Start with high-confidence philosophy of language books, then narrow by subgenre or adjacent topics.
On Certainty
Ludwig Wittgenstein, G. E. M. Anscombe
Language in Thought and Action
S.I. Hayakawa, Alan R. Hayakawa
Meaning of Meaning
C. K. Ogden, I. A. Richards
Language Vs. Reality
N.J. Enfield
Linguistics and Philosophy
Etienne Gilson
Language
Daniel L. Everett
The Archaeology of Knowledge
Michel Foucault
Culture and Value
G. H. Wittgenstein
The Spell of the Sensuous
David Abram
Language, Counter-memory, Practice
Michel Foucault, Donald F. Bouchard
Tractatus Logico-philosophicus
Ludwig Wittgenstein
Speaking in Tongues
J. M. Coetzee, Mariana Dimópulos
