I recently discovered Ze Frank's hilarious web show, named "The Show." I guess I'm a bit late to the game, since he did it in 2006, but wow - it's quite something.
It's occasionally not suitable for work, since he sometimes uses profanity, but it's just about the funniest and smartest thing I've seen online.
Check out this episode, which starts out as a critique of ugly MySpace pages, and ends up as a fascinating commentary on user-generated content and the whole Web 2.0 phenomenon. Or this one, about complexity, learning and playing.
Again, NSFW, but doggone funny.