From Hilarious To Controversial, Here Are 45 of the Most Iconic Moments in American Talk Show History

Discussing Paris Hilton’s Time in Jail

Paris Hilton had touched the heights of stardom at one point in her life. Nonetheless, she did experience low points as well and had to go to jail for a dirty incident. It became clear that she didn’t want to speak on the topic anymore when David Letterman kept asking her questions about the experience.

While she was on the show to talk about the new fragrance she had launched, Letterman started by asking how she liked being in jail. She tried to change the topic by saying it was a traumatic experience, but Letterman kept staring at her for a few more minutes.

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