I probably pick out most of the things you said Christy.
Most of all, probably his humility, honesty, his thoughtfulness, and his complexity.
He's gives a lot of thought and consideration to things other artists may not. It's the kind of quality that adds a dimension to his work. Hearing his whole thought process behind a song usually highlights some things you might not catch initially and it adds a new level of appreciation.
The humility...He's both appreciative of and uneasy about being the object of great attention. I think that's an incredibly honest reaction - particularly honest with himself. Despite his talents, he knows that he's just a guy and he isn't comfortable indulging a lot in the trappings of fame.
His honesty...He openly struggles to be himself and be comfortable about it. His shyness and insecurity and occasional social discomfort is endearing, especially to those of us who can appreciate the feeling. In his lyrics the honesty comes out in what feels like totally unfiltered emotions. Some of those emotions don't even paint him in the most sympathetic light, and I think that requires a bit of bravery to put yourself in that position. It also is somewhat thought-provoking for the listener to see some things about human interaction laid bare and it can motivate some self evaluation.
But he's not milk toast either. He's stubborn, snippy, not one to shy away from challenges or arguments. The artiste - for all the "bad" and "good" that entails. In the overall shell of a shy man are flashes of great confidence, some arrogance, and a steadfast attachment to certain primary ideals about art and life and what is truly important about each.
In 1997 he said something about always trying to aim for certain ideals - to be better than he was. He said something like, "I'm not saying I've always been able to do that, but I've always tried to do that. You make choices that you hope are the best choices. Over a period of time you can come to define yourself by the choices you've made." I like that. It's a statement that rolls up a lot of the things I said above into one ball.
Plus, I think he's got a very goofy sense of humor that peaks out at interesting times.
