Does anyone find his smile annoying?

yes, mrbrightside,
I know what you mean. It's hard to put into words,but we know it when we see it.(I see it in his eyes also)
Naturally, we are not supposed to be proud to admit,but if we feel this way,there must be others who feel the same...but people have to be 'shhhh' about it.

Keith Carradine's does the same thing.

"All our best men are laughed at in this nightmare land"
~Jack Kerouac~

I don't find it annoying but it is definitely distinctive. Perhaps it annoys you because you get the feeling he's been pulling it for years to appear charming and disarming. You know...like 'ain't I just cute as the dinkins?"...like he used to practice it in the mirror when he was a teen so he could turn it on for the girls. Considering that he is now 57, the effect is more one of snide, then charming. Does that say it for you?