The first Loebner Prize competition was held on November 8, 1991, at the Boston Computer Museum. In its first few years, the contest required each program and human confederate to choose a topic, as a means of limiting the conversation. One of the confederates in 1991 was the Shakespeare expert Cynthia Clay, who was, famously, deemed a computer by three different judges after a conversation about the playwright. The consensus seemed to be: “No one knows that much about Shakespeare.” (For this reason, Clay took her misclassifications as a compliment.) -Brian Christian, Mind vs Machine

I highly recommend his book Most Human Human, for an interesting perspective on how (most) humans pass the Turing Test.