30 most shocking late night scandals

14. David Letterman grills Paris Hilton hard about her jail time

For whatever reasons they might have, many people out there are not big fans of Paris Hilton. People just couldn’t wait to mock the rich heiress after she went to jail for driving on an expired license. And one of those people just so happened to be the late night talk show host David Letterman.

Hilton would join Letterman on his TV program as a guest, trying to put the bad stuff in her life behind her. But Letterman wasn’t willing to let it go so easily. From the moment he introduces her, Letterman treats Hilton in such a condescending manner. That makes things uncomfortable right away, but then he zones in specifically on her jail stint, which she clearly doesn’t want to discuss.

Eventually, Hilton has to clearly tell Letterman that she does not want to talk about prison anymore. Letterman jokes that they differ there because that’s the only thing he wants to talk about. Things go a little more smoothly from there, though an apparent tension stays in the air for the rest of the interview.

Afterward, Letterman would face some criticism for crossing the line with Hilton, prompting him to offer an apology.