Well, I don't know if they'd really fit the bill for you, but what comes to my mind is stuff by Jaron Lanier, and "When Google Met Wikileaks" by Julian Assange.

Well, I don't know if they'd really fit the bill for you, but what comes to my mind is stuff by Jaron Lanier, and "When Google Met Wikileaks" by Julian Assange. Assange actually seems similar to Chomsky to me because of the depth and breadth of his knowledge.