The 5 Best Books on Debating for Difficult Discussions

Critical thinking, vibrant debate, and an insatiable desire to find meaning in the world are three things that make human beings truly unique.

No other living thing in the known universe can look at the world around it and ask, ‘why are we here?’

This is what makes the mechanism of debate so captivating to me. On this page, I’ll explore some of my favorite books on the topic. From Aristotle to the modern-day – let’s get into it.

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The Best Books on Debating

1. Thank You For Arguing: What Aristotle, Lincoln, And Homer Simpson Can Teach Us About the Art of Persuasion by Jay Heinrichs

Thank You For Arguing: What Aristotle, Lincoln, And Homer Simpson Can Teach Us About the Art of Persuasion by Jay Heinrichs

Whether you’re debating at a podium or over a friendly drink, it can be easy for your passion to get the better of you.

When we feel our position is threatened, the powerful fight or flight response kicks in and we start to lose control.

In this refreshingly accessible read, Jay Heinrichs leads us through the myriad ways we can maintain rational, effective discourse with other people.

The reader encounters the likes of Aristotle, Lincoln, Homer Simpson, and many more.

If you’re looking for an introduction to the art of rhetoric, this can be a great place to start.

A wealth of perspectives and approaches are explored, providing an excellent overview of how debate and discussion can be shaped and moved.

Learn tricks that politicians and orators have been using for centuries.

Pros:

  • Very accessible
  • Refreshingly witty and fun to read
  • A well-considered selection of famous debaters and figures

Cons:

  • Not ideal if you’re not one for pop-culture references
  • The writing style can be a little ‘cutesy’ at times

2. A Rulebook for Arguments by Anthony Weston

A Rulebook for Arguments by Anthony Weston

This concise, engaging read is now in its 5th edition.

It begins by making a strong case for rational debate in the modern world and then continues to outline precisely how to argue the right way.

This is a great option for those interested in joining a debating society or public speaking forum.

It provides insights into standard etiquette, forming arguments, and maintaining debates that are rational and healthy.

At around 100 pages, it’s far from exhaustive, but it does offer a wonderful introduction to the world of debate.

It’s an excellent teaching tool too.

Each chapter has been written very economically with next to no ‘waffle’ or wasted page space.

Despite its length, I’d recommend reading this one when you can give it your full attention.

A lot of ground and plenty of terms are covered and it would be easy to overlook sections if you’re reading it on the go.

If you’re struggling to write essays at university or school, this book might be of help.

It has some stellar advice on how to structure and formulate what you’re trying to say.

You’ll learn how to provide examples that solidify and crystalize your arguments rather than obfuscating them.

Pros:

  • Mercilessly concise at around 100 words
  • Sharp insights into etiquette and standard approaches
  • An excellent teaching tool

Cons:

  • May be a little brief if you’re not new to the subject
  • Some may find the number of political examples used to be a bit trying

3. Crimes Against Logic: Exposing the Bogus Arguments of Politicians, Priests, Journalists, and Other Serial Offenders by Jamie Whyte

Crimes Against Logic: Exposing the Bogus Arguments of Politicians, Priests, Journalists, and Other Serial Offenders by Jamie Whyte

For most of us, it’s easy to see logical pitfalls in the arguments of other people.

When it comes to our own behavior, however, our perspectives can be considerably more myopic.

A great strength of this book is that it cuts through a lot of the everyday logical failings that most of us are guilty of.

Crimes Against Logic is refreshingly easy to read and is also packed full of wit.

While some might find the discussions of religion to be a little glib, the topics explored here are treated with a healthy dose of humor and eloquence in equal measure.

The reader is taken on a breakneck tour of the most common logical fallacies found in debate and modern discourse.

The chapter on ‘shocking statistics’ is particularly worthy of praise in my opinion.

It demonstrates superbly how easy it is to manipulate statistics to tell the story you want them to tell.

This is an excellent introduction to debate and logical discussion and will still prove entertaining to more experienced debaters.

Pros:

  • An entertaining read with plenty of wit and wry commentary
  • A great tour of common logical fallacies
  • It’s pretty accessible

Cons:

  • Levity is not in short supply here – topics such as religion are treated with an almost disdainful tone

4. Being Logical: A Guide to Good Thinking by Dennis Q. McInerny

Being Logical: A Guide to Good Thinking by Dennis Q. McInerny

A concise, expertly written primer to logic, this is another must-read for newcomers to the topic.

It’s worth noting, however, that this book’s analytical, efficient treatment of its subject matter means that more experienced critical thinkers may still find plenty to appreciate.

It’s got a refreshingly ‘no-nonsense’ approach to the question of how to be logical.

It gets right to the point and cuts through it with laser-focused precision.

Pros:

  • Boils logic down to its bare essentials and explains them effortlessly
  • An easy, short read

Cons:

  • It’s perfect as a primer but doesn’t delve much deeper

5. The Art of Always Being Right by Arthur Schopenhauer

The Art of Always Being Right by Arthur Schopenhauer

This treatise from 19th-century German philosopher Arthur Schopenhauer explores an oft-overlooked topic when it comes to logic – controversy.

Rather than methodically explaining the various logical fallacies and how to avoid them, Schopenhauer explores the many ways in which a person can win an argument while still being wrong.

The focus here is on gaining the upper hand in a debate, not necessarily on being correct.

To those interested in public debate, this is a fantastic, humorous read.

It’s a pertinent example of how when speaking publicly, the salient facts alone won’t be enough to guarantee success.

Pros:

  • A distinct perspective compared to the rest of this list
  • Full of lessons for public speakers to draw from
  • Remarkably humorous and captivating

Cons:

  • It won’t serve you too well as a beginner’s guide to logic

Summary

I hope you’ve found the recommendations on this page helpful.

Remember that most concepts in life only thrive when you put them into practice.

Once you’ve sunk your teeth into some of the reading on this page, get out there and see if you can hold your own on the debaters’ battlefield.