Ok, the idea I had was something akin to You Don't Know Jack, e.g. a little more real-time, quiz-showy type of interaction. I suppose we can do this, but the preparation is pretty colossal, and it's a skype chat!
The last time I was in something like this, a gamemaster compiles a list of questions, assigns people into teams, and at an agreed time posts the questions. Then allots a set amount of time to get people to answer them, to be submitted before a predefined deadline. Then the answers will be revealed, agony/ecstasy ensues. Repeat.