Several books which I have found particularly interesting.

Non-Fiction

• Retreat to Commitment by WW Bartley
• The Fatal Conceit by FA Hayek
• A Conflict of Visions by Thomas Sowell
• Order Without Law by Robert Ellickson
• Engines of Creation by K. Eric Drexler
• Out of Control by Kevin Kelly
• Consciousness Explained by Daniel Dennett
• Society of Mind by Marvin Minsky

Fiction

• Shockwave Rider by John Brunner
• True Names by Vernor Vinge
• Snow Crash by Neil Stephenson
• The Diamond Age by Neil Stephenson
• Atlas Shrugged by Ayn Rand
• Probability Broach by L. Neil Smith
• Pallas by L. Neil Smith
• The Moon Is a Harsh Mistress by Robert A. Heinlein
• The Illuminatus Trilogy by Robert Shea and Robert Anton Wilson
• The Crying of Lot 49 by Thomas Pynchon
• Gravity's Rainbow by Thomas Pynchon