I had some time to fritter and Skyped Chris to ask for some Youtube recommendations.
He recommended Return to the Source: Philosophy and The Matrix, which he has playlisted on one of the many interesting pages of his Floating World Web.
In this doco, various philosophy professors and writers deconstruct The Matrix with reference to a wide range of Western and Eastern philosophies.
Some quotes which touched me:
"Gnosticism frames the fundamental human problem in terms of ignorance, the solution being enlightenment, whereas traditional Christianity tends to frame the problem in terms of sin and repentance... Gnosticism would hold that the fundamental human problem is that we are diamonds in the mud... and we need to get out because we are divine sparks and we don't belong here."
"When we become passive consumerists, we are surrendering our lifeforce."
"Kant's point was that the mind has structures, that impose structure on the world and create worlds in certain ways... the structures of the mind actually bring forth phenomena... the structures of the mind bring forth the world."
"The herd mentality can be thought of as The Matrix - everyone's having a collective hallucination, everyone's thinking the same thing, which is an absolute nightmare for someone who wants to wake up, which would be a nightmare for Nietzsche."
"There's a whole school of spirituality... called Tantra, which basically maintains that neither men nor women can get final enlightenment without each other."
"Western philosophy, in a way, is a big head-trip.... In Hinduism, it's regarded as a spiritual path to really feel that enlightenment of really feeling that you're in Brahmin. Every human being carries, in the very centre of their being, this spiritual reality...."
"In all the Tantric traditions, love is what holds nirvana and samsara together. The simplest interpretation of that is that love can conquer all."