I saw Rorty in action, I believe, four times, three in debate-ish settings. He was an extraordinary speaker, so I count myself lucky.
He and Michael Sandel formed a two-man APSA panel just as Democracy's Discontent was coming out , and Rorty was a dazzling commentator--appreciative of the book and more generous to it than many commentators, but also jabbing at it with an incredibly effective rapier. (His commentary may have been a draft of his contribution to the volume of commentaries on the book, Debating Democracy's Discontent.) Here and in the other times I saw him, I got no sense of the melancholy air that apparently led him to be nicknamed 'Eeyore' in some circles. I remember having the sense that Sandel was standing still, very earnestly, and Rorty was dancing around him, amusing himself to no end.
But that was nothing compared with the Rorty-Habermas debate at ... Loyola University of Chicago, I think (might have been DePaul, but I think it was Loyola) some ten years later. It's famously true that the great theorist of communicative action is not the most effective communicator in person, particularly but not only in his nonnative English. He's a brilliant writer but simply not an effective public speaker. They were debating the obvious stuff: is there truth, including moral truth; can we know anything by reason; is Kantian enlightenment the way forward or an intellectual dead end. The official topic was in there somewhere, but it was basically just Rorty and Habermas doing their respective things about moral truth, moral knowledge, and the history of philosophy. In a packed, overheated room, Habermas's under-his-breath speaking style filtered through his accent added up to an absolutey soporific effect. There was probably no full sentence that I caught entirely, and there were whole paragraphs that I missed entirely. Yet I understood enough to know that he was making hard, important arguments that I found persuasive. Rorty, on the other hand, was a performer par excellence. Even at that stage when he was turning away from post-modernism I found the argument pointlessly nihilistic; but he was just dazzling to watch. Habermas made me wish I'd just sat home and read one of his essays. Rorty did anything but.
The third quasi-debate setting was the only one in which he met his match. It wasn't even really a debate. It was Rorty's Dewey Lecture at the University of Chicago Law School. The Dewey Lecture is an annual event there, but the pragmatist Dewey is a particularly important figure for the pragmatist Rorty. And Chicago Law is home to another famous pragmatist of a different sort, Richard Posner. So Rorty's Dewey Lecture on "Dewey and Posner on Pragmatism and Moral Progress" was a pretty special occasion. But if anyone in the world is not nonplussed by argumentative fancy footwork, it's Richard Posner, and Posner's very calm shrug of a question seemed to me to stop Rorty in his tracks.
The one time that I saw Rorty speak that I don't think of as having been a debate was a lecture at Chicago, giving the core of his "no Plato, no Kant, no Truth, and that's OK" position as it existed by then, and discussing its relationship to literature. If the basic position about moral knowledge still seemed to me entirely unsatisfying, I must say that I found the discussion of moral knoweldge and literature fascinating, deep, and even moving. It reminded me of what I had found best in Rorty's writings; he was capable of great insights beyond the headline projects of demolition.
I know he's often compared with Stanley Fish, but I have the sense that that's unfair to both of them treating their 'there's no such thing as' positions and their wits as constitutive of their intellectual lives. In my view he was a one-of-a-kind figure, and he'll be missed.
In my experience, there are two ways Great Men respond to strong critics, in Q & A. 1) By not listening. 2) By being willing to concede 'yes, of course, your fundamental critique of my position seems to have considerable force'. Then, five minutes later, they are back to saying whatever it was they were saying before. Rorty was definitely the latter sort - which is, I think, better than the former sort.