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This week we’re turning off the paywall and turning things over to Friend of the Newsletter Chandler Dean. Chandler is the writer, comedian, and speechwriter behind the comedy debate show Abolish Everything!, which has a new season out on January 29th on Nebula. He’s written short humor for all the cool places, performed at UCB, and leads the humor practice at West Wing Writers. And he’s guest-writing this edition to talk about persuasive humor and how it works.

After that, we’ve got a couple of recommendations of things we’ve been into lately: A daily trivia game and an archive at the intersection of punk and technology.

On Persuasive Humor

There are a lot of things you can accomplish with short humor—making your reader laugh, making your reader smile, making your reader quietly breathe to themselves slightly more heavily than they normally would—and generally speaking, funny should come first.

But humor is also a powerful tool of persuasion. We laugh at the things we immediately recognize to be true, but hadn’t thought—or dared—to express ourselves. So when we laugh, it can be an involuntary recognition that the joke we just heard contained a good point.

In my work as a speechwriter, I use humor all the time as a rhetorical tool to get a point across, and make it as memorable as possible. But the inverse is true, too: in my comedy, I often rely on evidence and persuasive techniques to get laughs—especially when a piece is topical or when I’m writing for my comedy-debate show Abolish Everything!

A lot of my favorite comedy I’ve ever seen or done falls into this subgenre that we could call “persuasive humor.” Here are a few big lessons I’ve learned in attempting it:

Having a Strong, Clear Point of View is Half the Battle

This is the engine of your persuasive piece. If you’ve heard the UCB motto for how to build out an improv scene or sketch—”If this is true then what else is true?”—then this is your “this.”

For the last few election cycles, I’ve written a topical Election Day piece for McSweeney’s, each of which was inspired by a strong, genuine feeling that I was eager to express, and could succinctly articulate:

2018: We Won? - The results that night were pretty good for Democrats, but it still felt difficult to believe it would make a real difference.

2022: The Time Has Come for Republicans to Take a Long Look in the Mirror and Keep Doing the Same Thing - Every time Democrats lose there’s all this introspection about what we need to change as a party and yet even on a bad night for the other party, Republicans don’t seem to have to do that.

2024: Lessons Democrats Can Learn from Trump’s Flawlessly Executed 2024 Campaign - Yup, Republicans didn’t need to do that.

It is certainly possible to come up with a funny concept that doesn’t come from an earnest place of passion, but I find that the likelihood of your audience caring about your point of view is much higher if you do.

This is why, in Abolish Everything!, I force myself and other performers to take the most extreme possible position on the silliest possible subjects. “Best man speeches are annoying” is just not as rich a starting point as “We need to abolish best man speeches.” (But both are true.)

Format is Your Friend

So once you have a strong, novel point of view, that’s enough to start building out a serious op-ed—but for short humor, you of course need some kind of satirical twist.

I’ve found, time and again, that one of the easiest and most effective ways to make a serious argument funny is to pair it with an unexpected writing format. This can be summed up with a simple “What If” statement—”What if X was like Y?” 

When Sarah Gruen and I wanted to write a piece satirizing annoying political fundraising emails, we literally made that “what if” statement our title: If I Emailed My Parents Like Democrats Email Me.

The nice thing about aping a specific format is that you don’t have to pull ideas for beats out of thin air. Instead, you can follow the format you’re parodying. What are the tropes of cover letters? Or election night speeches? Or, in this case Democratic emails? When we wrote this one, Sarah and I literally pulled full sentences from real Democratic emails and just swapped out specifics to fit our concept. (We were mad libs doing Mad Libs.)

Again, Abolish Everything! is built with this in mind too—everyone is encouraged to adapt their funny idea into the format of a passionate political speech, which constantly gives you somewhere to go. And what is that format? Well…

Steal From Speechwriters

In my experience as a speechwriter, many, if not most, persuasive remarks follow Monroe’s Motivated Sequence: Attention, Problem, Solution, Vision, Call to Action. (A format passed down to me by Newsletter of Humorous Writing Co-Founder Brian Agler!)

Not every set at Abolish Everything! follows this to a T, but when they come close, it tends to work: Here’s my idea, here’s why I believe it, here’s what will happen if my idea isn’t implemented, here’s what will happen if my idea is implemented, address some counterarguments, tell an emotionally resonant story or share a profound quote that supports your idea, get out of there.

