The actress faced a barrage of questions about her imprisonment from the host of the late night show and eventually refused to answer any of the pointed questions.
Asked whether she liked being in jail, the Simple Life star curtly replied: "Not too much", but she was still asked questions about everything from her meal plan in the slammer to what she learned from her experience.
Hilton, who previously vowed to be a better role model after her release, said she felt she could do anything after her "traumatic experience".
She told Letterman that meals at the prison consisted of a hard-boiled egg and an orange for breakfast, followed by a baloney sandwich for lunch and "jail mystery meat" for dinner.
Hilton, who recently announced that she would work to raise awareness about the plight of people in Rwanda, then told the chat show host that she was sick about talking about her imprisonment and had moved on.
But Letterman would not budge and continued to fire questions at her. He said: "This is where you and I are different. Because this is all I want to talk about."
The actress replied: "There's other stuff to talk about Dave. I didn't come here to talk about this. That was a long time ago."
But Letterman's questioning finally ended after Hilton smiled in response to further questioning.
His persistent attitude finally broke down the 26-year-old, who said: "Now you're making me sad I came because you're hurting my feelings."
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