I actually had that Pokemon Monopoly back in the day!

Some of the most fun I've had was playing the Game of Thrones board game with my family (the first time my wife won, then I won, and interestingly, each of the times we won each one of us was playing Tyrell ). I also really like Munchkin, however mean that game may be.

Ooh, and I think the coolest game we've ever played was this little card game one of our best friends bought on her trip to Italy for 1 euro - it's called Oriente and it's a small indie game that was so much more fun than anyone expected it to be.