Nostalgia
8.7k readers

Remembering David Letterman's Relentlessly Rude Paris Hilton Interview

Updated March 9, 2021 8.7k views10 items
Editor's Note: Voting and Reranking have been closed.

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

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

    Photo: The Late Show With David Letterman / CBS
  • Letterman Tried To Press The Subject By Asking If People Have Reached Out

    Photo: The Late Show With David Letterman / CBS
  • Letterman Joked That The Jail Time Could Be Hilton's Lasting Legacy

    Photo: The Late Show With David Letterman / CBS