5 Massive Books That Are Worth Your Time

When most people go on beach trips, they buy some trashy mystery or romance novel in the airport. Me? I cart Kant’s Critique of Pure Reason with me. In its own suitcase. Why? Because it’s like 800-and-some pages and dense as fuck. Then I take notes in my lounger on the beach while my girlfriend sunbathes. Sometimes I even bring my laptop to do research. My girlfriend tells me this should be embarrassing. I think it’s kind of awesome.

Because here’s the thing about gigantic books: they’re almost always amazing. No editor or publisher in their right mind would allow 1,000 pages of shit to get published.¹ They would force the author to either chop the beast in half or tell them to get the hell out of their office.

No, if a 1,000-page book has even survived the chopping block to see the light of day in the first place, that means it’s probably something special.

Writing/reading is like visiting another person’s brain. And a short book or article is like a short stay. You come in, have a coffee, talk about the weather or sports, and then move on.

But with big books, you’re not just visiting the author’s brain, you’re entering into a romantic relationship with it. You’re making out with their brain, enjoying quiet evenings in the park with their brain, staying up late crying and listening to all of the fear and guilt and joy and bliss pour out of their brain. It’s the most severe form of intimacy between two people who have never met and will never meet.

Now, I’m not saying every big book will do this to you. But many will. If you deep dive into them long enough, they will reorient the way you think and feel about this world, and you’ll come out of them better for it. Here are five brain busters that have made me better for it.

War and Peace

By Leo Tolstoy

Page Count: 1,296 pages

Before I had any idea what War and Peace was or what it was about, it had already achieved mythical status in my mind. Back in high school and college, if any of the kids ever complained about how long or hard a certain book was, the teachers would often say something like, “It could be worse; we could be reading War and Peace.”

The point was clear: Almost 1,300 pages. Written by some boring Russian dude over 100 years ago. Over 25 main characters and a story that spans almost 10 years. No thanks.

Jump ahead to 2013, I happen upon a David Foster Wallace interview where he says something about War and Peace being the best book ever written, period. Now, I love DFW (he’s on this list too), and by this time, I loved 1,300-page books. My mouth watered. And, like the sick fuck I am, I bought War and Peace to take with me on a three-week trip to the Philippines. Soon, I found myself ignoring pristine white sand beaches with their translucent aqua-green water day after day to stare into my Kindle for hours at a time with my jaw agape at how a human being could be capable of producing something so magnificent and amazing.

War and Peace may be the most epic thing ever created by a human being. I know the word ‘epic’ gets thrown around these days as if it means nothing, but I’m actually not exaggerating when I say that. The sheer scope of the story, combined with its unrivaled depth of humanity in each character — I have never seen anything like it anywhere else in any art form. It really is a book about life in all of its beautiful and horrifying forms.

The book is a historical fiction based on Napoleon’s fateful (and failed) attempt to invade Russia in 1812. Over half of Europe was decimated and Napoleon lost almost 90% of his army. The book focuses primarily on the Russian high society, how they react to their country crumbling around them, and how they cope with it in all of their unique and flawed ways. But what makes Tolstoy stand out as one of the best storytellers the human race has ever produced is his ability to psychoanalyze his characters and get to their deepest and most guarded motivations in a matter of a few sentences.

As Isaak Babel put it, “If the world could write by itself, it would write like Tolstoy.”

Why It’s Hard to Read: The length, primarily. It took me almost two months to get through it, and I’m a pretty fast reader. It also takes a couple hundred pages of work before it starts paying off. As I mentioned, there are over 25 main characters as well as a number of side characters. And to make matters worse, many of the first scenes of the book (which take place in the high courts of the Russian aristocracy) include passages in French, requiring you to check the footnotes for translations.

Note: There are as many translations of this book as there are pages and many of them suck. Be sure to grab the translation by Pevear and Volokhonsky. It’s widely considered the best one.

Why You Should Read It Anyway: Put simply, this is your favorite literary genius’s favorite literary genius. Tolstoy is the master. His two big novels War and Peace and Anna Karenina are both pretty much always in the top 3 of any “best books ever written” list. From Dostoevsky to Gustav Flaubert, from Ernest Hemingway to David Foster Wallace, they all raved like giddy little children at a birthday party whenever Tolstoy was brought up around them. Read it.

