The Late Show with David Letterman is going to be talkin' Sirius, at least twice before Christmas. Howard Stern will be on Letterman Nov 17 (the same night XM will be on NBC's "The Apprentice w/Trump") and Jay Thomas (a good buddy of Letterman) will be on Dec 19. Stern was on Letterman this time last year, showing off Sirius and talking about the move.. Howard and Dave also go back, Stern was a guest on Letterman back when both worked for NBC. Letterman has also been on the Stern Show.. Dave never goes on other shows, he has been on Stern and Live with Regis.. The photo of Letterman on Stern is from March of 1996.