37 Books Every Gentleman Should Read
World Book Day is coming up as it is every 23 April. Commit yourself to reach back to the classics, then begin reading. Some book titles included in this list are expected, though there are a handful of surprises. And, if you’re thinking what to read during a general free time on the sofa, or by a pool or an ocean, I’ve got you covered.
A well-read gentleman is also a good conversationalist. It’s the perfect excuse to get lost in a good book.
Self-Control: Its Kingship and Majesty by William George Jordan
The turn of the 20th century was the golden age of personal development books. In contrast to the self-help books of today, which are filled with flattering, empty, cliche platitudes, they’re direct, masterfully written, and full of profound and challenging insights that centre on the development of good character. Even in this golden age, one author stands supreme: William George Jordan. His Self-Control is full of beautifully written wisdom on self-reliance, calmness, gratitude, and more.
How to Be A Gentleman: A Timely Guide to Timeless Manners by John Bridges
Being a gentleman isn’t just being a nice guy, or a considerate guy or the type of guy someone might take home to meet their mother. A gentleman realizes that he has the unique opportunity to distinguish himself from the rest of the crowd. He knows when an email is appropriate, and when nothing less than a handwritten note will do. He knows how to dress on the golf course, in church, and at a party. He knows how to breeze through an airport without the slightest fumble of his carry-on or boarding pass. And those conversational icebreakers―“Where do I know you from?” A gentleman knows better. Gentlemanliness is all in the details, and John Bridges is reclaiming the idea that men―gentlemen―can be extraordinary in every facet of their lives.
A Confederacy of Dunces by John Kennedy Toole
A Confederacy of Dunces is one of my favourite books of all time. This New Orleans-based novel won author John Kennedy Toole the Pulitzer Prize. Its perfect comedy of errors is centred around the character of Ignatius J. Reilly, a lazy and socially ignorant, but very intelligent man, who still lives with his mother at the age of 30. A Confederacy of Dunces serves as a guide for what a man ought not to be while providing sound entertainment all the while.
Lord of the Barnyard: Killing the Fatted Calf and Arming the Aware in the Cornbelt by Tristan Egolf
A literary sensation published to outstanding accolades in America and around the world, Lord of the Barnyard was one of the most auspicious fiction debuts of recent years. Now available in paperback, Tristan Egolf’s manic, inventive, and painfully funny debut novel is the story of a town’s dirty laundry — and a garbagemen’s strike that lets it all hang out. Lord of the Barnyard begins with the death of a woolly mammoth in the last Ice Age and concludes with a greased-pig chase at a funeral in the modern-day Midwest. In the interim there are two hydroelectric dam disasters, fourteen tavern brawls, one shoot-out in the hills, three cases of probable arson, a riot in the town hall, and a lone tornado, as well as appearances by a coven of Methodist crones, an encampment of Appalachian crop thieves, six renegade coal-truck operators, an outraged mob of factory rats, a dysfunctional poultry plant, and one autodidact goat-roping farm boy by the name of John Kaltenbrunner. Lord of the Barnyard is a brilliantly comic tapestry of a Middle America still populated by river rats and assembly-line poultry killers, measuring into shot glasses the fruits of years of quiet desperation on the factory floor. Unforgettable and linguistically dizzying, it goes much farther than postal.
Treasure Island by Robert Louis Stevenson
I saw the theatre production of Treasure Island at the National Theatre not once, not twice, but three times. Then, I read the book again with much delight. Pretty much everything we think of when we think of pirates comes not from the pages of history but from this book: treasure maps with “X” marking the spot, deserted islands, peg legs, parrots, and more. Published as a children’s tale (and a rather adult one at that), American novelist Henry James praised it as “perfect as a well-played boy’s game.”
The Federalist Papers by Alexander Hamilton
Read Hamilton’s Federalist Papers, then read the Constitution. Composed of 85 articles, The Federalist Papers served to explain and encourage the ratification of the U.S. Constitution. The majority of the essays were penned by Alexander Hamilton and originally published in The Independent Journal and The New York Packet. While the Constitution lays out the laws of the land, these essays provide the 18th-century version of the ballot/blue books we get the mail around election time, explaining the laws that are being proposed. It is essential reading for any civically minded American. Forget the theatre production.
