Wittgenstein is for the person who suspects that most philosophical problems are actually problems of language — and that clarity about what we can and cannot say is the deepest kind of thinking there is. You've probably had the experience of an argument that felt irresolvable, then realised the two sides were using the same words to mean different things. Wittgenstein built two entire philosophies from this observation — the first showing what language cannot say, the second showing that meaning lives in how we use words, not in what they refer to. He is the most difficult thinker on this list, and one of the most rewarding.
the limits of languagelanguage gamesthe unsayablephilosophy as therapymeaning as use
Where to Start Reading
Philosophical Investigations
Wittgenstein's second masterwork — the argument that meaning is use, not reference. Written as numbered remarks, not chapters. Difficult, but passages can be read independently. Start with §1–100.
Tractatus Logico-Philosophicus
Wittgenstein's first philosophy — a crystalline attempt to show the limits of language. Seven propositions, 80 pages. The final line is one of the most famous in philosophy.
Wittgenstein's Poker (Edmonds and Eidinow)
Not by Wittgenstein but about him — a narrative account of his famous ten-minute confrontation with Karl Popper. The most accessible way into his life and intellectual world.
“Whereof one cannot speak, thereof one must be silent.”