Personal robots for human entertainment form a new class of computer-based entertainment that is beginning to become commercially and computationally practical. We expect that the principal manifestation of the robots' entertainment capabilities will be socially interactive game playing. We describe this form of gaming and summarize our current efforts in this direction on our lifelike, expressive, autonomous humanoid robot. Our focus is on teaching the robot via playful interaction using natural social gesture and language. We detail this in terms of two broad categories: teaching <i>as</i> play and teaching <i>with</i> play.