Book Review: I Wear the Black Hat by Chuck Klosterman
- Christian Farrell
- Nov 5, 2021
- 3 min read

Chuck Klosterman is one of the most successful writers of my generation. He first came to attention with his column in Spin (which I used to relish, even though I didn't know who he was), then wrote books that were equal parts heavy metal tributes and back country travelogues, and finally branched out to wrote some of the most thoughtful and inspired prose of any American writer (his fiction...is another story). It's hard to believe that the writer of Sex and Drugs and Cocoa Puffs would become the writer of The New York Times' "The Ethicist" column on writing ability alone, but...here we are.
By the way, I somehow feel it's important to point out that I'm writing this review while eating Cool Ranch Doritos. Can't put my finger on it, but I feel like Klosterman would be pleased.
Anyway, I Wear the Black Hat stems from, of all things, a discussion Klosterman had about Star Wars that I've had with myself many different times.
Quick - what's your favorite Star Wars character! My guesses below.
Keep scrolling!
Did you say Darth Vader or Boba Fett? I did (Darth, at least). Klosterman had posed that question to his agent and theorized that young kids see themselves as Luke, teenagers as the suave Han Solo, and adults as Darth Vader, when his agent said he still saw himself as Han. This caused Klosterman to ask the obvious question about himself: Am I a villain?
Klosterman spends this book examining villainy in all its forms and seeing how the lessons learned could apply to him. He establishes early in the book the basic rule of villainy: the villain is the one who knows the most but cares the least - as per one example he provides, George W Bush wasn't a villain, but Dick Cheney was. He then applies this standard to all forms of villainy.
There are definitely standout chapters. There is one where he examines people and groups who set themselves up to be villains (like NWA and the Raiders/Al Davis), there is another one where he shows how "Seinfeld" subversively obliterated both the left and right sides of the political spectrum, and there is one where he explains why tying a woman to a railroad track is the most villainous act a person could do (even though it has never actually happened). The standout chapter is one where he sets out five descriptions that definitely sound villainous - like con artist, drug dealer, and athlete using racist taunts - and provides examples of "heroes" who still fit those descriptions.
Overall, though...this book kind of dragged. While much of what he was writing was thought-provoking, none of it was anywhere near as exhilarating as But What If We're Wrong, one of the most genius books I've ever read (which also happens to be the book who wrote after this one). Klosterman, as a gifted writer, even let his gift get away from him in one chapter. He was writing about why he loves Kanye West but wants him to fail, while he also hates Lebron James but wants him to succeed; as he started providing his argument for his feelings on Lebron he abruptly stopped and said he realized he can't find any way to explain his feelings towards Lebron. As Klosterman points out, this is something you can get away with if you are having a discussion with someone face to face; however, after reading it as a chapter in a book, it just seems like a great waste of time.
It's possible that I'm holding Klosterman up to an impossible standard since the book after this one is one of the greatest books I've ever read, but I do think I Wear the Black Hat was better in theory than IRL. Still, I think we can muster up seven out of ten hot dogs.



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