David Letterman interviews Paris Hilton: makes her cry, makes the world laugh

This is truly one of the best interviews I've ever seen, as Letterman clearly despises Paris Hilton, clearly hates having to interview her on his show, and thus goes out of his way to make her as uncomfortable and annoyed as possible. The rumor is that she was in tears backstage after her segment, and vowed never to go on his show again. Wow. Mission accomplished, Dave. The transition from "Which do you like better, New York or Los Angeles?" to "So how did you like being in jail?" is one for the ages.