- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Reese Witherspoon, Harry Connick Jr.
Air Date: 2008-11-25
Dave calls out Tony for making him read the same monologue joke twice; after President Bush pardoned 14 convicted felons that week, Dave and Alan grant clemency to an audience member; Reese Witherspoon relives her 2005 Oscar win and plugs Four Christmases; Harry Connick Jr. performs "It's The Most Wonderful Time of the Year."