Here’s the problem with reading the books that everyone else has read. It makes you more like everyone else. Checking off the various books from your high school curriculum, and then, perhaps the “100 Greatest Books Ever Written” is the educational equivalent of skating to where the puck is and not where it’s going.
Reading is about insight into the human experience, about understanding. What does following in the footsteps of everyone else get you? It gets you to exactly the same conclusions as everyone else.
Not to say that the books in our “canon” aren’t valuable, because they certainly are. It’s just that you have to remember for every Great Gatsby out there, there were 10 others written at the same time about the same thing that for whatever twist of cultural fate and cumulative advantage are mostly lost to us (one of the books on this list fits that definition to a T).
The Western world has been publishing books for some 3,000 years. Memoirs, histories, aphorisms, essays, treatises, tutorials, exposes, stories, epics–it’s all there. Humble yourself to think that our grasp of the lists of the “best” of these books will always miss more than it captures.
Which is why I put together the list of books below in their rough historical order. They are all great pieces of literature or learning and at the same time, mostly unknown. Sure, you might have heard of a few of them (in which case, consider yourself part of the minority) but far too many people haven’t. Put down your David Foster Wallace and pick up one of these. See what happens.
1. Cyropaedia (a more accessible translation can be found in Xenophon’s Cyrus The Great: The Arts of Leadership and War)
Xenophon, like Plato, was a student of Socrates. For whatever reason, his work is not nearly as famous, even though it is far more applicable. Unlike Plato, Xenophon studied people. His greatest book is about the latter, it’s the best biography written of Cyrus the Great (aka the father of human rights). There are so many great lessons in here and I wish more people would read it. Machiavelli learned them, as this book inspired The Prince.
2. The Moral Sayings of Publius Syrus: A Roman Slave by Publius Syrus
The best philosophy comes from people who were not “philosophers.” Syrus was a slave and his moral maxims are far better than perhaps the most famous book in this category, those of Duc de la Rochefoucauld. Some favorites: “The mightiest rivers are easy to cross at their source.” “Avarice is the source of its owns sorrows.” And of course, extra-applicable to this list, “Many receive advice, few profit by it.”
3. Meditations by Marcus Aurelius (Gregory Hays translation, do not read the others, they suck)
Those familiar with my writing will not think this is an unknown book. But for far too many people it is. You can get a PhD in philosophy and not be forced to read this–and that’s a travesty. I imagine because it’s one of the few texts that wastes no time on pretension or explanations of the world. It simply tells you how to live a little better. Just wrap your head around this: At some point around 170 AD, the single most powerful man in the world sat down and wrote a private book of lessons and admonishments to himself for becoming a better, kinder and humbler person. And this text survives and you have access to it today.
4. The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari
Basically a friend and peer of Michelangelo, Da Vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. Unless you have a degree in Art History it’s unlikely that anyone pushed this book at you and that’s a shame. Because these great men were not just artist, they were masters of the political and social worlds they lived in. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic, but an actual artist and architect of equal stature to the people he was documenting.
5. The Man Without a Country by Edward E. Hale
Patriotism is not a concept that gets a lot of love today. But this essay/book makes you think a little. Released in 1863 during the height of the Civil War, the plot’s simple: an innocent man caught up in Aaron Burr’s treasonous conspiracy stands trial for his actions. When asked to address the judge, he bitterly remarks that he wishes to be done with the United States forever. So the judge grants his wish as a punishment–he’s sentenced to live the rest of his life in a cabin aboard ships in the US Navy’s foreign fleet, and no sailor is to ever mention the US to him again. He dies many years later, an old man like Rip Van Winkle, unsure of the changing world around him. For those with some understanding of historical, you’ll enjoy the meta-fiction of it, for those that haven’t it is still a very good look into early America.
6. 12 Years A Slave by Solomon Northup
This one won’t stay unknown for long as Brad Pitt’s doing a movie about it but please don’t let that scare you away. If there is one book you read about slavery in America, read this one. It’s the real story of a born freedman in the North who, as a traveling musician, was brought out of his home state on false pretenses in order to be captured, kidnapped, and transported South to be sold as a slave. It’s fucking harrowing and written lucidly and articulately by the person who experienced it. For 12 years, he was a slave–and not some border-state slave, but a bayou slave in the deep South. He was cut off from his family and his freedom, and even among the slaves he was different. He couldn’t tell anyone he could read and write, he couldn’t even tell anyone that he was formerly free because they threatened to kill him if he did. This book is just as good as Frederick Douglass’ memoir and I think illustrates the horrors of slavery in a much more undeniable way.
