David Letterman had a number of famous interviews while he was a late-night host, but one of his most infamous ones happened in 2007 when he interviewed Paris Hilton shortly after she was released from prison. The interview is all kinds of awkward as Letterman pushes questions about Hilton's time in lock-up while Hilton becomes more and more standoffish. Below is a breakdown of some of the questions Letterman barraged Hilton with without taking the hint to back down.
Letterman Opens The Interview By Immediately Asking How Hilton Liked Jail
He Then Brings Up That They Locked Up Her Friend Nicole Richie
Letterman Wanted To Know How Jail Changed Hilton
Letterman Was Particularly Interested In Jail Food