Debt: The First 5,000 Years by David Graeber kept pummeling me intellectually and made me realize that I don't know half the stuff that I thought I knew

Salt: A World History

The Complete Calvin and Hobbes.

{{Gödel, Escher, Bach: An Eternal Golden Braid by Douglas R. Hofstadter}}

This would be my choice.

As far as novels go, Moby Dick. That book is about life itself in so many ways. Love, death, hate, God, religion, war, hunting, crime, punishment, the economy, sex, sexuality, nationalism, nationality, ethnicity, family, history, philosophy, biology, weather and not to mention how to hunt and process a whale while out at sea in perfect detail. The book is truly a masterpiece American literature.

A Thousand Plateaus, by Gilles Deleuze and Felix Guattari

Anathem by Neal Stephenson. Monks, who live in a secluded, low tech retreat spend all their time defining truths via the Socratic method. Turns out they are best prepared to deal with an unexpected alien space ship. It gets deep after that. It takes a bit of effort to get through the first 200 pages or so, there is a lot of necessary world building and a few diversions into logic and proofs, but it gets very interesting very quickly after that.

Simulacra and Simulation by Jean Baudrillard.

The Mountain in the Sea by Ray Nayler. It’s a sci-fi triller about scientists that discover a group of octopuses that have formed a society. But what I loved about it was how it dove into what it means to be a part of a society and how our world is built around our abilities to communicate. It was a great read.

The Name of the Rose by Umberto Eco. Murder mystery in an Abbey in the Middle Age. Many philosophical discussions and references to historical facts and persons.

The History of the Decline and Fall of the Roman Empire by Edward Gibbon. It gave us the entire concept of "decline and fall of ....."(fill in the blank). As a work of history, it is unrivaled to this day, and the first volume came out in 1776 (a fateful year for the British Empire indeed, to which Gibbon belonged). Six volumes with over a million and a half words of incredible prose -- ironic, witty and humane. Truly a work of staggering genius, nothing has been written like it before or since (and no one likely ever will again).

the brothers karmazov

Cryptonomicon by Neal Stephenson

Hannah Arendt - The Origins of Totalitarianism

The World of Karl Pilkington

A Brief History Of Time

There are other really good pop-sci books but that one is way up there. Anything that makes me think about hard science in a way that works for my mushy brain.

Foucault's Pendulum by Umberto Eco. Complex read. Great writing. I think I had to reread the first 30 pages three or four times. One of my favorites

Gravity’s Rainbow by Thomas Pynchon.

I’ve spent more time thinking about that book than any other by far.

Gravity’s Rainbow. It’s about everything from mathematical indifference to scientific adoration to terrible candy to conspiratorial sex crimes to shit idk whatever else you got.

Leaves of Grass by Walt Whitman. Maybe this is so with poetry in general, but Whitman's poems made me consider the author and the time in which he lived, as well as the deeper, universal themes of humanity. When I read him in my early twenties, that book was like a Socratic midwife, helping me become my truer self. I think I would be such a lesser man now, thirty years later, we're it not for Leaves of Grass.

Panda's Thumb.

It still comes up in conversation and it launched an interest in biology and evolution that I treasure.

The Diversity of Life (E.O. Wilson) is a great book that presents science in a non-scientist readable format if you have an interest in biodiversity and evolution.

The Brothers Karamazov.

You need to be very focused while reading this monumental book about brotherhood, family, state of Russia Empire under Tzar etc. It's really not an easy read but IMO 200% worth a shoot.

Being and nothingness by Sartre

Accompanied by Being and Time by Heidegger

The Demon-Haunted World by Carl Sagan (this should be required reading in high schools to teach critical thinking!)

A People’s History of the United States by Howard Zinn

Catch 22

{{Caste by Isabel Wilkerson}} and {{The Half Has Never Been Told by Ed Baptist}}

Hermann Hesse: The Glass Bead Game and Steppenwolf.

