- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Will Ferrell, Ben Folds Five
Air Date: 2000-07-19
Dave continues to refer to Paul as Wayne ""Fat Boy"" Ewing; Alan shows Dave photos from his recent vacation; Maria confirms that Al Gore's interested in being a guest on the show; Ben Folds Five (in their last TV appearance) performs ""Regrets.""