The recent movie “Star Trek Into Darkness” offered not just one bad guy, but two: a reboot of the classic villain Khan, and a rogue commander of Starfleet. We need villains so we can root for heroes. Yet the bad guy is often so much more interesting — have you ever read John Milton’s “Paradise Lost”? The villain Darth Vader is at the very core of the “Star Wars” saga, which taken as a six-film narrative arc is about the rise, fall and redemption of Anakin Skywalker.

Prolific author and social commentator Chuck Klosterman takes on the question of villains and villainy in his thought-provoking nonfiction work, I Wear the Black Hat. The book is a series of essays examining villains of recent memory — some of whom are more villainous than others: Adolf Hitler, Al Davis of the Oakland Raiders, Bill Clinton, Howard Cosell, Jerry Sandusky, Julian Assange (“the most archetypically villainlike villain of the Internet age”), Kim Dotcom (and the rest of your company’s IT shop), Perez Hilton and many more.

Klosterman acknowledges that good and evil are social constructs, then proceeds to examine why we consider some things evil, while perceiving others as good. Why do we root for Batman, but despise Bernhard Goetz, even though both are psychologically damaged vigilantes? One is fiction, the other is real. “Why are the qualities we value in the unreal somehow verboten in reality?” he asks.

The author’s central theme, which he repeats over and over, is: “The villain is the person who knows the most but cares the least.” The inability to care shows that person’s psychopathic tendencies. A hilarious example is Newt Gingrich. “Gingrich loves who he is. He doesn’t care what other people think of him, because he doesn’t particularly care about other people,” the author writes. “This is why I always find myself rooting for him, even when I’m against what he pretends to desire. I know exactly what he’s doing. It’s like looking into a mirror I do not possess the capacity to smash.”

Klosterman has written a book of enormously engaging tangents. You may occasionally wonder where this is going, but you soon find out. The author never strays from the course, even if he takes you through the weeds to show you a new view. The chapter on profane comedian Andrew Dice Clay had me scratching my head … at first. Dice as a bad guy? An unlikeable comedian, perhaps, but hardly a villain. The author soon morphs the argument into the victory of political correctness.

In recent years, movies and television have built more nuanced, sympathetic portrayals of bad guys such as the drug dealers on “The Wire.” The late, great actor James Gandolfini, who played Tony Soprano, comes to mind. Surprisingly there are very few women mentioned or considered as villains in Klosterman’s book, though Sarah Palin’s name does come up over three short pages.

Witticisms abound in this book. The author dislikes the 1970s band the Eagles — and turns a critique of their song “Take It Easy” into an oblique takedown of Tiger Woods’ extramarital affairs: “It’s clearly the problem of a young man, as no one over thirty-five could sustain interest in seven simultaneous relationships unless they’re biracial and amazing at golf.”

Klosterman dissects two other black athletes: O.J. Simpson, who is commonly perceived as a villain, and Kareem Abdul-Jabbar, who is less so (“If he’s a villain, he’s the best possible kind.”). Abdul-Jabbar sounds refreshingly like a normal person, one who doesn’t embrace adulation or fame. O.J. Simpson, on the other hand, clearly is a bad guy, having murdered his wife and Ron Goldman. Klosterman makes light of Simpson’s book If I Did It in a brilliant takedown. If he did it?! Of course he did.

The author is fond of making lists. Given Americans’ fondness for lists, this mostly works out well. On the other hand, his use (and overuse) of parentheticals, although always spot on, can become distracting.

I Wear the Black Hat is a grab bag, a Whitman’s Sampler. There’s always something that you will enjoy, and it simultaneously gets to the heart of what is villainous while entertaining and humoring you. Klosterman writes at one point, “An author I know once explained why writing became so much more difficult in the twenty-first century: ‘The biggest problem in my life,’ he said, ‘is that my work machine is also my pornography delivery machine.’”

Ummmm … no comment.

Garrett Peck is the author of four books, including The Potomac River: A History and Guide and its sequel The Smithsonian Castle and The Seneca Quarry. He also leads tours to Seneca Quarry as well as the Temperance Tour of Prohibition-related sites in the nation’s capital. www.garrettpeck.com

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