Fresh out of the slammer in 2007, Paris Hilton, a frequent Letterman guest, made a big mistake and returned to the show. Letterman began with some simple banter about which coast she likes better, East or West. Then he went in for the kill:
Letterman: New York City is exciting, isn't it?
Hilton: I was born here. Yeah.
Letterman: Yeah. Good for you. How'd you like being in jail?
Zing!