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Ancient Wisdom for Modern Readers

How to Tell a Joke: An Ancient Guide to the Art of Humor

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Timeless advice about how to use humor to win over any audience



Can jokes win a hostile room, a hopeless argument, or even an election? You bet they can, according to Cicero, and he knew what he was talking about. One of Rome's greatest politicians, speakers, and lawyers, Cicero was also reputedly one of antiquity's funniest people. After he was elected commander-in-chief and head of state, his enemies even started calling him "the stand-up Consul." How to Tell a Joke provides a lively new translation of Cicero's essential writing on humor alongside that of the later Roman orator and educator Quintilian. The result is a timeless practical guide to how a well-timed joke can win over any audience.

As powerful as jokes can be, they are also hugely risky. The line between a witty joke and an offensive one isn't always clear. Cross it and you'll look like a clown, or worse. Here, Cicero and Quintilian explore every aspect of telling jokes--while avoiding costly mistakes. Presenting the sections on humor in Cicero's On the Ideal Orator and Quintilian's The Education of the Orator, complete with an enlightening introduction and the original Latin on facing pages, How to Tell a Joke examines the risks and rewards of humor and analyzes basic types that readers can use to write their own jokes.

Filled with insight, wit, and examples, including more than a few lawyer jokes, How to Tell a Joke will appeal to anyone interested in humor or the art of public speaking.

321 pages, Kindle Edition

First published March 30, 2021

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522 people want to read

About the author

Marcus Tullius Cicero

8,045 books1,954 followers
Born 3 January 106 BC, Arpinum, Italy
Died 7 December 43 BC (aged 63), Formia, Italy

Marcus Tullius Cicero was a Roman philosopher, statesman, lawyer, political theorist, and Roman constitutionalist. Cicero is widely considered one of Rome's greatest orators and prose stylists.

Alternate profiles:
Cicéron
Marco Tullio Cicerone
Cicerone

Note: All editions should have Marcus Tullius Cicero as primary author. Editions with another name on the cover should have that name added as secondary author.

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Displaying 1 - 28 of 28 reviews
Profile Image for Massimo Pigliucci.
Author 91 books1,176 followers
September 3, 2023
How to Tell a Joke is actually two books in one. The first part is based on Cicero's treatment of the subject matter, which is part of his On the Ideal Orator (specifically, book 2.216-290). The second part is from Quintilian's The Education of the Orator (book 6.3). So you get two ways of looking at jokes from two of classical antiquity's foremost experts! The translator, Michael Fontaine, does his best, but obviously not all jokes come across as funny, or even intelligible, two thousand years later. A surprising number does, though, and those that don't translate well are helped by the copious notes that accompany the text. But this isn't just a collection of jokes. It is telling that both Cicero and Quintilian wrote on the subject within the context of advice given to orators, because humor has always been part of the rhetorical arsenal of good speakers, in and out of a court of law. The general recommendations still hold up, and the modern reader learns both about humor per se and about the culture and customs of Ancient Rome. Highly recommended.
Profile Image for George Sr..
Author 15 books5 followers
April 30, 2021
Having read both Cicero and Quintilian in the Loeb Classical Library, I found this book a disappointment. It is more paraphrase than translation, and the translator went overboard trying to put the works in modern vernacular. The text abounds with words wholly unsuited to the subject matter and completely unworthy of such well-educated men as Cicero and Quintilian: “guy,” “jackass,” “wiseass,” etc. Anachronistic language is often used. I’m quite sure that the ancients had no idea what a “pit stop” or “political correctness” are. The most out-of-place anachronism came when someone was described as being “hoist on his own petard.” A petard was an explosive device used in assaults upon fortifications. Sometimes one blew up prematurely, “hoisting” the man trying to place it “on his own petard.” If, however, you can tolerate the cavalier approach to translation, you will find the book to be both enlightening and entertaining.
Profile Image for Dan Wilbur.
Author 2 books70 followers
April 5, 2021
This brief book has all you need to know about comedy. Well, all the Romans knew about it. Some advice is shockingly prescient. Some advice is odd and a few quips are untranslatable. I love to get to a footnote that says “no one knows what this means.” I bet it was funny at the time. Pretty good observations about what jokes work and what jokes don’t from someone who lived 2,000 years ago. Good stuff.
15 reviews1 follower
July 3, 2021
I have never rated a book 3 stars but here we go!
I love my Greek philosophers/orators, especially Marcus. But there is some unnerving unattractiveness about this one. From the start I got the characters very mixed up and the way the book was printed was funny to me more than the contents were at times! So, why would I need the Latin manuscript on the left pages and the English ones on the right at the same time?? Again, true of any other subject coming from ancient Greek writers, the material was outdated, true, but there is no old and dusty nostalgia to it in this one (or at least it seems to me like so this time!).
That's me though. Overall it is good to check it off from your bucket list but do not expect to be intrigued/blown away by your expectations because you will be heavily disappointed.
Cheers
Profile Image for ilse.
295 reviews23 followers
April 11, 2021
fun but not for me
Profile Image for Gene Z.
138 reviews8 followers
April 4, 2022
I recommend the audiobook where the narrator brings to life the modern phrases like “jackass” and “oh hell yeah!” and “sick burn”
Profile Image for David.
402 reviews
February 21, 2024
I was expecting a book about what the ancients said about humor. What I was not expecting, but was pleasantly surprised with, was a book that is simply a translation of the ancients' writings on the topic. No modern commentary, no summaries or long-winded explanations. The editor/translator included only a few comments when necessary to give proper context to something from the Latin. Other than that, the original stands or falls on its own.

