Kim Kardashian

In the 1990s Kim Kardashian (above right) and her older sister Khloe (above left) attended Marymount High School, a private Catholic school for girls in Los Angeles. In the 2000s, of course, Kim perfected the art of the "leaked" sex tape and parlayed her dubious fame into a successful reality television career with offshoots in modeling, acting and a fragrance line. Ms. Kardashian's surprisingly durable tabloid celebrity has also rubbed off on her entire extended family including, most hilariously, a wastrel douche from Long Island who knocked up her sister, Khloe.

Wastrel douche, Scott Disick

If Kim Kardashian's father, OJ Simpson enabler Robert Kardashian, had lived to see what has become of his dysfunctional brood, the expression on his face might look a little something like this...