I was at a ball game 3 days ago. To keep the crowd entertained they played the "Everybody clap your hands" line from Cha Cha Slide while the following was on the screen:
Ok I was thinking since I last posted in this thread. Previously I said Joker in the Dark Knight and I now say Darth Vader ties with Joker. Darth Vader tries to kill his family multiple times and has no qualms about it.
David Xanatos from Gargoyles, if TV show counts as movie. He's smooth, intelligent, manipulative, and charming. Not to mention just how much he got away with as a serious villain on a Disney show. Not many children show villains spend millions resurrecting the last of an ancient race to twist them to your will, even if stuck in jail at the time.