Times have not changed with regard to humor. It was just as effective then as it is now for making a point, winning over an enemy or attacking a bad idea. While Cicero mainly focused on the use of humor in public speaking (especially in the role of a lawyer trying a case), he does, in contrast, touch on the use of humor in other contexts. He traces out various forms of humor; he discusses whether something the humor is found in the language used or in the thing itself; he advises when it is appropriate to use different forms of humor. I would recommend this book for anyone who does public speaking and wants to inject some humor into his speaking.
Profile Image for Jorvon Carter.
82 reviews2 followers
December 12, 2023
Technically this is Cicero’s elitist opinion on what good humor is. That is, things like witty satire and witty puns within the context of a trial or senate debate. If he were alive today, he would consider stand-up, situational comedy, self-deprecation, slapstick, and sex to be trashy. So in that regard, guide isn’t wholly appropriate for the 21st Century. In addition, given the nature of humor, the author had to be fast and loose with the translation, since wordplay doesn’t translate directly. Finally, Cicero was quite pessimistic in regard that comedy is an innate skill which cannot be learned, so he focuses more on showing what’s funny as opposed to teaching how to be funny.

That being said, some of the insights of the book are appropriate 2000+ years later. For example, don’t maliciously insult people, know how to read a room, don’t tell a joke so stupid that people laugh at you, place punchlines at the end of your statement.
Profile Image for Mike Bright.
224 reviews3 followers
May 30, 2023
This is a translation of a work by Cicero and a work by Quintilian, including the original Latin for both. Cicero was evidently quite the funny guy, and Quintilian quotes him a lot.

The premise of the book is great, and I deeply appreciate the wonderful young lady who got this for me - great choice.

However, this is not so much about telling a stand-alone joke as about quick comebacks and situational humor. That means you have to understand the situation; explaining a joke decreases the humor significantly. Not being a classics scholar, much of the situation for each joke eluded me, so it wasn't all that funny a book.

I can't judge the quality of the translation since I don't speak Latin. However, the translation seems excessively modern and hip - clearly geared toward a young modern crowd. It seems a bit forced to me.
Profile Image for Eric.
208 reviews1 follower
February 17, 2024
This book would be less of a joke if it didn't include the Latin on the opposing page as the Loeb editions do. Painful to read for someone that knows Latin,
Fontaine even omits proper nouns.

Caput eum ad fornicem Fabium offendisse.
p210

"He bumped his head on a triumphal arch."
p211

Where is the Arch of Fabius? Why omit that?

