Graydon Carter used to be a hero. Along with Kurt Andersen and Tom Philips, the mysterious Canadian (yes, it’s possible) founded Spy Magazine in 1986, a much-needed satirical antidote to the self-important, status-mad 80s. Spy set the table for a humor-laden, media-savy approach to cultural criticism that would lead to everything from Gawker to The Daily Show–and then he became the thing he hated. Sure, he’s done some great work as the editor-in-chief of Vanity Fair, but he’s done a lot to contribute to celebrity-mad America, too. And then he opened an exclusive West Village celebuclub, the Waverly Inn. And then he started saying things like this: “I find it harder for anybody as they get older to feel 100 per cent strongly behind one party. There’s lots more grey than when I was younger. I’m a libertarian.” Sometimes, there’s nothing more villainous than when a hero gives up.