I'm glad people like the idea! It's not an easy one but I think it would pay off...
spinuntilyoufall's idea of each person submitting then passing their "clue" to the next person is right on - someone should probaly overview the ideas to make sure they are doable... though sometimes the hardest ideas give the best results!
I think we would have to ask people to limit their suggestions to a set number of words (no more than 10 for example) and disallow naming anything from a video game - that way the source of the result is totally random. Simple sentences, famous sayings/quotes, etc work best for this type of thing.
In case people haven't played this before, my friend scanned some our entries from the last session - I'll attach the best example. The words are either what someone had to draw or how they described the drawing when it was passed to them. I don't remember what the original sentence was, it was likely something mundane like "I enjoy drinking coffee when I program JAVA."
The handwriting is hard to read so...
Left: "a disgruntled stay at home mother cannot have her morning coffee and so instead she looks up images of hot java and is overcome with jealousy."
Right: "a man is watching p0rnographic material casually while enjoying a morning cup of Folgers (the best part of waking up) and is being judged by a nun walking past the open door."
The really famous example of this is "* fight". It starts with a pair of roosters... and goes downhill from there.