Check out 'Philosophize This'
I think we can all safely agree that, for most of us, a naked bearded guy shouting Eureka in his bathtub is the furthest extent of our grasp on philosophy. It is a subject rarely taught in schools or encountered in the mundane activities of adult life. Alas, philosophy is such a wicked beast, that even those interested in investing the time and effort in grappling with it, will be turned away by such gibber-gabber as 'One cannot step twice in the same river' . Even the definition of the field is widely disputed, with common substitutes being largely vapid linkages of words - "Philosophy is the study of general and fundamental problems, such as those connected with reality, existence, knowledge,values, reason, mind, and language. " 
Unfortunately, philosophy transcends definitions ... even the idea that something can be defined by a set of words strung together is a philosophical challenge. Being a product of the modern Indian school of rote-learning, I get queasy when I cannot define something in 20 words. After much pain, I have settled upon the tenuous understanding that philosophy is the discipline of asking questions, for the sake of asking them. My interpretation may seem callous and disrespectful, but trust me, it is not! I am a big fan of superfluous questions. Who among us would not desire to shut ourselves up in a Mediterranean beach-house and ponder the great questions of life over a bloody Mary, if given the chance? Some of the greatest philosophical breakthroughs in history have come about through questions that had no immediate value to that day and age.
I attempted to make sense of philosophy by reading the works of Kant and Aristotle. However, reading the works of great philosophers is like joining in the middle of a panel discussion. Each person is, overtly and covertly, referring to the ideas of his predecessors while putting forth his own. Without sufficient context, the arguments lose most meaning. Hence, random readings of philosophical texts proved to be ineffective. What I desperately craved for was a coherent presentation of all vital philosophical ideas in an edible fashion. Fortunately, I stumbled upon the perfect resource for that - Philosophize This, a podcast by Stephen West.
Philosophize This is one of the hottest podcasts right now, in which Stephen talks about the evolution of Western Philosophical thought. Starting from Pre-Socratic schools such as Pythagorean and Milesian, he explains the basic contributions and key insights behind each key advance in philosophical thinking. Despite the heady nature of its content, the podcast is surprisingly easy to follow and Stephen is an excellent story teller who uses highly effective allegories to help us understand. One example that I particularly enjoyed was comparing Empedocles to Captain Planet, a comparison to warm every geek's heart! I have been enjoying the show so much, that I began taking down careful notes of each show, with the goal of eventually constructing a mind-map of key Western philosophies. I'm not even halfway through the podcast, but it has become an important part of my daily routine. I highly recommend it!
A few of my notes ... (hopefully I will upload all of them soon)