* A THRIVE/SURVIVE THEORY OF THE POLITICAL SPECTRUM [1] - Still the best theory on the conservative/liberal divide. It changed how I view the conservative viewpoint and helped me understand it better.
* MEDITATIONS ON MOLOCH [2] - One of the most famous blog posts on the internet (certainly in HN circles at least). Part fantasy, part philosophy, part game-theory - all of it brilliant. It changed how I approach my life goals and what I need to optimize for in life.
A blog post so famous that it has it's own podcast[3]!