This is pretty damn old. It was popular here in Israel about 2-3 years ago. It can find a lot of obscure stuff, and almost never misses popular figures. If you want to have some fun answer all the questions the same. It used to have a picture of a girl having an orgasm if you answered YES to all the questions, but I'm pretty sure they removed that a while ago.
This is sweet. It got the first four guesses right (Ray Lewis, Jesus Christ, Samus Aran, and Dave Chappelle) but missed Alexis Texas. Too bad it's only limited to people and not objects or places.
Just did Matt Heafy (frontman of Trivium), and it got it on the 3rd try. The first time was really close, it chose Corey from Trivium and then Wayne Static.