39 Classic Books That Every Modern Gentleman Needs To Read

Man reading skylineReutersA man lies on his back as he reads a book in front of the London skyline April 24, 2014.

The modern gentleman doesn’t just know where to go and how to dress, he knows how to think.

The only way to do that — to learn how to make sense of the world with your mind — is to consider a lot of different thoughts. By and large, the best of those thoughts can be found in books that have stood the test of time.

For that reason, Business Insider has compiled a list of classic books that can teach you how to think — about politics, love, philosophy, bravery — everything a man should know about in order to face the world.

All of these books were written before 1980. You’ll have to wait for another list for more modern reads. In the meantime, check these out.

Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig

Pirsig's novel addresses the fundamental question of how to live life. Specifically, Pirsig suggests that no matter what a person is doing, he should do it with care, and without external distractions.

You can buy the book here.

The Prince by Niccolo Machiavelli

Machiavelli boldly asserts that it is better to be feared than loved in his 16th century mini-text.

Whether a leader should be feared or loved is a question that has yet to be solved -- which makes this work an extremely modern and relevant read for anyone holding (or looking to hold) a leadership position.

You can buy the book here.

To Kill a Mocking Bird by Harper Lee

Harper Lee's only novel is a heavy hitter. The book explores the moral nature of human beings -- how we all have good and bad within us -- and addresses the prejudices associated with social classes.

You can buy the book here.

For Whom the Bell Tolls by Ernest Hemingway

Hemingway explores the value of human life and the atrocities of war with his mega-novel. Despite the pervasive cynicism, the author provides a note of hope with love. Romantic episodes periodically rejuvenate the characters, even as they await their doomed fates.

You can buy the book here.

One Hundred Years of Solitude by Gabriel Garcia Marquez

Marquez's masterpiece blends realism and magic, emphasising the subjectivity of peoples' experiences -- aka we each see reality in our own unique way. Additionally, the author writes about several generations of the same family in an effort to create the illusion of timelessness.

You can buy the book here.

The Age of Innocence by Edith Wharton

Wharton examines the social constructs and scandals of New York City's 19th century society. What's especially impressive is that even the most minor characters are presented as multi-faceted individuals. Her wit and insightful writing style makes the book an incredible read.

You can buy the book here.

Palace Walk by Naguib Mafouz

Palace Walk is the first part of a trilogy by Naguib Mahfouz set in Egypt, which is brimming with tension before the 1919 revolution.

The book chronicles the daily life of a family consisting of a tyrannical father and his docile wife, and their sons and daughters. The question of revolution is addressed within the context of the family structure, and within the larger context of Egyptian society.

You can buy the book here.

Crime and Punishment by Fyodor Dostoevsky

Crime and Punishment is a murder mystery told from the point of view of the murder. If that's not enough to get you to read the book, then we don't know what will.

The murderer initially justifies his actions by saying that it was a 'societal good' but eventually reevaluates what it means to be a good person.

You can buy the book here.

Things Fall Apart by Chinua Achebe

The leader of a Nigerian village, Okonkwo, is the central character of the text and he deals with the question of 'what it means to be a man' and a leader.

Additionally, the work examines the effect of colonialism in Nigeria during the late 19th century -- namely, and the tension between tradition and cultural change.

You can buy the book here.

Fathers and Sons by Ivan Turgenev

Basically anyone who goes home for major family reunions during Thanksgiving will completely relate to this book.

As the title suggests, Turgenev's book deals with intergenerational relationships. Namely, how recently graduated, liberal (not to mention, nihilistic) students deal with their old school and equally flawed fathers.

You can buy the book here.

Animal Farm by George Orwell

This book will make you feel uncomfortable. And that's the point.

Orwell's dystopian novel deals with the corruption and naivety found within a society, and is a critique of totalitarian communism.

You can buy the book here.

All Quiet on the Western Front by Erich Maria Remarque

Remarque, a German World War I veteran, chronicles how soldiers truly feel in the war zone -- the incomparable stresses of combat and total detachment from civilian life.

You can buy the book here.

