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David Letterman Roasting Paris Hilton about Prison Is Uncomfortable to Watch

This 2007 interview between David Letterman and Paris Hilton resurfaced today after Paris claimed she'd been traumatized by the experience.

Supposedly before the interview took place, Dave agreed to not ask her about her recent stint in prison, but then he spends the entire interview just making fun of her for going to jail.

Some claim Dave went too far, but if he had avoided the topic, this would have just been another boring interview not worth remembering.
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