My dad used to love playing Red Alert 2 with me, he'd always pick soviet for the bigger tanks. He still plays games now, Diablo 3 and WoW mostly. My dad is 62 and has played games since I can remember, my first memories as a child were eating crisps and watching him play games on the Spectrum 64k
Most of the games my Dad plays are military strategy based, such as Real War: Air Land and Sea. I actually got into liking that game through playing it with him. Others include Super Power, which is a Cold War strategy game of U.S. submarines vs. Soviet Union submarines. Pretty challenging game.