Tim OBrien
May 2009
Sonia Sotomayor
I love fast turnaround jobs.  The client knows what they want, they might really need me, and though it will blast a hole in my day, the fallout is relatively minor.  I most often say yes, and then make my calls.  If I have work pending I call my agent to clear things for me and keep me in a protective bubble, and I call my wife to tell her I am going to be a nut for the next 24 hours.  MORE of a nut that is.
Time Magazine's Arthur Hochstein called on Tuesday and asked if I would do a cover.  The subject was Judge Sonia Sotomayor.  The photos of Sonia are quite varied and as she spoke at the White House during the announcement, photographers were clicking away.  In a way, THEY are my competition.  However, Sonia was NOT doing a photo-shoot, she was speaking.  She smiled broadly when speaking of her gratitude and was emotional when speaking of her family and mother.  It's great theater but not the best for a photographer hoping for an iconic pose.  I started this with reference provided by Time.  For the most part nothing was good on it's own but could work provided I piece it all together.  A black and white shot for her face that had a wonderful yet powerful smile, a great color shot for her updated hair, though not in the exact angle I needed, and finally I needed to put her in a judge's robe.  The last hurdle was the age she was in the black and white shot.  
She is a bit younger and her face was slightly less full.  
I worked like crazy Tuesday  and got approval by around 6 PM and worked all night and finished around 10 am.

Here is a trick I will divulge.  I hope it helps some of you out there who work in oil and hate when parts of your work go matte while it dries.  As I paint a portrait, I work  on the likeness first and stay on that until it's perfect.  The hair and robe can be off and rushed a bit but you can't do it with a likeness.  So, when I do that, as the night goes on, the face can start to go matte.  This would mean by the time I'm ready to start photographing the work in the morning, it looks odd on lacks depth.  My darks would photograph weak.  What I do is shoot the face WET then put the painting back up on my panel and paint the other parts.  I then would photograph the robe and hair WET as well and merge it all in photoshop.  
Perhaps this is no secret but there you have it.
Many things have to be aligned for a cover to run.  First, the art has to be stellar.  Next, photography has to be difficult to find or find the right shot.  If the cover is of people Time just can't have access to, you have a better chance.  
Finally a quick call when the painting is due in 24 hours is a good sign.

Time is a dream to work with and I've done many covers for Arthur.  He's super positive and always has smart advice as I go along.  One skill that he has that I hope I have learned is his ability to choose the right shots to work from.
Arthur also tells me what I'm up against always (I think he tells me all?) and always calls to let me know he's received the art.  That's a class move.  I hardly ever am able to take that call as I'm usually sleeping.
Yesterday I woke at 2 p.m., went for a run, then dinner in Battery Park with the family.  When I got home Arthur had called to say I got the cover and Rick Stengel will be revealing it on Morning Joe, MSNBC in the morning.

Visit for Breaking News, World News, and News about the Economy

I love when I do something that gets on TV.  I got a nice nod here.  Good for illustration in general I think.

When the phone rings I want to write down anything that is important to know. In this case, on the back of a piece of mail I write "TIME JUDGE SOTAMAYOR" (Spelled wrong). I clearly liked the call because I sketched a bird but it seems to have bashed it's head. Below is the thumbnail (Complete with red TIME boarder!) The pink splotches are Vitamin Water. I help keep 50 Cent rich.
This is the first sketch and the approved one as well.
An alternate. Got to show an alternate, right?
I liked this alternate. I had already done the first sketch and sent it when some new reference arrived. This one is iconic but perhaps the lack of eye contact sank it.
The full painting. There is a way to make someone have lines and wrinkles yet not look old. I keep them very warm and close in value. The information is there, just not in high contrast.
I think I forgot to paint her ear in, which is hinted at near her ear ring. Shhh.

Ella Underground
In the formative years of my career I have devoted time regularly to doing personal work.  These samples are among my most well known works and I have really gone too long without doing more.  I've built up a long backlog of images and this year I have blocked out time each season to doing a few.  If an illustrator steers their career skillfully, the work they are assigned will be just like their personal work.  Sometimes for me, assignments are great and fun and endless.  After months and months of these assignments I start to feel like the images in my head are not getting out.  I guess I don't always steer the career the right way.

The first is a painting of Ella.  Ella is my sweet niece and she is the definition of cute.  She is very aware of herself and as a result, always strikes a memorable pose.
I like contrasts and so I thought of a rough and rusty background behind a profile of her.  In playing around with this, I found the rust to come forward too much so I kept washing it out to the point of minimizing the impact while maintaining the look of pipes and gauges.
This is a portrait of an underworld urchin and Ella is perfectly cast in my opinion.  Her sister Molly said right away that she was a bit jealous so I have to do something of her soon.  She is also stunning.  Cassius has been in a few illustrations now to the bloom is off that rose.
So, this is a sort of 'steam punk' portrait I guess.  I was thinking of doing something similar to a portrait I did for Irene Gallo several years ago titled "Prince Ombra."

