1. Marilyn Manson
I dont know how this would work, as it would be difficult for the machine to tell that Marilyn Manson usually looked like a cross between Lady Gaga and a pack of icing sugar as his makeup would assumedly not still be attached to his skull. If, however, they do manage to get their hands on a picture of Manson in all his glory, one can only imagine that future generations will assume he was some kind of possessed vessel that temporarily housed the spirit of Satan as he rose from the ashes, commanding an army of people contemporarily referred to as goths, emos or losers to fight for him until, after a great war between good and evil, he was finally exhumed from earth leaving all but Mansons skull as a warning to humanity. But that's only if the machine picks up what he looked like with his makeup on of course.