I would totally play RISK with my siblings or friends. It's easy to play once one is used to the rules of the game, and it caters to invoke one to use more critical thinking skills. I for one, almost won the first time I played it with my friends, whom have had weeks of practice before-hand, but I didn't want to be a prick and thus didn't invade territories I could have easily taken over - I was in command over Europe, most of Asia, and most of Africa with two players [out of six total] left to conquer, and I took control of these areas for most of the game.
Chess would be the other game I would play, however, only if it is the chess set that was made with tiny shot glasses - I shall be reward one way or another, win or lose!