Money Quotes:

“Man cannot possess anything as long as he fears death. But to him who does not fear it, everything belongs. If there was no suffering, man would not know his limits, would not know himself.”

“[B]ut now, in these last three weeks of the march, Pierre had learned a new and more comforting truth–he had learned that there was nothing frightening in the world. He had learned that, as there can be no situation where a man is perfectly happy and free, so there is no situation where he can be perfectly unhappy and unfree. He had learned that there is a limit to suffering and a limit to freedom, and that those limits are very close; that the man who suffers because one leaf is askew in his bed of roses, suffers as much as he now suffered falling asleep on the bare, damp ground.”

“We can know only that we know nothing. And that is the highest degree of human wisdom.”

Other Things You Could Probably Do in the Time It Takes You to Finish This Book:

• Launch an ill-advised land invasion of Russia.
• Learn to speak French well enough to understand the passages in the beginning of the book without footnotes.
• Grow a beard as long and hideous as Tolstoy’s.

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The Better Angels of Our Nature

By Steven Pinker

Page Count: 832 pages

Chances are you’ve heard this book mentioned somewhere in the last few years. And chances are you’ve heard it mentioned because of how wrong or misguided the book must be.

That’s because Pinker’s argument in this book is so contradictory to everything we feel to be true, it’s extremely hard to accept (hence, him needing 832 pages to convince you.)

What’s his argument? It’s this: today, we live in the most peaceful, tolerant, and non-violent period in human history.

I’ll let that sink in a moment…

In fact, Pinker says, relative to the rest of human history, the past 70 years have been so peaceful and non-violent that historians, sociologists, and political scientists have no idea how to explain it.

Now, if you’re like most people, you immediately resist this argument. You think that there’s no way that could be true. And that’s why Pinker begins the book by deftly reminding us that the vast majority of human history included mass slavery, habitual torture, public executions, cruelty towards both animals and children, human sacrifices and honor killings, and so on. These things were the rules of the human experience, not the exceptions. He points out that in medieval Europe, there was an art form to torture and people took pleasure in public mutilations. Women and children were often sold off as slaves. Wars that killed hundreds of thousands of people were started for no other reason than some lord or king got his ego bruised. Hell, apparently people used to set cats on fire as a form of entertainment.

And once your stomach is queasy, Pinker then slams you with 600 pages of data. Page after page after page of charts, graphs, studies, historical quotes. The evidence he presents is massive (again, it’s 832 fricking pages). There are entire sections of the book where every single sentence is footnoted with references to studies. Pinker knew people were going to call bullshit on him, so he did his due diligence here.²

But don’t get bummed out by all the data. He spends the last few chapters taking a stab at why violence has declined and this is where the book gets really fascinating. I won’t spoil his answers, but here are a few hints: empathy is overrated, reason and literacy are way underrated, governments are better than people think, and religion is, well… hate to piss in the punch bowl, but religion is responsible for a lot of violence.

Why It’s Hard to Read: The hardest part of this book is just how exhaustive the data is. He doesn’t just show the decline in wars and violence within society; he spends many pages or even entire chapters showing the decline of things like torture, animal abuse, domestic abuse, hate crimes, even spanking children. There are hundreds of charts and graphs and it can all get a bit tiresome. Take it in measured doses.

Also, his description of some of the violence that was prevalent throughout history can get sickening at times. It’s eye-opening how cruel our species can be (and usually has been).

Why You Should Read It Anyway: It’s worth it for a few reasons. First, if/when you’re convinced of Pinker’s central argument, your whole perspective on the world and history changes. Yes, we obviously have huge problems today that need addressing, but comparatively, these are way, way, way better problems than people faced even a few generations ago. This is actually a significant shift in most people’s worldview that has real, tangible implications.

But secondly, Pinker’s arguments for why violence happens and why it has declined will likely change a number of your assumptions about life. “All we need is love,” Pinker argues, is actually likely far more dangerous than it is helpful. On the contrary, he argues for a classic, Enlightenment-era ethos: reason, tolerance, individual liberty, and a healthy dose of skepticism.

Money Quotes:

“Institutionalized torture in Christendom was not just an unthinking habit; it had a moral rationale. If you really believe that failing to accept Jesus as one’s savior is a ticket to fiery damnation, then torturing a person until he acknowledges this truth is doing him the biggest favor of his life: better a few hours now than an eternity later.”