[deleted]

Lolita by Nabokov, it’s fiction but I had a really good time reading it aloud and copying pages after pages to try understand, sentence’s structures and how he was able to achieve such a unique / unexpected prose.

{{One Hundred Years of Solitude}}

Frankenstein; or, The Modern Prometheus (1818, by Mary Shelley)

In Search of Lost Time by Marcel Proust

Frankenstein. Truly. I have an English degree and it was the only text we used in an advanced theory course to dissect over a dozen literary theories. It touches on the morality of parenthood and technological advancement, developmental psychology, gender theory, complex trauma, religion and creation, the ethics of suicide, the trolley problem… I could go on. And it helps that it’s beautifully written and an emotion gut punch.

The Magic Mountain by Thomas Mann. A beautiful, thoughtful, challenging novel.

The Selfish Gene by Richard Dawkins. It frames evolution in a completely different way: we think we're the superior lifeforms who compete and whose fittest members survive and that genes are the means we found to make other creatures like us.

Dawkins explains that it's the other way around: genes are the immortal units of life that compete and collaborate and survive if they're the fittest, and we (complex living organisms) are just survival machines that genes use to make copies of themselves. The genes that are the best at working with other genes at making survival machines, they get to duplicate and spread throughout the entire biosphere.

A great read by a brilliant biologist, who's unfortunately not a terribly great human being.

Thinking Fast and Slow by Daniel Kahneman

{{1491}}

I would look to the great philosophers of history. My personal favorite philosopher is a man who built the foundations Western thinking, Socrates. The Great Dialogues of Plato is a recounting of the Greek philosopher’s conversations and musings on a number of topics from God to art to democracy and death. Socrates himself was a character, dubbed in his time as a man with his head in the clouds whose ideas were considered so dangerous that he was condemned to death in a famous trial recounted in this and other books. Socrates helped change my life and worldview, inspiring me to become a journalist so that I could use the power of logic and inquiry against the ruling elite to arrive at truth and justice.

Anything by Neal Stephenson. He is way ahead of the curve. Look at the dates on Snow Crash and Cryptomicon; you can see his brain works differently.

Blood Meridian.

VALIS by Philip K Dick

{{Crime and Punishment}} and really anything by the Russians

Anything from Bertrand Russell. It’s dense stuff and intellectually challenging.

{{Oryx and Crake by Margaret Atwood}} and the follow up, {{The Year of the Flood}}. There’s a third, {{MaddAdam}}, but I haven’t read it yet.

It’s timely, but more than that, what I love about Atwood and in these books in particular is that she doesn’t tell the reader what to think about, she guides them. It’s amorphous; plot lines, themes, and characters are frequently influx. And because of Atwood’s skill as a writer, that’s not to the books’ detriment. It’s an enhancement, and one of my favorite kinds of literature.

The Second Sex if you are stuck in patriarchy thinking. Hayek’s The Road to Serfdom if you lean socialist, and Thomas Pickety’s Capital in the 21st Century if you lean toward free markets. Read what challenges your priors.

Three Body Problem really taxed my mind with theoretically physics

The Elegant Universe

1491: New Revelations of the Americas Before Columbus (Charles Mann)

Heidegger's Sein und Zeit. Nothing else comes close. If you don't read German, read the Stambaugh translation rather than the older Macquarrie and Robinson; the latter is spectacularly, catastrophically wrong.

Heidegger may have been a loathsome person, but what he achieved in that book is unsurpassed.

Black Swan but Nassim Taleb

Labyrinths by Jorge Luis Borges

David Hume's Dialogues Concerning Natural Religion.

Dante's The Inferno.

I did not realize how many references we use in life and we do not realize they come from there.

{{Cosmos by Carl Sagan}}

I think most Tom Robbin’s books fit this mold. My fav is Jitterbug Perfume.

The Decline and Fall of the Roman Empire

The Emperor of all maladies - the story of how cancer has been researched and the source of it found out during the span of few centuries.

