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

David Letterman takes it too far with Paris Hilton

Paris Hilton made headlines in 2007 after going to jail as a consequence of driving with a suspended license. The star wanted to leave her time behind bars in the past and went on Letterman's show specifically to promote her clothing line and new fragrance. However, Letterman simply wasn't having it. He wasted no time in grilling Hilton about her stint in prison, despite her obvious discomfort.

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Post originally appeared on Upbeat News.