More than fantasy or even science fiction Ray Bradbury wrote horror and like so many great horror writers he was himself utterly without fear of anything. He wasn't afraid of looking uncool - he wasn't scared to openly love innocence or to be optimistic or to write sentimentally when he felt that way.
As a father you immediately become uncool especially the older they get. The older you get it's inevitable that as cool as you think you are you're probably just as lame in your kids' eyes.
I never saw music in terms of men and women or black and white. There was just cool and uncool.
I think being a wealthy member of the establishment is the antithesis of cool. Being a countercultural revolutionary is cool. So to the extent that you've made a billion dollars you've probably become uncool.