We currently have a thread in progress concerning the greatest philosophers in history. This reminded me of a question I've been considering for a while.

Recently I realized that although I've spent a massive percentage of my time for the past few years reading, it's almost always been non-fiction, for example posts on Less Wrong, or posts on other forums or blogs, or old treatises on economics or philosophy. Although I feel as if I've stumbled onto some of the absolute best sources of insight the history of civilization has to offer, and some of the most brilliant thinkers to have ever walked the planet, it strikes me that the main optimization criteria that led to the popularity of most of these pieces of writing and most of these thinkers, and thus the reason they were visible enough for me to run into them, has been a matter not necessarily of the quality of writing style, but instead a matter of the level of insight perceived by whatever critical mass of people brought it to the forefront.

In other words, I've mostly ran into articles and books that have garnered their level of fame not by the eloquence of their prose, but instead by the insight contained within. I've ran into plenty of famous, highly insightful thinkers who just aren't very good at writing. They became famous for another reason: the ideas they brought to the table, however incompetently. This is in utter contrast to another section of the history of writing: what we call "fiction", and in some cases "poetry". Although fiction writers or poets are generally expected to bring some sort of insight to the table, or even a lot of insight, this certainly isn't the overwhelming criterion determining their fame. Most of the scientists who have become famous for their work have been at least decent at writing, or nobody would have been able to get through their stuff (though there are exceptions). In the same way, the great fiction books of history certainly have insight; it's just often not what carries them to success.

In non-fiction, the top contenders are usually there for their insight, though their writing is usually at least decent. And in fiction and poetry, the top contenders are usually there for their eloquence and writing style, though their insight is usually at least decent. There's at least one exception I can think of, where this person seems to be civilization class in both insight and writing style: David Hume. One of the greatest thinkers in history, and certainly also one of the greatest writers in history. Anybody who's read a decent amount of other famous writers and thinkers, and understands some of Hume's key arguments, would at least have some sort of sympathy for that characterization, despite the extreme level of praise I'm bestowing onto his work.

So here's my point, and my question: I'm mostly interested in insight, but I'm also interested in communicating this insight in an extremely effective way, with the most solid prose possible, and the highest level of eloquence that can be attained. For this, I can't simply limit myself to reading the most insightful, revolutionary non-fiction work, as the market test that led to the widespread adoption of this work was not necessarily one of requiring a high level of eloquence or poetic ability. I'll need to read works that became famous for their writing style. So we come now to the question: Who are some of the best writers in the history of civilization? Who should I read for the purpose of getting better at writing?

(TL;DR: I've spent a lot of time reading non-fiction books, but most of these books became famous for their level of insight, and not necessarily because of any sort of high level of competence in writing, or eloquence of style. I want to get better at writing, so although I've ignored fiction for a long time due to thinking my interest was scientific insight and not fiction stories, I've changed my mind, and realized I should probably be reading some fiction in order to learn from the masters of eloquence. So with that said, here's my question: Who are some of the best writers in history?)

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35 comments, sorted by Click to highlight new comments since: Today at 4:33 AM

Oh boy.

What are some of the tastiest foods in history?

Now that's just no fun, but fine.

Best cake in history.

And I am absolutely not biased!

Who are some of the best writers in the history of civilization?

Different writers have such different styles that I'm not sure it's possible to measure them all on a simple linear scale from "bad writing" to "good writing". (Or rather, of course it's possible, but I think it reduces the dimensionality so much that the answer is no longer useful.)

If I were to construct such a linear scale, I might do so by asking "How well does this writer's style serve his goals?" Or maybe "How well does this writer's style match his content?" For instance, many blogs seem to be optimized for quick readability, since most people are unwilling to devote too much time to reading a blog post. On the other hand, some academic writing seems optimized for a certain kind of eloquence and formality.

I guess what I'm trying to say is that you're asking the wrong question. Don't ask "What makes a piece of writing good?". Ask "How does the structure of this piece of writing lead to the effect it has on the reader?". The closer you come to answering this question, the easier it will be to design a structure that serves your particular writing needs.

My mental image of writing quality is somewhat like a many-dimensional moss ball branching out from a central point.

In the centre there is unequivocally bad writing, mostly written by writers with no experience writing. As you follow the moss outwards the writers get better, but they get better in different ways, and different readers have different requirements.

