If you want a fast introduction to lots of different philosophers for a hacker audience I would start with watching The Matrix trilogy and then the documentary

If you want a fast introduction to lots of different philosophers for a hacker audience I would start with watching The Matrix trilogy and then the documentary Return to the Source about philosophy in the films, while they miss out lots of things it's still pretty good, it's on YouTube here- http://www.youtube.com/watch?v=9ysbczEYvKY http://www.youtube.com/watch?v=9ysbczEYvKY there are also various books about philosophy in the trilogy. The Matrix and Philosophy: Welcome to the Desert of the Real by William Irwin Like a Splinter in Your Mind: The Philosophy Behind the Matrix Trilogy by Matt Lawrence More Matrix and Philosophy: Revolutions and Reloaded Decoded by William Irwin (Feb 8, 2005) Philosophers Explore The Matrix by Christopher Grau Taking the Red Pill: Science, Philosophy and the Religion in the Matrix by Glenn Yeffeth and David Gerrold Also personally a few of the books that I had me think about my philosophy- Poker Without Cards: A Consciousness Thriller http://www.pokerwithoutcards.com/ http://www.pokerwithoutcards.com/ Finite and Infinite Games: A Vision of Life as Play and Possibility by James P. Carse The Uncommon Sense of the Immortal Mullah Nasruddin: Stories, Jests, and Donkey Tales of the Beloved Persian Folk Hero Also you could check out Robert Anton Wilson documentary Maybe Logic http://www.youtube.com/watch?v=-gp4dha42ZA http://www.youtube.com/watch?v=-gp4dha42ZA Oh and I'll leave you with some weirdness from Timothy Leary on How to Operate Your Brain http://www.youtube.com/watch?v=SQq_XmhBTgg http://www.youtube.com/watch?v=SQq_XmhBTgg