- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Ted Koppel, Isabella Rossellini, Macy Gray
Air Date: 1999-07-26
Paul complains about the heat at Woodstock '99; Dave brags about Max Pappas and Team Rahal (a sign of things to come); Ted Koppel's evil twin Kenny is caught hosting Nightline in lieu of his more well-known brother.