People magazine reported that after welcoming Hilton to New York, Letterman got right to the point. He asked the star, "Uh, how’d you like being in jail?"
Audience members were surprised by this unexpected question. They were amused when Hilton replied, "Not too much."
Letterman pushed it by stating that they even put her friend Nicole Richie behind bars. He didn’t stop there and continued asking questions about her prison stay.
Hilton replied, "Well, obviously it was a very traumatic experience, but I did it, so I feel like I can do anything now."