS:
I admire so many talents for different reasons. If I start citing so many of my friends someone will be hurt that I missed them. Longevity has an obvious romance at this stage of my career so I tend to watch what friends in and around my age do to connect to the world. I also watch some as a cautionary tale and clearly won’t mention them here. As the new president of the Society of Illustrators and a member of that organization for so long, I know everyone. This is a wonderfully close community and we all inspire each other.

In the past three or four years I’ve watched the sharing of new work and process evolve on Facebook, Twitter, Instagram and Tumblr. That’s effective and some people do it well enough to make me interested in their work, so I follow that a bit.

HOW I STAY CURRENT:
I teach and through my students I see everything they are inspired by and learn who their heroes are and what inspires them. Through that process I can come to understand trends, where they come from and which artists are in their focus. I don’t think I’ve ever followed a trend.

I think many people might look at my work at the start of my career and what I do now and think I’ve changed very little, but I have. Earlier in my career I was more of a photorealist but over time I’ve let the tiny brushstrokes stay untouched and controlled my palette more, making the images more like paintings than photographic. My subject matter has changed too, I suppose.

These are stylistic changes but have little to do with the market. There are certain visual puns that I used to paint that are now easy Photoshop solutions. I went in another direction, attempting elegance and beauty.

SERVING AS PRESIDENT OF THE SOCIETY OF ILLUSTRATORS:
I clearly think that the Society of Illustrators is an important organization in the field of illustration. The mission is there to promote the work of illustrators past, present and future. This is a constant effort, and the staff and Anelle Miller, the executive director, work hard to make so many things happen in any given year, with multiple exhibitions, competitions, lectures, dinners, community outreach, and a myriad of other activities. My primary role is as a cheerleader and to lean on my colleagues to support the mission with membership. Ideally, every working illustrator would be a member, and I hope that others see the value during my presidency and join the Society.

HOW I PROMOTE MYSELF:
I had an agent for most of my career, and that afforded me the luxury of being able to just paint and let that part of the business fall in someone else’s lap. I’ve been solo for a year and a half now and am learning how to get my work seen and to connect with art directors. I do run up against not wanting to directly ask for work. I think we all like being asked first, and I grapple with wanting to work with certain art directors, and reaching out while making sure I don’t come off as needy. Most people I approach for work I do so out of respect for the work they assign and do.  

Direct e-mails are about the most I do. I don’t do mailers much, but I have portfolios on web directories all over the place. The combination of it all, plus a fortunate presence in competition annuals keeps me busy with work.

ADVICE FOR SOMEONE STARTING OUT:
Art directors LOVE finding new talent. That thrill of finding fresh energy and voices is strong with many people who use illustration. New illustrators should understand that if they are persistent, do brilliant work and if they keep being industrious they will get work. Also, I see many students with very targeted and personal work and one thing I’ve learned in my career is to use my style to work in many different markets.

See more Tim O'Brien illustrations, new work, and updates:
Tim O'Brien website
Twitter
Instagram
Tumblr
Drawger blog