War and Peace by Leo Tolstoy

War and Peace is filled with the never-ending drama of young adulthood. The story centres around three young adults trying to find the 'meaning in life.' They pursue adventure on the battlefield and aristocratic stardom, but ultimate discover that 'true meaning' lies somewhere else entirely.

You can buy the book here.

Reminiscences of a Stock Operator by Edwin Lefèvre

Reminiscences isn't just about Wall Street, or about one of the greatest traders of all time, Jesse Livermore. It's about collective thought and human behaviour. The playing field for all of that action just happens to be the stock market.

If you work in finance and you haven't read this yet, drop everything and read it. Now.

You can buy the book here.

The Autobiography of Malcolm X, as told to Alex Hayley

Malcolm X started out as a gangster known as 'Detroit Red' running the streets of Harlem and Boston. He went to jail. He found Islam. He evolved and evolved. The rest is the history of one of the greatest civil rights activists and misunderstood Americans of the 20th century.

You can buy the book here.

The Iliad and The Odyssey by Homer

The Iliad and the Odyssey are the original adventure stories. Both epics center around characters who learn that true heroism is not determined by the number of enemies that he kills.

You can buy The Iliad here, and The Odyssey here.


A terrible monster named Grendel goes on a merciless killing spree of the Danes, so their king calls in Beowulf for help. Uber-hero Beowulf takes on Grendel by himself and kills him with his bare hands. You don't get any more legendary than that.

In the sequel, Grendel's mum comes around to cause havoc...

You can buy the book

Siddhartha by Hermann Hesse

Siddhartha is the classic tale of a journey of self discovery. The protagonist pursues enlightenment, and ultimately discovers that it is experience that leads to understanding -- singular moments alone are meaningless.

You can buy the book here.

Why I Write by George Orwell

Orwell wrote this right on the eve of WWII. The book is a three essay meditation on the character of English, European, and global society on the brink.

It's an incredibly organised work, wherein Orwell lays out how he thinks social and political structures shape our collective understanding of ourselves.

You can buy the book here.

The Narrative of the Life of Frederick Douglass by Frederick Douglass

In his own words, Frederick Douglass describes how he escaped from slavery to freedom in the 19th century American south.

You can buy the book here.

King Lear by William Shakespeare

This play will kick you in the stomach.

Shakespeare addresses absolute human cruelty and meaningless pain, and asks whether or not 'true justice' can exist. The initially cruel Lear descends into madness over the course of the novel (he even literally attempts to battle a thunderstorm). Despite flickers of hope, the play ends on a bleak note.

You can buy the book here.

Don Quixote by Miguel de Cervantes

'What is the true object of Don Quixote's quest? ... We cannot know the object of Don Quixote's quest unless we ourselves are Quixotic,' writes the eminent Yale professor Harry Bloom.

This is arguably the greatest novel ever written.

You can buy the book here.

This Side of Paradise by F. Scott Fitzgerald

Fitzgerald's debut novel is about the disillusionment associated with growing up. The main love story is a thinly veiled account of F. Scott and Zelda's romance pre-first break-up. (You'll be glad to know that she took him back following the success of this novel.) But the real kick is the last chapter -- you'll never complain about the 'disillusioned boredom' of your happy life again.

You can buy the book here.

As I Lay Dying by William Faulkner

Faulkner's novel is told from the point of view of 15 characters via the stream of consciousness. What's particularly fascinating about the novel is the on-going tension between what the characters think and what they say.

You can buy the book here.

Night by Elie Wiesel

Wiesel chronicles his imprisonment at the Auschwitz and Buchenwald concentration camps. He struggles with maintaining his faith -- especially when 'God is silent' during moments of absolute human brutality.

You can buy the book here.

The Master and the Margarita by Mikhail Bulgakov

The devil is on the loose in Soviet Russia, but no one believes he exists.

Bulgakov's classic is part a mad cap adventure, part bizarre nightmare, part philosophical mind-bender.

You can buy the book here.

The Brother's Karamazov by Fyodor Dostoevsky

This is not a beach-read... to say the least. In this novel, Dostoevsky debates questions of morality, free will, faith versus reason, law versus truth, science versus spirituality -- and so much more. Just like with Crime and Punishment, the author centres this book around a murder mystery.

