This is a collection of books I've read and enjoyed. I've tried writing reviews, but I think I'm not critical enough: all I really want to do is share the good stuff, so here's some of that.
todo: finish writing descriptions + xrefs
One for the cynics. It is broadly considered common sense, especially in america, to assume that in a crisis situation people will instantly be at each other's throats. What's interesting is, this is the opposite of what happens in real life. A Paradise Built in Hell (subtitled "the extraordinary communities that arise in disaster") is a book about what happens in real life.
This might sound like depressing fare, but what saves it is the book's focus: on the people who survived, what their lives were like at the center of these moments, on what they did, who they did it with, and how they looked back on it after the fact.
The common themes are of people coming together, setting aside differences, uniting in a common struggle - basically all those cliche utopian ideals that we want to believe in but usually reject as naive. Well, here they are, writ large and told through first-person accounts.
The author, Rebecca Solnit, is one of my favorite authors currently working. This is sort of an outlier in her work, less autobiographical than usual, but somehow it feels just as personal because you can see the values reflected through the stories she has collected and shared here.
This gives you a full view of half of a field. It's a bit lopsided, but the stuff it covers, it covers very well.
I have had a couple people ask me, either personally or on behalf of friends, whether there's a path for math grad students to get into cryptography. My answer: yes, and it starts with this book.
It is part of the "undergraduate texts in mathematics" series, but don't let that fool you: some of the math it discusses is fairly heavy-duty. That said, it does a good job of building up to the advanced stuff, so if you come in with a basic undergraduate knowledge of concepts like modular arithmetic, it can get you the rest of the way there. Even so, YMMV depending on how much you like math.
My favorite Neal Stephenson novel. Incredibly long and discursive. Very chill.
There is a giant circular wall, which has stood for thousands of years. Inside lives an order of monastic academics. There is a gate in the wall; every year, this door to the outside world opens once. Within this circle is a second wall, with a second gate; this one opens every ten years. Likewise twice more, with the innermost wall's gate opening only on the millenium. Aside from these openings, these scholar-monks live in voluntary isolation from the outside world, eschewing advanced technology and leading simple lives of thought and study.
Of course, the plot demands that their isolation be interrupted; however, a good portion of the book takes place before that interruption. This portion just charts what life would be like inside these walls. What are the dramas of their lives? What are their goals and dreams? What are the big decisions they have to make? What might cause these people to come together or grow apart? How do they spend a lazy afternoon, or a lazy summer? This, to me, is the best part of the book.
That said, once the plot gets properly underway, it is very engaging and interesting.
This is the only book I've ever read where an important plot point hinged on the question of whether or not Platonic metaphysics is empirically verifiable.
Can a factual biography also be a hit piece? No one was asking this question, but nevertheless, here we have the answer.
This was written by Ray Monk, who also did the extraordinarily good biography of Wittgenstein that I've mentioned elsewhere on this page. Wittgenstein and Russell's lives intersected many times, and they corresponded heavily, so (as I understand the story) after Ray Monk finished his Wittgenstein book, he realized he was already halfway to a book on Russell and he figured, what the hell, let's finish it off.
The catch: He really does not like Bertrand Russell. And when you read this book, you will understand why. It's important to emphasize that Monk is not unfair to the man, but he is absolutely merciless in his choice of (for example) extended block quotes from Russell's absolutely mortifyingly cringeworthy unrequited love letters.
It might sound unfair to pull from those, but it's important to understand that Russell wrote a lot of letters, and a lot of these were love letters. My man was writing letters at the rate most of us send texts, and that is not an exaggeration.
The love letters aren't the worst of it, though: in one episode, Russell goes out on a walk, realizes on this walk that he no longer loves his wife, and does what any reasonable person would do in such a situation: he returns home and tells her the news. Monk's sympathy for her is palpable as he describes the impact this had on her life (she was devastated and, it seems, never fully recovered).
In fairness: Russell had a very traumatic childhood (which this book will tell you all about) and it seems he ended up as an emotionally malformed adult (which this book will also tell you all about). The man is lucky to have been a sharp philosopher and a member of the british aristocracy, both of which meant that he had a wider range of options than most of us who come from similar backgrounds, but nevertheless his life was full of a series of horrors and humiliations that feel cribbed from cringe comedy. In fact, if any TV writers are reading this: adapt this book. It'll kill.
