An interesting discussion of the Popular Culture and Philosophy series -- the series in which The Grateful Dead and Philosophy appears -- in the Chronicle of Higher Education a little while back by Stephen T. Asma. A fair and thoughtful discussion that ends with this argument:
[William] Irwin [the original series editor], whose writings on pop culture exude a somewhat charming and amusing sense of mission, sees the books as providing a significant service, "Citizens of a democracy are better citizens for the knowledge of of philosophy, as it teaches them to think critically and encourages them to dissent responsibly." He likens the pop-culture books to training wheels on a bicycle -- presumably readers will grow comfortable enough with The Matrix to read Descartes directly.What do you think? Is this blog pointless, not making any difference, just pissing in the ocean, if the idea is to try to contribute some philosophical content to the larger cultural discourse? Is philosophy doomed to be unpopular despite any and all well-intentioned efforts?
The track record for this sort of edutainment is dodgy and its future unclear. I remember, for example, curators at the Field Museum in Chicago once telling me that they had brought recent travelling exhibits about Harley-Davidson motorcycles and chocolate and couture jewelry and Jacqueline Kennedy's dresses in hopes that visitors would come to see the flashy stuff but then wander over to the more substantive permanent exhibits, too. The curators also spoke of sugar and medicine. Careful analysis of foot traffic, however, revealed that visitors came for the candy and exited the museum straight-way -- no additional nutrition was ingested.
In the end, I suspect that, despite the excellent new efforts, philosophy will remain intractable and estranged from popular culture. It will remain so not because it is biased or willfully elite, but because it is in an extremely self-reflective relationship with its own history, and it requires highly disciplined, systematic, abstract conceptualization, a skill that does not come easy to most people.
One can barely make a move within the oldest academic discipline without understanding its past. People who don't know its vast literature feel excluded from the import of any particular philosopher or problem. That kind of exclusion can be remedied by doing the requisite study -- by catching up, so to speak, on a body of knowledge. But philosophy is more than just a body of knowledge; it is an ability to examine the structures of thought itself. Simon Blackburn calls that "conceptual engineering," in order to distinguish it from regular empirical investigation. The requirement makes philosophy unpopular in the same sense higher mathematics is unpopular.