Reddit reviews The Routledge Guidebook to Wittgenstein's Philosophical Investigations (The Routledge Guides to the Great Books)

William Lycan's Philosophy of Language: A Contemporary Introduction is very helpful and comprehensive as an overview.

As for really famous primary works in the field, you might want to check these out:


Truth and Meaning

Tarski's The Semantic Conception of Truth and the Foundations of Semantics

Quine's Two Dogma's of Empiricism

Davidson's Truth and Meaning

Pragmatics

Austin's How to Do Things with Words

Grice's Logic and Conversation


Reference

Donellen's Reference and Definite Descriptions

Kripke's Naming and Necessity

Wittgenstein

Primary Lit:

Wittgenstein's Philosophical Investigations and Tractatus (obviously)

Secondary Lit (I'm only well versed on the secondary lit for the later Wittgenstein, so I'll give you that):

Marie McGinn's Routledge Guide

John McDowell's Wittgenstein on Following a Rule

Meredith Williams' Wittgenstein, Mind, and Meaning

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Hope that helps!

EDIT: Added a lot

Wittgenstein by William Child is really good. It covers all the major topics and is written in a very clear and easy to follow prose. A more advanced book is Marie McGinn's Guidebook to Wittgenstein's Philosophical Investigations.

But reading Wittgenstein himself is indispensable. I would recommend starting with the Blue and Brown books (it's a single book actually), and then reading his magnum opus Philosophical Investigations. You should keep in mind that there is no scholarly consensus even on the basics of W's philosophy and you should therefore be very cautious with any secondary literature that you read. It is better to make up your own mind based on Wittgenstein's own texts rather than what commentators say about them. Wittgenstein's later philosophy is non-technical and pretty much self-contained in that it doesn't presuppose much prior philosophical knowledge to understand (or at least to be able to follow it) so there's really no good reason why you shouldn't just start with the primary texts.

Start with the Tractatus, then the Philosophical Investigations, and then On Certainty. Read the source material at the same time as reading commentaries. Having read a large chunk of the many commentaries on Wittgenstein, the best on PI is Marie McGinn's. With Wittgenstein the style and the content of his work are two sides to the same coin, and McGinn understands that well.

I asked a similar question not so long ago and got some good answers. You might want to take a look at the thread.

I ended up going with The Routledge Guidebook to Wittgenstein's Philosophical Investigations by Marie McGinn which is designed to be read in parallel with the primary text.

I would start at the beginning, since Wittgenstein introduces themes and ideas and then builds on them throughout. Some of the most famous passages are in the the late 100s and early 200s (the "rule-following argument") and the mid 200s to early 300s (the "private language argument"). There's some sections in between the beginning and there that you might be able to skip, but it's hard to say exactly which ones.

If you end up being interested and want to study the book in any depth, I'd reccomend reading it along with Marie McGinn's Routledge Guide.