Grayson Perry is eminently quotable.Here he is on the subject of 'coolness'. He also makes interesting stuff.
Few groups are straighter or more conservative than teenagers, who take cool seriously. And what makes cool very immature in my book is that it's a binary judgment: hip v square; in v out. The other week, I quizzed my 15-year-old neighbour about what the current words for "cool" were. He told me that cool can be "sick" or "nang", and uncool is "wack". Or interestingly, considering the attention span of the modern youth, uncool can be "long". As in: "Man, that opera was long."
I'd like to make a plea for difficulty over cool. In the end, I think being difficult is the coolest thing you can be. One of my guiding principles in life has been to follow the path of most resistance: as soon as I start doing something well, I get bored. So I try to do something a bit harder.