I got the idea for Ask Dr. Smartypants after reading James Thurber's The Pet Department. I realized that we could use this format as the basis of yet another Chicken Game. However, I couldn't think of any way to generate sensible prompts using random juxtapositions. Eventually, I settled on the idea of having each player write a setup letter for someone else's drawing. This isn't exactly random, but at least it provides a juxtaposition of two different people's ideas.
I enjoy the fact that all of the answers in this game are written in the voice of a single character—Dr. Smartypants. It's interesting to see how the personality of that character evolves over the course of a session. One drawback to the game is that it's not always easy to come up with good setups. I recommend active pictures of people or animals, and relatively short and open-ended setup letters.