It seems to match reality, at least somewhat. There are a lot more ways to be good at writing than there are to be bad at writing. Unfortunately, while this means it's possible to warn people away from bad books, it makes it hard to recommend good ones.

The writer that I'd most like to be able to write like is Terry Pratchett.

Cervantes, the author of the first modern novel, widely regarded as one of the best books ever written

It's worth emphasizing just how modern and readable this book is, especially considering it is contemporaneous with Shakespeare. If you get a modern English translation, you will be delighted. Cervantes really invented modern literature.

What is this obsession with total orders?

Who are some of the best writers in the history of civilization? Who should I read for the purpose of getting better at writing?

The answers to these two questions are likely to be different. I think Nabokov is an incredible writer, but I wouldn't recommend emulating his style as a route to becoming a better writer. Still, if you're looking to read a masterful prose stylist, I don't think you can do better than Nabokov. Here's an excerpt from Lolita to give you a sense (although you should be aware that the narrator is supposed to be a pretentious pedant, so that's reflected in the writing).

Cormac McCarthy is another excellent writer, of a very different kind than Nabokov. Here's a bit I like from The Road (which I don't think is a great book all things considered, but it does have some beautiful writing):

When it was light enough to use the binoculars he glassed the valley below. Everything paling away into the murk. The soft ash blowing in loose swirls over the blacktop. He studied what he could see. The segments of road down there among the dead trees. Looking for anything of color. Any movement. Any trace of standing smoke. He lowered the glasses and pulled down the cotton mask from his face and wiped his nose on the back of his wrist and then glassed the country again. Then he just sat there holding the binoculars and watching the ashen daylight congeal over the land. He knew only that the child was his warrant. He said: If he is not the word of God God never spoke.

When he got back the boy was still asleep. He pulled the blue plastic tarp off of him and folded it and carried it out to the grocery cart and packed it and came back with their plates and some cornmeal cakes in a plastic bag and a plastic bottle of syrup. He spread the small tarp they used for a table on the ground and laid everything out and he took the pistol from his belt and laid it on the cloth and then he just sat watching the boy sleep. He'd pulled away his mask in the night and it was buried somewhere in the blankets. He watched the boy and he looked out through the trees toward the road. This was not a safe place. They could be seen from the road now it was day. The boy turned in the blankets. Then he opened his eyes. Hi, Papa, he said.

I'm right here.

I know.

An hour later they were on the road. He pushed the cart and both he and the boy carried knapsacks. In the knapsacks were essential things. In case they had to abandon the cart and make a run for it. Clamped to the handle of the cart was a chrome motorcycle mirror that he used to watch the road behind them. He shifted the pack higher on his shoulders and looked out over the wasted country. The road was empty. Below in the little valley the still gray serpentine of a river. Motionless and precise. Along the shore a burden of dead reeds. Are you okay? he said. The boy nodded. Then they set out along the blacktop in the gunmetal light, shuffling through the ash, each the other's world entire.

Also John Le Carre, and I'll second Terry Pratchett.

[-][anonymous]11y60

Several writers come to mind, but if I have to pick one, I'd vote for George Orwell. Among other things, he has penned a very lucid essay on how to write eloquently and clearly: http://www.orwell.ru/library/essays/politics/english/e_polit I am sure you will find reading it to be of tremendous value.

404'd. What was the essay's title?

[-][anonymous]11y30

Sorry about that. I have edited my comment to include a working link. The title is "Politics and the English Language".

For a critical take on this essay, check out this post on languagelog.

[-][anonymous]11y30

I have read it. It is an interesting post, though I am inclined to agree with the commentator here.

Note that even in fiction, some people present truly amazing ideas while having certain technical difficulties with writing. Philip K. Dick springs to mind as an author who, on the one hand, had an especially fecund imagination for original ideas. On the other hand, his ability to write dialog was absolutely awful. The plots are fascinating enough that one is willing to overlook this, though.

Terry Pratchett will get mentioned many times here, I'm sure; his facility at playing with language is basically peerless.

I also suggest Peter S. Beagle -- particularly The Last Unicorn, but also everything else he's written. I've never seen any other writer with such an impressive use of cadence in their prose.

Gene Wolfe's Book of the New Sun is a fantasy work I most identify with quality of writing rather than having clever ideas. It has a fascinating invented, but not arbitrary, vocabulary, as well as an unreliable narrator that rewards close attention. You can read an excerpt of the beginning here.

