As far as living musical artists go, Jimmy Page and Herbie Hancock are like eternal coolness personified. Siouxsie Sioux as well. Oh, gotta throw in legendary bassist Tony Levin, who's played with like everybody. Met him once, and even though I know better, I would've sworn he invented the gangsta lean that evening. Bill Bruford gave him a run for the money than night, though. They were both funny as hell.
I don't think Bono was ever cool, but Edge and Adam sure af were. Hell, they still are.
More on this later, when I figure out just how I want to say something.