The "Free to Choose" television series is really great, second that. They're all on google video, search for the obvious keywords and "long" duration (20+ mins) to find them easily.
I especially liked the debate segment in each show, where Friedman argues his points with both supporters and detractors. It struck me while watching it, you really can't find stuff like this on TV anymore.
I'll second the Econtalk podcasts. Russ Roberts does a great job of looking into everyday phenomena with a guest and looking at how economics influences so much. Really a good listen.
Basic Economics by Thomas Sowell
Applied Economics by Thomas Sowell
Free to Choose by Milton Friedman (video series, too)
Use of Knowledge in Society by Hayek (short, non-technical paper which is full of brilliant insights): http://www.econlib.org/library/Essays/hykKnw1.html
Not a book, but the Econtalk podcast is fantastic: http://www.econtalk.org/