Dune is widely regarded as the greatest fantasy novel of all time. Although you should be warned that the quality does decline somewhat in the series of books following, and the story is incomplete if one ignores the crappy continuation by Herbert's son.

Hitch Hiker's Guide to the Galaxy is considered a gold standard in humorous sci-fi writing.

1984 is of course a must read for its use of language, but most have already.

Ernest Hemmingway isn't everyone's cup of tea, but it would be hard to argue his use of language doesn't belong somewhere near the top. Try some of his short stories to get a feel for whether the bigger commitment of his novels will be worth your time.

I would definitely read something by Tolstoy and something by Dostoevsky. The contributions of these authors to the modern narrative style is hard to overstate. Again I would recommend some short stories as many people find themselves unable to commit to novel length "classic" works for various reasons.

Something by Philip K Dick, I'd recommend either Ubik, The Three Stigmata of Palmer Eldritch, or the classic Do Androids Dream of Electric Sheep?

And lastly I have to recommend the comic Watchmen. It deserves every bit of its acclaim.

Actually, one of the things that impressed me most about the Book of the New Sun is that none of the words in it are invented, although many are extremely obscure, some use unusual lexical constructions, and at least one is an editing error.

Regardless, it's a fantastic series. I'd actually call its worldbuilding quite good as well, though I have a particular fondness for the dying Earth subgenre, and although its impact is magnified by the way ideas are introduced: setting-wise, it does perhaps the best job of implementing the old "show, don't tell" adage for writers that I've ever seen.

Shakespeare usually ends up on lists of "best writers ever", but the style is so different from contemporary fiction that I don't know if reading Shakespeare would be at all useful for absorbing writing skills.

It's worth pointing out that Shakespeare wrote for a medium that doesn't really exist any more in quite the same sense. He is still worth investigating. His work hasn't endured for centuries without reason.

I read primarily non-fiction but in search of the kinds of aesthetic, literary, stylistic merits which you seem to associate with fiction and poetry. (For the record, I also have a lit degree, just in case that gives the following any more authority than it would carry otherwise.) As such, here are a few writers of nonfiction I consider worth a look:

  • Orwell has already been mentioned, and rightly so. Although he's primarily known for his fiction (especially the Big Two), to me he excels as an essayist and writer of nonfiction. If Politics and the English Language hadn't already been linked to, I'd be linking it here. He has plenty of other classic essays, though, and his book-length nonfiction is great too. My favourite of these is Homage to Catalonia, which is about as rigorously clear and honest a bit of political reportage as I can conceive of, not to mention being an account of a really interesting part of history (the Spanish civil war).

  • Borges also springs to mind. Penguin publish a wonderful selection of his essays, and it's absolutely one of my favourite books - easily as good as his fiction. (I mention his nonfiction since I'm on a roll with that, but really, his fiction is just as stylistically great. Plus, reading Borges' stories is a mind-expanding and beautiful experience that everyone should go through anyway.) He has this wonderfully understated and laconic prose style, and his subordinate clauses can express ideas that other writers would belabour for a paragraph. His essays cover an unbelievably broad range of topics, discussing, for example, Zeno's paradox, Citizen Kane, artificial languages, and many, many, many other writers. (He's so well-read in world literature, and interpolates so much from other writers, that one feels well-read by proxy after being in contact with him.)

  • I'm a great fan of Douglas Hofstadter, for his linguistic whimsy, puns, form-vs-content gags, and other surface details, but it's possible that these might not be everyone's cup of tea.

  • I've also been digging Montaigne lately, whose book Essays is responsible for the noun essay meaning what it does. His style, though, is quite flowery and circumlocutory, interpolating references to a lot of latin and greek. If you're looking for concision and directness of thought, you probably won't find it in him. The cultural gulf of all those centuries passing also makes him quite tricky to read. But on the whole I was surprised by how much I felt I had in common with him, and there's something deeply heartening about finding that across such a deep gulf of time. And he is an important pre-enlightenment source of skepticism, which might be of interest to LW types.

  • Last but not least, I've always held Bertie Russell to have a nice clear, direct style.

If I had to pick out one writer from the above, it would be Borges, with no question.

