Quite generally, the familiar, just because it is familiar, is not cognitively understood. The commonest way in which we deceive either ourselves or others about understanding is by assuming something as familiar, and accepting it on that account; with all its pros and cons, such knowing never gets anywhere, and it knows not why. Subject and object, God, Nature, Understanding, sensibility, and so on, are uncritically taken for granted as familiar, established as valid, and made into fixed points for starting and stopping. While these remain unmoved, the knowing activity goes back and forth between them, thus moving only on their surface.
Georg Wilhelm Friedrich Hegel, Phenomenology of Spirit §31
Behold the superfluous! They are always sick; they vomit their gall and call it a newspaper. They devour each other and cannot even digest themselves.
Friedrich Nietzsche, Thus Spoke Zarathustra, On The New Idol
Amusing Ourselves to Death - Neil Postman
The Culture of Narcissism - Christopher Lasch
Dialectic of Enlightenment - Max Horkheimer and Theodor W. Adorno
Hate Inc. - Matt Taibbi
The Image - Daniel J. Boorstin
Manufacturing Consent - Edward S. Herman and Noam Chomsky
The News - Alain de Botton
Propaganda - Edward Bernays. I recommend the edition that contains an introduction by Mark Crispin Miller.
Propaganda - Jacques Ellul
Public Opinion - Walter Lippman
Simulacra and Simulation - Jean Baudrillard, translated by Sheila Faria Glaser
The Society of the Spectacle - Guy Debord, translated by Ken Knabb
Understanding Media - Marshall McLuhan
Armed Struggle - Richard English
The Big Machine - Robert Jungk
Big Wonderful Thing - Stephen Harrigan
Desert Solitaire - Edward Abbey
The Global Cold War - Odd Arne Westad
The Half Has Never Been Told - Edward E. Baptist
Inglorious Empire - Shashi Tharoor
The Jakarta Method - Vincent Bevins
The Outlaw Bank - Jonathan Beaty & S.C. Gwynne
A People's Tragedy - Orlando Figes
The Power Broker - Robert A. Caro
Capital, Volume 1 and Gundrisse - Karl Marx. I found it fulfulling to read these in coordination with David Harvey's lectures, linked here for Capital and Gundrisse. I enjoyed the Ben Fowkes translation of Capital and the Martin Nicolaus translation of Gundrisse.
The Iliad - Homer, translated by Robert Fagles
Mediations - Marcus Aurelius, translated by Martin Hammond
Norse Mythology - Neil Gaiman
The Odyssey - Homer. I found both the Emily Wilson and Robert Fagles translations rewarding.
The Prince - Niccolò Machiavelli, translated by George Bull
The Prose Edda - Snorri Sturluson, translated by Jesse L. Byock
The Conspiracy Against the Human Race - Thomas Ligotti
The Affirmation of Life - Bernard Reginster
Friedrich Nietzsche - Julian Young
The Portable Nietzsche and Nietzsche: Philosopher, Psychologist, Antichrist - Walter Kaufmann
Phenomenology of Spirit - Georg Wilhelm Friedrich Hegel
My personal highlights:
Antifragile - Nassim Nicholas Taleb
Crowds and Power - Elias Canetti
Future Shock - Alvin Toffler
Deep Work - Cal Newport
Your Brain at Work - David Rock
The Cost of Loyalty - Tim Bakken
Lying to Ourselves - U.S. Strategic Studies Institute
The Manager's Path - Camille Fournier
Turn the Ship Around! - L. David Marquet
Brian Cantrill's Software Values Trilogy
Gitlab's writeup on directly responsible individuals (DRIs)
The Art of Rhetoric - Aristotle, translated by Robin Waterfield
Farnsworth's Classical English Rhetoric - Ward Farnsworth
Making Your Case - Antonin Scalia and Bryan A. Garner
Recommendations below include all sequels, if applicable.
Children of Time - Adrian Tchaikovsky
Dune - Frank Herbert. The first installment is a fulfilling standalone experience, and if you want more time in the world everything through Chapterhouse: Dune is worthwhile. Skip the Brian Herbert additions.
Eisenhorn - Dan Abnett
Leviathan Wakes - James S. A. Corey
Revelation Space - Alastair Reynolds
The Three-Body Problem - Cixin Liu
The Way of Kings - Brandon Sanderson
The Wheel of Time - Robert Jordan
Mallmann on Fire - Francis Mallmann
Oaxaca - Bricia Lopez
Tartine - Elisabeth Prueitt and Chad Robertson
Tartine All Day - Elisabeth Prueitt
Tartine Bread - Chad Robertson and Eric Wolfinger
Carl Griffith's 1847 Oregon Trail Sourdough Starter
The King's College Cambridge Undergraduate Reading Lists
St. John’s College Great Books Reading List