I'm sorry if this type of stuff was discussed before I got on board here.
With Maya's question for her story, it got me thinking more about who Kelly is. He is a very complicated character, true, and I think there is a problem seeing him first and foremost as "cool".
You know, I've been giving their coolness some thought lately, because I think it is actually a very shallow aspect of a personality. Is Kelly really that "cool" as an individual--partly, yes, but it's not really "who" he is. Yes, he is amazingly cool when it comes to races and working with a black man and allowing that man to be equal to him. Kelly simply isn't racist or bigoted in any way, shape, or form, which was an incredibly progressive attitude in the mid-65s. He was also cool at times with women, being charismatic, charming, handsome, courteous and no doubt conscientious of sharing the enjoyment of their time in bed.
He also dressed cool, being fashionable, and even making some new fashion statements.
However, as B-L wrote as usually so well, Kelly is damaged goods psychologically. One could positively debate that he is not innately a happy man, and his addictions to tobacco, alcohol, and women are, as they are with so many others, trying to fill a void that life itself cannot. He had a very problematic childhood, being a single child, with relatives dying early, probable divorce, and estrangement from his Aunt and Uncle. Although he enjoys the excitement of his work, he doesn't actually enjoy doing much of it, especially when friends need to be stopped, and violence happens to friends and him. He is (in my opinion) much more attached to Scotty than Scotty is to him, since Scotty does have a large, close family back home in Philadelphia, including siblings, mom and extended family members. Anyway, is it cool that Kelly drinks too much, gets into depressions, is otherwise moody, uses and leaves women (we can assume some wanted him to stay), is addicted to his job because he is hesitant or fearful or unwilling to love a woman and set up a normal life? Not really. Perhaps the action of his job is necessary to keep him out of his mind, a mind which doesn't easily give him happiness. I imagine others interpret his avoidance of getting out of spying in their own ways.
This is why Culp was so masterful in his portrayal of the complexity of Kelly Robinson. For a prime time ratings winner, having so emotionally labile a character in charge of "I Spy" is amazing. What we see in the show are two very realistic humans, with flaws and virtues, in a very flawed yet virtuous profession. But, I can't see Kelly as the "epitome" of cool, except superficially. Which is why, no doubt, I love him as a character even more. Nothing is more interesting and fascinating than a psychologically multi-layered character. Kelly Robinson was, indeed, the epitome of a real human and as UNcartoonish as James Bond.