As might be expected, there is some intellectual posturing and some people seem to have conflated "Important to me" with "Most page-for-page wisdom." Similarly there is some confusion between important for the development of world knowledge versus wisdom. All that said, it is an interesting list. I have omitted duplicates and a handful of what seemed simply improbable selections.
The first six are Cowen's nominations and then the rest follow from the comments section.
The Stoics
Democracy in America by Tocqueville
Pensees by Pascal
Enquiry by David Hume
Gulliver’s Travels by Jonathan Swift
Moby Dick by Herman Melville
A Dance to the Music of Time by Anthony Powell
Constitution of Liberty by Friedrich Hayek
Mestizo Logics by Jean-Loup Amselle
The Blank Slate by Steven Pinker
The Better Angels of Our Nature by Steven Pinker
The Stuff of Thought by Steven Pinker
The Language Instinct by Steven Pinker
How The Mind Works by Steven Pinker
Theory of Moral Sentiments by Adam Smith
Screwtape Letters by C.S. Lewis
Beyond Backpacking by Ray Jardine
Antifragile by Nassim Nicholas Taleb
The Life-Changing Magic of Tidying Up by Marie Kondo
William Shakespeare
The Bible
The Prophet by Kahlil Gibran
Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig
Shopcraft as Soul Craft by Matthew B. Crawford
The World Beyond Your Head by Matthew B. Crawford
Capitalism and Freedom by Milton Friedman
Free to Choose by Milton Friedman
Pragmatism by William James
Beyond Good and Evil by Friedrich Nietzsche
The Prince by Niccolo Machiavelli
The Discourses by Livy
Epictetus
Meditations by Marcus Aurelius
Seneca
The Consolation of Philosophy by Boethius
On Liberty by John Stuart Mill
Political Theology by Carl Schmitt
Concept of the Political by Carl Schmitt
Disquisitiones Arithmeticae by Carl Friedrich Gauss
Republic by Plato
Hamlet by William Shakespeare
Wolf Hall by Hilary Mantel
Gödel, Escher, Bach by Douglas Hofstadter
Groundwork for the Metaphysic of Morals by Immanuel Kant
Twilight of the Idols by Friedrich Nietzsche
On Certainty by Ludvig von Wittgenstein
Heart of Darkness by Joseph Conrad
Pride and Prejudice by Jane Austen
Collected Fiction by Jorge Luis Borges
The Feynman Lectures on Physics by Richard Feynman
The Selfish Gene by Richard Dawkins
On Human Nature by E.O. Wilson
The Structure of Scientific Revolutions by Thomas Kuhn
The Sayings of the Desert Fathers (Apophthegmata Patrum)
Waste Books by Georg Christoph Lichtenberg
Essays by George Orwell
The Old Regime and the Revolution by Alexis de Tocqueville
Don Colacho by Nicolás Gómez Davila
Never Trust a Calm Dog, and Other Rules of Thumb by Tom Parker
Discourse on Inequality by Jean-Jacques Rousseau
Flatland by Edwin A. Abbott
Stephen Jay Gould
The Rational Optimist by Matt Ridley
Critical Rationalism: A Restatement and Defence by David Miller
Jacques the Fatalist and his Master by Denis Diderot
Zero To One by Blake Masters and Peter Thiel
The Use Of Knowledge In Society by Friedrich Hayek
The Downing Street Years by Margaret Thatcher
Walden by Henry Thoreau
Omar Khayyam’s Rubaiyat translated by Fitzgerald
Extraordinary Popular Delusions and the Madness of Crowds by Charles Mackay
Essays by Montaigne
The Good News Is the Bad News IS Wrong by Ben Wattenberg
Perpetual Peace by Immanuel Kant
The Emile by Jean-Jacques Rousseau
Gargantua and Pantagruel by Francois Rabelais
The Book of Disquiet by Fernando Pessoa
Mysteries by Knut Hamsun
Rasselas, Prince of Abissinia by Dr. Samuel Johnson
Maxims and Reflections by Francesco Guicciardini
Les particules elementaires by Michel Houellebecq
Thinking, Fast and Slow by Daniel Kahneman
Betraying Spinoza by Rebecca Goldstein
Collected poems of Wallace Stevens
The Federalist Papers
Augustine’s Confessions
Best short stories by Anton Chekhov
Gods Of The Copybook Headings by Rudyard Kipling
Last Call: The Rise and Fall of Prohibition by Daniel Okrent
Liar’s Poker by Michael Lewis
The Superior Man by David Deida
Maxims by La Rochefoucauld
