My favorite philosophers

I'm a bit surprised not to see Daniel Dennett on the list. Were you trying to highlight lesser-known people, or are there actually issues you have with Dennett?

Also, Michael Bishop is at Florida State, not Florida.

Now, to business:

As soon as I read this, I winced in the knowledge that all of the comments were going to be about Chomsky.

Chomsky's name appears to be something of a boo light here on Less Wrong. I attribute this to two things:

(1) Chomsky is well known for writing about politics, which we all know is the mind-killer. This is a probably a good reason to be suspicious of him. I have never really bothered to look into the details of his political theories, due to a lack of interest, but I suspect that he may not be wrong so much as not even wrong: political analysis as usually understood is unlikely to be the appropriate level on which to look at the world for the purpose of formulating theories that have a chance of being true. However, the fact remains that while Chomsky is perhaps best popularly known for his political advocacy, it has nothing to do with his place in intellectual history, which rests on his work in linguistics. (It should also be remembered that leftist politics -- particularly of a radical variety -- serve specific signaling functions in academic circles in contemporary America.)

(2) Misunderstanding of his linguistic and psychological theories and their context -- in particular, a notion that Chomsky is "anti-empirical" or some such. This is simply wrong. I suspect this impression mostly results from hearing about Chomsky's ideas second- and third-hand via less sophisticated commentators. I don't know to what extent Chomsky's various technical ideas in linguistics will ultimately prove correct, but I tend to be unimpressed by his critics -- it's as if they haven't reached the third-level and are stuck on the first.

Ironically (in view of his "anti-empirical" boo-light status), he played a crucial role in establishing some of the most important ideas that we take for granted here regarding the biological nature of our minds and the limitations of introspection, among other things. Behaviorist psychology was wrong, and Chomsky was responsible for its demise. And he's a critic of postmodernism.

For a general overview of his ideas from the man himself, I recommend this excellent TV interview from the 1970s, which puts them in a philosophical context. (This is just one of a whole series of interviews with various philosophers and historians of philosophy, which can serve as an extremely useful crash course in the subject; here's Quine, for example.) Some of the things he says are clearly wrong (such as the idea that there's no hope for using scientific knowledge to improve our brains), but others just as clearly refute certain uninformed misunderstandings of his positions.

If you could make people read one book or up to three shorter papers from each of these people, what would you pick?

Chomsky? He is something of a bellwether for specious reasoning, which is a contribution of sorts. The obviously inconsistent logic of the various beliefs he holds makes his philosophy, such as it is, seem disjointed and arbitrary.

As a philosopher, he plays a "crazy uncle" character.

Chomsky: The most important linguist of the 20th century

Yes, but perhaps in the same sense that Freud was the most important psychologist of the 20th century. Sending your field of study on a wild goose chase for half a century certainly qualifies as important but maybe not ultimately productive.

But I suppose the jury is still out on how many geese this particular expedition managed to hunt down.

Alain Badiou? He would have my vote.