Compilation of clips where Late Show where Dave interviews guests with tough questions. Hilary Duff, Paris Hilton, Lindsay Lohan, Nicole Richie, Martha .\rbr\rbrParis Hilton appearing on David Letterman - he insists on talking about her jail time. Paris is not pleased!\rbr\rbrThe longest-serving late night talk show host in history has had some memorable moments over the years! Join as we count down .\rbr\rbrFunny clips with Dr Phil McGraw and Dave Letterman insulting and mocking each other on the Late Show. 3:56 - The origin of the phrase Ill hold your wallet .