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.
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.