The most compelling - and most painful - parts of the book come from Russell's interactions with background characters, like the prison guard (while Russell was jailed for protesting) who was unexpectedly nice to Russell, but who was the target of almost unlimited scorn in the latter's letters after his release in a series of passages that reek of british classism exacerbated by a total lack of self-awareness.
I still respect Russell's writings (I have his History of Western Philosophy on this list, and I've read and enjoyed some of his other works as well, like his Introduction to Mathematical Philosophy) but I was completely floored at this biography's picture of him. That said, I simply could not put it down, either. It's that classic dilemma: You don't want to look, but you can't look away.
One of Neal Stephenson's masterpieces. A book that defies description. Spans multiple generations of multiple families, whose fates intertwine in all kinds of fascinating ways.
A young mathematician befriends Alan Turing and goes on bike rides with him; later, he helps Turing in the war effort by building a hydraulic computer. Two characters - one of whom might secretly be immortal - are imprisoned in adjoining cells, and pass encrypted messages using a cipher that is calculated using a deck of playing cards (and which was invented for the novel by Bruce Schneier). A commando and his civilian lover hook up under increasingly surreal circumstances. Several characters collaborate to build an offshore data haven and, in passing, invent Bitcoin (this book was published in 1999!) A character's computer gets Van Eck phreaked. And that's not even half of the crazy stuff that happens in here.
I can barely keep up with Stephenson's new stuff, but when I finally get caught up I'm going back to this one. It's not his only masterpiece - I'd also recommend Anathem and Interface, among others - but this is a great book.
I read this as a kid because I accidentally requested it from the library when I was intending to get a copy of Neuromancer. In my defense, both titles have an unreasonable number of syllables, and anyway, it turned out to be exactly what I was looking for.
Schneier's best book (in my opinion). And yes, I'm including the books on cryptography, which were epochal but are showing their age. This book is encyclopedic. I wrote about it in more detail here, though I might have laid the praise on a little heavy (it's amazing what six years of perspective can do).
This is the book on big data and surveillance circa 2015. It is comprehensive and packed to the stitches with detail. It's one of the most information-dense books I've ever read. I was amazed by how many of the projects described in it were unfamiliar to me, even though I do my best to be aware of what's happening in this space.
This book is almost a decade old at this point, and I'd really like to see an updated edition; that said, it is still worth reading.
I'd never seen a poem written in sign language until I read this book.
I don't read a lot of poetry, but I was lucky enough to read this and I was blown away by it. Excerpts from it have gone viral (you may have seen "we lived happily during the war"), but they sell it short. Each poem stands on its own, but they are anything but disjointed; the whole is greater than the sum of its parts.
One of the many books that has been bought for me as a joke, but that I have thoroughly and unironically enjoyed. This book helped me decide where to place my desk, and it worked perfectly.
Among other things, Feng Shui is (in basic, westernized terms) concerned with the balance of flows of "energy" within a space. You don't want a space to feel too chaotic or too stagnant - you want areas of rest and areas of motion, with balance between them.
By watching how your cat engages with your space, you can see what they understand to be the areas of rest and motion - where do they sleep, and where do they go to run around when they've got the 2 AM crazies?
Your cat is engaged in constant dialogue with the space around them, and you can listen in on this dialogue and use it to help inform how you craft your space. This sounds kind of crazy, and maybe it is, but it actually works.
A cat's input can be surprisingly grounding. Your cat (allegedly) doesn't understand language, so they are completely incapable of being taken in by any new-age nonsense, which makes them an excellent collaborator.
The rest of the book goes into way more detail and is a surprisingly approachable, down-to-earth, and even convincing exposition of something that I always thought to be kind of hand-wavey and even disreputable. If I'm being honest, I still kind of see it that way, but I can't deny the results.
Diane Williams is a treasure. These are tiny stories, and this will be a tiny note. The book is good. It's easy to read and rewarding to dwell on. I've written about it before. It comes via McSweeney's, which as a publishing house tends to be terminally twee, but they really scored big on this one.
