It got President Obama in 12 guesses. I next thought of my Member of Parliament, and it guessed the Premier of British Columbia, which was the right ballpark but wrong. The next question was "Is your character a dog?" It guessed Jack Layton, the leader of the New Democratic Party, after a few more guesses. It repeatedly asked "Is your character American", so it must have gotten confused. The next guess was Danny Williams (Premier of Newfoundland and Labrador).
Apparently this thing knows major Canadian politicians, but not MPs. I'm not impressed, honestly. Plenty of humans would be much better.
It did figure out Bill from Left 4 Dead in 15 questions. Apparently it knows popular video games pretty well. It was cool to watch it narrow down the possible answer - "Does you character fight monsters?" Yes. "Is your character related to zombies?" Yes, ruling out many space marines and RPG characters. "Is your character made by Capcom?" No, ruling out Frank West. "Is your character part of a team?" "Is your character old?" "Does your character wear a hat?" At that point, I knew it would get Bill.
I was thinking of Lizzie Borden, but the first guess was Pocahontas. Nope. Then it guessed Helen Keller. After repeatedly inquiring if my character was real, is she fictitious, was she a real person, the computer ignored my answers and said it was Domino Hunter.
This program is bad with real people, apparently. Much worse than the people I used to play 20 questions with.
It also can't handle obscure video game characters. It couldn't get Rex Chance.
It's really bad at asking questions. Rex Chance has brown hair. It asked if my character had black, white, or blond hair, then hilariously stopped before asking if he had brown hair. It guessed Kratos, a bald guy. It asked if he had brown hair, on question 30, then it guessed Balthier. I had specifically said that my character was not from Final Fantasy. After that, he guessed James Sunderland from Silent Hill 2. A respectable guess, but completely wrong again.
Overall, I am unimpressed. Once it stops contradicting obvious questions, it might "trip me out."