I figured I’d give a run down of important essays of Rorty to read for people who like reading lists. The essays I’ll be choosing from are the ones that are anthologized, ones that are easily accessible. If you’ve never read Rorty and want a general intro to him, there’s no better place than the beginning of his Philosophy and Social Hope (PSH):
1. “Trotsky and the Wild Orchids”: his autobiographical essay, this gives a brief synopsis of his philosophical motives and his general project. Probably the best overall single essay for getting one oriented with Rorty.
2. “Truth without Correspondence to Reality”
3. “A World without Substances or Essences”
4. “Ethics Without Principles”: these three essays taken together probably outline succinctly the effects of pragmatism Rorty foresees in the broad areas of philosophy, roughly metaphysics and ethics (meaning, "What happens to the other two traditional branches of philosophy, metaphysics and axiology, when you take out the third branch, epistemology, at its knees?"). I also leaned on these three essays for my Intro to Richard Rorty.
Outside of that, the single best essay for seeing the broad brush of pragmatism is:
5. “Pragmatism, Relativism, and Irrationalism” in Consequences of Pragmatism (CP)
Aside from that essay, the next best two are:
6. “Solidarity or Objectivity?” in Objectivity, Relativism, and Truth (ORT)
7. “Philosophy as Science, as Metaphor, and as Politics” in Essays on Heidegger and Others (EHO)
The best essay for Rorty’s philosophy of science is:
8. “Is Natural Science a Natural Kind?” in ORT
The best essay for Rorty’s mature views of materialism is:
9. “Non-Reductive Physicalism” in ORT
The best essay on Rorty’s political philosophy is:
10. “The Priority of Democracy to Philosophy” in ORT
The two best essays for Rorty on literary criticism are:
11. “The Pragmatist’s Progress: Umberto Eco on Interpretation” in PSH
12.“The Inspirational Value of Great Works of Literature” appended to Achieving Our Country
Aside from that, everything else is cake. Of Rorty’s two books, Contingency, Irony, and Solidarity (CIS) is the most important and probably worth reading straight through after reading several of the above, or first (if you have the time) because it (somehow) blends together pretty much every preoccupation Rorty has ever had. Everything before leads up to it and everything after leads out of it. The first third blends Davidsonian philosophy of language, Freudian moral philosophy, and Rawlsian political philosophy into a pragmatist picture of language, self, and community. The second third blends this all together with his preoccupations with Heidegger and Derrida. And the last third takes the mess and throws in his love of literature. I say “mess”, but the result, in my opinion, is very successful. He somehow manages to include quite a lot of subjects and gear them all in the same direction, and all under 200 pages. For something that can be seen to be so comprehensive, it is by far the shortest great work of philosophy in the 20th century.
Philosophy and the Mirror of Nature (PMN) is worth reading on its own merits, but for people just looking around for extra tools or a little excitement, you can probably neglect it. It is something of a Mystery Tale for Pragmatists, and most philosophers consider it to be a classic, but those philosophers are professional philosophers. For amateurs (like myself), one can neglect it unless (a) you’re really jiving for more Rorty and want to work your way backward into the older stuff, (b) you want more specific, technical arguments for some of the issues raised in his later work, or (c) you want to learn about the history of early 20th century analytic philosophy.
If (c), then I couldn’t suggest a better place, though just remember that it all ends in Rorty’s lap. If you want other suggestions about the history of analytic philosophy I would suggest John Passmore’s comprehensive A Hundred Years of Philosophy and Ian Hacking’s Why Does Language Matter to Philosophy?.
If (b), then knock yourself out, just remember that they are technical, which means it will be difficult to understand them without understanding what analytic philosophy is up to. Thankfully, my answer to (c) suggests that PMN does that for you along the way, which it does, but, in my experience, it is still difficult to get into. PMN was definitely not the first thing I read.
If (a), then oddly enough I don’t think reading PMN is the best place to start unless you already understand some technical, analytic philosophy. What this means is that, if you want to read back into Rorty, start further back, not with PMN—again, unless you already understand some analytic philosophy. I seem to be repeating this a lot, but you won’t understand why until you try getting into technical analytic philosophy. I didn’t find it easy. I still don't find it easy. I still don't understand it and I still don't like it. God, I'm reading a paper right now by Michael Williams, one of Rorty's former students, and it's about Davidson and it's all like "Convention-T" and "if and only if" and some other incomprehensible words all strung together.
My advice for amateurs looking for a way into Rorty’s old stuff is his three papers of 1961, pretty much the first things he ever wrote: “Recent Metaphilosophy”, “The Limits of Reductionism”, and “Pragmatism, Categories, and Language”. The last is technical, but if I remember correctly it’s readable and a great lead on a number of issues. Aside from them, there’s no better entry point for Rorty’s old stuff then the heavily anthologized “Mind-Body Identity, Privacy, and Categories” of 1965 which is the paper that made Rorty’s name.
If you want to read PMN, or back into his corpus, my advice is to read CP’s “Is There a Problem about Fictional Discourse?” and the volume's large Introduction as a litmus test. If you can read the former, you’re good to go. If you can only read the latter, then you’re almost ready and could give it a run. But if you still can’t get into PMN, try reading the beginning of Richard Bernstein’s Beyond Objectivism and Relativism. That book parallel’s PMN and Rorty and Bernstein disagree on very little. The latter half of the book has more to do with Continental philosophers than analytic, but the first half is about analytic philosophy of science which may help gear one into the terminology. Another outlet is some of Hilary Putnam’s later work. I’ve suggested The Collapse of the Fact/Value Dichotomy before, but there is also Putnam’s Reason, Truth, and History. I haven’t spent a lot of time with that book, but it sees Putnam at his closest to Rorty and it even suggests that you can read the last half before the first if you aren’t acclimated to technical philosophy.
Okay, I’ll close with three more essays. The first is the best about Dewey, the second the best about Derrida, and the third is an important essay about education.
13. “Dewey Between Hegel and Darwin” in Truth and Progress
14. “Deconstruction and Circumvention” in EHO
15. “Education as Socialization and as Individuation” in PSH