“I am sometimes asked, “How do you know there won’t be a war tomorrow (or a genocide, or an act of terrorism) that will refute your whole thesis?” The question misses the point of this book. The point is not that we have entered an Age of Aquarius in which every last earthling has been pacified forever. It is that substantial reductions in violence have taken place, and it is important to understand them. Declines in violence are caused by political, economic, and ideological conditions that take hold in particular cultures at particular times. If the conditions reverse, violence could go right back up.”

“In this way of thinking, the fact that women show a lot of skin or that men curse in public is not a sign of cultural decay. On the contrary, it’s a sign that they live in a society that is so civilized that they don’t have to fear being harassed or assaulted in response.”

Other Things You Could Probably Do in the Time It Takes You to Finish This Book:

• Throw a woman in a well to see if she’s a witch. If she floats, then fish her out and burn her alive for that week’s Friday night entertainment.
• Be grateful approximately 12,031 times that you weren’t born in previous generations.
• Commit genocide or some other atrocity. Blame it on people with a different skin color than you.

Godel, Escher, Bach

By Douglas Hofstadter

Page Count: 824 pages

My love for paradoxes dates back to my teenage stoner days where we’d lay around in my friend’s garage, get high, and say shit like, “Dude, the only thing that’s constant in the world… is like… change.” And then sit there spacing out to Pink Floyd as if something life changing just occurred.³ As I got older, the prevalence of paradoxes behind a lot of situations in life became more apparent and I couldn’t help but feel they represented some sort of limit to the human brain’s ability to process certain types of information.⁴ I even went so far as to write an entire post about paradoxes that are strangely true on this site a few years ago. I made self-referential jokes and thought myself kind of clever.

Then I read Godel, Escher, Bach and realized that I didn’t even begin to know what the fuck I was talking about. In fact, I’m still closer to that blabbering stoned idiot in my friend’s garage than I am to Hofstadter’s monumental work.

This book. This fucking book, man. Its brilliance is indescribable. At its core, Godel, Escher, Bach is an investigation into how components of a system can come together and create something greater than the sum of their parts — or essentially, how something like a self-referential consciousness (a brain that can have thoughts about itself, or even have thoughts about thoughts about itself) could ever come to exist from a slimy pile of a few billion neurons.

Hofstadter employs a boatload of clever gimmicks, analogies, and fun mental games to get his point across — the most prominent ones being Godel’s incompleteness theorems in mathematics, Escher’s paradoxical drawings, and Bach’s recursive musical inventions.

Why It’s Hard to Read: It’s intellectually intense. A single chapter may take a piece written by Bach, analyze it, use that analysis to make a point about systems theory which then results in a paradox which is then made fun of with a fictional dialogue between Achilles and a turtle. It’s an intellectual rollercoaster, impossibly dense in places, and an epiphany spree in others.

If you don’t have a background in mathematics, the set theory sections will be difficult to follow. If you don’t have a background in music, a lot of the analogies to Bach will be lost on you. If you don’t have any knowledge of philosophy, some of the references and discussions will come up blank. But it’s worth taking the time to stop and understand everything.

It took me three tries to finally get through it, and even then I don’t think I completely understood everything he was getting at. At some point, I just went with it. I found it helpful to set the book down for days or even weeks at a time, let it sit with you, and then return to it when you’re ready for more. It’s like eating chocolate mousse, it’s rich and deep and filling, but you can only handle small portions at a time.

Why You Should Read It Anyway: I feel like everyone should be handed a copy at some point in their life — even if they don’t like it, even if they don’t understand it — just to see what it’s possible for a book to be, to see the dizzying genius the human mind is capable of creating.

But here’s really why you should read it: philosophy, in general, is incredibly dense and boring, and this is perhaps the only book I’ve ever seen that applies the same creative genius required to understand deep philosophical concepts to the actual writing and explication of those concepts. In many ways, GEB is a pure joy to read and I guarantee it’s unlike anything you’ve ever come in contact with. It stretches your brain in ways you didn’t know it could be stretched.

Money Quotes:

“Meaning lies as much
in the mind of the reader
as in the Haiku.”

“How gullible are you? Is your gullibility located in some “gullibility center” in your brain? Could a neurosurgeon reach in and perform some delicate operation to lower your gullibility, otherwise leaving you alone? If you believe this, you are pretty gullible, and should perhaps consider such an operation.”