I'd also note that there is a fairly good cached answer to the question of who the best writers in history are, in the form of the literary canon. You'd do well not to ignore it. Literary types might be quite different to LW types, but their implicit consensus about which writers of the past are worth paying attention to is basically trustworthy, I think. In other words, reading pretty much any 'classic' (roughly speaking, 'well-known work from before the twentieth century or so') is likely to expand your horizons and teach you something new in terms of style. On the other hand, changes over time in language and culture form barriers to easily reading sufficiently old books, and I suppose one could argue that this outweighs what one stands to gain from it.

Borges also springs to mind. Penguin publish a wonderful selection of his essays, and it's absolutely one of my favourite books - easily as good as his fiction.

Borges is also my favorite top author, and I also think his nonfiction is at least as good as his fiction, which hardly anyone else does! Were we separated at birth?

We undoubtedly were. I've also been enjoying his poetry lately, since I found a nice bilingual edition of that. I can't read the Spanish, but it's nice to have it there for comparison's sake, to be able to see what kinds of choices the translators made.

For style, some diverse picks: Joyce, McCarthy, Nabokov, Carlyle, Heller, Nietzsche, Adams. Of course if you try to emulate any of those writers you'll likely just make a fool of yourself, with the possible exception of Adams. For stuff that's even less emulable: Dostoyevsky, Hofstadter, Eliot.

You may be interested in this Quora answer by Venkatesh Rao. An excerpt directly relevant to your question, with which I wholeheartedly agree:

When I read a [David Foster Wallace] passage, it is like looking at a pinprick-sharp photograph, compared to my own blurry photographs. He unerringly picks words to use that simply work 100x better than my choices. It's like he has a 15 megapixel camera and a tripod, while I am using a 3 megapixel point-and-shoot. A bigger vocabulary isn't enough. The skill lies in matching words to needs.

In fact his language is so precise that it makes his writing almost too rich to read. I've never finished any of his novels because they are too rich for me. My brain can't handle it.

And this isn't just at the word level. His sentences, paragraphs and chapters are massively precise as well. James Joyce is another example. His prose has been described as having the precision of poetry (an amazing feat, given that typical good poetry is generally 100x more precise than typical good prose, and Ulysees is HUGE).

Here's a sample of David Foster Wallace and of Joyce. I'm surprised not to see at least the former mentioned here already.

I'd add that DFW's precision doesn't extend to conceptual precision: he engaged in a fair amount of bluffing in his writing.

I can add my own example here, actually. In Infinite Jest, the character Michael Pemulis is supposed to be a maths whiz, but both times Pemulis discusses basic calculus in any detail, he screws it up. In endnote 123 he waffles about using the mean value theorem to find an average, even though the mean value theorem is only an existence proof, and in endnote 321 he screws up the derivative of x^n ("Function x, exponent n, the derivative's going to be nx + x^n-1 for any kind of first-order rate-of-increase thing they're going to ask you."). (There are ways to explain these away as typos or unreliable narration but in the context I don't find those that plausible.)

This bluffing might be one reason DFW hasn't been mentioned already, although he does roughly fit Crux's criteria here (at least for people, like you & I, who generally like DFW's writing style a lot).

Okay, so it seems pretty clear that he can't do math (or lacks a good math editor). That's disappointing, especially since he has a degree in it.

But I don't think either of the other two speaks to lack of conceptual precision: the Language Hat post is essentially complaining that he's a prescriptivist, which seems conceptually fine (if possibly wrong) to me. Meanwhile the eXiled one is an extensive (and in places unbelievably hatchet-y) attack on him for I'm not quite sure what--pretending to be folksy and chummy while secretly using big words?

(I admit that I skimmed because the author didn't seem to have a point other than rambling about how the sponsor of the guy who made a movie of a book in the same genre as Infinite Jest once did some questionable political things. So maybe I missed something.)

the Language Hat post is essentially complaining that he's a prescriptivist, which seems conceptually fine (if possibly wrong) to me

That's probably LH's essential point, but some of the specific holes they pick in what DFW wrote suggest DFW had a blurry idea of what various words & phrases mean ("à clef", "q.v.", "bethought", "sub" vs. "infra"), and of what people in a particular job/demographic do or say (like thinking that descriptive linguists merely describe people's beliefs about language rather than their usage, or that a "Young Urban Black" pronounces "on" with "that NYCish oo-o diphthong").

Meanwhile the eXiled one is an extensive (and in places unbelievably hatchet-y) attack on him for I'm not quite sure what--pretending to be folksy and chummy while secretly using big words?

(I admit that I skimmed [...]