7. Civil War Stories by Ambrose Bierce
Mark Twain, for all his bitterness and sarcasm, was just more fun for average people to read than Ambrose Bierce. But Bierce is the one who truly captured the Civil War–a terrible and awful conflict in which death and destruction and stupidity were far more prevalent than strategy or heroism. This book (half fiction and half memoir) contains the story “An Occurrence at Owl Creek Bridge,” which Kurt Vonnegut called the greatest short story ever written. Too many books about the Civil War are inaccessible, with their flanking movements and war vocabulary. This book is all people. Must read.
8. Forty Years a Gambler on the Mississippi by George Devol
The memoir of a professional gambler, fighter and criminal who rode the riverboats of the Mississippi and Red Rivers. It’s a true and vibrant snapshot of a period of American life that you can’t get anywhere else. Gun fights, brawls, cons–it’s all here. Fascinating, peculiar and very easy to read.
9. Hunger by Knut Hamsun
A dark and moving first-person narrative, about the conflicting drives for self-preservation and self-immolation inside all of us. Hunger is about a writer who is starving himself. He cannot write because he is starving and cannot eat because writing is how he makes his living. It’s a vicious cycle and the book is a first-person descent into it. Strangely modern for being published in 1890 and ultimately inspired a lot of great stream-of-consciousness writing since (but influence goes unacknowledged because Knut was a Nazi sympathizer).
10. Letters from a Self-Made Merchant to His Son by George Horace Lorimer
This book is the preserved correspondence between Old Gorgon Graham, a self-made millionaire in Chicago, and his son who is coming of age and entering the family business. The letters date back to the 1890s but feel like they could have been written in any era. Honest. Genuine. Packed with good advice.
11. My Life and Battles by Jack Johnson
This is the lost and translated book that came out of a series of pieces Johnson–perhaps the greatest boxer who ever lived–wrote for a French newspaper in 1911. It’s not very long but it is full of really interesting strategies and anecdotes. You get the sense that he was an incredibly intelligent and sensitive man–clearly had a thirst for drama and attention. Who knows what place he would occupy in our culture and history had he not been taken down so thoroughly by racism and genuinely evil people? But despite all that, he was always smiling. As Jack London put it after Johnson’s most famous fight: “No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today.”
12. Company K by William March
Far and away the best book ever written about WWI. Better than All Quiet on the Western Front or Goodbye to All That or any of the other classics. But that’s the problem–WWI was awful, perhaps the most awful thing of the 21st century. And this book is forgotten precisely because it portrays the war and its pointlessness too realistically. We want to know, but we don’t really want to know.
13. Babbitt by Sinclair Lewis
I don’t think there was anyone in the 1920s who would have believed that this book would be completely forgotten. By all accounts, it was destined to be a classic critical novel of the American Dream. You can’t read anything about the ’20s and ’30s that doesn’t comment on Babbitt (sold 130,000 copies its first year, HL Mencken loved it, it won Lewis a Nobel Prize). Calling someone a “Babbitt” was considered an insult and the phrase became a constant topic of conversation in the media and literature. Yet, here we are 80-90 years later: you’ve probably never heard of the term or the book. Perhaps it’s because the biting satire of American suburban middle class life cuts deeper now than it did then. It doesn’t matter if the book is old, it’s still very funny and at its core, a critique of conformity and what Thoreau called the “life of quiet desperation.”
14. Asylum: An Alcoholic Takes the Cure by William Seabrook
In 1934, William Seabrook was one of the most famous journalists in the world. He was also an alcoholic. But there was no treatment for his disease. So he checked himself into an insane asylum. There, from the perspective of a travel writer, he described his own journey through this strange and foreign place. Today, you can’t read a page in the book without seeing him bump, unknowingly, into the basic principles of 12-step groups and then thwarted by well meaning doctors (like the one who decides he’s cured and can start drinking again). On a regular basis, he says things so clear, so self-aware that you’re stunned an addict could have written it–shocked that this book isn’t a classic American text. Yet all his books are out of print and hard to find. Two of my copies are first editions from 1931 and 1942. It breaks your heart to know that just a few years or decades later, his options (and outcome) would have been so very different (he eventually died of an opium overdose).
15. Ask the Dust by John Fante
This is the west coast’s Great Gatsby. Fante has benefited from some recognition–mostly thanks to Bukowski championing him in his later years–but because the book is about Los Angeles and not New York City, it is mostly forgotten. Better than Gatsby, it is a series. Bandini, the subject of the series, is a wonderful example of someone whose actual life is ruined by the fantasies in his head–every second he spends stuck up there is one he wastes and spoils in real life. He’s too caught up and delusional to see that his problems are his fault, that he’s vicious because he can’t live up to the impossible expectations they create, and that he could have everything he wants if he calmed down and lived in reality for a second. This is the series in order by my favorites: Ask the Dusk, Dreams from Bunker Hill, Wait Until Spring, Bandini and The Road to Los Angeles. (DO NOT watch the movie version of Ask to Dust, it is embarrassingly bad.)
