Tim O’Brien & His Knack for Pop Culture

Graphis Master Tim O’Brien paints intricately detailed illustrations and portraits from his Brooklyn studio. His art has appeared numerous times on the covers of TIME Magazine, Der Spiegel, Rolling Stone, Mother Jones, and Smithsonian Magazine, and has been featured in Esquire, GQ, National Geographic, and countless others.

Introduction by Arthur Hochstein, Designer, Arthur Hochstein Design+Image

I first met Tim O’Brien in 1989; I needed a photo-realistic painter to bring a tear to George Washington’s eye, defiling a famous Gilbert Stuart portrait for the cover of Time Magazine. His work brought tears to my eyes and readers’ ever since. I really think Tim’s greatest gift isn’t just about the astounding quality of his work—the spot-on likenesses and the thoughtful contexts he creates—but how and why he does it. Most realist portraitists need many days or weeks to accomplish their magic. With Tim, it’s more like hours; so fast that even after all these years, I wonder how the hell he does it. That ability and the incredible discipline it takes to use it are what make Tim an ace in the hole for art directors. In my bleakest professional hours, when I’m staring into the abyss of failure, Tim has always been there—friendly, calm, and self-assured as ever—to help me get the job done by making a beautiful portrait, so expertly done that the speed of its creation becomes a non-factor. In all our years, he has never, ever failed me or himself. And for all those nights that I slept better because he wasn’t sleeping at all, I thank him.

How did you begin as an illustrator?
I was always a gifted artist, technically. I could accurately draw what I saw, remember how I drew something, and knew I could do something not everyone could do. As high school was ending, I reluctantly pursued art in college, perhaps hoping I would be something else, like a boxer. Once in college, all the possibilities of image-making opened wide, and my dream of making a living as an artist seemed possible as an illustrator. I was pretty good—I won some student awards, got an agent upon graduation, and started my career.
 
What professional goals do you still have for yourself?
I’ve not been much of a self-promoter over the years, so I generally wait for jobs to come to me and feel pretty satisfied with the many clients I’ve had over the years. There are no dream jobs above all others… perhaps a Muhammad Ali postage stamp, but in general, career longevity is my overriding goal at this point, and perhaps to feel like the work I’m doing is making me happy.
 
What part of your work do you find the most demanding? 
Being organized is my biggest challenge. In any given week, I have dozens of emails to write to various people, sketches to do, revisions to sketches, final art to complete, competitions to enter, bills to pay, Society of Illustrators duties to fulfill—the list goes on and on. I do all of this alone, running my own business, and it never ends. It’s fun, but it never ends.
 
What is your work philosophy?
Work hard, play hard.

Who do you prefer to work with: an art director, designer, or client?
They’re all people, but often, they are only emails. I approach them all the same way; I write clearly and without attitude. I work with my clients and aim to be easy to work with while trying to create stunning work. Still, working with confident and talented ADs who hire me because they love what I do is the best.
 
What would be your dream assignment?
Apart from a Muhammad Ali postage stamp, I think a career as an illustrator provides anyone with many opportunities to turn assignments into meaningful moments.
 
What is your greatest professional achievement?
Longevity in this business.
 
What are some challenges you’ve overcome to gain success?
I didn’t have a hard time starting in this business. What I’ve learned to deal with and understand are the ups and downs of my career. I have strategies for dealing with slow periods that used to freak me out. Now, I chill and do personal work, fix my house, run more, and enjoy the periodic breaks. Now, they don’t last for long, but years ago, they felt like career-ending moments.
 
What inspires you?
My students, my talented friends, and beautiful paintings.
 
Whose art do you most admire?
I have so many talented artist friends that I could fill a book listing them and not be lying. The art that inspires me comes from all directions and does not need to be from a genius or the walls of a museum. Things get into my head passively: a color scheme, a design structure, a clever idea, or appreciating some sort of ambitious undertaking. So, when I look at the work of all the people I admire, I take in elements.
 
What and who are some of your influences?
There were so many, but I followed the work of Gottfried Helnwein, George Tooker, Paul Cadmus, and Guy Billout when I was in college.
 
Who do you admire most in your profession?
I have a strange answer to this. I grew up without a father and entered this profession as somewhat of a rube. I have always looked for clues about how to be, how to talk, and how to operate in this business and in life. I have always admired the eloquent people I’ve met, the charming people, and those who are generous. When you’re finished speaking with them, you feel energy. The first person I met in this business who was that to me was Marshall Arisman. I met him when I was about 20, and today, when I meet young artists, I’m mindful of how these small first meetings carry so much weight.
 
Would you have any advice for illustrators just starting out? 
Work very hard, become undeniable, and when sending out emails or postcards, or however you promote yourself, no reply does not mean “dislike” or “hate.” Very few ADs ever write back; if you’re not aware of that, you feel as if you’ve been rejected. It’s not like that. If you’re undeniable and persistent, you will get work.
 
What do you value most? 
My family.

Aside from illustration, what is your favorite pastime?
I love running.
 
Do you have any hobbies?
I suppose, besides running, I love boxing, boats, antiques, steak, booze, and friends.
 
What is the biggest personal challenge you’ve ever had?
It’s so big I can’t share it here, but we all have to deal with things, sometimes in silence, and sometimes the challenge lasts far too long. We get through it by seeking help, looking to close friends, and moving forward.
 
What is your greatest personal achievement?
Career longevity and relevancy. I’d like it to continue for a few more decades.
 
What would you change if you had to do it all over again? 
I have not much to say about my career choices, but I would have loved to have lived through the initial years of my son’s life again. I was always just trying to get through it, and now, as he’s about to go to college, it feels like it was a blur.
 
Tell us about your state of mind when you’re working.
I start with some anxiety, a healthy dose, followed by a peaceful quiet or Zen that comes from knowing what I’m doing.
 
What do you wish to convey in your work? 
Elegant ideas.

Tim O’Brien paints intricately detailed illustrations and portraits from his Brooklyn, New York, studio. His art has appeared numerous times on the cover of TIME Magazine, Der Spiegel, Rolling Stone, Mother Jones, and Smithsonian Magazine. It has also been featured in Esquire, GQ, National Geographic, and countless others. Tim has illustrated several US Postage Stamps. Tim received an honorary doctorate from Lyme Academy of Fine Art in 2013. Tim is the current president of the Society of Illustrators. His numerous speaking engagements include the United Nations, BYU, the Norman Rockwell Museum, the Society of Illustrators, Syracuse University, SVA, Pratt, RISD, CCA, Western Connecticut State University, College of Creative Studies, MICA, and the University of the Arts. Tim has been an educator for almost 30 years and is an adjunct professor at Pratt Institute in Brooklyn.

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To discover other talents in issue #358 of the Graphis Journal, click here.