My Way
niemann.blogs.nytimes.com
niemann.blogs.nytimes.com
This is a fairly content-free post, and I'd hate to see too many like these on the front page (what's next? Lolcats?), but very once in a while, a tasteful "funny illustrations" post that's a bit geeky and original is not too bad.
However, I personally don't find any of the individual maps particularly clever. It's originalish, but I prefer
http://strangemaps.wordpress.com/
It's a blog of real maps, so a slightly different idea. I've just submitted the latter, so it'll be interesting to see what kind of response that gets.
To be honest, I'm worried more about videos like John Stewart. But it hasn't happened enough to be truly worried.
I'm sure it violates the Google Map TOS to modify their maps so it would be an interesting two-weekend project to create a mashup of OpenStreetMaps and phrases/sets of concepts/questions to generate these automatically. It could go viral.
First step would be calculating intersections and the angle of intersection for a limited geographic area. Then build a UI that lets users rate the "divergence" of the statements or entities they want to visualize. Then map the set of user input to your intersection db. It might be hard to teach an algorithm how to make it visually appealing but that Words app did it.
Word cloud: http://neoformix.com