Your Car’s Owner’s Manual
Yep, that dusty book in your glove compartment. Come on, bring it out and get to know your car better. So, it’s not exactly “literature” but it’ll teach you something that will come in handy. Guaranteed. By the way, I was shocked to learn the battery in my Mercedes is located under the driver’s seat.
The Wealth of Nations by Adam Smith
The fundamental work on free-market policies: “It is not from the benevolence of the butcher, the brewer or the baker, that we expect our dinner, but from their regard to their own self-interest. We address ourselves, not to their humanity but to their self-love, and never talk to them of our own necessities but of their advantages.” Want an education in economics? This book is a great start.
How to Win Friends and Influence People by Dale Carnegie
The granddad of books about people skills, the advice found in How to Win Friends and Influence People is still sound and applicable 80 years later. Carnegie writes about skills like making people feel valued and appreciated, ensuring you don’t come across as manipulative (which happens unintentionally more than we think!), and essentially, “winning” people to your viewpoints and ideas. While it can sound a little disingenuous in its description, these are true skills that people use every day, and this book is a great resource for boning up your social game.
The Republic is a Socratic dialogue, written by Plato around 380 BC, concerning the definition of justice and how a just city-state should be ordered and characterized. It is the great philosopher’s best-known work and has proven to be one of history’s most influential works of philosophy and political theory. In it, Socrates and other various interlocutors discuss the meaning of justice and examine whether or not the just man is happier than the unjust man, as well as the theory of Forms, the immortality of the soul, and the role of the philosopher in society.
For Whom the Bell Tolls by Ernest Hemingway
Robert Jordan is a young dynamiter in the Spanish Civil War. He’s an American who’s volunteered to fight against Franco’s fascists and is sent behind enemy lines to take out an important bridge to impede enemy forces from advancing. He lives in a rudimentary camp with anti-fascist Spanish guerillas and comes to embrace their hearty way of life and love. And of course, there are some incredible battle scenes, which were informed by Hemingway’s own time as a correspondent in the Spanish Civil War.
A defining novel of the Beat generation, On the Road, is fictional, but a semi-autobiographical account of two friends’ road trips across America, against the backdrop of a counter-culture of jazz, poetry, drug use, and the drunken revelry of back-alley bars. Along with their travels, they’re searching for what many young men are: freedom, ambition, hope, and authenticity.
Travels With Charley In Search of America by John Steinbeck
To hear the speech of the real America, to smell the grass and the trees, to see the colours and the light—these were John Steinbeck’s goals as he set out, at the age of fifty-eight, to rediscover the country he had been writing about for so many years. With Charley, his French poodle, Steinbeck drives the interstates and the country roads, dines with truckers, encounters bears at Yellowstone and old friends in San Francisco. Along the way, he reflects on the American character, racial hostility, the particular form of American loneliness he finds almost everywhere, and the unexpected kindness of strangers.
A Moveable Feast by Ernest Hemingway
Ernest Hemingway’s classic memoir of Paris in the 1920s. A Moveable Feast brilliantly evokes the exuberant mood of Paris after World War I and the unbridled creativity and unquenchable enthusiasm that Hemingway himself epitomized.
Swiss Family Robinson by Johann David Wyss
After a terrible storm, the Swiss family Robinson becomes shipwrecked on a deserted island. With teamwork, ingenuity, and a bit of luck, the group strives to overcome nature’s obstacles and create some semblance of community and civility within their new environs. A truly classic survival and adventure tale.
While there’s plenty of political, moral, and economic philosophy in this book, it’s coated in an action thriller of a story. Set in the near future, our protagonists are Dagny Taggart, heir to a transcontinental railroad empire, and Hank Rearden, the head of a steel company who’s invented a revolutionary new alloy. Together, they battle against evil government bureaucrats and socialists to hold civilization together, while all the while powerful industrialists are mysteriously disappearing, leaving behind only the cryptic phrase “Who is John Galt?” Though this book is associated with passionate libertarianism, the story is an interesting one to ponder no matter one’s political persuasions.
The Count of Monte Cristo by Alexander Dumas
The ultimate tale of betrayal and revenge. Edmund Dantes, days before marrying his beloved Mercedes, is brutally betrayed, arrested for treason, and consequently taken to a prison on an island off the French coast. The story goes on to tell of his escape from prison (don’t worry, it’s early in the novel and doesn’t ruin anything) and his becoming wealthy and re-entering society as an educated and sophisticated Count. He plots his revenge, eyes reclaiming his love, and ultimately…well, you’ll just have to read it.