Human, All too Human by Friedrich Nietzsche
The Ghost Dance by Weston LaBarre
The Man without Qualities by Robert Musil
Jude the Obscure by Thomas Hardy
The Mayor of Casterbridge by Thomas Hardy
Niklas Luhmann
The Abolition of Man by C.S. Lewis
Pilgrim’s Regress by C.S. Lewis
Theology and Sanity by Frank Sheed
Fahrenheit 451 by Ray Bradbury
Man, the State, and War by Kenneth Waltz
Lucretius
Six Records of a Floating Life by Shen Fu
Enjoy Calculus by Eli S. Pine
I, Pencil by Leonard E Read
The Strategy of Economic Development by A. O. Hirschman
Dialogo dei due massimi sistemi del mondo by Galileo Galilei
The Wit and Wisdom of Mark Twain
Georgics by Virgil
Brothers Karamazov by Fyodor Dostoyevsky
The Restless Universe by Max Born
Origin of Species by Charles Darwin
Wittgenstein’s Vienna by Allan Janik and Stephen Toulmin
The Old Man and the Sea by Ernest Hemingway
Aesop’s Fables
The Island of the Day Before by Umberto Eco
The Little Prince by Antoine de Saint-Exupéry
Other Men’s Flowers by Wavell
Thoughts and Reflections by George Savile Halifax
Discourses by Epictetus
H.L. Mencken
Sun Tzu
Liberty, Equality, Fraternity by James Fitzjames Stephen
Up the Organization by Peter Townsend
The Mythical Man Month by Frederick Phillips Brooks
Sex and Character by Otto Weininger
Death on Credit by Louis-Ferdinand Céline
The Old Man and the Boy by Robert Ruark
The Prince by Nicolo Machiavelli
The Moon Is a Harsh Mistress by Robert Heinlein
Human Action by Ludwig Von Mises
Lila: An Inquiry into Morals by Robert Pirsig
Les fables de La Fontaine
The Art of War by Sun Tzu
The Construction of Social Reality by John Searle
The Logic of Scientific Discovery by Karl Popper
Meditations of Marcus Aurelius
Devil’s Dictionary by Ambrose Bierce
Edward Mills and George Benton: A Tale by Mark Twain
The City of God by St. Augustine
The Small Catechism by Martin Luther
1984 by George Orwell
The Forgotten Man by Amity Shlaes
Alexander Hamilton by Ron Chernow
Man’s Search For Meaning by Victor Frankl
The Unteathered Soul by Michael Singer
Flow by Mihaly Csikszentmihalyi
Decline of the West by Oswald Spengler
On Power by Bertrand de Jouvenel
Pilgrim at Tinker’s Creek by Annie Dillard
Back when we were grownups by Anne Tyler
Han Feizi Zhuanzi
Word and Object by Willard Van Orman Quine
Sermons of Meister Eckhart
Cat’s Cradle by Kurt Vonnegut
The Traditions of the Western World by J. H. Hexter
Death of Ivan Ilyich by Leo Tolstoy
The Canterbury Tales by Geoffrey Chaucer
A Pattern Language by Alexander Ishikawa
The Ultimate Resource by Julian Simon
Life at the Bottom by Theodore Dalrymple
Benjamin Franklin’s Autobiography
Guns, Germs, and Steel by Jared Diamond
War and Peace by Leo Tolstoy
To a God Unknown by John Steinbeck
The Beginning of Infinity by David Deutsch
The Art of Worldly Wisdom by Baltasar Gracian
The Invisible Man by Ralph Ellison
Bacon's Essays
The Imitation of Christ by Kampis
The Kural
The True Believer: Thoughts on the Nature of Mass Movements by Eric Hoffer
2nd Treatise by John Locke
Heraclitus Fragments
Euthyphro by Plato
Pride & Prejudice by Jane Austen
The Underground Man by Fyodor Dostoyevsky
Self-Reliance by Ralph Waldo Emerson
If by Rudyard Kipling
The Death of Ivan Ilyich by Leo Tolstoy
Pale Blue Dot: A Vision of the Human Future in Space by Carl Sagan
Gulliver’s Travels by Jonathan Swift
How to Win Friends and Influence People by Dale Carnegie
The Little Prince by Antoine de Saint-Exupéry
Vision of the Annointed by Thomas Sowell
To Kill a Mockingbird by Harper Lee
The Name of the Rose by Umberto Eco
The collected essays of Frederick Bastiat
The Sciences of the Artificial by Herbert Simon
Lives of the 12 Caesars by Suetonius
Iliad by Homer
Odyssey by Homer
How Proust Can Change Your Life by Alain de Botton
Alice’s Adventures in Wonderland by Lewis Carroll
The Happiness Hypothesis, by Jonathan Haidt
The Machinery of Freedom, by David D. Friedman
The Death and Life of the Great American Cities by Jane Jacobs
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