I Wear the Black Hat: Grappling with Villains (Real and Imagined) was my least favorite Chuck Klosterman book so far. I've read both Eating the Dinosaur and Sex, Drugs, and Cocoa Puffs along with parts of other essay collections and some of his online essays. Typically, I'll read one of his books and begin to think and write like him but can't sustain the imitation because he's far too smart. This book reads like that, but instead of being like his other books, which are closer to playful bar banter, this was like a doctoral dissertation defense.
The discourse seemed heavier but the content didn't help matters. The things Klosterman wrote about were things I didn't understand culturally. He's ten years or so older than I and the essays on Andrew Dice Clay, Don Henley, and Monica Lewinsky were too bland because I didn't grow up with the ideas that surrounded those people and didn't experience their impact. I had nothing to draw on and say, "Oh yeah, I remember that."
The essays are loosely based around villains, so loosely that Klosterman shares the musical acts he hated from 1984 - 2003.
There's never been an artist I didn't like as much as I didn't like Bruce Springsteen as a twelve-year-old. I hated all his songs, including the ones I'd never heard of. I hated music about roads and I hated his generic-yet-kinetic clothing and I hated whoever it was I thought he represented...I just thought he was so fake, which is the most backward possible reason for hating Bruce Springsteen. - Page 27
If you like Klosterman, look for this book. His discourse and humor are still there, it was just too much for me.