Well, I thought "
Winston Churchill", it took 25 questions, one wrong guess (N. Chamberlain). The 14th question was "Is your character from the 'A Song Of Ice and Fire' series?" and the 24th question was "Has your character been hired by another club in summer 2007?"
All my answers were "expected" except for four "Don't know" for very specific / simple / non-sense questions for which I would have to go into Sir W. Churchill's biography (all the expected answers were "?" anyway). I can't think of anything more simple.
EDIT: On the second attempt with the same person in mind it took him only 14 questions. Some of the questions were different. His 6th question was "Is your character in Shake It Up?", I said "No" and the expected answer was "?". Oh, my, I think these guys should feed their databases with some more data.