Thank you Ella!

I think if this was for a client there might have been suggestions to make her a bit more determined and conversely pleased. I like the slightly weary feel to it as is. "Ella Underground" Oil and Gouache on Panel.
I liked the angle of her 'bob' hairstyle, and kept that part in, but the hand holding something had to go.
My sketches are on anything BUT my sketchbook. This one on a scrap piece of paper was the first time I thought of a square and industrial pipes as a motif behind her head.
At this point I had some solid ideas of clothing and the pipes. The inside of PRATT is very old and industrial and I think I was influenced by that. I would often suggest my students USE that stuff as reference. None did, so I did. Here is a watercolor to set the mood.
The pipes are mostly a drawing with gouache and oil glazes.
I must always hold back on going overboard with surface texture of faces of those with soft skin. The lines are there on close inspection but the contrast between the brush strokes and the area beneath is much closer.
I get a ton of work from this illustration. Irene Gallo, AD extraordinaire commissioned me several years ago to do this kid. I always wanted to do an other in the same neighborhood.
Starting My Career
This quick sketch shows the car on the parkway overlooking Westville, New Haven.
I just finished teaching for the semester.  Many of my students are graduating this coming week and will soon start to be illustrators without a net.  It's a frightening time for a young artist.  The soft cocoon of a class is broken and and out they flutter, unfurling their new wings but quickly getting buffeted by the swirling winds of life.
We all were in their shoes at one time.  
In 1987, the week of my graduation in late May, I thought it a brilliant idea to paint my hematoma blue 76 Ford Granada gold.  Armed with some house painting money, I purchased 12 cans of metallic gold spray paint and in 'swirling winds', painted this iron giant gold.
Of course, it wasn't quite the bling I was hoping for, but thinking back, it indicates to me just how care free or silly I was at that moment.
The first order of business after graduation was to pack my portfolio and head off to Jellybean photographic.  I needed my work shot for a hard portfolio (the only kind in existence at the time.)  My senior portfolio instructor, Ken Davies said a few things before I graduated.  He suggested I get some nicer clothes and shoes. My pal Steve Brennan and I decided on the first Monday after graduation to drive in my gold Granada to NYC, dressed in our 'Ken Davies' clothes and shoe's we called, 'cachinkas' for the sound they made while walking.
We boarded the S.S. Granada in New Haven and drove on the Merritt Parkway headed for Manhattan.  Just out of New Haven and the incline out of the tunnel I noticed that the car, never too peppy in the first place, was driving in an odd way.  The power was fading.  It was as if it had a extension cord attached to my home town and I was pulling the plug.
What was that?
Looking at the rear view mirror I could see a huge cloud of white smoke that shot from the back of the car.  The vehicle died.  I steered this glorious golden paperweight to the shoulder and wondered what happened?  Did I blow a tire, hit something or worse?
It was worse.  The car threw a rod and I could see it sticking out from the pan beneath the engine.
We gathered our portfolios and I left the car on the Merritt.  This meant that we had to either walk home (1987, no cell phones) or scamper down the embankment to the houses below and appeal to someone to help us.  We scampered down in our cachinkas and got covered in dirt and nettles to the unsuspecting neighborhood below.  Door after door these two frightening salesmen went, ringing doorbells hoping for a good Samaritan.  Finally, an older couple let us in.  They believed we weren't going to harm them and let us sit in their kitchen and drink ginger ale.

We called for a ride, the car died and that was that.

I lost a certain care-free attitude that afternoon (thankfully).  I was aware of how silly my gold care was, sitting on the highway.  I had to start to think like an intelligent person.
I soon got an agent, received assignments, and with my older brother Dan's help, bought a truck.   I grew up.

I wish my former students well on your journey and I hope you're all ready for how unpredictable it will be.  Work every day on your art, invest in your career, make connections, and don't give up.

Innocent and foolish pride in a pathetic attempt at standing out from the crowd. I laugh when I see this. Details are funny. One, the car in the garage I bought for parts and the wooden speakers on the back ledge of the car. I do look proud though. Sheesh!
Note the intelligence to wear a respirator. I lost those photos.
It almost gleams. This car was called "Neutral" by my friends. You had to put it in neutral at a light in order to not stall.
1987 Paier College of Art Graduates. Steve Brennan, Tim O'Brien and Mark Castellitto. We are sitting at an opening at the Society of Illustrators, our first. This is 1988.
Toe in the Water
Tuesday, 8:30 am.
Get in the car and drive Cassius to school.  Drop him off and head home.
Up to the studio, the answering machine light is blinking.
It's BusinessWeek and they are asking me to do a specific cover.

I need to think about it.  I have to go to Pratt and do final evaluations for the semester and am supposed to stay until 1 PM.

I call the AD, and find out the particulars.  He is seeking a cover and the idea is sounding weird for me and the deadline is the next morning. 
I think many would walk away from this kind of job but I've learned that these kinds of jobs are adrenaline boosters.  In a quick turn-around job the decisions are quick, the way it affects other jobs is minimal and the income is great on a per hour basis.