Can't say I blame you. The eXiled article does make a number of points, some of them cogent — Dave Eggers really is wrong to treat IJ as a flawless alien artifact with no literary precedents — and some of them silly — like Glazov complaining about pretentious language in IJ's first chapter, which plays out from the POV of a dictionary-reading prodigy with an eidetic memory — but the cogent points are hard to get to because they're mixed with cheap shots and the article as a whole is pretty nasty. (I usually have more of a problem with that kind of nastiness, but for some reason I don't mind it so much in that piece. Maybe because I haven't read Selby or Vollmann or Eggers? Dunno.)

The most relevant bit here is the blockquote with a list of a dozen drug bloopers, which I reckon shows DFW puffed up his drug knowledge with old drug manuals and memories of his alcoholism. DFW mixed up millilitres & milligrams, made a mushy reference to "lightweight tranqs" that doesn't seem to map to pharmacological reality, didn't know what is or isn't a benzodiazepine, and didn't know the abuse potential (or effects) of antipsychotics.

To me, the Language Hat and eXiled posts indicate DFW suffered from conceptual imprecision about language & drugs respectively, just as the Everything and More flubs and IJ's calculus errors indicate fuzziness about mathematical ideas.

Hilarious and possibly useful: How To Write Badly Well

Just to calibrate your expectations, I don't think I have the same metrics for appreciating prose as most literary folks - I read fiction for the story(and, to a lesser extent, clever moments) much more than I do for the description. Dense clouds of jokes, references, and plot points are what I like to see. The Nabokov and McCarthy excerpts below I just find to be utterly boring.

With that being said, the first ones who come to mind as examples are actually television writers, not novel writers - Joss Whedon and Matt Groening(or the associated writing staffs, but to my understanding both of those guys set the tone for their shows). I'll jump on the Pratchett bandwagon as well - I find his endings underwhelming, but his style is magnificent. In the "archaic, but still cool" category, I'll nominate Shakespeare and Milton.

The only authors who have managed to impress me to the NaN point with raw authorial formidably, without an auto-win choice of subject matter, that I can remember right now:

  • Andrew Hussie
  • Terry Pratchett

Isaac Asimov wrote a ton of both fiction and non-fiction and was very good at explaining things. He's generally considered impossible to imitate, though, because his writing takes pretty much everything that's considered part of a writer's "style" and entirely leaves them out.

As a sample of his writing, I present to you the greatest short science fiction story ever written.

the greatest short science fiction story ever written

Picked that just to emphasise my belief that there's no such thing, did you? :P

It's a good story, certainly, and a lot of people seem to think it's one of the greatest, but.. to me, it grates. Too.. religious, whether or not that was the intention.

Well, it was Asimov's favorite. ;)

[-][anonymous]11y-30

Kim Stanley Robinson. Seldom-changing human conditions (love, family, aging, conflict) projected into science fiction settings, science fiction settings used to project in convincing ways the near future based on existing tools and events.

The Three Californias

  • The Wild Shore (1984)
  • The Gold Coast (1988)
  • Pacific Edge (1990)

The Mars Trilogy

  • Red Mars (1993)
  • Green Mars (1994)
  • Blue Mars (1996)
  • The Martians (1999) (a collection of bits that didn't make it into the trilogy)

Antarctica (1997)

Science in the Capital

  • Forty Signs of Rain (2004)
  • Fifty Degrees Below (2005)
  • Sixty Days and Counting (2007)

It doesn't make sense to me that everyone I know hasn't read The Mars Trilogy several times. KSR has written many books before and after these, I find these the best written and the most relevant for readers of LW.

I read Red Mars, and had to struggle just to finish the first book. Had no desire to read any further. I recall it being a whole lot of ham-fisted social commentary and not much of actual value.

I can definitely see why the Mars Trilogy isn't on everyone's multiple-read list. The premise that they wouldn't have sorted out more of the philosophy of the expedition while still on the ground is shaky. The premise that they'd send a bunch of scientists with little in the way of a command structure is credence-breaking. The way so many scientific developments come out of these scientists on Mars who have to spend so much time just staying alive as opposed to the dozens of millions of scientists and engineers on Earth who can pay others to keep them alive is absurd.

At that point, the odd gratuitous sex scene or scientific oddity (windmills to run electrical resistive heaters? multiple-meter-thick beanstalks?) is barely a blip on the radar.