I'll put in another recommendation for Homestuck. I learned of it from here and it's as good as advertised.
It's basically a web comic of sorts presented in the form of a text-driven adventure game. It starts simply but eventually gets pretty epic, and has very well-developed characters. The general intellectual attitude is pretty compatible with LW. You'll have to be able to enjoy or at least tolerate a high dose of silliness at frequent intervals, however (which results from the partially audience-driven nature of the story. See explanation).
edit: I should say what it's actually about too: It's a drama/comedy about some kids that get sucked into a powerful video game, with loads and loads of meta (and eventually, loads and loads of characters, although it starts off gently enough).
There was a recent discussion considering the idea of a monthly Book (later expanded to movies, links, etc) thread. The poll was pretty unanimous that this was A Good Idea (tm). The past two threads have had a decent amount of activity, so let's keep going.
Post what you're reading, listening to, watching, and your opinion of it. Post recommendations to blogs. Post whatever media you feel like discussing!
Rules: