The Problem with Monopoly
This recent Wired article by Andrew Curry lays it out perfectly:
Monopoly, in fact, is a classic example of what economists call a zero-sum game. For me to gain $100, you have to lose $100. For me to win, you have to be bankrupt. Gouging and exploiting may be perfect for humiliating your siblings, but they're not so great for relaxing with friends. Monopoly also fails with many adults because it requires almost no strategy. The only meaningful question in the game is: To buy or not to buy? Most of its interminable three- to four-hour average playing time (length being another maddening trait) is spent waiting for other players to roll the dice, move their pieces, build hotels, and collect rent. Board game enthusiasts disparagingly call this a "roll your dice, move your mice" format.
Apparently Settlers of Catan is a worthy alternative. I had no idea that board games were so mathematical; that's pretty sweet. The article also poses an interesting question: If all of the world's copies of Monopoly were replaced by Settlers, would the world be an objectively better place? My initial intuition was a resounding yes, but now I wonder whether I am merely falling victim to the underdog bias.