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Tim OBrien
Jon Stewart for Esquire
posted:

I was asked by Esquire to do a painting of Jon Stewart like the famous portrait of JFK by Aaron Shikler.
His portrait of JFK is a somber and reflective one, a true break from presidential traditions.  I love it so relished the opportunity to learn a bit working from it.  I learned that Shikler's brushwork is wonderful.

Esquire wanted to do a piece on Jon Stewart, who I think is brilliantly funny and perhaps the best political media watchdog working today.  The article discussed his view of what he was doing on Comedy Central on his show and even suggested he had a slightly inflated view of his role or importance.  Though I cringed ever so slightly at poking fun at Jon, I knew he had thick skin.

The assignment was simple;   a master copy of this portrait.
First issue was finding reference of Stewart with his head down and NOT smiling.  Very long and labored searches brought up various shots that when combined, offered the best hope at matching the original.

Finally the brushwork.  As I was painting I thought that it would be a breeze.  No.  Brushwork is fluid the first time around but copying brushwork is hard.  I tried to stay with the pose and color key but allowed for my natural style to work it's way in.
The end result worked well and this piece currently resides in the Esquire offices.

Thanks Jon for your sense of humor and for all that you do. 





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