Serena Williams, Tom Arnold, Dave Matthews Band Dave admits to being in a disproportionatly good mood during a segment called "Late Show Newsmakers;" the Dave Matthews Band becomes the second band ever to perform on the roof of the Ed Sullivan Theater. Details Casts Title Serena Williams, Tom Arnold, Dave Matthews Band Genres Talk Comedy Release Date 2002-07-15 Episode Runtime 01 Hours 03 Minutes Season Number 9 Episode Number 185 Production Companies Worldwide Pants, CBS Entertainment Productions, CBS Productions, CBS Studios David Letterman Self - Host Paul Shaffer Self -Musical Director Alan Kalter Self - Announcer (voice)