“What is an “I”, and why are such things found (at least so far) only in association with, as poet Russell Edson once wonderfully phrased it, “teetering bulbs of dread and dream” — that is, only in association with certain kinds of gooey lumps encased in hard protective shells mounted atop mobile pedestals that roam the world on pairs of slightly fuzzy, jointed stilts?”

Other Things You Could Probably Do in the Time It Takes You to Finish This Book:

• Listen to all 125 CDs of Bach’s complete works.
• Build a computer that is conscious that could then build exponentially more computers that are conscious that could then build exponentially more computers that are conscious and so on…
• Resolve Zeno’s Paradox.⁵

The Origins of Political Order + Political Order and Decay

By Francis Fukuyama

Page Count: 1,280 pages (608 book one + 672 book two)

(I’m kind of cheating because this is two separate books: The Origins of Political Order and Political Order and Decay. But Fukuyama intended them to be two parts to a single grand work, so that’s how I consider them here. If that bothers you — fuck you, it’s my list.)

Fukuyama is most famous for brashly declaring after the Cold War that “the end of history” had arrived. One could say that he spent most of the intervening 20 years trying to restore his reputation from that overly bold (and unfortunately, completely misinterpreted) statement.⁶ I believe that with this work, his admitted magnum opus, he’s done just that and more.

Fukuyama’s desire with these books is to answer two big questions: 1) How and why did governmental systems develop across the world? 2) Why did some governmental systems become more functional and just than others?

To construct his argument, Fukuyama literally traces the evolution of all of the world’s major civilizations: Chinese, Indian, Middle Eastern, European, and the New World up to present day. The first book follows world history up until the French Revolution and analyzes the differences between the pre-modern state systems in each major civilization and why they developed in the direction that they did.

Book two then starts with the French and American Revolutions (the invention of modern democracy, basically) and looks at why western nation/state systems have come to dominate the planet, why North America, Australia, and much of Asia have caught up with the West in terms of development, education and economics, and why other regions of the world such as Latin America, Africa, and the Middle East struggle in their own unique cultural ways.

As someone who has traveled the world many times over and wondered things like, “Why are Latin countries so corrupt?” or “Why is there very little violent crime in Asia despite large amounts of poverty?” or “Why do democratic movements never take root in the Middle East even though it’s clear the majority of people there support them?” this book provided mind-blowing answer after mind-blowing answer.

Why It’s Hard to Read: If you are a history nerd, you will love this shit. If not, it can be rough.

Fukuyama is constructing a massive thesis here, and so to support that thesis well, he needs to be thorough. You’ll get about 100 pages of ancient Chinese history, followed by about 100 pages of ancient Indian history, followed by 100 pages of Middle Eastern history, followed by 100 pages of medieval European history and so on. If you’re like me, it will get stale at times and you’ll have to force yourself through it so you can finally get to the good stuff. ⁷

Why You Should Read It Anyway: In terms of pure ideas and the gained understanding of the world and humanity, this is probably one of the most illuminating books I’ve ever read in my life. That is no exaggeration.

Seriously, why is China the way it is? That sounds like such a dull and vague question that a nine year old would ask his Dad, but after reading this book, you know exactly why China is the way it is.

This book also gave me a much-needed respect for governments. As someone who had a libertarian bent throughout college, Fukuyama bitchslapped me with hundreds of pages of explanation of why centralized governments, despite their obvious flaws and dangers, are probably one of the best things humanity has ever created. No joke.⁸

Money Quotes:

“Many people, observing religious conflict in the contemporary world, have become hostile to religion as such and regard it as a source of violence and intolerance. In a world of overlapping and plural religious environments, this can clearly be the case. But they fail to put religion in its broader historical context, where it was a critical factor in permitting broad social cooperation that transcended kin and friends as a source of social relationships. Moreover, secular ideologies like Marxism-Leninism or nationalism that have displaced religious beliefs in many contemporary societies can be and have been no less destructive due to the passionate beliefs that they engender.”

“Human beings are rule-following animals by nature; they are born to conform to the social norms they see around them, and they entrench those rules with often transcendent meaning and value. When the surrounding environment changes and new challenges arise, there is often a disjunction between existing institutions and present needs. Those institutions are supported by legions of entrenched stakeholders who oppose any fundamental change.”

