[QUOTE=keithwms;846245]The obvious counterexample being Karsh's photograph of Alfred Krupp... not sure if we should really consider that to be a portrait though :rolleyes:
I believe you mean Arnold Newman's portrait of Krupp?
And I'm inclined to agree, a great portrait needn't necessarily flatter. The best one's always seem to reveal something essential about the sitter. And it really is all about the relationship you have as a photographer with the sitter.
That said, I think it's possible to make a good portrait by being more observer than engaging the sitter in a lot of small talk. It's all in how you relate to other people that is true to yourself.