Here is the heavier stuff in my idiosyncratic list. Some of it is still a pleasure to read, but some is too heavy even for me.
Books with a “realist” view of human nature and how to deal with people:
* Il Principe by Machiavelli (the Discourses should also be worth reading)
* The Art of War by Sun Tzu
* The Icelandic Sagas have been described as a working-out of the fundamental laws of human nature, and the praise is fully deserved. A bit difficult to keep track of all those Viking names: get editions with name indexes and family trees at the back
* Extraordinary Popular Delusions and the Madness of Crowds, by Charles MacKay (highly recommended to Obama supporters)
* Any economic history, e.g. Angus Maddison
* Any history, as long as it is written with a realist perspective: no nationalist/romantic or anti-nationalist/politically-correct history
Cultural history:
* English Culture and the Decline of the Industrial Spirit, by Martin Wiener
* Tocqueville: I have read only his Memory on Pauperism, but want to read more.
* Rodney Stark has written several books on the rise of Christianity and the benefits that Christianity has brought to Western civilization
* Arthur Brooks: I did not read his books, but his research shows that conservatives are happier, live longer, have more children, give more money to charity, and donate more blood
* Learned Optimism, by Martin Seligman: actually this is a self-help book, but chapter 11 is highly relevant to cultural history
History of ideas:
* Popper: The Open Society and Its Enemies (or anything by Popper for that matter)
* Hayek: The Road to Serfdom
* Isaiah Berlin should be worth reading, although I have not done so
* Jonah Goldberg: Liberal Fascism (Goldberg looks odd in this august company, but probably wrote the most accessible book — although I have not yet read it)
Economics, political or not:
* The Armchair Economist, by Steven Landsburg
* anything by Milton Friedman
Finally, I should say that writing long computer programs has taught me the most important conservative principle: be careful when you mess around with complex systems.
