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 Then Asked If Hilton Even Knew What She Did
Hilton Tried To End The Jail Talk
Letterman Tried To Press The Subject By Asking If People Have Reached Out
Letterman Joked That The Jail Time Could Be Hilton's Lasting Legacy