90s90s90s:

Drew Barrymore flashes David Letterman on The Late Show - 1995 [x]

indigozeal:

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.

recspecs:

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.

chainedandperfumed:

He’s so good!

ramseyesscom:

This Splitsider article about the time David Letterman had 13 cameras in his studio came out pretty good, and, if nothing else, it reminded me to watch this clip on YouTube, which is the best:

GETNAKEDMILEY