Compilation of clips where Late Show where Dave interviews guests with tough questions. Hilary Duff, Paris Hilton, Lindsay Lohan, Nicole Richie, Martha .\r<br>\r<br>Paris Hilton appearing on David Letterman - he insists on talking about her jail time. Paris is not pleased!\r<br>\r<br>The longest-serving late night talk show host in history has had some memorable moments over the years! Join as we count down .\r<br>\r<br>Funny 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 .\r<br>\r<br>
