Villainy is the ostensible topic of I Wear the Black Hat: Grappling with Villains (Real and Imagined), but the real subject is Chuck Klosterman. Is he a sage or a wise guy, a hero or villain? Is he a modern philosopher, inching ever-closer to answering the big questions—what is reality? what is the meaning of life? does god exist? does free will?—or a dude who draws pop culture parallels for pure entertainment? “My job is kind of to be confused about things other people don’t even think about,” says Klosterman, author of eight eclectic books and the “Ethicist” column for The New York Times Magazine. He recently moderated a barstool debate about whether or not Kim Kardashian is a “good person.”

Riffing on reality TV stars, teen idols, comic book characters, professional athletes, politicians and the Eagles in what sometimes seems like a single breath has earned Klosterman many acolytes and some opponents. Readers may find themselves cuckoo for Sex, Drugs, and Cocoa Puffs (Klostermania) or not (Klosterphobia), but one thing to laud is his refusal to rest on dichotomous thinking. “So much of American culture is built around storytelling—the way we describe our lives is,” he says. “In anything where you use narrative, you’re going to have this sort of protagonist and antagonist. I think that a culture that used some other means to express ideas would probably be less black and white than ours,” says Klosterman, who uses hero vs. villain simply as a springboard to the great grey ocean of inquiry.

Among those getting the hypercerebral treatment in I Wear the Black Hat are, in no particular order of villainy: Taylor Swift, O.J. Simpson, Sarah Palin, Perez Hilton, Joe Paterno, Julian Assange, Muhammad Ali, Andrew Dice Clay, Morris Day, Snidely Whiplash, Niccolò Machiavelli, Bono, Sharon Stone, Ice Cube, Eazy-E, Fred Durst, Wilt Chamberlain, Seth MacFarlane, Joseph Stalin, Michael Stipe, Kenneth Starr, Bill Clinton, Linda Tripp and Hitler. Klosterman’s mind must shred like a snowboard.

The chapter on vigilante justice begins: “Let’s pretend Batman is real.” He self-consciously adds, “(I’m aware that this opening is enough to stop a certainI wear the black hat kind of person from reading any further ...)”—typical Klosterman. In such a world, where Gotham is New York City and some guy in a winged suit without a law enforcement affiliation pummels criminals on the daily, “do you root for this person, or do you want him arrested?” he asks. Meanwhile, back in 1984, real-life vigilante Bernhard Goetz escapes prison time for shooting four black youths in a subway car, and Klosterman writes, “If Goetz was still at large and Batman was somehow real, we’d have to assume Batman would be trying to stop him.” Factored into this determination are social climate (New York was a dangerous place in the ‘80s), emergent details (the youths were unarmed) and prevailing attitudes (it’s not generally a good idea to take the law into one’s hands). Klosterman agrees that George Zimmerman, currently on trial for the vigilante killing of Trayvon Martin, would fit well in this chapter, though he is reluctant to claim him as a villain until more details are known. “The object of this book would be that we are less willing to call people villains. We [as a society] are making decisions about people I don’t know, and I guess I just feel increasingly unsettled by how I feel about people I don’t know,” says Klosterman.

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A second side to this discomfort is explored in the book: “I care about strangers as abstractions, but I feel almost nothing when they’re literally in front of me,” he writes. “They seem like unnamed characters in a poorly written novel about myself, which was written poorly by me.”

Does his observation, plus a strong identification with Chevy Chase and Darth Vader, mean that Klosterman is a villain? “As I’ve matured, inevitably I find myself more sympathetic toward bad people because I see my own problems in these characters,” he says. “I don’t really see myself in Luke Skywalker anymore.” Do we? Is he? Are we? What do you when you have all these questions? “The end result is you wind up writing a book like this,” says Klosterman. 

Megan Labrise is a freelance writer and columnist based in New York. Follow her on Twitter.