I Wear the Black Hat by Chuck Klosterman

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“The true value of a human being is determined primarily by the measure and the sense in which he has attained liberation from the self.” – Albert Einstein

Chuck Klosterman gives us with this new book a series of essays that discuss various men and women (mostly men) ranging on a scale from the critically maligned (Fred Durst) all the way to very, very bad (Adolf Hitler). As you might imagine, the lion’s share of his focus resides on the less important but more playful end of that spectrum. To put it in perspective: O.J. Simpson serves as Hitler’s mini-boss, and Don Henley gets like 10 pages.

These passages don’t individually stand alone as well as those in Klosterman’s previous essay compilations, but rather serve as clothespins on a narrative string where he dissects the dirty laundry (if you will) of well-known figures and airs it out for everyone to get a whiff. He serves up Andrew Dice Clay, Julian Assange, Joe Paterno and Kim Dotcom, among others, as tributes to the court of public opinion.

Despite Klosterman’s role as “The Ethicist” for The New York Times—the epitome of a White Hat, one assumes—he delivers his verdicts in Black Hat less with journalistic precision than in the style of his classic, winding pop-labyrinths that either delight or infuriate (and often do both simultaneously).

He starts many of these essays with a main character. He summarizes the general ins and outs of this character’s alleged villainy. Before getting to an ultimate point about the subject’s guilt, he splinters off into some wild non-sequitur that translates to something like this: “In order to understand Bill Clinton, we need to understand Ted Bundy.” Then he processes the entire Ted Bundy history before leading back to deliver the complete Clinton world-view. [To risk an unsophisticated summary of this one: The reason we remember Ted Bundy as the only serial killer with a human personality instead of simply as another sub-human genetic monster is because he had good looks—the same reason a lying, cheating president escapes being remembered as an entirely pathetic joke…like, say, Linda Tripp.]

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If these pop-culture connections don’t dazzle quite as much as they did in some previous books, it actually serves to Klosterman‘s advantage. You get more of a sense that you’re reading a real conversation rather than some rhetorical magic trick. Think of Tarantino’s Bill conjuring Superman to explain his feelings about Beatrix Kiddo. The teenagers may be bored that heads don’t fly, but adults appreciate the intimacy of straight personality.

I Wear The Black Hat feels very much like the end of Klosterman’s innocence (if you’ll allow me to hit a second Don Henley note). This ain’t no ‘sports car and a blonde co-ed’ styled midlife crisis. It’s more of a High Fidelity, Rob Gordon, “What’s it all mean?” kind of thing. Klosterman prefaces the book with a latent philosophy-student rumination on how “good” and “bad” ultimately stand as meaningless constructions. He even non-ironically asks, “Am I a psychopath?” The Ethicist doesn’t feel comfortable with what he learned about his morals while writing his privacy-invasion fantasy The Visible Man, and yet he still doesn’t feel wrong. Just uncomfortable.

New York Times readers need not be alarmed. You don’t have to actually feel ethics in your heart to thoroughly understand ethics in your brain. One of Klosterman’s best theses asserts that the worst villains are “the people who know the most but care the least.” You wouldn’t get nearly as mad at a 5-year-old kid who severely injures his twin brother—even if he meant to cause harm—as you would at a 45-year-old man who gives the kid a wound across the face with a switch-blade. One person causes a worse injury…but the other person is worse, ya know?

(Coincidentally, Klosterman would point out, you wouldn’t vilify a face-slashing psychopath as much as, say, an informed Penn State football coach who did just enough to cover his own ass, and that’s it.)

For worse or better, I Wear The Black Hat shows Klosterman embodying this generation’s Lester Bangs—despite a more realistic standard for authenticity, he’s at his best when most navel-gazey. At one time, this might have been (and for some critics, always will be) a problem, except we’ve fully entered the Marc Maron era. To understand Klosterman, you need to understand Marc Maron.

Maron, and virtually all of today’s top standup comedians—Louis C.K., Patton Oswalt, Bill Burr and Paul F. Tompkins—toiled in mixed career successes for a while after they had already mastered their art. In a very technical sense, none of their most recent specials is as funny as their crafted material from back when nobody cared about them. But they’re so much better now. Because once you say fuck it and just grapple with your inner life for an audience, people who already like you are going to love you. Craft never resonates as much as intimacy.

Klosterman’s Black Hat essays drip with a certain type of self-reflection. He seems to be at the point in his career where complete objectivity—something he knows ranks as pretty much the most important part of his job—is the thing he’s least capable of achieving. Frequently smug prose can’t cover over the suffering of his inner identity crisis; it’s why I Wear The Black Hat is one of his best books yet.

Ryan Carey performs amateur cultural psychology at The Inappropriate Thesaurus (www.dolphindentist.blogspot.com) and on Twitter @SlackerDIYtoday.