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Likeness vs. character
Well, it may sound strange but I don't think about it at all. I just worry about values, shapes and color and the likeness just seems to come.
The hard part for me is not getting a simple likeness but in capturing the character of the individual. This is more than just capturing the forms of the face. Also in portraits we tend to have very subtle expressions. So it is very easy to come very close but, have something be not quite right. Sometimes when working from a photo, I can work for days and I can't seem to get that special something that instantly identifies the person. But I can do a quick study from life and get it in a hour. It may be that the photo just did not capture that fleeting expression that comes and goes as the person sits. Also the mouth moves as does the area around the eyes depending on expression. As Sargent was quoted as saying "A portrait is a painting with something wrong with the mouth".
I know this probably does not help you any but really there is no secret to capturing the likeness. It all comes down to hard work: the more you paint the more consistently you will get a painting you are happy with. Also you know even the best artist at times have had to do more than one attempt before they and the client were happy with the final painting. I love the story in E. R. Kinstler book about the Katharine Hepburn commission. In one of the captions it says that he filled forty pages with pencil drawings and color studies. Now I think that there is a lesson in that. How many artists try to go from photo reference to finished portrait with out any drawings or studies?
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