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).