Translating jokes is a tall order, but Fontaine tries too hard throughout this book often using far more profanity than the Latin calls for. Like the brilliant Joel Christiansen at Brandeis, Michael Fontaine tries to make Latin edgy to appeal to college students. His writings end up sophomoric as a result.
164 reviews1 follower
December 3, 2024

This book includes many jokes from Ancient Rome. Either I did not get the jokes at all or they weren’t very funny. How to tell a joke splits humor into lots of different categories. One category is spur of the moment humor. These are quips and jokes that come up in daily conversation. Some people can be funny without rehearsing jokes, for others it is very difficult. Many years ago I came up with the idea of a disability called humorlessness. I believe there are people with no sense of humor at all. I suggested that these people might hire a seeing humor person to go around with them and point out when something is funny.
189 reviews
June 23, 2025
If I ever needed a reason to learn Latin, this book’s translation would be it. Translating jokes is not a simple task, but transforming Cicero’s humor into a cheap-sounding American sitcom diminishes it too much. The audiobook narrator reinforces this even further by using a different tone whenever a joke is said - just in case you miss it. I wonder why they did not add clips of laughing public, just to make sure.
The advice from Cicero and Quintilian themselves is very good, if you bear through the narration and forgive the cheap language used in the translation. If the translator and narrator actually had paid notice to it the audiobook would be much better.
Profile Image for Rhea Kassiopea.
14 reviews1 follower
December 7, 2022
Translation takes way too many liberties and does not represent the original well enough for my liking. Luckily the edition is double-sided and has original Latin texts to compare it to.

There are way too many unnecessary modernisms in this book when there are perfectly fine english words that would give justice to the original - I read ancient texts to better understand the thought process of someone writing 2000 years ago, not to make fun of them!
I strongly recommend reading Latin if you are going to pick up this book.
6 reviews
February 14, 2022
It's a short read and a great introduction to incorporating humor into public speaking. I found myself laughing through the examples and I find it a necessity for anyone interested in being a representative speaker. Oddly enough the examples of what not to do stick with your memory better than the best practices, so a reread may be worth while.

The best lesson I took from it, try to make the people around you laugh before you do it for an audience.
Profile Image for Matt.
202 reviews8 followers
November 5, 2022
Pleasant enough, and a nice reader-friendly bilingual edition. It's hard to get much real humor from it, though, because the jokes are hard to translate and/or require so much cultural context to set up. It's a credit to the translator that even when it's impossible to fully appreciate, it's not dull to read.
Profile Image for Julier.
880 reviews28 followers
May 10, 2024
This short book was interesting, but I found it odd when jokes were updated to modern language. Cicero had thought about when to use humor and when not to use humor, including being a stand-up comedian. A few jokes were funny today. I couldn't give the audio my full attention throughout. I forget when it was written but it was B.C.
Profile Image for JuanK Russo.
73 reviews2 followers
December 30, 2024
Mas que un tratado sobre el humor, un testamento del ingenio humano. Sorna, burla, chiste y aneccionario, han acompañado al hombre desde la adopción del lenguaje. Los estudiantes de latin deberían leer esta obra solo por la calidad de la traduccion.
Profile Image for MG King.
147 reviews3 followers
May 31, 2025
2.5 stars. I don’t really understand the point of a dual facing text when you’re being extraordinarily liberal with translation to the point that the content of the Latin itself is altered, but I had a good laugh now and then.
Profile Image for Michael Jeffries.
167 reviews2 followers
August 29, 2025
Comedians today could learn a thing or two from Cicero, the stand-up statesman. He was apparently a man of quick wit, a sharp tongue and mind, and also thought that profanity was beneath a quality humorist.
Profile Image for Don.
220 reviews
August 27, 2021
Cicero had a sense of humor. Now I know.
Profile Image for Tania .
727 reviews19 followers
March 5, 2023
What is funny? While some humor doesn’t translate, it’s remarkable when it does! Especially after thousands of years!
Profile Image for Yvonne Lacy.
432 reviews
January 10, 2024
Yes, this not a joke. The translator has used the most relaxed and colloquial English but has based it on Cicero's short piece on effective humor in public speaking. Very enjoyable!
Profile Image for Michael Barros.
211 reviews3 followers
May 12, 2024
“When people keep asking you a question and are practically badgering you for a reply, it’s also funny to slowly give them an answer they don’t want.”

This guide is invaluable.
Profile Image for S.Ach.
686 reviews209 followers
June 15, 2025
Instead of titling this book as "How to tell a joke", the narrator (yes, I listened to it on Audible) could have titled it as "How to bore someone to deep slumber."
Profile Image for Scott Satterwhite.
162 reviews
June 16, 2025
This was not quite a joke book, but akin to one, and I enjoyed it. I never thought Cicero could be so funny, and it made me think of stand-up comedians during the Roman era.
Displaying 1 - 28 of 28 reviews

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