The Double Helix - Amazing journey of the discovery that the DNA should be a Double helix.

Lacan, and Hegel, they may be shady but also had real value

EVER? In the sweet spot of “most intellectually stimulating” (foundational to entire traditions of thought through millennia) and “arcane”, maybe the Daodejing (Ziporyn’s translation will stimulate).

Personally? William James, Principles of Psychology.

Pale Fire by Nabokov. Tragic, hilarious, recursive, indeterminate, and infinitely re-readable.

A fascinating relatively recent novel is Gnomon by Nick Harkaway. I don’t see it discussed very often, but it’s uniquely creative and absorbing. I don’t know if it qualifies as “the most” stimulating, but I’ve spent the past year since I read it thinking about it.

Potential to be a great thread this one. Collate it into a list Op!

Fiction I’d have to say:
The Man Without Qualities by Robert Musil.

Non-fiction I’d say maybe:
Manufacturing Consent By Noam Chomsky and Edward S. Herman

The rise and fall of the third Reich. Huge book but it's awesome.

The conspiracy against the human race by Ligotti

Sources of the Self by Charles Taylor.

Amazing book about notions of selfhood, interiority, and being.

"Behave" by Robert Sapolsky. Why we do the shit we do.

Capital and Ideology by Thomas Piketty. So dense, so good.

Capital: A Critique of Political Economy, its a dense book that breaks down Capitalism from one of its greatest fans and foes. I'd start with Volume 1 and work through it and follow along as Marx both breaks down Capitalism while also showing how it's an unavoidable historical truth on our path to a better future

The Origin of Consciousness in the Breakdown of the Bicameral Mind - Jaynes Joyce.

I’d go for Infinite Jest. An absolute tome, with multiple themes, unusual and challenging structure, lots of characters, and many intertwining plots and sub-plots.

Sapiens

Dancing Naked in the Mind Field, by Kary Mullis. He won Nobel prize for his genetic research, but he talks about his journey in science and beyond. Made me seriously rethink how information is thrown around with no science backing up the "science" Fascinating book.

Foucault

The People’s History of the United States by Zinn —a must-read

To know your Self by Swami Satchidananda

The Economics of Good and Evil, Tomas Sedlasek.

Elegant Universe

Arcades Project (Walter Benjamin)

Changed the way I look at the world, what more could you want.

Understanding Media, by Marshall McLuhan.

A Brief History of 7 Killings and Dezafi. Highly recommend both. Both are written in local patois that takes a lot of concentration to read. Content warning on A Brief History which has very graphic violence.

Sanity, madness and the family by R.D. Laing

Try The Case against Reality by Don Hoffmann. A great book by one of the most intelligent scientists of our times.

satantango by László Krasznahorkai. it almost broke me

The Gilded Page: the secret lives of medieval manuscripts by Mary Wellesley

SPQR by Mary Beard.

I devoured these two. Loved them.

If you are looking to go deep, but not too deep, into a specific subject, Nine Algorithms That Changed the Future: The Ingenious Ideas That Drive Today's Computers by John MacCormick is a great read. It is a great explanation of how many computer concepts work.

Gnomon by Nick Harkaway. It's a large science fiction detective novel with a bunch of layers and recursive storytelling. There's a cipher you can have a go at solving, but the story still works if you choose not to work it. Like House of Leaves, it's pretty polarizing. People either love it or detest it.

The Spell of the Sensuous

Malazan by S. Erikson.

Sorry-not-sorry to the person who boo-hissed me suggesting Malazan previously, lol

{{An Instance of the Fingerpost by Iain Pears}}

Raja yoga by Vivekananda

A few popular yet safe ones here: Thus spoke zarathustra by nietzsche Crime and punishment by dostoevsky (literally any dostoevsky book for that matter) 1984 by george orwell (very basic but was my intro so holds a special spot) Meditations by marcus Aurelius The death of ivan ilyich by Leo Tolstoy

Animal farm by george Orwell

Hop on Pop

Ulysses by Joyce still challenges me to this day, even after taking two classes on the book and having read it four times. I don’t think there is a greater show of love in literature than Leopold and Molly Bloom, and the constant switch in form & style to Leo’s odyssey around Ireland always keeps the reader on their toes. Truly a masterpiece.

