Why Dictators are Never Cool

even when they really, really want to be

Apr 18, 2025

Another big week of new people coming to join us here! So just a quick note to say hello (hi!) and to tell you that this is my mostly-weekly newsletter where I talk about WHATEVER I FEEL LIKE even if it’s COUNTER CULTURAL and that even if you HATE IT I will keep my emotions in control because I’m just cool like that. But also I will usually talk about my latest projects, stuff I like, birds, also birds, sometimes birds, and pretty much always a picture of my bunny Bruce.

So let’s see what we have to discuss first!

God With Us: Bible Stories on the Road to Emmaus

My graphic novel GOD WITH US has now been out for almost three weeks!

We talked all about it on the Fascinating Podcast this week. You can listen here:

If you’ve read God With Us and you’re willing to take a few minutes to leave a review on Amazon or GoodReads it’s a huge help to me!

Why a dictator can’t — by definition — be cool

President Bukele — the self-proclaimed “coolest dictator in the world” — hung out at the White House this week, where he did a lot of uncool things like talk with President Trump about building more prisons in El Salvador so that the US can incarcerate some American citizens there in addition to the immigrants who are currently illegally held there.

I was so struck by the idea that President Bukele thinks that he is cool, and the fact that I had an almost visceral response to this idea, that I spent a lot of this week doing a deep dive into the history of “cool”… where it came from, what it means, why we disagree about what is cool and what is not.

I legitimately got to the point that I could write a book on this. Okay, a third of a book, maybe. So please know that I am simplifying here so that we can get to what is an uncontestable truth: A dictator cannot, by definition, ever be truly cool.

Believe it or not, there’s been scholarly studies on this. Here’s my favorite one if you want to be a big nerd and go read more on your own.

So, here’s the problem: lots of people want to be cool. And they want it so bad that we actually have two conflicting definitions of cool.

Let’s boil it down, simplified, like this:

Cool: someone who is stylish and/or popular.

Cool: someone who is countercultural and/or rebellious, and calm in the face of injustice.

You can see where these are in conflict right out of the gate. Someone who is cool (stylish) almost certainly is embracing a majority culture of some kind… they’re wearing the “right” clothes, have the “right” look and tend to have a lot of social capital.

Whereas someone who is cool (countercultural) is almost certainly rejecting a majority culture of some kind. They’re in opposition to the majority trends and dress how they want, do what they want, and they don’t really care what you think or say about that.

Miles Davis, definitely one of the coolest

Using the word “cool” in these ways comes to us out of the African American experience, and specifically through the jazz music of the 1920s. If you know anything about the history of jazz, you know that it came into being largely as enslaved peoples in the US played music together and blended traditional African and European musical styles into a whole new thing.

It’s difficult to even imagine this today in the age of elevators that play smooth instrumental jazz, but jazz started out as a controversial and counter-cultural musical movement. Cops would bust up jazz clubs, arrest musicians, cancel permits letting them play music. Was it because the musicians were Black, or because of the jazz? The answer was often, “Yeah, both.”

And in that musical movement — probably on the front end, but with increasing frequency after World War 2 — the idea of coolness came to life. The idea was to be relaxed, be chill, to be in control of your emotions, even in the midst of opposition or oppression. People don’t like our music? That’s fine, man, don’t worry about it. Don’t dress the right way? Don’t look the right way? Cops busting up your jam session? Be cool. You can’t control what those other people think or do, but you can control what you think or do.

Nearly always connected to this counter-cultural ideal of coolness was a protest-centered idea that we can build a society outside of the unjust one. They can arrest us or hate us or even kill us, but they can’t force us to become like them.

Interestingly, this counter-cultural coolness spread into the white counter-cultural movement through people like the Beat poets, and singers and actors who were connected into the jazz scene.

And from there, it eventually spread to folks who *wanted to be popular* and would take counter-cultural styles and ideas and drag them into the mainstream, often leaving behind the counter-cultural values and ideas but taking the music and clothes and slang, which created this sort of soulless coolness that was based completely around stylishness and popularity.

Of course the counter-culture would have moved on by then to create new social markers for the outsiders, and the cycle starts again.

So you can see why a dictator can’t be cool any more than they could be counter-cultural. If you’ve brought the whole culture under your thumb, you can’t really rise up and resist yourself. So in El Salvador, where an astonishing TWO PERCENT of the population has been incarcerated — the highest per capita imprisonment rate in the world — it’s not the jailers and politicians or the head dictator who is cool, it’s the people who resist them.

It’s impossible to be cool if you’re a dictator. And it’s very, very difficult to be cool if you’re a world leader or a billionaire or something like that… who are you going to fight? Who are you going to stand up for? It’s always Robin Hood who’s cool, not Prince John.

That’s why we see someone like Elon Musk — the richest man in the world and a guy I consistently just feel sorry for — struggling so hard to be cool. He just wants people to love his jokes and think he’s awesome, but when you’re the richest guy on earth the one thing it’s hard to be is cool. He COULD be cool, but he doesn’t understand it. He does things like hire a team of video game players to make it look like he’s good at video games, not understanding that “good at stuff” is not enough to make you cool (and “paying people to make it look like you’re good at stuff when you’re not” is super uncool). He COULD become cool if he chose some sort of massive, unbelievable goal that would make things better for humanity and went after it… like the time he said he’d fund the end of world hunger, but then took that money and donated it to his own non-profit, probably as a tax dodge.

Someone like that can be popular, can be stylish, can be liked or admired, but ya just can’t be cool. Which is very upsetting to someone who wants it so desperately. And people who are too eager to be cool… well, you know. Ya gotta just BE cool.

I’ve done like three drafts of lists to show kind of who is cool and who isn’t, and how rich or powerful people CAN be cool and how it’s almost always linked to their care for the outcast or vulnerable, but I think at the end of the day it’s better if people think of their own examples.

So think about some of the coolest people… rebels with or without causes, people who stand up for others in the midst of unfair authoritarianism.

Mr. Burns

I was in NYC and Connecticut very briefly this last week so I could go see a play called Mr. Burns that my daughter Allie did all the choreography for.

The play is about the Simpson’s as a cultural artifact after the apocalypse. Allie and the other students and staff did a great job on it, and I have to say I’ve been thinking about it a lot since I saw it.

I somehow managed not to get a single picture (at least on my phone) of any of my friends who I managed to see briefly, including Clay and Jen, who I stayed with, my writing partner Hugh and his wife Shay, my new friend Chris McCumber, and also my sister Dawn and brother-in-law Todd and OF COURSE MY DAUGHTER ALLIE and despite this embarrassing wealth of people I love in a very short period of time I really only managed to get a picture of an idol of Bart Simpson. D’OH!

JAILBREAK

Apparently yesterday I did not sufficiently lock the door on Bruce’s hutch.

It’s not really a “jailbreak” as Bruce happily puts himself to bed every night, but I do usually lock him in to keep him safe from raccoons, which are disgusting omnivores that would gladly eat a gigantic bunny. Anyway, here’s a picture of the fugitive as I saw him this morning:

He was pretty pleased with himself. I don’t know how long he was out running about that night or into the morning, but when he saw me, he came inside, ate some pellets, and then stretched out for a lovely nap on the porch.