“Many of these problems could be solved if the United States moved to a more unified parliamentary system of government, but so radical a change in the country’s institutional structure is inconceivable. Americans regard their Constitution as a quasi-religious document, so getting them to rethink its most basic tenets would be an uphill struggle. I think that any realistic reform program would try to trim veto points or insert parliamentary-style mechanisms to promote stronger hierarchical authority within the existing system of separated powers.”

Other Things You Could Probably Do in the Time It Takes You to Finish This Book:

• Found a country and develop your own civilized state system.
• Actually live through all of ancient Chinese history.

Infinite Jest

By David Foster Wallace

Page Count: 1,092 pages

In 40 years, when I’m old and crapping my pants, I will gather my grandchildren around the hearth and proudly tell them how their dear old granddad read Infinite Jest not once, but twice. Yup, that’s right. Your dear old granddad was a total self-hating masochist.

For whatever reason, when it came out in 1995, Infinite Jest became a cultural event. It was the massive book that was “cool” for all the Gen Xers to read. Wallace’s book readings were overflowing with people and he soon found himself invited onto major TV shows to be interviewed nationwide.

This all made him uncomfortable, of course. Aside from his anxiety, his book was a parody of this exact facet of American culture — blindly pursuing the hot new thing, ignorant of any depth or meaning or significance. DFW once joked that everybody seemed to love his book, including the few people who actually read it.

Infinite Jest takes place in a fictional near future. The United States and Canada have merged. A cheesy singer is elected president. And there’s so much pollution that giant catapults launch toxic garbage from New England into nearby Quebec.

The story loosely revolves around a few plotlines: a child prodigy who studies at a tennis academy owned by his family, a recovering drug addict trying to make a clean life for himself, and a mysterious cartridge simply referred to as “The Entertainment” that is apparently so entertaining that anyone who views it will forgo everything — eating, sleeping, pooping — just to keep watching it.

I say the story is loose because really, there’s not much of a story going on here. You’re mostly reading this for hundreds of pages of Wallace’s creativity and unique voice. Some people find the book tedious (the first time through, I did at times), but once you fall into his style, Wallace’s unique ability to constantly observe life in ways you didn’t know existed makes you feel as though you’re getting smarter simply by reading him, even if it’s a paragraph about something mundane like tennis shoes and chewing tobacco.

Why It’s Hard to Read: Convoluted and disjointed plot. Over a dozen main characters. Oh, and there are over 200 pages of footnotes for Wallace’s tangents.

This book takes time. It is fiction, but it reads as slowly as some of the densest non-fiction. That isn’t to say that it’s hard to read. It just requires patience. Let it come to you… whatever the fuck that means.

Why You Should Read It Anyway: Because this book really does let you jump into a warm bath with one of the most creative and unique brains the English language has seen in the past 100 years. Sure, there are some really insightful commentaries about American excess and the deleterious effects of pursuing happiness at all costs. There are some heartwarming sections about addiction and some incredibly moving passages that find characters at their best and worst moments.

But, usually, the book is exactly what it’s parodying: it’s excessive, entertaining, addictive, and all-consuming to the consumer.

Money Quotes:

“Everybody is identical in their secret unspoken belief that way deep down they are different from everyone else.”

“Like most North Americans of his generation, Hal tends to know way less about why he feels certain ways about the objects and pursuits he’s devoted to than he does about the objects and pursuits themselves. It’s hard to say for sure whether this is even exceptionally bad, this tendency.”

“Mario’d fallen in love with the first Madam Psychosis programs because he felt like he was listening to someone sad read out loud from yellow letters she’d taken out of a shoebox on a rainy P.M, stuff about heartbreak and people you loved dying and U.S. woe, stuff that was real. It is increasingly hard to find valid art that is about stuff that is real in this way. The older Mario gets, the more confused he gets about the fact that everyone at E.T.A. over the age of about Kent Blott finds stuff that’s really real uncomfortable and they get embarrassed. It’s like there’s some rule that real stuff can only get mentioned if everybody rolls their eyes or laughs in a way that isn’t happy.”

Other Things You Could Probably Do in the Time It Takes You to Finish This Book:

• Start a professional tennis career.
• Start and then kick a brand new meth habit.
• Get out of the house and actually have a life.

Looking for More Books to Read?

I’ve put together a list of over 200 “best books” organized by genre, as well as my all-time recommended reading list that includes the book(s) I’m reading each month. Check them out.