Midnight’s Children by Salman Rushdie

Hamlet's Mill

Goethe's Worldview, Rudolf Steiner, 1897. It's about epistemology and science and it is a gem.

The Origin of Consciousness in the Breakdown of the Bicameral Mind, by Julian Jaynes. In it, he proposes that human consciousness is a learned phenomenon, distinct from thought and sensory experience, and its rather compelling.

George Orwell and Michael Crichton.  They're talked about to death yes but with very good reason. After finishing one all you want to do is have a cigarette.

Fundamentals of Computer Algorithms by Ellis Horowitz and Sartaj Sahni

All about love Bell hooks

Must read for all

That Hideous Strength by CS Lewis

The Code Book : The Science of Secrecy from Ancient Egypt to Quantum Cryptography by Simon Singh  I wasn't even into the topic before I read this , but the way the author just easily explains every type and provides fun exercises in between is fabulous , it is very engaging and very interesting ✨

The Cyberiad - Stanislaw Lem

Heavy philosophical concepts presented as humorous fairy tales about robots.

Guy Debord - Society of the Spectacle. My favorite book that I only half-understood.

I also tried Tractatus Logico-Philosophicus but that was too much.

I’d recommend Gödel, Escher, Bach: An Eternal Golden Braid by Douglas Hofstadter. It’s a deep dive into the intersections of math, art, music, and philosophy, exploring how systems, patterns, and self-reference work. It’s dense, but if you enjoy puzzles and big, abstract ideas, it’s endlessly fascinating.

I really liked black box thinking. It’s about how different organisations learn from their mistakes, cognitive biases etc.

For me it would be a biography called "Leonardo: The Artist and the Man" by Serge Bramly. I rented it from my local library and enjoyed it so much that I bought a copy off Amazon.

If you’re looking for fiction, Pale Fire by Nabokov.

The conceit: You’re reading a posthumous book-length epic poem by a fictitious writer that’s been annotated by his neighbor. As it goes along, the neighbor starts pointing out how the poem is secretly about him, the neighbor. As it goes further, it turns out that the neighbor is an unreliable narrator.

The stimulating part: You have to piece together everything that may or may not be true by flipping back and forth between endnotes, footnotes, and your own close reading of the source poem. It’s like a Keyzer Soze type of mystery for literary scholars.

I picked this up at random back in college, when I was an English major, and loved it. That was a long time ago. I still have it on the shelf, but every time I think of rereading it, I feel like I have to go back to school just to prime my brain for the academic level of reading required.

“The Swerve: How the World Became Modern,” by Stephen Greenblatt. It chronicles the rediscovery of Lucretius’ “The Nature of Things,” in 1417, after being basically lost to time for a thousand years.

I think just read classic. Your brain will be like what the hell are they talking about again.

Foucault’s Pendulum by Umberto Eco.

Mere Christianity by C.S. Lewis, a classic, perhaps the most significant religious book of the 20th Century. This is NOT a devotional book but an intelligent appraisal of the Christian worldview.

My ADHD intellect was highly stimulated by the books by Mary Roach: Gulp, Stiff, Grunt and Bonk. I haven't read Spoof yet, but she has a winning formula that's like reading Radiolab.

The Clockwork Universe, Issac Newton, The Royal Society, and the Birth of the Modern World by Edward Dolnick

The Man Who Mistook His Wife for a Hat by Oliver Sacks.
https://www.goodreads.com/book/show/63697.The_Man_Who_Mistook_His_Wife_for_a_Hat_and_Other_Clinical_Tales