Political cartoonist and writer Tim Kreider is known for telling it like it is. An unabashed critic of George W. Bush’s administration, which he covered in his cartoon strip The Pain—When Will It End?, Kreider gained fans for his darkly funny take on some very serious times.

Kreider’s comics have been published in such colorfully named collections as The Pain—When Will It End? (2004), Why Do They Kill Me? (2005) and Twilight of the Assholes (2011), which combined his essays with his cartoons. In addition to being an artist, Kreider also contributes essays to the New York Times. His work has gained fans such as Judd Apatow, Rolling Stone’s Matt Taibi and the late, great David Foster Wallace.

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Here, Kreider talks about his latest, We Learn Nothing, an essay collection that covers a close brush with death; attending a Tea Party rally; and figuring out how to let a friend-turned-peak-oil-fanatic go. We called the book, “earnest, well-turned personal essays about screw-ups without an ounce of sanctimony—a tough trick.”

How did We Learn Nothing come about? Many passages and ideas seem to have stemmed from your New York Times work?

I wrote a few pieces for a blog series in the Times. The first piece I wrote was on a series on alcohol. The editor liked my writing a lot and invited me to be a regular contributor on the next one on happiness, a subject among my friends I’m not generally an authority. I wrote five or so pieces, and on the strength of those, I got some interest.

There are several short essays in the book of ones that first appeared in the New York Times, but all the longer ones were wrote originally for the collection…I would take a theme and run with it for couple thousand words, longer ones for book, and they tend to be personal experiences…I mostly wrote about people I’ve lost in one way or other over the years. In some cases, they just stopped being my friends, or it became impossible to be friends with them anymore.

There is a sort of bittersweet tone to the book, to growing up and leaving behind youth…

The tone surprised me. I spent years as a political cartoonist and polemicist, and I got very practiced at being funny and mean. I found myself trying things in this book that I wasn’t necessarily sure I was good at. It’s scary enough to try to be funny and fail, but trying to be sad or moving and failing in a way is more embarrassing.

I started writing this two years ago, in my early 40s. It’s an odd time of life, when you turn 13, there are all these pamphlets and filmstrips that tell you that your life will be changing now. There’s none of that when you turn 40, but it’s kind of the same—your life starts to change in ways that no one has prepared you for. When you start to realize that, you start to do some rough calculations that, yes, time is not endless. You can feel it in your cells, the hangovers last for days. Now I feel like I’m not getting anything done.

And that’s another thing, somewhere in your 30s, people’s fates start to diverge, the chickens come home to roost. One reason I started to lose people, one of the delusions you cherish when you’re young, is that everyone is going to be OK, they’ll meet someone, etc. Eventually you realize that not everybody is going to do that, good things do not come to everybody. That’s another thing that accounts for that evangelic tone that crept into this book—it’s a lot about people I loved a lot and lost in different ways.

What do you like about writing that illustrating doesn’t provide?

Writing is what I was supposed to do, what I studied in school, what I majored in. But I spent several years trying earnestly to be a writer, way done back then. I wrote short stories and sent them to literary magazines, and nobody published them.

But then I got positive reinforcement for my cartoons from the local alt-weekly [Baltimore City Paper] and then continued what I got positive reinforcement for. I published essays called the “artist’s statement” along with my cartoons each week, and they got longer and more polished and lot more like essays. I was very iffy about including that with the cartoons—I’m personally of the opinion that artists should shut up about their own work…frankly artists are usually in the dark about what they’ve accomplished. I admire people like Stanley Kubrick who don’t talk, but my publisher at Fantagraphics [Books] wanted to include them and did.

One essay deals with attending a Tea Party rally. In this election year, any plans on more political work?

No, I suppose if someone asked me to and paid me money for it, I would write or draw something about it, but mostly for emotional reasons and the emotional hell that entails, I don’t need to get sucked back into it. I know that nobody is very happy with Obama, but the Republicans have no one. Romney is not liked. I think it will be like a Clinton and Dole blowout [in 1996]. Matt Taibi wrote in the last issue of Rolling Stone that this might be the most boring election of all time.

Molly Brown is the features editor of Kirkus.