This is the thing though, the assignment was about private equity and how these investors were about to get back in the game.  They are timid but once they get back in, it could revive the economy.  They had other covers in play but wanted me to paint a realistic portrait of a wealthy, mid 50's man.  ON TOP of his face a cartoon mustache, monocle, and top hat like the character in Monopoly.  I think many illustrators could have knocked that one out  of the park (Taxali, Bower...)  but there is a vital skill that illustrators don't talk about enough that thankfully I have.  One must be able to hear a pitch and know if they can or should do a certain idea.  Do you take it and do it even though you think it's not right?  Do you do a sketch hoping they won't like it but like your idea?  Tough call and really hard if it's an artist's first cover.  I've done countless covers so that was not the case, but what to do?
Before I could do anything about the call,  I had to go to Pratt and do my final crit and then a faculty meeting.  Just prior to the meeting I called my agent and though many talk about how they don't need one, I find that as a sounding board, among his other roles, he is invaluable.  
I can come off as reasoned and calm, even charming because I rant and complain to him.  I wanted to do the cover but thought the idea was not right.  I whined some more.  Finally, as he listened I devolved into talking about how bad I thought the idea was (for me) and that it was odd and if they wanted to talk about private equity getting back into the game, use a "toe into the water or something."  I said "That's it, a well tailored pant leg and shot dipping into the water, with concentric circles rippling out from the toe"
My agent, Peter Lott paused then said, "You know, Tim?  That's it,  let me call him."  I said yes, offer that idea.  As I thought it out I sketched it on some paper in front of me.
Three minutes later Peter called back to say perfect and to go with it.
That's a cool rush and a great payoff.  The other way it could have gone is the AD really insists on his version and calls some other artist to do it.  In this case the idea was a better and more direct way to convey the thrust of the story.

The next step is the process.  I went home and did a sketch and got it approved but I was urged to find a great shoe and a non-cuffed, pinstriped pant leg.
I don't have wing tipped shoes so I went out to pick up a pair.  I went to sears which is near my home and of course the shoes there were cheap looking.  7pm and I still don't have a shoe.  My wife called her friend to ask if her husband could loan me a shoe.  The shoe belongs to Janno Lieber who is the president of World Trade Center Properties, and is overseeing the rebuilding of the World Trade Center.  He is also my marathon pal and for the past 3 years we go to the start together and wait in the cold for the start of the race.  He's a great guy.  My neighbors are used to being asked for clothing or to model for things.  Janno is also a giant compared to me, well over 6 feet tall and big feet.  
I would have to set up the shoe and photograph it off a foot.  The shoes were also aged a bit but the illustration should be crisp, smooth and new.  I don't have any of the reference anymore, I am trying to keep iPhoto leaner recently and 50 shots of a shoe are not worth the hard drive space.
Elizabeth modeled the leg in the pinstripe pants and I stuffed the shoe with paper to help smooth it out a bit.
After shooting everything it was 9:30 and I had to start putting it all together.
This is essentially a still life and I drew it  and painted it fairly quickly.  The water ripple is a combination of freehand airbrush and oil paint.
I finished about  6 AM.  I gave up caffeine last fall but save it for all nighters.  MAN is that drug powerful when you give it up.  I was WIRED all night with my knee bouncing.  Part of it was the caffeine and part of it was the fun of doing an one night cover assignment.
A few days later in a doctor's office I saw that my cover ran.  That's always a thrill.
Thanks to the folks at BusinessWeek for giving me the opportunity and for being so great to work with as usual.

This is sketched as I hear the pitch from the client. I drew that wall street guy first and and then lost interest as I heard the rest of the details. The sketch of the horse car is the indication of my distraction. After hanging up with the AD I talked to my agent and did that toe thumbnail.
Working the idea out more at home I do a sketch and then talk to the AD and hear his comments. Flop the foot, crisp pant leg, no cuff and pinstripes. I always doodle when I'm on the phone and many other ideas are born that way. Tortoise and giraffe may show up in the future.
A bit out of order, but here is the sketch I sent. I grabbed a shoe off of an internet shoe store for reference.
Final art, a close-up of the toe. I had to ignore all the great wrinkles the shoe had. I paid Janno for the use of the shoe with the great shine I gave his shoes.
When the art is just a foot, there is still a beauty to find in the details. Pinstripes next to the lines of the socks contrasted against the smooth shine of the shoe. Patiently I add a highlight to many of the tiny parts of the stitched and stamped leather. I snuck in an "OB" on the heel.
The hardest part was shooting the pant leg. Elizabeth had to stand on a pile of 3 unopened Workbook tear sheet reams and dangle her leg down to a piece of white foam core. It's hard to do as I fuss with the pants and try to have just the right shape and not too many wrinkles or waves to the pants. Realist painters must all torture the people they live with, or is it just me?
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