Elinor Ostrom's book on how the Tragedy of the Commons is some made-up bullshit that's not real (my words, not hers, unfortunately), and on how commons can be managed in real life.
The book takes a ton of case studies of shared resources: pastures, fisheries, water supplies, etc - the exact places where conventional economic wisdom would tell us to expect cutthroat behavior, backstabbing, sociopathic scheming, and so on, and it finds that the only people who actually behave in this way in these settings are economists, who tend to quickly get shown the door.
OK, that was a bit glib, let me try again. She goes through case studies of how communities manage commons across the world, and synthesizes a series of observations on what the necessary and sufficient conditions are for preventing the tragedy of the commons. Fascinating stuff that flies in the face of a lot of conventional "wisdom".
The writing is fairly dry and technical - understandably so, considering that it was written to predict and deflect criticisms from the absolute worst types of pedants, including but not limited to economists - but clearly that strategy worked, because Ostrom won the Nobel Prize in Economics in 2009.
If you need any more reasons to like her and her work, try these quotes from Wikipedia:
Since the 60s, Ostrom was involved in resource management policy and created a research center, which attracted scientists from different disciplines from around the world. Working and teaching at her center was created on the principle of a workshop, rather than a university with lectures and a strict hierarchy.
Ostrom studied the interaction of people and ecosystems for many years and showed that the use of exhaustible resources by groups of people (communities, cooperatives, trusts, trade unions) can be rational and prevent depletion of the resource without either state intervention or markets with private property.
Another of the many books that someone bought for me as a joke, but that I have enjoyed in earnest. I don't (have enough space to) grow weed, but if I did, this book would be my bible. It also contains a lot of interesting information that is useful for the more casual enjoyer.
A famous book written by a famous mathematician, George Pólya. This book is to mathematicians what The Breakthrough to Shodan is to Go players. It's a series of short chapters, each of which describes a problem-solving strategy - or in some cases a meta-strategy or heuristic - followed by a series of problems for which the strategy at hand is unreasonably effective.
We're talking here about proofs and derivations, not arithmetic, to be clear. This isn't about how to add numbers together, but rather about how to come up with formal arguments for specific formal results - and in that sense much of this book is applicable to a much broader group of people than just mathematicians.
Computer scientists don't need to think this hard nearly as often as mathematicians do, but if you practice this stuff, you'll be way ahead of most of the pack. And besides, it's just a fun read.
Many well-known mathematicians have named this as their favorite book. I would love to see a follow-up stat on how many of them have only read one book, but that's just me being catty. If you had to pick one book to read, you could do worse than this one.
One of my favorite books on cryptography. Outstanding. Very thorough. Detailed but readable. Includes lots of trivia (like - no pun intended - a discussion of the freakishly simple-yet-unbroken stream cipher Trivium as a companion to the discussion of LFSRs).
Do note that it is an introduction, rather than a treatment of the full field. The topics covered are covered thoroughly, but there are some notable omissions: elliptic curves are one, and post-quantum algorithms are another (in fact, the third edition seems to have added 20 pages on PQC, but I have not yet read them). The latter omission is understandable given the pace of research; the former is, in my opinion, a weakness. It is however in keeping with the theme of the book, which is more interested in concepts than implementation details. ECC has a lot of important implementation details, but it also is just flat-out important: These days, almost all serious cryptographic engineering involves elliptic curves.
Consequently, a lot of the topics discussed feel interesting in the same way classical cryptanalysis is interesting: you don't need to know all of it, but it provides an accessible example of the types of ideas and reasoning you'll need to be comfortable with, and in that sense there still is real value in teaching it before moving on to the harder but more practically relevant stuff.
Would be an excellent textbook for an introductory class on cryptography. I'd be comfortable putting it in front of anyone from grad students to (motivated, non-math-averse) high schoolers.
This is "the one book every professional Go player has read" and with good reason. Shusaku is probably the most famous Go player of all time.
Quoting from Wikipedia: "He is known for his undefeated streak of 19 games during the annual castle games; his thirty-game match with Ota Yuzo; the eponymous Shusaku opening; and his posthumous veneration as a "Go sage". Next to his teacher, Hon'inbō Shūwa, he is considered to have been the strongest player from 1847/8 to his death in 1862."
