I've never played, but I've read a lot of interesting post play narratives of the video game Dwarf Fortress. It is notorious for it's bad UI, but also for its eerily verisimilitudinous, emergent dwarf behavior.
Boing Boing has a nice post today about artist Tim Denee's pics of the saga of the fortress Bronzemurder. The maps, the situation, the randomness of it all feel very oldschool to me. I thought if you never play the game you might enjoy taking a gander at these pictures.