16. Why Don’t We Learn from History? and Strategy by BH Liddell Hart
These are two very short books but will help you understand the topics more than thousands of pages on the same topic by countless other writers. In my view, Hart is unquestionably the best writer on military strategy and history. Better than von Clausewitz, that’s for sure (who for all the talk is basically useless unless you are planning on fighting Napoleon). His theories on the indirect approach is life changing, whether you’re struggling with a business or just office politics. I can’t say much more than read these books. It’s a must.
17. The Crack Up by F. Scott Fitzgerald
If you like Asylum, read The Crack Up, a book put together by Fitzgerald’s friend Edmund Wilson after his death. It is such an honest and self-aware compilation of someone hell-bent on their own destruction. At the same time, Fitzgerald’s notes and story ideas within the book make it undeniably clear what a genius he truly was. It’s a sad and moving but necessary read.
18. On the Rock: Twenty Five Years in Alcatraz by Alvin Karpis
John Dillinger was played by Johnny Depp. Most people know who he was–mostly because he died in a hail of bullets. But they forget that the other Public Enemy #1 at the time was Alvin Karpis and he didn’t die. In fact, he lived up until the 1980s. Just enough time to do a couple decades at Alcatraz with guys like Al Capone. During a temporary transfer to an alternate prison, Karpis met a young weirdo named Charlie Manson and taught him how to play guitar.
19. Death Be Not Proud by John Gunther
Written in 1949 by the famous journalist John Gunther about his death of his son–a genius–at 17 from a brain tumor, this book is deeply moving and profound. Every young person will be awed by this young boy who knows he will die too soon and struggles to do it with dignity and purpose. Midway through the book, Johnny writes what he calls the Unbeliever’s Prayer. It’s good enough to be from Epictetus or Montaigne–and he was fucking 16 when he wrote it. It’s reading the book for that alone.
20. The Harder They Fall by Budd Schulberg
Budd Schulberg’s (who wrote On the Waterfront) whole trilogy is amazing and each captures a different historical era. His first, What Makes Sammy Run? is Ari Gold before Ari Gold existed–purportedly based on Samuel Goldwyn (of MGM) and Daryl Zanuck. His next book, The Harder They Fall is about boxing and loosely based on the Primo Carnera scandal. His final, The Disenchanted is about Schulberg’s real experience being attached to write a screenplay with a dying F. Scott Fitzgerald. All you need to know about Schulberg’s writing is captured in this quote from his obituary: “It’s the writer’s responsibility to stand up against that power. The writers are really almost the only ones, except for very honest politicians, who can make any dent on that system. I tried to do that. And that’s affected me my whole life.”
21. Losing the War by Lee Sandlin
This is an essay, not a book, but if you have to read one thing about WWII, this is it. Sandlin is a master and the essay is free, read it.
22. The Measure of My Days by Florida Scott Maxwell
The daily notes of a strong but dying woman (born 1883, written in 1968) watching her life slowly leave her and wind to a close. The wisdom in this thing is amazing and the fact that most people have no idea exists–and basically wait until the end of their life to start thinking about all this is very sad to me. Also I love her generation–alive during the time of Wyatt Earp yet lived to see man land on the moon. What an insane period of history.
23. The Power Tactics of Jesus Christ and Other Essays by Jay Haley
The title essay in this book is peerless and amazing. The rest of the essays, which talk about Haley’s unusual approach to psychotherapy are also quite good. If you’ve gone to therapy, are thinking about going to therapy, or know someone going to therapy, this book is a must-read.
24. The Tiger: A True Story of Vengeance and Survival by John Vaillant
I’ll end with this book because it’s the most recent. The (true) story is simple: man in Siberia wounds tiger while hunting to feed his family. Tiger goes on killing spree while hunting the man down, and is stopped only when the Russian government dispatches a special SWAT team to track and kill it. This is probably the single best piece of nonfiction journalism I’ve ever read. I suppose it’s not totally unknown but I’m guessing you haven’t read it and that needs to change, now.
I’ve tried to capture most of the major eras and epochs above, from classical Greece to the Renaissance to the great wars of the 20th century. Yes, it is heavy on American history. But guess where most of the people reading this live?
Like I said, there are certain classic texts that we must read–books that have become cultural rites of passage. No one is saying you should skip your high school reading list. The problem is thinking that that’s enough. In order to work for “everyone,” those books had to be safe, they had to be accessible, they had to be provocative but not too provocative. There is a very understandable reason that we read All Quiet on the Western Front and not Company K. Or that we read Huckleberry Finn to understand slavery and not Solomon Northup’s real memoir.
Because the latter books are real. The others keep us comfortable, even when they make us think.
The next step is digging a little bit beneath the surface, leaving the road and exploring parallel or divergent paths. I hope some of these books do that for you. They certainly did for me.
For more book recommendations like this, try Ryan’s monthly reading newsletter where all these books have been featured at one point or another.