Monica Lewinsky (Molly Shannon)
Most folks treated the intern who had inappropriate relations with the then–commander-in-chief as little more than a one-note punchline – basically, the sum of all her stained-dress jokes. SNL went a slightly different route, with Shannon playing her less as a Lolita than a wide-eyed girl caught up in a situation she was too young to understand (ditto the consequences). This Lewinsky was more of a sounding board for other people's bad behavior, whether it was Bill Clinton's Saddam-baiting phone chats or Linda Tripp (played grotesquely by John Goodman) trying to gather information to use as collateral. Then you get to this 1998 sketch in which Lewinsky visits Oprah to promote her book "How to Give the President a Hummer," and suddenly, the gloves had come off.