Albert Einstein reportedly said: the Brothers Karamazov is 'the most wonderful book I ever laid my hands on.'

You can buy the book here.

Sir Gawain and the Green Knight

One day a 'Green Knight' shows up at King Arthur's court and declares that if anyone strikes him with an axe that day, then the Green Knight will strike that knight the same way in exactly 366 days. Sir Gawain takes up the challenges and beheads the Green Knight.

The Green Knight picks up his decapitated head and tells Sir Gawain that he will see him in exactly one year and one day. Sir Gawain then spends the rest of the story debating whether he should show up within a year and be a chivalric knight, or skip out on his promise.

You can buy the book here.

Julius Caesar by William Shakespeare

'Cowards die many times before their deaths; the valient never taste of death but once,' declares the titular character in this historical-ish Shakespearean play.

Caesar isn't the major character of the text, however -- he is assassinated after only five appearances. In the aftermath, the other characters deal with the complicated questions of free will and public versus private life.

You can buy the book here.

On the Origin of Species by Charles Darwin

Darwin's seminal work implied deeply controversial theological and political ideas and must be read as serious philosophical text. The idea of natural selection implies that people and other animals are not 'already perfectly created' -- which challenges the idea that there was a preordained natural hierarchy in nature and that humans.

You can buy the book here.

The Art of War by Sun Tzu

Sun Tzu believes that war is a necessary evil, and if possible, it should be avoided. He writes: 'The supreme art of war is to subdue the enemy without fighting.'

Nevertheless, he also believes that if one is in a state of war, strategic positioning is critical, and he meticulously describes war tactics.

You can buy the book here.

The Epic of Gilgamesh

The Epic of Gilgamesh is the oldest surviving book out there -- it dates back to as early as 2100 BCE. In the text, the king of Uruk, Gilgamesh attempts to discover the secret to physical immortality, but ultimately fails. When he returns home, he realises that his kingdom will be his 'immortality' and that a part of his legacy will live on forever.

You can buy the book here.

On the Road by Jack Kerouac

Kerouac chronicles the journey of several friends across America -- it's the defining novel of the Beat generation that addresses the search for meaning in the post-World War II United States.

You can buy the book here.

Oedipus Trilogy by Sophocles

You know the story: hapless Oedipus unknowingly kills his good ol' dad, marries his mother, and then gouges out his eyes when he realises the truth. AKA it's only when Oedipus is blind that he truly 'sees' the truth.

However, you've probably never read the third part, Antigone. It's a masterpiece, too.

You can buy the book here.

Fahrenheit 451 by Ray Bradbury

In this dystopian novel, Guy Montag lives in a universe were books are the enemy and nobody thinks for themselves -- oh, and he's a fireman who burns books for a living. Over the course of the novel he comes to realise the emptiness of his formulaic and censored life -- and then does something about it.

You can buy the book here.

The Autobiography of Theodore Roosevelt by Theodore Roosevelt

The life of one of the greatest American Presidents told from his perspective.

You can buy it here.

The complete works of Chekhov

Chekhov is the undisputed short story master, but his plays are worth the read as well.

'The Lady with the Dog' is the one you absolutely need to read, if for no other reason than the fact that's it's a passive aggressive takedown of Tolstoy's Anna Karenina.

You can buy the book here.

I, Robot by Isaac Asimov

Maybe you saw the Will Smith version, but the movie only kind of incorporates pieces of one part of I, Robot.

This nine-story collection ny Asimov -- a master of science fiction -- is way more mind-blowing, and way worth the read.

You can buy the book here.

Great Expectations by Charles Dickens

Great Expectations is your typical story about growing up -- told in the first person by principal character Pip. The basic thesis of the work is that love and loyalty are more important than social advancement and class, which Pip learns along the way.

You can buy the book here.

And now, time to complement that scholarly mind with...

Business Insider Emails & Alerts

Site highlights each day to your inbox.

Follow Business Insider Australia on Facebook, Twitter, LinkedIn, and Instagram.