So a nice example of "the pessimistic induction" is from Larry Laudan's "A Confutation of Convergent Realism." Briefly, it claims that the history of science is a pretty sad story in terms of scientific theories getting it right about what exists (because most (all?) theories in the history of science are strictly false on subsequent theories) and this repeated past failure should make us skeptical that current scientific theories refer to real entities.
Now, whether or not it is a fallacy - as Peter Lewis (apparently falsely) claims - the argument form itself is kind of interesting. Let's just call an argument which infers from repeated past failures to current (and perhaps future) skepticism of success a "pessimistic induction." Timothy Williamson makes a somewhat similar pessimistic induction (although he doesn't call it this) in Knowledge and its Limits regarding an analysis of knowledge in terms of truth, belief and any other condition(s). This partly motivates his claim that no such analysis is possible - knowledge instead is semantically unanalyzeable. John Norton, in "Causation as Folk Science," makes another pessimistic induction on our past failures at explicating any adequate notion of causation. This motivates his seemingly correct relegation of (scientific) causation to the status of a folk science without any "fundamental" reality not derivative from acausal scientific theories (much as newtonian gravitational force can be recovered from general relatavity although gravity is not a newtonian force in general relativity).
I'm sure there are many other such examples of "pessimistic inductions" out there, even if the one against scientific realism is the one that is often associated with the actual phrase. So, this leads to two questions. First, what degree of support should such arguments lend to their conclusion? Presumably they cannot be decisive or else the history of philosophy should probably lead us to abandon philosophical inquiry about any given topic. But in terms of establishing the burden of proof (for instance), they seem like they work. Second, what other examples of such "pessimistic inductions" can everyone think of? Any particularly good ones? Finally, if anyone has actually read these articles (or the book) do they think the arguments work as intended?
The Laudan article is from Philosophy of Science, Vol. 48, No. 1 (Mar., 1981), pp. 19-49. The Peter Lewis article is from Synthese 129, pp. 371-380, 2001. The Norton article is from Philosophers Imprint, Vol. 3, No. 4 (Nov., 2003) and is available
here.