Greg Kinnear, Jake Johannsen CBS Mailbag: Dave teaches grade school, while "AP writer Adam Klymer" (the scribe Dubya referred to as a "Major League Asshole," as played by Gerard) gives the future president the finger. Later, Greg Kinnear promotes "Dinner with Friends." Details Casts Title Greg Kinnear, Jake Johannsen Genres Talk Comedy Release Date 2000-09-08 Episode Runtime 01 Hours 03 Minutes Season Number 8 Episode Number 15 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)