I enjoy listening to philosophers I respect talk about the life and thought of other philosophers. Below is a discussion between the popularizer of philosophy Bryan Magee and the great John Searle.
Magee is an under-appreciated philosopher. His books The Philosophy of Schopenhauerand Confessions of a Philosopherhave always impressed me with their lucidity and originality. Also, his book Story of Philosophyis a wonderful introduction to the history of philosophy.
John Searle is an influential thinker--and from the few times I've met him, a pretty cool dude. His Chinese Room arguments against artificial intelligence are still discussed in philosophy of mind circles, and his 1970s debates with Jacques Derrida about Speech Act theory are the stuff of legend.