At the risk of sounding like a coffee table book about coffee tables in the shape of a coffee table...
I have just completed Scott Rosenberg's new book, Say Everything. If you have the time, it's a really interesting history of the development of blogging, and of the criticisms launched at blogging over the years. As someone who teaches cyberlaw and is trying to update a casebook for the Web 2.0 generation, it has some really useful thoughts that build upon commentaries and criticisms about the early Internet. Will the ability to communicate online polarize us all in our views rather than broadening our horizons? Does the Internet spell the death of traditional media and, if so, why? Can the Internet in general, and blogging in particular, ever be successfully commercialized? Should it be?
The book also contains an impressive amount of information gleaned from interviews with bloggers and from blog archives over the years that range from early blogging, to military blogging, to mommy-blogging, and to being "dooced" (ie losing your job because of something you said on a blog).
I particularly liked the last few chapters where Rosenberg makes analogies between blogging and other forms of corporate and social media over the years - the telephone, the television, Twitter (miniblogging), and online social networks. Really good food for thought - and there might be a few potential cyberlaw essay questions lurking in there.