You've probably seen this before, but one of my favorite web games, and one of the few semi-early Internet staples to survive all these years, is Guess the Dictator or Sitcom Character. As with any database system, there are some flaws; some questions don't have clear answers (if you don't know the answer, I think you're supposed to just choose "no"). But in general, no matter what dictator/politician or sitcom character you have in mind, it will guess it. You can go hours trying to stump it on a constistent basis.
If I had to analyze the fun of it, I think it's that it proves that a) Politicians, whether they're evil dictators or not, appear to us very much like TV characters -- a collection of easily-identifiable, TV-worthy traits and catchphrases -- so grouping them together makes sense, and b) TV characters whom we thought of as generic, cookie-cutter creations turn out to have enough distinctive, unique characteristics that a computer database can distinguish between, say, Chrissy Snow and Kelly Bundy by asking a few simple questions.