Thanks for all the suggestions so far.  A nice combination of things I've already read, would never read, very much am interested in, and things I'd be willing to give a go at.  Nice well-rounded syllabus. :)

I suppose I should offer up some of my recommendations.  It is a difficult task, isn't it?  Hmmm.  The thing is, there all all these quirky things that might not fit everyone's tastes.  For example, I have this book, Inside the Film Factory, which is a collection of reproduced documents, source material, from early Soviet Russia.  Gives a lot of insight into important things like the role of media and the State and how highly intelligent creative and well meaning individuals can get sucked into supporting a totalitarian regime...  Brilliant, and I find myself thinking of it often.  But it's pretty niche material.

Hmm.  "Imagined Communities" by Benedict Anderson, "Instance of the Fingerpost" by Iain Pears, "The Plague," "Candide," "1984," Heidegger, The Federalist Papers, ... some of the usual suspects on my list.

Just googling around I see that Dubravka Ugresic has a new book coming out this month!!  I'd put any of her work on my life syllabus.

Those who can make you believe absurdities can make you commit atrocities. -Voltaire