Philosophers seem to have a prodigious output. One masterpiece follows upon another. And in order to understand one you usually have to read all of the others that came before it. So you can imagine the difficulty of winnowing down the list to the absolute best books in the genre. I’ve settled on including the most alluring works that will hopefully lead you on a journey through each thinker’s larger body of work as this is often necessary to really understand the fundamental thinking of each philosopher.
These books are essential reading and will take you through the major schools of philosophy from Ancient Greece all the way to the dark pensuers of Postmodernism.
The Republic by Plato
The Republic is a common starting point for Plato and Philosophy in general as it introduces many key concepts regarding the nature of reality, justice, and living the good life. As Plato himself says, “the beginning is the most important,” and reading this first will set you off on the right foot as you explore the intricate city of philosophy.
The Symposium by Plato
Wonderfully lyrical as well as deeply thoughtful, this is some of Plato’s finest work. As with many of the Platonic Dialogues, it takes place as a recollection of an event at which Socrates and a few famous poets of the time were discoursing on the nature of Love. There are more than a few clever speeches and even more clever replies and Alcibiades even makes an appearance as Socrates’s jilted lover.
The Parmenides by Plato
This is Plato’s heady book on concepts that will eventually go on to capture most of the philosophers that come after him and which he earnestly grappled with. It is the ancient and hallowed battle between giants and gods or, the debate between Being vs. Becoming. If you are captivated by this debate between Zeno of Elea and Parmenides and a young Socrates then you should proceed quickly on to the Theatetus which is another masterpiece about the Being vs. Becoming and where Socrates articulates his metaphor of being a midwife most beautifully.
The Metaphysics by Aristotle
While we are only left with what amounts to dry notebook entries, Cicero is said to have described Aristotle’s style as “like a river of flowing gold.” Like many, I was actually introduced to Aristotle through The Nicomachean Ethics but The Metaphysics (which is likely a scholastic assembly of texts written by Plato’s best student) is far, far more important especially as you go on to deal with the weighty debates of later philosophers. The Metaphysics is Aristotle’s account of primary causes and starting points and if you like it a great follow on is On Coming to Be and Passing Away.
Outlines of Pyrrhonism by Sextus Empiricus
Written in sparse and scientific prose, the Outlines of Phyrronism is the most comprehensive articulation of the ancient Sketptical school of philosophy that exists to this day. It is an essential read especially if you want to further study metaphysics or engage with later thinkers whose thought spring from these dark waters (Nietzsche especially). The Loeb edition should always be your go to for these kinds of works.
Moral Essays by Seneca
The ancient philosophy of Stoicism had many prominent followers in Rome including Cicero and Marcus Aurelius. Seneca here is eminently wise and bold in the face of a mutable, indifferent, and lethal Nature and an ambitious populace bent on chasing worldly possessions and satisfying fleeting passions. His thoughtful writings on things like Death, Wealth, Happiness, and Anger are worth eternal attention and as applicable today as they were when he was setting them down on papyrus.
On the Nature of Things by Lucretius
More a work of philosophy wrapped in elegant language than a poem, On the Nature of Things is indisputably brilliant and enchanting while also being a fundamental articulation of the Epicurean school of thought.
Meditations on First Philosophy by Descartes
Kierkegaard once quipped that ancient philosophy begins in wonder while modern philosophy begins in doubt. And its founder is undoubtedly Rene Descartes. If you have ever found yourself questioning the nature of reality and asking yourself how you can be sure that anything is real, Descartes was wrestling with those same questions in late 16th century France.
The Prince by Niccolo Machiavelli
A masterstroke of political philosophy that utterly shocked and terrified most of Europe once it was published. Machiavelli explores the art of statecraft as an antagonist to Plato arriving at a realist doctrine best expressed by his phrase “the ends justify the means.”
The Phenomenology of Spirit by G.W.F. Hegel
An unmissable entry in German philosophy that every major philosopher has had to grapple with since its publication. This particular text comes with an in-depth explication of Hegel’s masterwork and you will be thankful someone has taken the time to help you through it because you will be reading this piece over and over again and still won’t fully understand it.
The World as Will and Representation by Arthur Schopenhauer
By turns clever and deeply insightful, Schopenhauer’s classic entry of philosophy builds off his interpretation of Kant and arrives at a powerful and dark articulation of pessimism. Nietzsche found this book randomly while browsing in a bookstore, and the world would be forever changed.
Maxims by Francois duc de La Rochefoucauld
This is one of the most treasured gems in all of philosophy that most Americans have no idea even exists. It made a huge impact on Nietzsche and indeed is perhaps the most potent and witty modern articulation of pessimism ever written. Reading La Rochefoucauld is like watching a master swordsman cut down an entire troupe of highway bandits at dawn while sipping champagne. The grace is breathtaking. You’ll never see it again and it will never happen again.
Oprette Morali by Giacomo Leopardi
Combining sparse witty language with deft philosophical commentary, Giacomo Leopardi articulates bleak philosophical insights through a series of fables. Leopardi is often celebrated as one of Italy’s greatest poets, but these fables crafted in the spirit of Aesop prove he was a harbinger of a philosophic pessimism that understood the indifference of Nature to human suffering, the agony of tedium, and the utter futility of humanity to change it’s lot in the cosmos.