And just like a real speech is more effective with strong research, so too is a good Abolish Everything! set. One can get away with just popping off with takes unsupported by evidence, but a lot of the best moments on the show have come when people can point to headlines or statistics or visuals or real stories from their lives that bolster their claim. 

People both loosen up and pay closer attention when encountered with a compelling fact or truth they hadn’t considered before, which are both excellent conditions for getting a laugh. And people are also blown away when they hear or see something funny that is also completely real. (See also: Luke and James’s great breakdown of Found Humor.)

Advance the Argument with Every Joke

This is something I wouldn’t necessarily worry about until you’re going back and editing. I don’t think it’s good for the creative process to constantly be keeping track of The Rules as you crank out your first draft. 

But once you’ve got that draft, it’s a useful exercise to go back and ask, for every line, if it meets two criteria: 1. Does this joke serve the point of view that the overall piece is expressing? and 2. Is it serving that POV in a unique way that no other line in the piece is doing already?

Following Rule #1 ensures that your piece isn’t meandering or confusing. And following Rule #2 ensures that you don’t just circle the drain, rephrasing the same joke over and over again.

With a lot of persuasive humor pieces, I’ll embody a character—let’s call him “Guy Who Idiotically Thinks the Opposite of What I Believe.” Or GWB for short. You can get a lot of mileage out of just putting GWB in different situations with each paragraph and playing out how he would react.

So in writing I Am a Disappointed Trump Voter Who Was Told It Would Be the Past By Now, I started by researching all the most ludicrous reasons that people voted for Trump—like reversing inflation, ending the male loneliness epidemic, vanquishing woke, and (gulp) taking over Greenland—and then it was just a matter of popping off on each of these subjects from the point of view of GWB.

What Are Some Examples of Great Persuasive Humor?

To atone for all of the talk about my own work I just did, here are some other pieces from this subgenre I’ve enjoyed lately:

Mike Drucker is particularly adept at this particular combination of a sharp POV with simple, elegant, delightful execution, as in his post-Dobbs piece We Would Do Something, But Then We Wouldn’t Have the Power to Do Something, So We Can’t Do Something.

Josh Gondelman captured the absolute insanity of getting inundated with diet and fitness culture right now with The Apocalypse is No Excuse to Give Up on Your Wellness Regimen.

And I felt seen in a really tough way after reading McKayley Gourley’s DUDE CORNER: Hey, Have You Seen This Thing I Haven’t Started Looking for Yet?

But also: in Abolish Everything!, we’ve designed a whole show for this kind of persuasive humor—making it one of very few TV or streaming shows practically engineered to showcase the talents of satire and short humor writers. And I’m proud to say that this season features a bunch of incredible talent from the satire and short humor community, whose work has been featured in this very newsletter—including Johnathan Appel, Adam Chase, Sam Corbin, Meredith Dietz, Ben Doyle, Sean McGowan, Jason Siegel, Cara Michelle Smith, and Milly Tamarez. So if you like persuasive humor, I hope I can persuade you to watch Abolish Everything!—returning to Nebula this Thursday!

Some Recommendations From Luke and James

Luke recommends Catfishing - The Wikipedia Guessing Game. This is a nifty little trivia game where you try to guess the titles of Wikipedia articles based on the categories the articles belong to. The articles are well-curated and the game tracks all kinds of stats that I find tremendously interesting to pore over.

The game can be pretty tricky at times (according to the stats “the all-time average daily score” for everyone playing the game is “3.6 out of 10.”), but unlike other daily games where you can drive yourself nuts and spend way more time than you want trying to figure out a solution, I find it refreshingly easy to know when I’m not going to get the right answer and accept that I’ve got to throw in the towel. Plus, even when you don’t get the correct answer, you often come away having learned something fun. For example, until I played the January 24th game, I never knew [redacted] went on to become a princess by marriage.

One last bit of trivia: According to the site’s extremely thorough FAQ page, versions of the game have been around since 2006—back before “catfishing” had any other meaning!

James recommends this JSTOR Daily article by Alex Houston on xeroxed punk fliers. Two Queens inventions, the Xerox machine and punk (thanks to The Ramones), are forever linked. The copy machine and its signature aesthetic of black and white, high contrast, visually lossy images have long been associated with punk. Alex pulls together academic articles and selections from a very cool archive at Cornell of fliers to tell the story of how the office copier and rock and roll collided and intertwined.

And if it isn’t on your radar already, I really recommend JSTOR Daily. They’re always surfacing interesting things like this that might otherwise remain hidden in academia.