One-on-One (Larry Bird vs. Dr. J) (1983)
This is where the rubber starts to meet the road. While only a game of one-on-one, it's the first game that makes some attempt to incorporate the character of actual players: Larry Bird is good at 3-point shots while Dr. J is good at dunking. That doesn't mean there aren't weird things about this game. For one, the 3-point arc is cut off, meaning there are no corner 3s, a future staple of video game basketball. But on the bright side, you can break the backboard and a grumpy janitor will come sweep up the glass.