Probably Oregon Trail, back when I was in first grade. What was that, 1989? Our first grade teacher would invite a pair of us during lunch to have a special gaming session where he would play the game but ask us to make decisions. Do you want to be a doctor? a blacksmith? a hunter? etc. The best part was shooting your musket at virtual buffalo, squirrels, rabbits, and other animals for meat. Back in those days, interactive media was very rare. It was such a neat treat!

I played Might and Magic 7 all the time. Fantasy RPG in a dungeons and dragons universe? Sign me up! The twist? In the end your universe is being controlled by a horde of cybernetic robots and you had to level up your lazer shooting skills. All your efforts into leveling magic were for nothing. Then you go around and fight dragons with laser guns. Its just ridiculous and OP. Then end ruined the game.