You find what you look for
Jeff, your question has motivated me to work out in my own mind what I think is the paramount goal of a portrait - to reveal the intelligent humanity of a subject. All the surface considerations of painting - of style, technique, painterliness, classicism, underpainting, etc. - matter little to me compared to what appears to be going on in the subject's head.
What matters most to me is than an artist has found the subject to be an interesting, compelling and intelligent human being. All people have some kind of intelligence which has nothing at all to do with level of education, social class or physical appearance. It's the duty of the artist to find it and reveal it. When I see a painting of a person who looks vapid, insipid, dull or sappy, I NEVER blame the subject. I blame the artist for either: 1. not finding the better part of the subject; 2. not having the technique to portray expression; or 3. not having the taste to know what's going on.
I think portraying intelligence on canvas is very difficult and maybe indefinable. Take a look around the artists on the SOG site and ask yourself which artists have managed to find intelligent, interesting, personable and intriguing subjects. When I make my own private lists of artists I love and artists I can't stand, invariably it's the artists who can articulate intelligent human expression that make the grade.
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