In the aftermath of Derrida's death, a lot of people mentioned how Derrida couldn't be pinned down on any topic and one thus couldn't disagree with him. (Because there was never a position to disagree with) I think this unfair, although honestly I think Derrida himself bares a lot of the blame for this. He is consistently so intent on demonstrating his points that the clear arguments sometimes get lost. One place to both see what Derrida is getting at as well as to see a place where one can disagree with Derrida is in the Gadamer - Derrida debate. For those interested, the debate has been translated and is available along with some supporting documents in the book Dialogue and Deconstruction: The Gadamer-Derrida Encounter.
Gadamer is probably the most famous of those influenced by Heidegger. His basic position is sometimes termed universal hermeneutics. He's often described as being influenced primarily by the early Heidegger. Derrida, on the other hand, is often described as being more similar to the later Heidegger. I'm not sure those characterizations are correct. But they're common enough so as to set the stage for the debate, or perhaps more accurately the non-debate.
Derrida, following his style of the 80's and 90's, decided not to debate by directly challenging Gadamer's positions, per se. Rather he goes through a demonstration of his points, much like he did with Searle in Limited Inc.. This has led to many to characterize the debate in rather negative terms. (Somewhat understandably) Yet I also think that it helps illustrate the problem. First Derrida arrives at his position not via Heidegger but via Husserl. It is Derrida's semiotic critique of Husserl that really leads him to reject the kind of hermeneutics Gadamer adopts.
Probably the best overview of the debate can be found in Behler's Confrontations: Derrida Heidegger Nietzsche. I'll largely follow Behler's reading.
Gadamer's position basically can be characterized as a charity of interpretation. Clearly we are able to understand one an other. Thus the main point Gadamer establishes is that hermeneutics functions on a "good will to understanding." That is, we assume that the person we communicate wishes to be understand and attempt to understand them. Derrida critiques this view by suggesting that "good will to understanding" as a theory, depends upon a metaphysics of will. Clearly to have good will so as to understand, one must have a will. Regarding this statement of Gadamer's, Derrida replies, "how could anyone not be tempted to acknowledge how extremely evident this axiom is?" The problem is, according to Behler, that if Derrida acknowledges this axiom, then the debate really is over. All the metaphysical implications Gadamer asserts follow rather logically. Thus Derrida, in tune with his critique of metaphysics and will, calls Gadamer's position the "good will to power" with the obvious allusion to Nietzsche.
The basic point of contention between the two ends up being the nature of the expansion between the two speakers in a communication. Gadamer view it in terms of merging horizons (context) that allow a shared context - or close to it - in which communication becomes possible. Deconstruction, in contrast, appears to be based on a notion of interruption, breaks, and the suspension of mediation. In other words the two views are at polar opposites in terms of the functioning of the will. Derrida's question of Gadamer thus becomes, how can a speaker come to know that he is understood if, to be understood they must share contexts? In other words, if a shared context is necessary to understand, how can one know when the context is shared? We might assume that we are converging on truth - much like the scientific realist who claims our answers get better and better with time. However it also seems fair to critique a view of evolution that depends upon only forward progress. Instead it may be that change is not continuous and not always in one direction. Rather we may take two steps forward and one step back. Progress may be interrupted by misunderstanding and radical miscommunication. We may arrive at agreement not via a continual line, but by false steps and many different ways of entry.
This isn't that radical a position, even if Derrida sometimes doesn't explain himself terribly well. I think most of us have been in conversations, especially philosophical ones, where we think we've reached a shared language and the discussion can proceed, only to find out we understood by similar terms radically different things. Indeed I've often found myself to have been more misunderstood even when I thought I was being understood. Perhaps this doesn't happen to everyone. But I've especially found it in discussions with Evangelicals since Mormons share many of the same texts and use a lot of the same terminology, only with radically different contexts and often very different understandings. Eventually as the conversation proceeds, we may reach that point where we recognize the break - an abyss between us. But that very fact may indicate that the charity of interpretation Gadamer advocates can't be taken as foundational for hermeneutics.
Now, I think it must be said that it is here that Derrida is most controversial. He is, according to many, best characterized not in terms of Heidegger but as being in the line of Nietzsche and the hermeneutics of suspicion. While that is the thesis of Behler's book, I think it can be pushed a little too far. Indeed I think a lot of these positions can be found even in the early Heidegger, although I'm not prepared to argue for it.
The second critique of Gadamer that Derrida uses is that of psycho-analysis. Now I'm not a big fan of Freud nor his use within the Continental tradition. So I'll not comment on that, as it just doesn't convince me too much. (Even the useful notions associated with Freud, in my mind can be better found in earlier figures such as Leibniz) However Gadamer's notion of hermeneutics does rest on an assumption of a "shared lived experience." That is, there is something universal and present for all people. Yet this assumption can be undermined not only by some of the questioning in psycho-analysis (the approach Derrida uses) but by the very nature of perspectivism. Put an other way, even if we are all in the same "world" that world may not be the same in lived experience. (Those of you familiar with Being and Time should quickly recognize the notion of different worlds there - I think Derrida's notion can thus be found in Being and Time) Without this shared living experience, there can be no shared context. Gadamer, as I mentioned, allows for a shared context by having the two speakers merge their contexts through speech. Yet if in a certain sense my experiences are uniquely mine and thus not shareable, is this possible? I suppose one might see this as a return to the question Wittgenstein raised of whether a private language is possible. In a certain way, Derrida suggests that it is and that this private language undermines hermeneutics.
In the debate, Gadamer appears to have understood this difference, describing Derrida's notion of understanding as "a break, a rupture" and not as the "continuous understanding of another person." This breach (following Behler) is akin to the Heideggarian "blow [stoss]...which thrusts itself upon us."
To be helpful, I should note an earlier post on semiotics and the Derrida/Peirce connection. It is helpful for understanding some of the above.
Just as an aid, here are two extended quotes from Gadamer and Derrida from their debate. It's from an excellent Derrida site some might find interesting.
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