Rolling Stone contributing editor Tim Dickinson popped up on Countdown with Keith Olbermann Friday to discuss Donald Trump's latest incarnation: debate moderator. Olbermann asked, "How does Donald Trump, who makes his living off not listening to other people, moderate a debate?" Dickinson attributes Trump's inexplicable rise to political relevance to his "accessible billionaire" persona, quipping that "he’s the guy that Joe the Plumber thinks he might be some day if his plumbing business were real and then took off.” This joke of a debate, says Dickinson, "builds on the joke of the Herman Cain campaign. Just when you think it couldn't get any weirder, the Donald comes in." Watch below.