Chuck Klosterman is curious about villains and villainy; he has been for a long time. For his generation, and generations since, Star Wars provides a useful template: As kids, everyone pulls for Luke Skywalker. He’s the hero, pure and good. But, as those kids come of age, Han Solo commands their attention. He’s a bad boy, but with a good heart. Then, as the lives of that audience grow more complex, Darth Vader becomes the most interesting character. His motivations are the ones that need to be understood. Vader is a good person who has chosen evil. Klosterman asks, in a variety of entertaining and provocative ways, who are the bad guys? Why does society embrace some of them and hate others? What was so Machiavellian about Machiavelli? Is the vigilante a villain? It depends. In sports, some individuals are villains on the field and others are villains off the field. Popular musicians often become objects of scorn. Political sex scandals, gangsta rap, and comedians who go too far—all of these phenomena produce rosters of culprits, some more vilified than others. And then there’s the rise of the online villain. I Wear the Black Hat mixes cultural criticism and self-interrogation with reality and imagination, and the book marks Chuck Klosterman’s most intriguing work to date.