The book contains not just game records but professional commentary and a biographical preface as well. It is quite a good read, as long as you like Go and have a board at home to play along to the games with. Shusaku's style is captivating and generally considered to be an excellent example for amateur players to emulate.
Ray Monk is an incredible biographer and he might have had a history-crush on Wittgenstein. I don't want to make any assumptions, but, having read this book, I can't rule it out.
This book is exactly what a biography should be. It's fun, engaging, full of anecdotes and details, but it does not compromise on its technical content at all. The author is a full-on decorated professor of philosophy who is more than capable of explaining every stage of Wittgenstein's thought. The framing device of biography allows him to do so "in real time", so to speak, explaining the ideas as they occur to Wittgenstein, and contextualizing them against his life at the time. This is especially valuable because he was unusually prone to arguing against his own earlier ideas, and charting the development of these arguments historically makes his self-dialogue much more approachable.
What emerges is a compelling portrait of someone who wanted, more than anything else, to do something remarkable. This book's subtitle, "The Duty of Genius", might feel a bit, oh, pretentious, or extravagant, but it's an accurate description of how Wittgenstein seems to have understood his own life: he was brilliant, he had incredible potential, and he felt that it was his duty to live up to that. (The fact that he spent his formative years in the shadow of his incredibly precocious older siblings probably did not help with this.)
But at the same time, he was a fucking nerd - he picked out doorknobs and chandeliers for his sister's house and then put "architect" on his letterhead for years afterwards. He was crazy - in one of the book's funnier anecdotes, he enlists in the army after deciding he hasn't experienced enough hardship (which, to be fair, was probably true), but due to his family's influence he is assigned a desk job. After a while he goes to request reassignment, confusing the officer on duty who takes a while to understand that Wittgenstein wants to go to the front lines! And he was maybe-very-probably gay - though we don't have conclusive evidence afaik, it's like, come on. The guy did some of his best work while sharing a two-person rowboat with his guy friend who happened to come visit him in the mountains for a while. There is a neverending parade of scenes like this, each more rife than the last. If it were fiction it would be accused of queerbaiting.
Wittgenstein has a reputation as one of the more difficult, if not impossible, of the modern philosophers - undeniably brilliant, but hard to read even on a good day. If you're interested, this might be the most approachable introduction to his work (and life!) that you'll find.
This book has the most boring title imaginable, and the writing style is a little dry, but the actual subject matter could not be more interesting.
I often describe books as having broad scopes, but this time I really mean it. Look up the table of contents and see for yourself. No, really.
If you want to get started as a security consultant, you should read two books: one for whatever speciality you want to develop, and one to get you conversant in the rest of the field. This book fills that second role better than any other book I know of.
If you're a developer who doesn't want to do cryptography, but does want to have an idea of what it involves, this is the book for you. If you've been tasked with doing something crypto-related, this is the book to read first (and then once you're done, I very strongly recommend hiring a consultancy to check your work - like, for example, my employer - but I digress).
I've written more about this book previously, so I'll cut this note off here. It's a good book.
I loaned this to a friend of a friend, then never saw them again. Clearly the book works.
Extraordinarily depressing. The Earth is doomed, we have to go to space asap, but it's gonna be really hard and not everyone can make it. Once we're in space, we'll have to stay there for a long, long time. The survival of humanity is uncertain. The one thing we know for sure is, it's gonna take a lot of hard sci-fi to get us through this.
Fairly long and discursive, as Neal Stephenson tends to be. This one is set over a very long time scale. It plays with a lot of ideas, though I can't expand too much on that without giving away plot points. This is Stephenson's take on classic sci-fi, writing about spaceships and astrophysics and thruster burns and all that nerd shit. If you're into that, you'll find a satisfying number of fresh ideas here. If you're not into that, you'll probably get bored pretty quickly.
One of the first books on security that I ever read, and, to this day, one of my favorites.
Ignore every synopsis of this book online. They undersell it. It seems to me like no one was quite sure how to sell this book because no one was quite sure what it was or who it was for. The answer is, it's a grab bag with a few cool ideas at every level of abstraction in a computer system circa 2005. There are a few nominal through-lines connecting these ideas, but really it's just a masterclass in discursive exposition. As for who it's for, the answer is - hackers. In the classic sense, where a "hacker" approaches a computer with curiosity and tries to do surprising things with it, this is the clearest expression of a "hacker mindset" that I've ever seen.
