Guess the Dictator/Sit-Com Character is a game where you choose a dictator or sitcom character and the computer asks you a bunch of yes/no questions while it tries to guess who you are thinking of (very similar to 20 questions).

Some of the results are actually quite impressing, it almost always guessed who I was thinking of, sometimes quite fast. It gave up on me just two times (and I then contributed a question of my own to help it guess the next time).