50 Mortifying, Awkward, Yet Incredibly Entertaining Moments You’ll Ever See In Talk Show History

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When David Letterman Made Paris Hilton Feel Utterly Humiliated

Dazed

Paris Hilton was the topic of most tabloids back in the early 2000s for a number of reasons, but one of the biggest stories to hit the headlines was when she was put in jail due to a suspended license. She was invited as a guest on Late Night with David Letterman, and while she was hoping to talk about her new fragrance and clothing line, Letterman had other ideas like grilling her about her time behind bars. Despite her attempts to change the topic, Letterman insisted on making a mockery of her experience. Good thing she decided to fight back a little and tell him she was done talking about it, which is probably something Letterman didn’t expect from the heiress. Regardless, it was not a great moment in his career.