The Most Iconic (and Cringeworthy) Moments in Talk Show History

Although she attempted to laugh it off, Letterman pursued the topic anyway, barraging her with questions and mocking her for the experience. Hilton finally snapped at the talk show host, telling him that she moved on with her life and no longer wanted to discuss the topic. The interview is easily among the most uncomfortable of Letterman's career.

The More You Know

Growing up, Eva Mendes wanted to be a nun, but she changed her mind when she found out they didn't make any money.
Leonardo DiCaprio's mom was looking at a Leonardo da Vinci painting in a museum in Italy when Leo first kicked. That's why he's named Leonardo.
Ashton Kutcher, who has always been a hit with the ladies, has webbed toes, and has revealed them on TV.
Walter White Jr. never encountered Jesse Pinkman in all 62 episodes of Breaking Bad.

Post originally appeared on Upbeat News.