In fact, I'll go further: this book is, to me, the high water mark for accessible technical writing. Many people would tell you that it's possible for technical writing to be either precise or conversational but not both at once. Zalewski proves those people wrong. It reminds me of how some great teachers can ramble for an hour and somehow manage to hit every beat in their lesson plan, while you're so drawn-in that you don't even realize you're learning.
If you look this book up up online, you can find a preview for the first couple chapters and the table of contents. Check it out and see if it hooks you. I really recommend it.
This is a sleeper pick in the Cory Doctorow bibliography. It probably wouldn't be in most people's top 3. That said, I liked it. The thing is, most of his books feel like vehicles for ideas; this might be the only one I've read where it felt like the characters came first. I found it to be disarmingly sincere and evocative.
I read this as a kid and I enjoyed it very much. I've revisited it many times - it might be the most heavily worn book on my shelf. This book - I guess it's technically a graphic novel, but who cares - paints a beautiful, compelling, personal view of Niels Bohr. He was a talented physicist, but also one who was in the right place at the right time with the right ideas; what makes him interesting is the degree to which those ideas, which were mostly correct, seem to have come to him by something other than the scientific method.
This is not to talk down on him as a scientist: he was definitely a scientist, and a very good one. He was also a philosopher and a poet, and someone who was not afraid of proceeding by guesswork. It is interesting to see how this played out in his interactions with his colleagues and students.
In his personal life, he seems to have been - according to the picture painted in this book - gentle, soft-spoken, moral, kind, diplomatic, and just an all-around great guy. This is an easy image to maintain during peace, but Bohr lived through the second world war.
One of the book's most compelling sections deals with his wartime walk and conversation with Werner Heisenberg, a colleague and former friend of his who was working for the germans. The depiction is haunting, historically accurate, honest about the limits of what is known about their conversation, and beautifully drawn.
I love stories about the lives of scientists. These are people who give themselves over completely to one thing. Why do they do it? Who are they? What drives them? What is the rest of their life like? What relationships do they have with their colleagues, their friends, their partners, their children? These are the questions I want to see explored, and this book shares my interests.
For people who read How to Solve It and say "I want more". This book was written as a textbook for students competing in math olympiads. It is extraordinarily comprehensive and detailed. If you know a kid who's really into math but doesn't have the right resources, get them a copy of this book, and do it as soon as possible.
I'll admit that I have not finished the book, because it is long and dense, but I have a very high opinion of it. It also gave rise to an online forum (The Art of Problem Solving, or AoPS) where a lot of olympiad types and former competitors hang out.
I've read many books on Go. This is the book I recommend. It is not an introductory book (for that, Kaoru Iwamoto's book would be a good choice), but once you've reached single-digit kyu strength, this is what you should read. One pro player has quipped that the book should be titled "The Breakthrough to Professional Shodan" (i.e. approximately 9 Dan).
A point of disambiguation: "Shodan" is an overloaded word. In Go, it refers to the changeover point where a former Kyu-ranked player earns their first Dan rank. This is analogous to the shift from a colored belt to a black belt in some martial arts (which, in fact, seem to have borrowed the kyu/dan system from Go). For most amateur players, achieving a dan rating is their ultimate aspiration. It certainly is mine.
I'm currently rated around 3 Kyu on OGS (feel free to send me a challenge if you play, by the way!), so I can't say the book has worked for me yet, but that's my own fault. I can say with confidence that it has measurably improved my game.
A very famous book. Unfortunately considered cliche to recommend to people, but it's good enough that I don't care. You've probably already heard of it, and probably have your own opinions about it. Just in case you haven't: this book's author, Peter Kropotkin, is one of the best-known historic anarchists, and this is his most famous book. It is the most accessible book of anarchist political theory that I'm aware of.
This book is from the 1890s, but for the most part it has aged extraordinarily well. Kropotkin was a revolutionary, but he does not touch on that here. This book does not deal at all with how-we-get-there - rather, in a move that is almost cliche, it picks up immediately "after the revolution", asking a simple question: now that we're finally reshaping society, what value should we place at its core?
