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!
Table of Contents
How Often Should You Reread Books?
There’s no definitive rule on how long you should wait 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.
It comes down to individual preference, and there’s no concrete number you should adhere to. I’ve read books again that 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
- This Saddle Tan Faux Leather Super Giant Print King James Version Bible, with its easy-to-read 17-point type print, is bound to be the Bible you reach for when you need a larger font
- The front cover features a simple design with an elegant heat-debossed St John’s cross framed by a heat-debossed double border
- The border is repeated on the back cover
- Gilt-edged pages and an attached tan satin ribbon bookmark enhance the beauty of the simple design
- The spine is decorated with six decorative gold-foiled and heat-debossed faux spine ribs and also features the gold-foiled title and heat-debossed version reference
The Bible is the best-selling book in history, and arguably the most important too. A majority of the rules and morals 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.
Even if you’re not religious, there’s still a lot to be learned from these texts.
Metamorphosis by Franz Kafka
- Metamorphosis by Franz Kafka — Complete and Unabridged“As Gregor Samsa awoke one morning from uneasy dreams he found himself transformed in his bed into a gigantic insect
- He was laying on his hard, as it were armor-plated, back and when he lifted his head a little he could see his domelike brown belly divided into stiff arched segments on top of which the bed quilt could hardly keep in position and was about to slide off completely
- His numerous legs, which were pitifully thin compared to the rest of his bulk, waved helplessly before his eyes
- ” — Opening lines of The Metamorphosis, by Franz KafkaMetamorphosis is a German novella written by Franz Kafka which was first published in 1915
- One of Kafka’s best-known works, Metamorphosis tells the story of salesman Gregor Samsa, who wakes one morning to find himself inexplicably transformed into a huge insect and subsequently struggles to adjust to this new condition
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’s coming 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 epic tale of Odysseus’s journey home—one of the earliest and greatest works of Western literatureSoon to be a major motion picture directed by Christopher NolanA Penguin ClassicIf the Iliad is the world’s greatest war epic, the Odyssey is literature’s grandest evocation of an everyman’s journey through life
- Odysseus’ reliance on his wit and wiliness for survival in his encounters with divine and natural forces during his ten-year voyage home to Ithaca after the Trojan War is at once a timeless human story and an individual test of moral endurance
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- Rieu’s translation has long been beloved and celebrated by scholars and readers alike, and for this Penguin Classics edition, classicist D
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: It speaks to many fundamental truths about what it means to be human and is 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 is a standalone book in Nassim Nicholas Taleb’s landmark Incerto series, an investigation of opacity, luck, uncertainty, probability, human error, risk, and decision-making in a world we don’t understand
- The other books in the series are Fooled by Randomness, Antifragile, Skin in the Game, and The Bed of Procrustes
- A black swan is a highly improbable event with three principal characteristics: It is unpredictable; it carries a massive impact; and, after the fact, we concoct an explanation that makes it appear less random, and more predictable, than it was
- The astonishing success of Google was a black swan; so was 9/11
- For Nassim Nicholas Taleb, black swans underlie almost everything about our world, from the rise of religions to events in our own personal lives
I could have listed any of Nassim Taleb’s books here, but the one that stands out 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, The Black Swan wins hands down.
On Liberty by John Stuart Mill
- In powerful and persuasive prose, Mill asks and answers provocative questions relating to the boundaries of social authority and individual sovereignty
- This new edition offers students of political science and philosophy, in an inexpensive volume, one of the most influential studies on the nature of individual liberty and its role in a democratic society
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
- Written as a moral essay to his friend Paulinus, Seneca’s brilliant, timeless essay still packs a powerful punch two thousand years later
- With its brash rejection of materialism, conventional lifestyles and group-think, On The Shortness of Life is as relevant as ever
- Seneca anticipates the modern world
- It’s a unique expose of how people get caught up in the rat race and how for those stuck in this mindset, enough is never enough
- The ‘busy’ individuals of Rome Seneca makes reference to, those people who are too preoccupied with their careers and maintaining social relationships to fully examine the quality of their lives, sound a lot like ourselves
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
- The basis of the Sundance TV series Gomorrah A New York Times Notable Book of the YearGomorrah is a bold and important work of investigative writing that holds global significance, one heroic young man’s impassioned story of a place under the rule of a murderous organization
- A groundbreaking, unprecedented bestseller in Italy, Roberto Saviano’s insider account traces the decline of the city of Naples under the rule of the Camorra, an organized crime network more powerful and violent than the Mafia
- The Camorra is an elaborate, international system dealing in drugs, high fashion, construction, and toxic waste, and its influence has entirely transformed life in Campania, the province surrounding Naples
- Since seeing his first murder victim, at thirteen, Roberto Saviano has watched the changes in his home city
- For Gomorrah, he disappeared into the Camorra and witnessed up close the drug cartel’s audacious, sophisticated, and far-reaching corruption that has paralyzed his home city and introduced the world to a new breed of organized crime
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 exposé 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 unleashed in and around Naples is just as 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
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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 can 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
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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 indicates that even the less well-trod path is sometimes the best.
On Living and Dying Well by Cicero
- Philosophical writings on “the good life” by the great Roman orator, in a vital new translation In the first century BC, Marcus Tullius Cicero, Roman orator, statesman, and defender of republican values, created these philosophical treatises on such diverse and trenchant topics as friendship, religion, death, fate, and scientific inquiry
- This lucid and lively new translation renders the great Roman’s writings accessible to modern readers as never before
- Cicero was a pragmatist at heart, but his philosophies were frequently personal and ethical, drawn not from abstract reasoning but from careful observation of the world
- The resulting work reminds us of the importance of social ties, the question of free will, and the justification of creative endeavor
- For more than seventy years, Penguin has been the leading publisher of classic literature in the English-speaking world
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.