The Popular Culture and Philosophy series of books look at the philosophical undercurrents in many manifestations of popular media such as The Simpsons, Buffy the Vampire Slayer and The Matrix, as well as other popular cultural icons like baseball, the iPod and the video game Halo. One edition features the British comedy classic Monty Python entitled Monty Python and Philosophy: Nudge Nudge, Think Think.
A series of sample podcasts of Monty Python and Philosophy and other titles are available. Looking at this makes one wish a similar series could be made available with a more theological bent.