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10 Best Books To Reread

Creating a list of the best books to reread isn’t easy. There are so many great books you could read and then read again, the list could contain 100 books.

I’ve managed to get this one down to ten that I feel offer a lot of value and wisdom that you should read again and again.

Looking to reread books isn’t what most think of doing when it comes to reading. It’s easier to go and buy some new books and just read those. I know, because I’ve done this a lot.

But there’s a lot of value to be had when you reread a book and go back through some old classics, especially if you haven’t read them for a long time.

So, here are my ten selections of books to reread that you should pick up if you haven’t read them in a while!

How Often Should You Reread Books?

There’s no definitive rule on how long you should go between reading a book for the first time and reading it again.

If the book is chock full of useful info such as Meditations, for example, then a good rule of thumb might be a year. A book such as the Bible could be reread multiple times in a year especially if you’re religious.

In the end, it comes down to individual preference and there’s no concrete number you should adhere to. I’ve read books again I first read ten years ago and found a lot of value in doing so.

Do what works best for you.

Best Books To Reread

The Bible

KJV Holy Bible, Super Giant Print Faux Leather Red Letter Edition – Ribbon Marker, King James Version, Saddle Tan
  • Christian Art Publishers (Author)
  • English (Publication Language)
  • 1804 Pages – 03/07/2017 (Publication Date) – Christian Art Publishers (Publisher)

The Bible is the best-selling book in history, and arguably the most important too. A majority of the rules and morals that we live by in the Western world, and further afield too, are inspired by what’s inside this book.

It’s incredible that passages written two thousand years ago, and thrown together to form the Old and New Testaments are still widely read today. I doubt the authors realised how influential their words would be when they put pen to paper.

Putting the Bible on this list is a catch-all for most religious texts. Whether it’s the Koran, Bhagavad Gita or the Talmud, there’s a lot to learn from religious texts. This is why it’s important to re-read them again.

Even if you’re not religious, there’s still a lot to be learned from these texts.

Metamorphosis by Franz Kafka

The Metamorphosis
  • Kafka, Franz (Author)
  • English (Publication Language)
  • 51 Pages – 12/01/2022 (Publication Date) – Independently published (Publisher)

Metamorphosis is my favorite of Franz Kafka’s short stories. The surreal nature of the story is what makes it so enjoyable and it’s short enough that you can reread it in less than an hour.

Without spoiling the plot, a man wakes up one day to find he has been turned into a beetle. He can understand what his family says, but he’s unable to communicate with them no matter how much he tries.

The remainder of the book shows what happens as both parties come to terms with the transformation.

It’s a masterpiece of literature and a profound meditation on what it means to be human. The struggle of the man transformed into a beetle, and his family to come to terms with what happened is a testament to how quickly things can change in life.

Kafka has written plenty of fascinating stories, and you should read as many of his stories as you can. The Trial is another favorite, but Metamorphosis is the one that I find myself coming back to time and time again.

The Odyssey by Homer

The Odyssey (Penguin Classics)
  • Homer (Author)
  • English (Publication Language)
  • 416 Pages – 04/29/2003 (Publication Date) – Penguin Classics (Publisher)

The Odyssey is another fantastic book that’s stood the test of time. At over two thousand years old, it’s even older than the Bible!

There’s a reason Homer’s story has resonated for so long and that’s because it speaks to a lot of fundamental truths about what it means to be human. As well as being fun to read.

The story sees Odysseus trying to return to his homeland of Ithaca to his wife and warn off the many suitors flocking around her. On his journey back he encounters many obstacles, which reflects the bumpy nature of life and how nothing ever goes the way we imagine it to.

The Odyssey is a useful reminder that life is an adventure and one that we often have little to no control over.

The Black Swan by Nassim Nicholas Taleb

The Black Swan: Second Edition: The Impact of the Highly Improbable: With a new section: “On Robustness and Fragility” (Incerto)
  • Taleb, Nassim Nicholas (Author)
  • English (Publication Language)
  • 444 Pages – 05/11/2010 (Publication Date) – Random House Trade Paperbacks (Publisher)

I could have listed any of Nassim Taleb’s books here, but the one that stands out for me is The Black Swan.

I remember reading it for the first time and being blown away. I had to stop and reread multiple parts during my first reading because I was astounded by what I found.

The Black Swan refers to events that hardly anyone predicts, but have huge consequences. Think of 9/11 or the 2008 financial crash. Only a handful of people saw these events coming, and even all these years later, we’re still living with the consequences.

You should read all of Taleb’s books, known as the Incerto. But if I had to choose one to recommend, it would The Black Swan hands down.

On Liberty by John Stuart Mill

On Liberty (Penguin classics)
  • Mill, John Stuart (Author)
  • English (Publication Language)
  • 187 Pages – 02/28/1975 (Publication Date) – Penguin Books (Publisher)

Given the political turmoil we’ve been through in recent years, a political text I find myself turning to is John Stuart Mill’s classic work, On Liberty.

