Risk Risk Risk...
I used to play Risk...
Then I discovered Diplomacy, the most Machiavellian political game ever!
www.diplom.org
My strategy game of choice is Abalone, an obscure but brilliant French game.
I used to play a lot of Monopoly, but since I played it like Diplomacy and beat the crap out of my family by exploiting all the loopholes I placed in my web of contracts and agreements, nobody really plays me anymore.