- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Kate Winslet, Darrell Hammond, Mandy Barnett
Air Date: 1999-04-14
The secret word is ""quadricentennial,"" and after doubling the stakes on last night's show, Dave ""raises"" them to an even hundred million; on a variation of a recurring bit, Biff goes out in traffic, harassing people with a bullhorn; Dave increases the jackpot again to $150,000,000; Darrell Hammond does his trademark Clinton impression.