George Clooney, Merle Haggard A man from Charlotte, North Carolina plays "Know Your 2003 Boston Red Sox;" ten Hooters Girls present the Top Ten; George Clooney plugs Intolerable Cruelty. Details Casts Title George Clooney, Merle Haggard Genres Talk Comedy Release Date 2003-10-09 Episode Runtime 01 Hours 03 Minutes Season Number 11 Episode Number 24 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)