Join Date: Aug 2005
Posts: 3,760
I'd say that
chess
draughts (checkers)
backgammon
Should be mandatory
You'd need a good reason to not play Go as well.
I'd put Settlers over Monopoly or Risk any day, and would *hate* to have to play all three. (play 3-man games if your structure will allow it, as they are more fun and faster than 4-man games)
Team games like pictionary, trivial pursuit, cranium are all good games, but I think you would have to employ some weird scoring system to find an overall winner in these games.
Don't forget connect 4 or other solved games that should be a lock for skilled opponent who studies, but could differentiate the good from the best quite well.