His simple answer: "well-being for all". This might sound obvious, but he argues compellingly that previous revolutions have failed precisely because they failed to uphold this value. In his words, they all forgot to account for bread. A revolution can only sustain itself so long on ideals alone; it needs to back them up with material improvements in quality of life - in other words, it needs to look after well-being for all.
Well, ok, but what does that mean? This is the question that he spends the rest of the book answering, in incredible detail, often with empirical figures to back up his arguments.
He argues that (using 1890s technology!) we could feed, house, clothe, and entertain everyone without asking anyone to work more than five hours a day. As an aside, I would love to see someone come up with an update to this figure that accounts for modern technology. It would not be an easy task, but I'm sure the figure would be striking.
My favorite thing about this book is the writing style: It's a very casual form of rhetoric, where many of the lines of argument feel like they could have been workshopped in barroom debates. I have no idea if that's historically accurate, but it's endearing - it offers the text a certain unpretentious accessibility that a lot of political writing just doesn't have.
If you have opinions about anarchism, you probably already know this book. If you don't, this is the book to read. Also, he talks about trains a ton, so if you're the kind of person who likes that, you'll have a great time.
If this book had found its way to me a decade or two earlier it would have significantly changed my life for the better. Perfect gift idea.
The gist: It's set on an earth-like planet (Urras), and that planet's moon (Anarres); the moon has been colonized by utopian anarchists who have now spent a couple centuries up there. Their stance towards Urras is isolationist. It's a hard but good life, but with limited opportunities for academic life, and so Shevek, a brilliant Anarresti physicist, decides to take the unprecedented step of leaving the moon to study at the universities of Urras. Chaos ensues. This narrative is interleaved with flashbacks to his earlier life on Anarres.
The narrative engages with an incredible range of themes: anarchism, personal and collective freedom, capitalism, social control, colonialism, revolutionary politics, sexuality, friendship, physics, metaphysics, class struggle, environmentalism, and more - all of which I would say it navigates maturely and clearheadedly. Somehow, despite that intense fare, it is never pretentious.
Solid chaos pick for a book club, especially a politically diverse one.
Absolutely fascinating stuff. Robert Axelrod (if the name sounds familiar, it might be because his son is David Axelrod, known for managing Obama's campaigns) ran an experiment in the 80s. Before we can describe it, let's lay some background.
The Prisoners' Dilemma is a classic thought experiment which uses game theory to argue for disturbing ends. The premise is that two players are each chosen to decide whether to "cooperate" or "defect"; the game's incentives are set up to encourage defection. Depending on who you ask, the game has been claimed to show that cooperation is irrational, that individuals will ultimately revert to serving self-interest over group interests, that war is rational, and all kinds of other absurd and disturbing claims. It is beloved by the types of people who claim to be "rational" when they really just mean that they're "jerks". It was thought up by some people at the RAND Corporation, which is extremely on-brand for them.
Now, the Prisoners' Dilemma is a one-shot game. But it gets more interesting if you iterate it. Suppose you have two players who play the game over and over with each other, and while they don't know the other player's move in the current game, they do know what they've chosen to do in every previous round of the game. We call this the Iterated Prisoners' Dilemma, or IPD.
This complicates things: the arguments for the one-shot strategy of "always defect" don't clearly apply here, and in fact it can be argued that there is no "perfect" strategy for the IPD, in the same way that there is no perfect strategy for poker.
So Axelrod had an idea: he wrote to everyone he knew who knew how to write a program, and he asked all of them to implement strategies for the IPD. They would implement their strategies and send them in to him. He would then take these and hold a round-robin tournament between them.
The results were incredible. The so-called "conventional wisdom" strategy of "always-defect" was in fact one of the worst-performing strategies sent in. The winner was "tit-for-tat", a strategy which simply starts out by trying to cooperate, then proceeds to do whatever the other player did on their last round. It cooperates as much as possible, but gives proportionate responses for betrayal. This, to me, is such a simple and beautiful result. It is not "optimal" becaues, as discussed, no strategy can be, but within the context of "rational" human behavior it was disproportionately high-performing.