Self-Reliance & Other Essays by Ralph Waldo Emerson
“Self-Reliance” contains the most prominent of Ralph Waldo Emerson’s philosophies: the need for each individual to avoid conformity and personal inconsistencies, and to follow their own instincts and ideas. You’re to rely on your own self versus going with the ebbs and flows of culture at large. Other essays in the collection focus on friendship, history, experience, and more. Is it just me, or is this Self Reliance a necessity in today’s world? I’m anything except a conformist.
The Master and Margarita by Mikhail Bulgakov
There is nothing more manly than a bout with the Devil. Mikhail Bulgakov wrote this entertaining commentary on the social bureaucracy in Moscow during the height of Stalin’s reign. Lucifer himself pays the atheistic city a visit to make light of the people’s scepticism regarding the spiritual realm. The novel also visits ancient Jerusalem under Pontius Pilate’s rule. Even for the non-religious, this book will provide plenty of food for thought.
Cyrano de Bergerac by Edmond Rostand
This 1897 play follows French cadet Cyrano de Bergerac. He’s a poet, musician, and expert swordsman — a true Renaissance Man. Unfortunately, Cyrano has a tragically large nose, which hinders his confidence to the point that he’s unable to profess his feelings to Roxane and feels he isn’t worthy of anyone’s love. What is a man to do in such a situation? Read and find out.
It’s all well and good to be a dreamer, but a man must also be grounded in reality. It’s a lesson that Don Quixote comes to learn in the 17th-century eponymous book, which is widely considered to be the world’s first novel. Quixote, along with his squire Sancho Panza, travels the world in search of grand adventures and heroic deeds which would earn him the title of Knight. He continues against all odds, and in some cases, against all common sense. It’s funny, surprisingly easy to read given the fact that it’s over 400 years old, and can provide a man many lessons on the aspirations of heroism.
This short, but ever-popular tale is a young woman’s take on humanity and horror. Mary Shelley was just 21 when Frankenstein was first published in 1818, and the book is widely regarded as the first popular science fiction/horror novel. While you surely know the monster and the story of mad scientist Victor Frankenstein bringing him to life, it’s a much darker and more philosophical book than what pop culture has made it out to be. You learn about science, ego, pride, and ultimately, what it means to be human.
A Tale of Two Cities by Charles Dickens
Dickens should be a part of every man’s reading life, and A Tale of Two Cities is a good starter. It’s set in London and Paris during the French Revolution and depicts the plight of the French peasantry, their turn to violence towards the aristocrats who marginalized them, and the parallels to London society during the same period.
The Great Railway Bazaar by Paul Theroux
In this travelogue, Paul Theroux recounts his 4-month journey through Europe, the Middle East, India, and Southeast Asia on the continent’s fabled trains: the Orient Express, the Golden Arrow to Kuala Lumpur, the Mandalay Express and the Trans-Siberian Express. His well-documented and entertaining adventures have come to be considered a classic in the travel literature genre. This journal satisfies the vicarious traveller and inspires the adventurous man.
The Iliad & The Odyssey by Homer
These epic poems are some of the world’s oldest pieces of literature. They’ve been read, enjoyed, and studied for thousands of years, and for good reason. They are not only beautiful to the ear, but contain lessons that every man can learn about heroism, courage, and manliness. The Iliad takes place during a few weeks of the final year of the Trojan War and details the heroic deeds of both Achilles and Hector, as well as a variety of other legends and stories. The Odyssey, a sequel of sorts, is about the great warrior Odysseus’ voyage home after the Trojan War. He faces various obstacles in his return to Greece, and we also see how his family back home dealt with his assumed death.
The Sun Also Rises by Ernest Hemingway
The novel that catapulted Hemingway to worldwide fame and success. The Sun Also Rises follows Jake Barnes and a group of ex-patriot friends through Spain and France, with plenty of wine-drinking and bull-fighting. The novel is a bit semi-autobiographical in that the main character is trying to deal with his war wounds — both physical and emotional — and escape to the supposed romanticism of travelling and eating and drinking to your heart’s content. Does Jake find happiness? You’ll have to read to find out.
The Brothers Karamazov by Fyodor Dostoevsky
While the book’s plot centres on an ageing, disinterested father and his three adult children, the substance found within goes much beyond that. Dostoevsky’s final and greatest novel, this book also involves spiritual and moral dramas and debates regarding God, free will, ethics, morality, judgment, doubt, reason, and more. It’s a philosophical work clothed as a novel — which of course makes Dostoevsky’s weighty ideas easier to digest. The McDuff translation gets rave reviews.
