It didn’t know my trump card for this kind of game: Theophilus.
Stumped it with Eduard Shevardnadze.
It failed to get Eddie Cochran after three wrong guesses (nearest was Roy Orbison), ubt he was in the database about 4 times over already (with different descriptors). I am pretty sure my answers were accurate, I checked Wikipedia.
Incidentally, here is a similar site that has been around a long time, so it should have a pretty big database by now: Guess the Dictator or Sit-Com Character
It got Bobby Fisher, after asking if my character was kinda creepy 
Seems that playing a variation of How Not to Be Seen is the key here-i.e. choose someone who doesn’t stand out much from the group in which he can be classified. He got Scorpius (Farscape), Barney the Dinosaur, and Elric of Melnibone’ very easily, but T. S. Eliot and Mark Messier stumped him (it did give me 3 hockey players, including Gretzky & Yzerman tho). There are probably tons of sitcom dads which can easily stump him…ok, going to try Mike Brady…
…and he guessed Herman Munster, Bewitched’s Darrin, and Clark Griswold (Chevy Chase’s character in the Vacation movies). QED.
I stumped him with Kerry King from Slayer, but then he got Lorena Bobbitt in the first round. (his exact words were “Lorena Bobbitt, penis chopper”)
It got Pompey the Great in 30-odd guesses. Stumped it with Professor Bernardo de La Paz. Stumped it again with Jamie McPheeters.
It doesn’t seem that good on English arts. It did get D G Rossetti, but failed with Elizabeth Siddal, John Everett Millais, John Ruskin, Bridget Riley (the op-art artist, not the porn star that’s in the database) and Evelyn and Auberon Waugh.
So, if it’s in an area that it knows about, it’s amazing. Otherwise, not so hot.
At 20 questions it guessed (wrongly) Cal Ripken, Jr. With one more question it got it right: Ryne Sandberg.
It missed Thing 2 (from Cat in the Hat). I would have taken either Things (or even a Who), but to no avail. Great program though, I love those things. First one I was ever aware of was the sitcom character or dictator.
I almost had a freaky insight-question yesterday when I was thinking of Claudio Sanchez of Coheed and Cambria and it asked “Is this character involved with the metal scene?” I answered “probably”. I thought that might throw it off, but after it got Claudio after around 20 questions I looked at the details and “probably” is exactly the answer it was looking for, so my answer really helped it.
It did get Pug, though.
Also got Charlie Bucket (in 19).
Stumped in with Beniamino Gigli. There was a “gigli (singer)” in the database, but no Beniamino.
Also stumped it with Douglas Hofstadter, although he was in the database.
The weirdest question was in going for “my cat”, after it narrowed it down to a non-famous cat who was a member of my family, asked me if my character was a singer or worked with singers.
Trying the Thing from the err Thing movie (1982)…by question 17 it is asking me if it lives in a snowy region, after already asking me if it can transform, so I’m toast: got it on question 18.
…and stumped him again, this time with a baseball player (Dustin Pedroia)-I’ve noticed he’s fixated on concrete signifiers, so when tested T. S. Eliot, he didn’t ask me anything about existentialism or such. Found a bug: it asked me if Dustin was less than 30 (yes), then it asked me if he was older than 50.
Took it 39 questions to get me. The fact that I sing threw it off. It kept trying to figure out which famous singer I was talking about until it finally asked (in question 36) “Is your character famous?”
Why, no. No I’m not.
I stumped it on “your mom” (that is, Akinator’s mom rather than your mom.) Although I should have said “yes” when it asked “is it a member of your family”. It’s not, it’s a member of Akinator’s family. I also should have taken “your mom” (as in my mom) instead of “my mom” (as in akinator’s mom) if it had said that, but it never even tried.
It found Henry Clay on a second guess and Garry Kasparov easily. I stumped it on Lt William Calley, though. I think it got confused that he was still alive, but not famous anymore. It did ask “…famous from the 70s?” That’s pretty close.
This time I followed Cecil Adams to the end. I stumped it, but it did have Cecil on its master list. I think I’ll try again and see if it does anything different this time.
ETA: Yup, got Cecil first try.
It’s hit or miss on famous authors. It got Isaac Asimov and Agatha Christie easily, but missed on Leon Uris and Herman Wouk.