His famous one is “Manufacturing Consent”, if you are into foreign policy and geopolitics/general US politics. It’s analysis on US media in relation to the power structure. That media content is very much created to manufactured perception about the power that be (corporations, ruling power). (eg. soft propaganda, as oppose to hard propaganda in most totalitarian countries.)

For general into: “The Chomsky Reader” (cheap and fun), “Language and Politics” (collection of writings, another cheap and fun book)

I think his best work is all on the web (radio interview, TV clips, his smaller writings.) Those are tightly related to events. He is at his best, IMHO when he is on live conversation setting. Very engaging.

His linguist/post structuralist works are way over my head.

so here is another linkie..

http://www.chomsky.info/interviews/19760725.htm

but a society that was organized on the basis of organic units, organic communities. And generally, they meant by that the workplace and the neighborhood, and from those two basic units there could derive through federal arrangements a highly integrated kind of social organization which might be national or even international in scope. And these decisions could be made over a substantial range, but by delegates who are always part of the organic community from which they come, to which they return, and in which, in fact, they live.

QUESTION: So it doesn’t mean a society in which there is, literally speaking, no government, so much as a society in which the primary source of authority comes, as it were, from the bottom up, and not the top down. Whereas representative democracy, as we have it in the United States and in Britain, would be regarded as a from-the-top-down authority, even though ultimately the voters decide.

CHOMSKY: Representative democracy, as in, say, the United States or Great Britain, would be criticized by an anarchist of this school on two grounds. First of all because there is a monopoly of power centralized in the state, and secondly — and critically — because the representative democracy is limited to the political sphere and in no serious way encroaches on the economic sphere. Anarchists of this tradition have always held that democratic control of one’s productive life is at the core of any serious human liberation, or, for that matter, of any significant democratic practice. That is, as long as individuals are compelled to rent themselves on the market to those who are willing to hire them, as long as their role in production is simply that of ancillary tools, then there are striking elements of coercion and oppression that make talk of democracy very limited, if even meaningful.