A review of 'The Serious Guide to Joke Writing'

Some key takeaways (not to be confused with edible keys to go)

Hi people reading this! This article is something different than my previous ones. With that in mind, lower your expectations, and give it a read.

I recently picked up The Serious Guide to Joke Writing by Sally Holloway. While reading, I noticed some overlap with How to Write Funny by Scott Dikkers (Henceforth referred to as HTWF). This isn’t a bad thing—if anything, it added depth to concepts I initially glossed over in Dikkers’ book.

Here are some of my key takeaways:

Don't gloss over wordplay

Without going on a rant about word-play, I'll say this: Wordplay isn't unique to this book. Scott Dikkers talks about it in HTWF, and it's incredibly common in comedy writing, both new and old.

Sally has a bunch of interesting exercises that revved my brain up. I did those exercises in the margins of the book and it's been one step in the process of every joke I've written this week.

Here's a weird wordplay joke I wrote while half asleep this morning, that I decided to run through chatGPT and caption:

The Brain's background processing function

The way I originally learned about it was as 'Focused thinking' vs 'Diffused thinking', which is easily found on google.

This felt like an important reminder to step away from certain jokes and ideas and to let my brain think about it in the background. The way Sally spoke about it in the book also reminded me of this quote from "The Book of Beautiful Questions":

Surrealist Questions

Questions like “How would you explain this to an alien?” or “How would a 4-year-old see this?” are useful for examining ideas from a fresh perspective. These kinds of questions can lead to unexpected insights, making them effective tools in joke writing.

I associate this technique with Madcap or Reference categories from Dikkers’ funny filters, though I won’t dive into it here, as the next section is more relevant to me.

Joke Webs (or mind maps)

Joke webs are mind maps. They can be used to freely think about how our core focus for a joke connects to objects in our mind and how those objects connect to more adjacent ideas.

This is a way to find specificity through free thinking.

In HTWF, we speak about funny filters as a way to take an idea (subtext) and filter it through a mechanism that heightens the subtext.

Example subtext: Crying babies are annoying.

• Ironic filter: “Nothing makes me want kids more than the crying baby on the plane.”

• Hyperbolic filter: “I wouldn’t hurt a baby, but if it’s crying, I might accidentally book it a flight to Siberia.”

• Reference filter: “Have you ever noticed that babies are usually crying, or sleeping? They’re either annoying, or drooling. Sometimes both!”

These example jokes are deliberate applications of a specific comedic lens.

Joke webs are much less deliberate in the beginning. We can start at the same place but this time, we start thinking about subtext through free associations:

I stopped myself at 1 or 2 layers deep here, but even that led to several joke ideas, such as…

• Do you think that when Obama was a baby and he pooped his diaper, he was like “What I need. What the American people need… is Change. A change of diapers.”

• They say you need to change a baby’s diaper right away but I think it’s like changing tires. You can push it off a little if you can’t afford it right away.

• The only thing scarier than a crying baby is crying bay bees.

• When I have company, my guests are usually very concerned my baby is crying, but then I explain to them that it’s passover, money is tight, and we need his tears for the celery.

• My baby is crying because he is hungry, but it’s ramadan and if I can’t eat, neither can he!

• Don’t go near my crying baby if you have any open wounds, unless you want to be a crying adult!

A lot of these jokes are bad, but that’s the name of the game when it comes to comedy writing. I still wrote them, and I wrote them in a few minutes while trying to prove a point.

What’s really interesting is that joke webs allow for a less structured approach. You start with a core idea and follow free associations, leading to new joke opportunities without adhering strictly to formulas.

Primary lessons learned:

The key lesson isn’t a secret to writing better material—it’s about using more tools. Sally Holloway provided me with additional ways to think about joke writing, particularly in terms of free association and mind maps. These tools haven’t replaced traditional editing practices, but they’ve helped me approach jokes differently.

A good joke still needs strong subtext and effective editing. No technique replaces the process of trying jokes on stage, refining them, and cutting what doesn’t work. Also, not all jokes work for every performer. Some of the jokes I’ve written through this process wouldn’t land well in my own stand-up, but they could be valid for other formats like sketches or scripts.

The things I left out:

Sally’s book has 15 chapters. I spoke about 4. I sincerely recommend you give it a read and decide for yourself what the important bits of the book are.

You can purchase the book here.