I used to like Monopoly, then I became a board game geek and got into games made by germans, and found Monopoly to be quite a "stupid" game with no skill. Just roll the die, move your piece, pay the money for rent or decide to buy it. Ifyou want to play good games, look for games made by Reiner Knitzia. Also, Hasbro is one of the few American game makers that make great games. Look for Heroscape(brand new about $40), Battleball(about $10), or Star Wars Epic Duels($10)
p.s. not to advertise but for more info on boardgames go to www.boardgamegeek.com and there is a complete listing of every board game availible, complete with pics, review, etc.