- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Kristin Davis, Ali G
Air Date: 2004-07-12
In the debut edition of "Where They Would Have Gone For Their Summer Vacation," Biff tells Dave that Charles Bronson would've gone to Mohegan Sun Casino in Connecticut; Jeopardy! super-contestant Ken Jennings presents the Top Ten; Dave admits to Kristen Davis that he was "watching hard" while viewing Sex & the City reruns on TBS.