The Prince by Niccolo Machiavelli
Written in the early 1500s, this is the classic guide on how to acquire and maintain political power (even if those methods are sometimes unsavoury) — a so-called “primer for princes.” Its precepts are direct, if not disturbingly cold in their formulaic pragmatism. It asks the classic question: “Do the ends justify the means?” A worthy read for any man wishing to better understand the motivations and actions that tend to rule modern politics.
The Great Gatsby by F. Scott Fitzgerald
Set among New York City elites in the roaring ‘20s, this book is considered one of America’s great literary products for a reason. Narrator Nick Carraway is befriended by his mysterious millionaire neighbour, Jay Gatsby, and proves to be a crucial link in Jay’s quixotic obsession with Nick’s cousin, Daisy. The metaphors, the beautiful writing, and the lessons one can garner about reliving the past all make The Great Gatsby worth reading, again and again. Our interview with NPR’s Maureen Corrigan is worth a listen. She is the author of So We Read On: How To Great Gatsby Came To Be and Why It Endures. We discussed her research into why a novel was written about Jazz Age New York that resonates with Americans nearly a century later.
Read 1984, then go delete your Facebook account. Perhaps the most essential to re-read today, 1984 sets stage in an oppressive futuristic society monitored by the ever-watching Big Brother. Protagonist Winston Smith goes to work every day at the Ministry of Truth, where he rewrites and distorts history. However, Smith decided to begin a diary — an action punishable by death. Amid modern-day data mining, the fall of Net Neutrality, and lunatic leaders, we cannot forget the toll of tyranny and totalitarianism.
Of Mice and Men – John Steinbeck
Another assigned high school read you probably didn’t appreciate when you were sixteen, it’s time to revisit the ambling of George Milton and Lennie Small, migrant workers who search for jobs throughout California amid The Great Depression. And with all great novels, it’s been banned time and again for its mention of violence, swearing, racism, sexism, the works, but it’s an essential commentary on the nature of The American Dream, the dichotomy of strength and weakness, and the loneliness of isolation.
The Adventures of Huckleberry Finn – Mark Twain
Often called “the greatest American novel,” The Adventures of Huckleberry Finn proceeds Twain’s The Adventures of Tom Sawyer and is renowned for its use of written vernacular in imitation of southern antebellum society. The story follows teenager Huck Finn and his friend Tom Sawyer as they navigate themes of race and identity. So, yeah, you should re-read that one today, especially given that the original novel has been the subject of censorship in schools for years.
If you need an “excuse” to read some of the best love poems ever written about oceans and women and the earth, say you’re brushing up on your dating one-liners. But the words by Chilean poet, diplomat, and politician Pablo Neruda are so much more than kindling. They are pure fire and combustion. This book will wake up your soul. It also mends broken hearts.
An ordinary man finds himself on trial after committing a murder in one of the greatest novellas of the 20th century. A dissection of morality and the philosophy of the absurd, The Stranger is particularly relevant today as we face a world of heightened sensitivity and, perhaps, a society that makes no sense to us.
The Call of the Wild – Jack London
Try this: Take the novel on a long, boring, or otherwise dreaded journey. Close the last page a changed man (it’s that phenomenal) with a new outlook on struggle and bonds. Set in Yukon, Canada, during the 1890s Klondike Gold Rush, London writes of Buck, a dog that is abducted and forced into the chaos and brutality of frontier life. In a word: rugged. Secretly: a tear-jerker.
Lord of the Flies – William Golding
A band of British boys are shipwrecked on an island and try to maintain order and normalcy the way governments do. As you might guess, it all goes terribly, terribly wrong. Lord of the Flies, the first novel from Golding, is a perfect glimpse at the nature of savage inclination. It’s a short read but it’s a damn good one.
Catcher In The Rye – J.D. Salinger
We’ll bet you first glimpsed the vibrant red cover of Catcher in the Rye some time in high school. But don’t let your memory fool you into thinking it’s a kids book. Possibly the best coming-of-age tale in all of literature, Salinger writes of the young and relatable protagonist Holden Caulfield and his first-person commentary on the world as he struggles between embracing adulthood and hiding in his childhood memories.
How To Be A Gentleman