Remember that time Terry Gilliam forgot how chairs work?
A much younger David Letterman with a (dirty) Royal Empress Typewriter.
David Letterman @ The Comedy Store
My favorite Letterman bit: Dave steals balloons from T.G.I. Friday’s, holds them for ransom. Bruce Willis gets involved later. Kudos to the encoder for capturing the whole saga, which was spread out over the course of the program.
Dave Letterman on Late Night With Conan O’Brien on 9/16/1998
Classic Letterman: Gene Siskel and Roger Ebert go door to door in Jersey with David Letterman, circa 1996.