it took it quite a few questions, but it eventually nailed one of my favorite literary characters "Captain Ahab"
I'm not sure the bot realized quite how loaded the question of "Is your character bad?" was. Hundreds of thousands of words have been written debating that :-P.
It's kinda weird like that. For instance, it took it no time at all to identify Idra, but it took it nearly the entire allotment of questions to get Dr. Watson (from Sherlock Holmes). I managed to stump it with Elia Martell (from Song of Ice and Fire), though it seemed to get close because it's first guess was Dany.