The Normal Well-Tempered Mind - I never knew the AI community had a favorite philosopher, but I can see why Daniel C Dennett is it. There are so many ideas in this conversation that made me think about how our minds work in a very different light. Even better is his disclaimer: "Everything I just said is very speculative. I'd be thrilled if 20 percent of it was right." That's an attitude I'll try hard to emulate.
Space Station Challenge - Figure out how to eke more power out of the solar panels by carefully changing their positions over an orbit. It's all the constraints that make this coding challenge so much fun.
Understand the favicon - A purist would be appalled, but the hacker within me loves how we're learning to push the limits of what's possible thanks to a deep understanding of platform quirks. Like the space station challenge, a complex but ultimately understandable set of constraints makes fertile ground for artful programming. Check out this beautiful subversion of browser's text rendering engines if you're into that sort of thing.
Love and other conspiracies of the X-Files - I have a confession - I've watched all nine seasons, and I'm gearing up to rewatch them soon. They're not all good in a conventional sense, but almost every episode is interesting, and Josh captures some of the roots of why they could be so compelling.