In search of cool examples for Stanford Law School class

I'm teaching Privacy and Free Speech Online at Stanford Law School in the Spring Quarter.  The course description:

Privacy and free speech values frequently conflict. Protecting one individual's privacy often requires preventing another's speech. The Internet has created significant opportunity for users to express themselves in chatrooms, on the web, and through new social network applications. With this increased expression has come increased disclosures of personal information that may be saved, searched, and republished. Courts are currently grappling with the privacy- speech tension in cases where individuals as opposed to media institutions are the publishers of personal information about themselves and others and where people are publishing information on public networks but intended for limited groups of readers. This seminar will explore the tension between protecting privacy and free speech online, with specific emphasis on the legal rules and social norms around user initiated communications and social networking and other web 2.0 applications.

I have a fairly hefty set of legal readings, but I'm also looking for interesting apps, websites, non- legal papers and innovative policies or business models that bring the privacy-speech conflict into focus.  Any ideas?

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