Remembering David Letterman's Relentlessly Rude Paris Hilton Interview

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

    Letterman Opens The Interview By Immediately Asking How Hilton Liked Jail
    Photo: The Late Show With David Letterman / CBS
  • He Then Brings Up That They Locked Up Her Friend Nicole Richie

    He Then Brings Up That They Locked Up Her Friend Nicole Richie
    Photo: The Late Show With David Letterman / CBS
  • Letterman Wanted To Know How Jail Changed Hilton

    Letterman Wanted To Know How Jail Changed Hilton
    Photo: The Late Show With David Letterman / CBS
  • Letterman Was Particularly Interested In Jail Food

    Letterman Was Particularly Interested In Jail Food
    Photo: The Late Show With David Letterman / CBS
  • Letterman Then Asked If Hilton Even Knew What She Did

    Letterman Then Asked If Hilton Even Knew What She Did
    Photo: The Late Show With David Letterman / CBS
  • Hilton Tried To End The Jail Talk

    Hilton Tried To End The Jail Talk
    Photo: The Late Show With David Letterman / CBS