AYN RAND. She was very determined, and the story about how she summarized the entire philosophy of Objectivism while standing on one foot shows a certain level of ballsiness that is not without its charm.
CHARLES MANSON. If we have to have serial killers, they should be people like Charles Manson. He's entertaining, and unlike a Bundy or a Dahmer, he doesn't fool you with an outward appearance of normality. He's quite clearly a bugfuck-crazy maniac, and sends out huge signal flares to stay away just by existing.
PAULY SHORE. His appearance on Futurama was, like everything else he's ever done, worthless and unfunny, but it at least connotes a slight willingness to engage in self-mockery.
COURTNEY LOVE. She had one really great single, even though she didn't write it, and her movies are no worse than those of, say, Cher.
BRET EASTON ELLIS. For all my talk about how he's the worst novelist I've ever read, he's at least ambitiously bad -- that is, his badness is that of a pretentious, self-impressed douchebag who thinks he's a great writer, rather than that of a formulaic hack who can barely string a sentence together like Clive Cussler.
PARIS HILTON. If you can momentarily erase from your conscious mind thoughts of what a soul-deadening experience it would be to actually have sex with her, she does have a pretty nice body.
HENRY KISSINGER. Like Richard Nixon before him and Hitler before him, Henry Kissinger is so cartoonishly evil and awful that he embodies a certain comical archetype that our culture needs.
CELINE DION. She seems to be a good mother.
GEORGE W. BUSH. Like William Murderface, Bush acts like he's turned being a dick into both an art and a science and perfected both aspects. This ability to drive people nuts with what a horrible person he is could come in handy to use against other people if he was your friend.
ROB LIEFELD. He...okay, let me get back to you on this one.