The book continues with other experiments, such as, what if we have initial populations of agents using each strategy, and we adjust the populations based on how well they do in the tournament, then run the tournament again, etc. He came up with a variety of distinguishing qualities for "cooperative" strategies, and identified necessary and sufficient conditions for them to survive and thrive even when the overwhelmingly dominant strategies are non-cooperative.
To me, this provides a serviceable philosophy of life and how to live it. Give everyone a chance, see how they respond to that, and go from there. If they respond negatively, don't forget that; ideally, cut off contact; if that's not possible, don't leave yourself open to them again unless they extend an olive branch first.
The book goes into much more detail, and it's nearly impossible to summarize. Douglas Hofstadter tried, and you can read his take on it in Metamagical Themas, or in this PDF excerpt here, which comes with my highest recommendations.
From Rebecca Solnit (see also A Paradise Built in Hell). A delightful combination of memoir, literary analysis, biography, and more. It defies description and feels almost like stunt-writing, like something that shouldn't work but does, like she picked five or ten topics from a hat and committed to writing about all of them at once, just to see if she could - and it turns out that she can! The book is a nonstop series of unexpected threads that combine and weave these topics together into a coherent whole. You almost can't believe your eyes as you're reading it. She is so good at this. A delight to read, as always.
I have more detailed notes that I'll dig up and put here eventually, but for now this will have to do.
Full disclosure: I read this cover-to-cover in high school, and I went back to it in college as my classes required. Other than that, I haven't gone back to it since, so I'm writing from memory here. But I recall this being a very good book. In particular, it's like a cheat code for undergrad philosophy classes.
Bertrand Russell's greatest skill was repackaging others' ideas for a lay audience. That sounds like an insult; I haven't made up my mind on whether I mean it as one. But the fact is, this is a useful skill and it makes him the ideal author for this type of book. - The book's scope is startlingly broad. It starts in pre-Socratic Greece, and just continues forward from there, recounting the views and ideas of everyone who Russell thought to be worth including. He limits the scope to western philosophers, which is unfortunate but not surprising, and still leaves him with plenty of good material.
In particular, he never fails to point out what he perceives to be the flaws in other philosophers' works. Sometimes I agree with him and sometimes I think he is arguing against strawmen; that said, either way, this stuff is great essay fuel and is consistently entertaining.
A collection of essays by David Graeber on the subject of bureaucracy. Sounds dry, but it isn't. He had a freakish, prodigious capacity for analysis, and it's on full display here. Thought-provoking stuff.
This was part of a trifecta of books I read (Walkaway - A Paradise Built in Hell - The Conquest of Bread) that quite literally reversed my outlook on life. I was a very cynical person, and one of the things that dragged me out of that particular tar pit was the experience of seeing my own ideals reflected back at me through this book. Never before had I read something and agreed so thoroughly with it.
I've written about it at more length here. Suffice to say I recommend it highly - I think there's something in it for just about anyone, at least as long as they're mature enough to not be scandalized by a handful of sex scenes.
If I were somehow suddenly placed in charge of distributing a billionaire's fortune, I would start a foundation dedicated to trying to make every piece of sci-fi technology from Walkaway real. That would be my plan. No more, no less. Can't happen soon enough.
The most quietly radical aspect of this book is the argument it makes in favor of having a place to fuck off to. There are whole parts of their world that are so unpleasant as to have been abandoned in favor of walled cities. This might sound bad, but it leaves room for experimentation, which is something we have painfully little of today.
I wrote more about this book here, so I'll try to avoid rehashing those notes. In brief, this is DeLillo in top form, dealing with themes like information overload, the way horrifying realities can become trivialized under scrutiny, the ways power structures impose themselves through systems of communication, the way those structures become mirrored in interpersonal dynamics, the implicit hazards of all of the above, and the ways these themes shape our subconscious desires.
If you can't tell, I'm having a hard time describing what it's about. It gets into big themes. If that all sounds too high-concept for you, I don't blame you, but I promise the book itself is surprisingly readable. It doesn't hit you over the head with this stuff; rather, it just provides an extremely rich text to dig into. DeLillo is the master of suggesting this stuff without outright saying it. I admire his restraint.
The perfect novel to write an overambitious college essay on.