- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Harry Connick Jr., Sean Astin
Air Date: 2004-02-03
Dave announces that after 22 years on the wagon, he would like to start drinking again, but only during the show. Later, he wishes Oprah a belated happy 50th birthday.