Bruce Dickinson’s not cool. He’s awesome, but he’s not cool.
Terry Pratchett, he was cool. Started out, let’s be honest, as a total hack knocking out unfunny fantasy pastiches. Found a voice, and what a voice, then built and populated a world. Then once he became ill became a huge force for alzheimers awareness, research and support, and absolutely fearless in the right to die debate. Cool.
Also, when I’m gambling I like to have a safe bet and a wild card so I’m also going with Macklemore, mostly because Downtown and its video are genius. But I like his style in general, he reminds me of MC Tunes.