9. "Look, I Love You Jimmy, But You're An A**hole." - Michael De Santa To His Son
This was one of the first truly hilarious moments in the game. Michael and Franklin are about to get a drink together and relax when Michael receives a phone call from his frantic son, Jimmy. You see, Jimmy, in his infinite wisdom, has decided to try and sell his father's boat in order to help make some money for the family. His "buyers" subsequently steal the boat...with Jimmy inside. What follows is a madcap mission where you race Michael and Franklin down the highway in order to stop the thieves from stealing the boat. In the end, you've managed to get Jimmy back safely while the thieves make off with Michael's boat. To call Michael devastated is a gross understatement. The entire ride home with Franklin and Jimmy is an exercise in family dysfunction. Jimmy alternates between pleading with his father for understanding and blaming his father for not being good enough to teach him how to be a man. Michael eventually reaches his breaking point and unleashes a tirade upon his son, resulting in one of the funniest and most unforgettable moments in the game.