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.


Self Control It's Kinship and Majesty William Gordge Jordan

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.


How To Be A Gentleman A Timely Guide to Timeless Manners John Bridges

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.


A Confederacy of Dunces John Kennedy Toole

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.


Lord of the Barnyard Tristan Egolf

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.”


Treasure Island Robert Louis Stevenson

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.


The Federalist Papers Alexander Hamilton

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.


The Wealth of Nations Adam Smith

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.


How To Win Friends and Influence People Dale Carnegie

The Republic by Plato

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.


The Republic Plato

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.


For Whom the Bell Tolls Ernest Hemingway

On the Road by Jack Kerouac

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.  


On the Road Jack Kerouac

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. 


Travels With Charley In Search of America John Steinbeck

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.


A Moveable Feast Ernest Hemingway

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.


The Swiss Family Robinson Johann David Wyss

Atlas Shrugged by Ayn Rand

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.


Atlas Shrugged Ayn Rand

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.


The Count of Monte Cristo Alexandre Dumas

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.

Self Reliance Ralph Waldo Emerson

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.


The Master and Margarita Mikhail Bulgakov

Cyrano de Bergerac by Edmond Rostand

This 1897 play follows French cadet Cyrano de