Actually, I've never thought those pictures with him and Kelly looked natural at all. They just look like posed, publicity stunts to me---just studio pics with a good photographer, meant to further their careers at the time, both of them.
Since most of the pictures we see these days are with him at some "event", being snapped as he's trying to exit or enter a vehicle or building, it's impossible to tell if he's "happy". You can't really tell happiness from a cold picture. I don't smile in the few pictures I have taken of me, and I'm happy most of the time.
In the interviews he did on A&E Biography, he appeared sublimely, peacefully, blissfully happy and content--serene, if you will.