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In his beautiful 2011 book The Most Human Human: What Talking to Computers Teaches Us About What It Means to Be Alive, Brian Christian shares his experience as a "human confederate" in a quirky contest known as the Loebner Prize. It's inspired by Alan Turing's proposal for how to gauge computer intelligence. In each round of the Loebner event, human judges sit at a computer and carry out text chats with two unseen interlocutors. One is a human and one is a software program--a chatbot. The judges must guess which is which, and the chatbot that most often gets mistaken for a human wins money for its programmer.