In elementary school, we would always play "Oregon Trail" on the Apple IIs they had...
But the game itself wasn't fun. The fun part was when you would name the characters after people you knew, and seeing things happen to them.
"Jessica has developed a fever"
"Adam has died of malaria"
"Jimmy drowned in the river"
"Jenny was run over by a runaway garbage truck"
Well, okay, maybe not that last one, but you get the idea.