Either Emperor: Battle for Dune, Sonic the Hedgehog 2 or Madden 09 depending on your definition of beating a game. If Superbowls count as beating Madden then Madden 09 is by far the game I beat the most. If not, I've been playing Emperor: Battle for Dune for at least 8 years and it's an easy game to beat. On the other hand I've played Sonic the Hedgehog 2 through three generations of consoles (Sega Genesis, PS2, Xbox360) so it's really hard to say which one I've beaten more.