From Controversial to Memorable: 40 Iconic Moments in Talk Show History
Letterman Rips Paris Hilton For Her Time in Jail
The words Paris Hilton and trouble are almost synonymous which has also led to the “Stars Are Blind” singer spending time behind bars on multiple occasions. Shortly after her arrest and subsequent release, Hilton decided it would be a good idea to make an appearance on “Late Show with David Letterman.”
As it turned out, the interview quickly became one of the most awkward yet totally hilarious moments on television. Letterman didn’t let his guest off the ropes at all, cracking jokes about her time behind bars, or as he put it, “the slammer.” Paris later commented that Letterman hurt her feelings, and we really feel for her in this instance.
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