Mill’s work is a foundational text that informed many of the laws and customs we live with today, in particular, the relationship between authority and the individual. A relationship that’s coming under increasing attack in some countries.

It’s hard to state just how influential Mill’s text is, and it should be read more widely than it is. Even though it was written in 1859, many of his points still resonate today.

There has been a slide towards authoritarianism in recent years, and On Liberty shows how respecting the liberty of individuals as well as the collective is key to living in a fair and democratic society.

On The Shortness of Life by Seneca

On the Shortness of Life: New Revised 2018 Translation
  • Seneca (Author)
  • English (Publication Language)
  • 42 Pages – 02/07/2018 (Publication Date) – CreateSpace Independent Publishing Platform (Publisher)

On The Shortness of Life is, you’ve guessed it, an essay on why life is short and how it’s important to make the most of it while we still can.

Like many of the other texts on this list, it was written two thousand years ago by the Roman philosopher Seneca.

As much as we like to think of ourselves as way more advanced than our ancient predecessors, it’s incredible just how much they get right about the human condition.

Reading Seneca’s work, you’ll find yourself agreeing with almost everything that he says. Even if the times have changed, what it means to be human is fundamentally the same.

On The Shortness of Life is an important text to read in good times and in bad, to remind yourself just how short and precious life is.

Gomorrah by Roberto Saviano

  • English (Publication Language)
  • 318 Pages – 10/03/2017 (Publication Date) – Picador (Publisher)

Gomorrah is one of the most harrowing books I’ve ever read, and I’ve read a lot of books. 

Written by the investigative journalist Roberto Saviano, it’s an expose of the Camorra, the Neapolitan mafia. What follows is a sordid tale of murder, extortion and sheer violence.

You may be more familiar with the Sicilian mafia, but the violence the Camorra unleash in and around Naples is just incredible. As is the amount of money they make from illicit activities.

To understand how important this book is, Saviano now has to spend his life under 24-hour police protection due to the threat against his life from the Camorra.

There’s a lot wrong with the world, and Gomorrah highlights some of it. But it’s one of the best books to reread as it highlights the importance of standing up to what’s wrong and what can happen if we don’t.

Essays by Michel de Montaigne

Michel de Montaigne – The Complete Essays (Penguin Classics)
  • Montaigne, Michel de (Author)
  • English (Publication Language)
  • 1344 Pages – 09/07/1993 (Publication Date) – Penguin Classics (Publisher)

Essays isn’t the most well-known book out there, but you’ll find a lot of wisdom in this collection of pieces written by the French philosopher Michel de Montaigne.

What’s great about Montaigne’s essays is that they cover a wide range of topics from solitude to an essay about posting letters.

He’s one of those writers, like George Orwell, who’s able to take mundane topics and make them interesting.

This is what makes Essays useful to reread over and over. You’ll find insights into a lot of different topics that you can dip in and out of when you need to.

Siddhartha by Hermann Hesse

Siddhartha: A Novel
  • Hermann Hesse (Author)
  • English (Publication Language)
  • 160 Pages – 01/01/1982 (Publication Date) – Bantam (Publisher)

Siddhartha is one of the best novels I’ve ever read. It tells the tale of a man, Siddhartha, looking for spiritual enlightenment in ancient India.

He travels around trying to find enlightenment in various places and from various people. Reading Siddhartha was a fascinating insight into the world of Eastern philosophy.

Siddhartha’s journey takes him to many different places and shows there’s more than one way to live your life, and you never know when you’ll find fulfilment.

One of the important points I took away from the book is that there’s more than one way to live your life.

No matter how much people might say they know what’s best for you, the plethora of routes and life choices indicate that even the less well-trod path is sometimes the best.

On Living and Dying Well by Cicero

On Living and Dying Well (Penguin Classics)
  • Cicero, Marcus Tullius (Author)
  • English (Publication Language)
  • 240 Pages – 11/27/2012 (Publication Date) – Penguin Classics (Publisher)

Cicero is one of the most important Roman philosophers and statesmen. He may not be as well-known as Seneca or Marcus Aurelius, but his writing is just as useful.

On Living and Dying Well is one of the most useful of his books you can read. As you might have guessed, it deals with how to live your life so that when you do leave this planet, you can do so with your head held high.

Interestingly, today death is seen as taboo. It’s rarely talked about, and many of the leaders in Silicon Valley are looking at ways of delaying the inevitable. The contrast with the ancients is remarkable.

They were under no illusions about what their ultimate fate would be, which is why this is one of the best books that make you think about life. Death is unlikely to be conquered anytime soon, and the prospect of living for hundreds of years isn’t as appealing as you might think.

Rereading On Living and Dying Well will provide you with ancient wisdom on how best to live your life. Remember, for all that’s changed since the fall of the Roman Empire, humanity remains remarkably familiar.

Looking For More Books?

Books by Plato – A collection of the best works by one of the most famous philosophers in history. Books that should be reread again and again.