Beyond Good and Evil by Friedrich Nietzsche
If there were any two thinkers I would recommend simply reading all their books, it has to be Plato and his eventual archnemesis, Friedrich Nietzsche. At the end of the day, you will either side with the god of Being (Plato) or the puckish giant of Becoming, Nietzsche. Beyond Good and Evil is also his most forthright articulation of what he calls perspectivism where instead of things existing in absolute categories, Nietzsche explores the very appealing and modernly resonant notion that truth is plural, contingent, and highly subjective.
The Gay Science by Friedrich Nietzsche
It was in this book that Nietzsche made his most famous declaration that “God is dead. And we killed him.” The Gay Science is also where Nietzsche most forcefully articulates his life-affirming philosophy and concurrently his notion of The Eternal Recurrence, the “heaviest burden.”
Either/Or by Soren Kierkegaard
By far Kierkegaard’s most accessible and lyrical work, this is equally important as the foundation of many of his thoughts. Kierkegaard’s first pseudonymous work, the first volume expounds a poetic and aesthetic point of view of living and the second volume explores the ethical point of view in the form of letters from a judge to the young poet from the first volume. Fear and Trembling/Repetition and Kierekgaard’s thesis On The Concept of Irony with Continual Reference to Socrates would also be good reads if you enjoy this vein of Kierkegaard (which is almost assured).
The Concept of Anxiety by Soren Kierkegaard
Kirkegaard has the best titles in my opinion, with Nietzsche coming in as a close second. In this work Kierkegaard explores the modern concept of angst or despair, the moment and eternity, and of course how we as humans relate to these concepts.
Concluding Unscientific Post-Script to Philosophical Fragments by Soren Kierkegaard
In Philosophical Fragments Kierkeggard wrestled head on with the major concern of modern philosophy: Doubt. In The Concluding Unscientific Post-Script to Philosophical Fragments, he wraps up his pseudynmous authorship and gives the fullest and most systematic articulation of the subjective view of truth. While this work is a lot more technical, it contains crucial concepts for understanding existentialism as well as many important jumping off points for understanding what Kierkegaard’s project was all about in the first place.
Being and Time by Martin Heidegger
Writing in gnomic prose, Martin Heidegger’s Being and Time is a text you both experience and will need to reflect on often. His project of de-struction is important to be at least familiar with in you intend to press on to recent thinking of post-structuralism and postmodernism. Here, in Being and Time Heidegger goes all the way back to the Pre-Socratics to call for an entirely different way of understanding truth, as something that is dis-closed. After reading this I would recommend Poetry, Language, Thought and the Question Concerning Technology which are a little more accessible and also eminently pertinent. If you are really interested in following Heidegger, then you will have to wrestle with On the Way to Language as well.
Margins of Philosophy by Jacques Derrida
This showcases many of Derrida’s important early entries of deconstruction, kicking off which an essay playing with form (something that he would continue to do in other works listed here as well). It’s a good entry into his unique style of thinking.
Of Grammatology by Jacques Derrida
One of the great texts of deconstruction that serves as a great follow on to Margins of Philosophy. Derrida gets more comfortable with his tools as he engages and probes marginal texts from JJ Rousseau Ferdiand de Saussure, and Claude Levi-Strauss (and many others). Derrida adeptly argues that in the binary opposition speech/writing, speech has always been valorized as the full presence of the self and writing basically devalued; the work of a grammatology would be to engage with this hierarchy in a new way that destabilizes it and reworks the hierarchy but does not try to escape the boundary.
Dissemination by Jacques Derrida
Throughout Derrida’s work there is a consistent desire and willingness to play and experiment with the space and structure of a philosophical text. In addition to Glas, that will to play is on display here throughout, with footnotes taking up more space than the actual text, with quotes running for pages. A thrumming romp through a great text of postmodernism.
The Postmodern Condition: A Report on Knowledge Jean Francois Lyotard
You will witness the collapse of “meta-narratives” while reading this book (which is a modern and clever repackaging of much of what Nietzsche had to say throughout his philosophical ouvere). This is a crucial text to read in order to understand the world as it is today, and one of the clearest and approachable articulations of postmodernism available.
Simulacra and Simulation by Jean Baudrillard
If you have ever wondered what the term hyperreality means, or that sly reference to this book in the Matrix (the desert of the real) then Baudrillard, a key figure in postmodernism, has been waiting for you. Baudrillard adeptly argues that we no longer experience reality but only the “hyperreal” which is essentially the simulacrum of the reality we once believed to be reality, but has no real relation to reality itself as such. If your head is spinning, that’s fine. In the clearest case towards the end of the book I believe, he uses a short story by Borges to illustrate his point. In “On the Exactitude of Science” Borges tells of an empire which has a map depicting all of its territories. The people once took the map of the empire to be a symbol for the empire, but with the passing of time the map has become the empire itself as such. Intrigued? It’s time to jump into this hallowed postmodern tome!