Klosterman's breakthrough uses cereal, soccer, The Sims, and Pamela Anderson as serious philosophical raw material — arguing that what a culture throws away tells you more about it than what it keeps. A manifesto for treating low culture with the same rigor you'd give to high culture.
Klosterman's breakthrough book, and the one where he established the mode he's been working in for twenty years now. Sex, Drugs, and Cocoa Puffs is a collection of essays about low-stakes pop culture subjects — cereal, The Real World, soccer, Pamela Anderson, internet dating, The Sims — treated with a seriousness that most critics reserve for high culture. The move is deceptively simple. Klosterman notices that the things a culture marks as trivial are often where its actual values are hiding, and he writes about those things with enough rigor that you come away thinking about them differently.
The famous essay is the opening one, on romantic comedies. Klosterman argues that watching too many romantic comedies has given a whole generation a warped expectation of how love actually works — that the cinematic logic of a misunderstanding followed by a chase at the airport has seeped into real lives in ways that make real relationships disappointing by comparison. The argument is funny. It is also, when you let it settle, alarmingly plausible. Every subsequent essay does something similar: takes a piece of pop culture most people would be embarrassed to think about, and shows that the embarrassment is the tell.
I bring this book up on the river when somebody's doing the thing where they're being snobbish about a thing somebody else loves. Klosterman's lens is useful here. The question isn't whether the thing is good. The question is what work the thing is doing for the person who loves it, and once you ask that question, a lot of judgment collapses into curiosity. That's a useful shift, and the book trains you to make it.
The voice is the other reason to read. Klosterman has the single driest comic instrument of any contemporary American essayist. He doesn't raise his voice. He doesn't strain for the joke. He lays down a sentence that has the joke embedded in the clause structure, and either you catch it or you don't, and he's not going to help. That restraint — combined with a willingness to write seriously about things other critics wouldn't touch — is the Klosterman signature, and this is the book where he figured out how to do it.
Read it when you need a mental break that isn't just vegetation. The pieces are short, self-contained, and individually satisfying in a way that long-form criticism often isn't. You can read one at camp, think about it while you're washing dishes, and by morning you have a new argument to bring to the crew. That's the book working.