The Serious Guide to Joke Writing, by Sally Holloway

Jack Thompson
7 min readJun 27, 2021


How to Say Something Funny About Anything

If you go by the reviews, this book is a modern classic, with plenty of recommendation for it online. Even the praise for the book is positive.

What I mean to say is, let’s find out if the praise is deserved.

The format of the book is good. It’s of short to medium length, interspersed with quotes and plenty of exercises for you to try out. You’ll get through it pretty quickly and have a lot to keep you engaged while you read.

A good chunk of the book is dedicated to Sally Holloway’s ‘Joke Webs’. It makes sense, because it’s the foundation for her writing process.

What are joke webs?

If you know about mind maps, this is the comedic form. Feel free to give the author some credit, because while visually mapping topics is nothing new, this is the first time they’ve been presented exactly like this.

Author Sally Holloway explains how she’s used this way of thinking — throughout her own successful career — to produce material for different shows and paid gigs. Where as my earlier reviewed How to Write Comedy filled a single page to show this at work, Holloway’s book goes much further and gets lot more specific.

With that, we’re underway, and using the experience of classes she’s taught joke writing to, she steers you, the reader, through the process of using joke webs for your own writing.

Very quickly, you’ll see this is a practical book, and to get the most out of it, you have to join in. There are 15 exercises to work through in total. From the bases of joke webs, you’ll be playing with words and phrases, redefining their existing meaning, and taking hem in unexpected directions.

While she could leave you to get on with it, her clear instructions guide you through the process. To add to it, there are ways to think about words, how to use the associations properly, and what to do if you get stuck. So you don’t get lost, instances from her classes are transcribed, which lets you see how other beginners get on.

Going through the book, you get to come up with jokes from a single topic, a mixture of two topics, while you’ll see jokes dropped in from famous comedians.

Which has been done purposefully to make you feel bad. Or possibly to inspire you.

It’s no matter if you get in trouble while coming up with jokes; most chapters end with a form to work though, a signed confession for the police.

In reality, chapters end with a troubleshooting section.

These cover typical issues that arise with students from her classes, and given that you’re following the same processes, hopefully these apply to you.

But if they don’t, too bad, your career’s over.

Author Sally Holloway. Her hair seems pretty straight, while I bet her mind’s tangled in joke webs.

While joke webs form the core of the book, there are some more things inside. As previously mentioned, there’s mixing of two topics discussed, with double joke webs. Moving on from that, there’s how to think about, and approach, joke writing from news stories.

Along the way, you’ll find the book to be motivational. That starts with the front cover; the font is clear, and in parts, bright and friendly, the kind that will even get kids going.

What I mean to say is that Sally Holloway talks about the challenges of joke writing as a paid job. From these pages, you’ll see that if you want to succeed, you basically need to stop complaining and get on with it.

However, she’s nicer than that about things.

The author highlights the time pressures to get things done and the work that has to go in. She informs you about panic, and how to approach it when it strikes. She talks of the nerves that afflict performers, and the feeling of dread you can get while writing, that your work isn’t good enough. She provides encouragement, to help you carry on with carrying on writing.

As you work through the pages, you’ll note the book doesn’t go into techniques you’ll find in other books on writing, those like exaggeration, irony, reverses etc. What it does provide is more ways to search for jokes.

She gives you a chapter called The Surrealist Inquisition, which prompts you to find different angles for topics . Provided in it are prompts and questions to stretch your thinking, for you to take a different perspective, to uncover material which otherwise may not have shown itself.

In the Stream of Consciousness chapter, Holloway describes how uninterrupted writing can help you find more ideas and jokes. Once more, there’s a page of handy prompts, while a transcription to an in class answer, highlights how you should follow the process and how you might get on.

While the questions hopefully help you discover some comic material, making jokes from them isn’t discussed. The questions open up topics and you can apply the things you’ve found to a central idea.

But how do you make it funny? It’s the hardest part of any instructional on joke writing.

It’s where a writing partner might help. If you’ve got one, you can immediately hear laughter. Those tears, your joke hit the mark. The two hours of talking without punchlines, they killed. If you haven’t got that, and it’s hinted in the book, you can write something and drop it into conversation. If you’re confident, exclaim it’s a joke (but the reaction might be different).

Without any audience, how do you know your idea is funny? These are just associations after all. Comedy relies on associations, but how do you get it to be funny?

That’s not answered.

In the author’s defence, maybe there isn’t an answer. In fact, long time comedy writer Gene Perret mentions this same issue in Comedy Writing Step by Step. He says the final item, the joke, must come from you.

In Holloway’s book, it seems that associations are the key to humour and comedy, and you, as the joke writer, are tasked with finding them.

Towards the end, honing your jokes is discussed. It gives some real examples of jokes which are changed ever so subtly, to alter the audience reaction, or because a reaction is lacking. One is given slight modification to avoid offence (because of the nature of the topic). Another is altered and it no longer gets any laughs. There’s a brief analysis as to why.

The book ends with a case study.

It’s interesting to see this laid out. 12 and a bit pages of an occasion the author had to write jokes to a tight deadline. Seeing how the submission date approaches and how she goes about getting the work done is a nice touch to finish the book. There’s a real feeling of how quickly you would need to move and the constraints which can get in the way before you can get your work submitted.

Nicely done.


A pretty succinct look into the world of joke writing. This book offers you plenty of scope to approach any topic, explore it deeply, and pull things out you wouldn’t necessarily find otherwise.

Recommended for:

Creatives who feel they haven’t got enough to write about

Thinking of different ways to approach material

Not for:

Going into formulas. The F word is mentioned, but there isn’t a special section dedicated to them.

Page 52 & 53 of the physical book. The double page spread of the joke web gets a little bit crushed at the centre fold, meaning some words are partially obscured.

Other thoughts:

Perhaps a few formulas could have been added here and there, just to complete the process and to give you further options to work with.


Short, medium. 194 pages, but it feels about 3/4 of that. There are diagrams, some white space, quotes sprinkled throughout the book. Either way, there’s a fair amount here and you won’t feel cheated.

Quicker readers should be done in a day or two.

Slower, dedicated readers, should be about a week.


Some ideas I’ve written with my own joke webs. Sort of. The A4 sheet of the webs was sitting in my lap while I thought of the associations, and how to put them together.

One joke web with the central topic of Ministry of Defence, the other with the central topic of bus stop.

The headline, and also the setup, for each joke is: Classified MOD documents found at bus stop

Classified MOD documents found at bus stop

Keep up with the story on the BBC website. Updates are scheduled every hour, on the hour, until the service stops at eight tonight.

Classified MOD documents found at bus stop

In order to find the person responsible, high level discussions have already started - on the top floor of a double decker.

Classified MOD documents found at bus stop

Internal interviews will be conducted to find any potentially responsible employee. The suspicion for this bus incident surely falling on the one that doesn’t turn up.

Classified MOD documents found at bus stop

This has led to high level discussions about why such a well paid employee is taking the bus.

Classified MOD documents found at bus stop

Leaving the documents at the stop was a lapse in judgement. They’d only put it down temporarily, to prioritise their other important heavy items; 5 boxes of the big Iceland pizzas.



Jack Thompson

Writes serious book reviews. Other ideas in the works.