Another anime series that asks big questions is Serial Experiments Lain.
It's about a young girl who gets into computers and learns about a parallel world of networked communication called the Wired. The Wired is like VR/AR/internet/chat rooms all in one.
It's only 13 episodes, so it's not a huge time investment, but really interesting. It covers computer hackers, Vannevar Bush's Memex, and more. It's also a bit like a David Lynch story, as it has its own dream logic that doesn't always correspond to what you expect.