Game: Final Fantasy VI (1994)

Some games really just want to screw with you. Much like Castlevania: Symphony of the Night, Final Fantasy VI is one such game. Just when you think you know the world backwards and frontwards, the villainous Kefka succeeds in his quest to destroy it. That's right. The dude commits planetary genocide. He's a walking Death Star. The rest of the game (20 hours or more) is spent acclimating yourself to this new and ruined world. It is truly a mind-blowing event for anybody playing it for the first time. They don't make 'em like they used to.