Why Speechwriters Take Humor Seriously

How leaders can land a joke that packs a punch — and proves a point

West Wing Writers
5 min readFeb 27, 2023


As leaders of West Wing Writers’ humor practice, satirists who have been published in the pages of The New Yorker and McSweeney’s, and veterans of the political comedy world, we’ve dedicated our careers, in part, to crafting jokes that serve a higher purpose — whether it’s helping progressives advocate more effectively for a cause, or helping business leaders make their messages more memorable.

We believe humor is a singularly powerful way for leaders to educate and endear. And you don’t have to take our word for it. Our perspective is confirmed by the most hilarious of disciplines: research.

One study found that people are seen as warmer and more competent when they disclose negative information about themselves with a joke, rather than delivering it straight. Another found that business leaders who used humor had happier, more effective employees. History is filled with examples of public figures who cracked a joke to show off their self-awareness and ease critics’ concerns. And if you’ve ever been to a conference where someone finally makes a quip after hours of self-serious presentations, you know first-hand how restorative a well-timed witticism can be.

And yet, thought leaders — from politicians to philanthropists, activists to academics — often tell us they avoid cracking jokes because they see being funny as risky. Some fear inadvertently offending a listener or making the wrong kind of headlines. Others simply doubt they’re funny enough to pull off a one-liner.

Which makes us… sad. Because, you don’t need to be a professional comic to deliver humorous remarks that pack a punch, prove a point, and stay firmly in the realm of good taste.

Here are six proven comedy writing techniques that anyone can apply to make ’em laugh…and make an impact.

1. Aim for cutting, not cruel.

One question we’re often asked is how to poke fun at someone without anyone getting hurt. The comedian Hasan Minhaj has a helpful heuristic for evaluating whether a joke is fair game: “My rule is I will make fun of your character” — as opposed to immutable characteristics.

Indeed, the jabs that got the biggest laughs at the 2018 White House Correspondents Dinner hit at politicians’ choices, rather than their appearances. Take this quip about the former president’s Twitter habit:

“[Donald Trump] tweets at 3 a.m. sober. Who is tweeting at 3 a.m. sober? Donald Trump, because it’s 10 a.m. in Russia. Those are business hours.”

Certainly cutting — but, as Minhaj points out, “not cruel.”

2. Stick your landing.

End your joke with the funniest or most revealing words. Otherwise, you risk talking over (or worse, abbreviating!) any laughter elicited earlier on in your joke’s structure. Tina Fey and Amy Poehler ran into this challenge when delivering their opening monologue at the 2015 Golden Globe Awards.

“Amal [Clooney] is a human rights lawyer who worked on the Enron case, was an advisor to Kofi Annan regarding Syria, and was selected for a three-person U.N. panel commission investigating rules-of-war violations in the Gaza strip.

So tonight, her husband is getting a lifetime achievement award.”

It’s a hilarious joke — and indeed, the audience roared with laughter. But that laughter began at “husband,” forcing Fey to speak over the noise to finish. It’s not every day that we try to punch-up a joke written by SNL alums, but if we may be so bold, here’s an easy fix for this one:

“Amal [Clooney] is a human rights lawyer who worked on the Enron case, was an advisor to Kofi Annan regarding Syria, and was selected for a three-person U.N. panel commission investigating rules-of-war violations in the Gaza strip.

So tonight, we’ll be giving a lifetime achievement award to her husband.”

3. Obey the rule of threes

In comedy, three really is the magic number. It allows you to establish a pattern with two items — any more would be overkill — and then subvert the audience’s expectations by breaking that pattern with the third.

Former CEO of IBM Ginni Rometti put this tactic to the test during her commencement address at Northwestern University. Quoting Franklin Delano Roosevelt, she told students that when it comes to public speaking, “you be brief, you be sincere, and you be seated.”

Which is a perfect segue to 4…

4. When in doubt, borrow

If you can’t think of a funny thing to say, reference a funny thing someone else said! Just be sure to give them credit.

5. Escalate

The Upright Citizens Brigade, the legendary sketch comedy and improv group co-founded by the aforementioned Amy Poehler, boasts the motto: “If this unusual thing is true, what else is true?” In other words, one way to turn a funny premise into a series of funny jokes is to paint a picture of the world in which that premise exists — and escalate to the absurd.

Take comedian Craig Ferguson’s remarks at the 2008 White House Correspondents Dinner. A recent immigrant to the United States, Ferguson, a Scotsman, noted that he was often asked why he didn’t move to Canada instead. “Canada,” he explained, “it’s not the party…it’s the apartment above the party.”

So, if that personification is true, what else is true? Ferguson plays out the scenario: Canada is the polite upstairs neighbor who just wants an evening of peace. The United States is the noisy but well-meaning party host. And the next floor down is — you guessed it — Mexico, who has long since joined the party.

6. Punch Up, Not Down

Tearing down people who are above you on the societal ladder is satire. The other way around is bullying. And if there is no one above you on the societal ladder, you can’t go wrong with self-deprecation.

Of course, there are innumerable techniques one can add to their toolkit of comedy — and like any other skill, it takes practice. So, start thinking seriously about thinking unseriously…and let the gags begin!

Sarah Gruen and Chandler Dean

If you want to learn more about the power of levity — and how you can harness it — feel free to reach out to us about our intensive (and fun!) humor workshops.

In “Orations Worth Ovations,” professional speechwriters analyze great speeches (real or fictional, historic or personal) and explain what makes them so good.

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West Wing Writers

A progressive communications-strategy firm led by former Clinton, Obama, and Biden Administration speechwriters.