Finish any 50 games of Pictionary and this achievement will unlock. The easiest way would be to play Family Fun mode and set it to Point Limit, with 5 points necessary to win the game. Once you start it up, simply press A and say they got it correct as soon as you start drawing. This will give you three points. Repeat and you will win one game. Keep doing this until the achievment unlocks. Each game takes around 5 minutes tops to complete so it will take you around 3 and a half hours to get this if you boost this way.