DailyDish - Monopoly still the king of board games
Starting with Monopoly, Jr., even young children can learn about money, Finance, and, sure--real estate. Newer models of the game provide a calculator to help with the tabulations, which can be difficult for both kids and adults (they can graduate to the manual version later).
Monopoly also comes with enough pieces to allow a larger number of players, making it a great option during the holidays or other times when family gatherings tend to be larger (and kids need to be occupied).
Monopoly also comes in endless themes, including sports teams (go Yanks!), fun locations (how about a New Orleans version to commemorate your last vacation?) and even cartoon and television versions like The Simpsons, which may just be the thing that catches, and keeps, your eye.
The only sour note to Monopoly? Not everyone gets to be the little silver hat--someone is going to have to be the iron.