Tim O'Brien

Where are you from and how long have you been illustrating?
I'm from New Haven Connecticut and I've been illustrating since 1986.

Its hard to know where to really begin, you're such an iconic illustrator. I suppose I'll start gently and ask you about some of your passions...
You speak a lot on drawger about your love for boxing, what does it take to be a great boxer?

What made Ali the greatest?
If your skills in the ring would have allowed it, would you have ran with boxing as a career?
There is a fair amount of info on the web about my love of boxing, that I used to box and train fighters. I got into it as a young teenager and kept boxing until around 40. I still love watching it but don't box anymore. I started running at 40 and find it just as challenging and perhaps a better sport to do as I get older. In the past few years I became more of a trainer and therefore was not getting as good a workout as I need to. I fantasized about being a boxer before I went to college and became an illustrator and never considered it after that. However, boxing is like illustration in that it is a solitary endeavor and each fight or job is a way to show off some skill and adhere to the fundamentals.
Still, there are natural artists just as there are natural boxers. Some just scribble and it's brilliant. Ali was an artist like that. He understood the show of boxing and in the ring was mentally stronger than most.

How much of boxing / running / illustrating is dedication, and how much is skill?
Who knows? It's different for each person really. I think most successful people are extremely dedicated and focused. The real hard part is KEEPING the focus. Fighters lose it and so do artists.
What drew you towards running? is it the idea of pitting yourself against yourself - or the act itself...
As I wrote earlier, I began running initially to find a new way to get into shape but on a whim committed to running the NYC marathon, then I HAD to train for it.

do you find listening to music motivating when doing long distance runs - if so, any specific bands / songs?
I listen to rock when I run. A good, driving beat. Mostly mixes and I get into phases with a playlist where I need to hear that specific list. For a long time now it's been a driving Pearl Jam list. I've started my marathons with these songs: 'The Real Me', The Who, 'Krafty' New Order, 'Beautiful Day' U2, and 'Given to Fly' Pearl Jam.

your work is amazing to look at. detailed to perfection, but behind every striking image is a great idea - Would you consider yourself more of a thinker than a draftsman, or vice versa?
I like to think I'm thought of as a problem solver and craftsman. If a client needs a home run portrait, I aim to be the guy. I do like conceptual work too, but with realism it can be the road to extinction since so many solutions can just be photoshopped just as easy. I determined that my skill had to be the thing I highlight the most. Not everyone needs my work but enough do that I have a career.
You've worked with Time pretty much your entire career, what makes that relationship so special? how have they helped you develop / mold your work?
I started doing covers for Time in 1989. Over the years I've learned how to make a powerful cover through working with Time and specifically Arthur Hochstein.

You cover a lot of political topics in your work and come off as a proud democrat in your speech- are you happy with the job President Obama has been doing?
If you could change / improve anything about America, what would it be?
Yes, I'm a proud democrat. I have a firm belief that we as a people can make life better for those less fortunate. That basic principle, that we are our brother's keeper is at the heart of the democratic party. This notion seems to go against republican platforms these days.
I do think Obama is doing VASTLY better than what preceded him. I'm proud of our country and our president's intellect. It's nice to have that feeling. I also think that Obama had to almost waste his first year TRYING to listen to republicans. He bent over backwards trying to bring them into his cabinet, hear their ideas and on health care, let them have at it. In the end he had to be a forceful and decisive president and insist on a course of action. I think that for the rest of his term we might see this more driven and less apologetic Obama. He now knows that his ability to have achievements will only come from being more forceful and seeing less of a compromise.

What are you loving about illustration right now, and what are you not so in love with?
I love the work that is being done. I feel as I did when I was a student. That I have so much to learn and everything being done is so good. I am just blown away by the talent out there today. Most of it. The bad is obvious. Fewer venues for published work. We all hope that when magazines and books live more and more on tablets and screens that the work pays as much. For a craftsman like me I need a certain fee to make it worthwhile. As I said earlier, I don't need everyone to use me, just enough.
You've already been an illustrator for more than two decades but still seem far from your peak - whats the key to longevity as an illustrator.?
That's nice to hear. Illustration careers don't really build up like they used to. An illustrator needs to accept the fact that they will have to reintroduce themselves again and again. They must accept the fact that young ADs won't care about an artist's amazing achievements, they just want the illustration they are assigning NOW. I think an artists can be knowledgeable without coming off as a grumpy, seasoned illustrator and I know too many grumpy illustrators, pining for the old days. I don't want to be one of those illustrators.

You seem to have a real dedication to young / new illustrators. what drives that?
If you make it good for the next generation you are helping out your industry. I also teach so I work with a select few to hone their skills learn from them. They are my science lab.

Are you still learning as a painter / image maker?

Do you ever doubt yourself / your abilities?
Yes. Not abilities as much as doubt my sensibilities.

Whats the most important advice you can give to new illustrators?
Art directors love finding new talent. That's an advantage. The key is to be seen and to have enough great work to put you over the top. Young artists tend to have a few good pieces with too many mediocre works thrown in to increase the size of the portfolio.

Any advice for the older / established ones?
Stay young and humble and make it your job to learn the names of the kids coming up. They will have your future in their hands in many respects so make it a point to meet new artists and be interested. That's not easy to do for many. They love what they love and may not like where current trends are headed. I try to understand what is going on today and just be in the mix.

all images copyright Tim O'Brien - check out tims work on drawger: http://drawger.com/tonka/
you're in for a good story and some amazing work!!


  1. AMAZING ...... thanks Pete and Tim

  2. The images are incredible. This was like looking at photographs.