30 most shocking moments in late night history
By Jeremy Dick
24. David Letterman uncomfortably grills Paris Hilton over jail time
In 2007, Paris Hilton made national headlines when she went to jail as a consequence of driving on a suspended license. Upon getting released, the star of The Simple Life only wanted to put the experience behind her and focus on moving her life forward, starting with focusing on her career with her clothing line and the introduction of a new fragrance.
To promote her new endeavors, Hilton appeared on David Letterman’s show, and probably immediately regretted that decision about ten seconds into their incredibly awkward interview. Wasting no time, Letterman greeted her by asking about her time in jail, which Hilton was able to essentially laugh it off. Letterman refused to let the topic go, however, and only barraged her with more and more questions mocking her about doing time behind bars.
Finally, Hilton had to snap at Letterman, literally telling him that she has moved on with her life and just doesn’t want to talk about it anymore. Letterman continues to grill her about it anyway, and the entire segment quickly became of the most uncomfortable interviews to watch in television history. No matter how you feel about Hilton, the entire segment is much more awkward than it is amusing.
Next: 23. The President as a musical guest?