I'm sure the joke responses are deliberate, just as Infocom text adventure games were programmed to be 'smart' enough to respond to predictable human input.
The best version of Monopoly I've played is the Mega version. A third dice speeds up the game start and finish by forcing players to move to the next unowned property, or to the next property where they must pay rent.
http://en.wikipedia.org/wiki/Monopoly:_The_Mega_Edition
+1 for those who recommended Settlers. Ticket to Ride is also fun, and Diplomacy does not have to destroy friendships. (Anyone willing to devote 5-7 hours to a game is a friend forever, no matter how long I remember that time they switched sides without warning and wiped me out.)