As you may have heard already, David Lettermen announced his retirement from The Late Show earlier this week. The best moments of the show always came when you could tell that Letterman was genuinely enjoying himself. Nothing seemed to bring Letterman greater joy than going out of the studio and bothering people. In honor of Letterman’s 67th birthday, here are five hilarious clips of Letterman having fun while he annoys TV hosts, his bosses and people at restaurants.
Dave was a little upset that his primetime special got less publicity from NBC than the The Today Show’s special received. He could have aired his grievances privately through a meeting or phone call. Since the show was filming right outside his office window, Dave figured it was easier to just use a bullhorn.
We doubt that any other host of a late night talk show would have the balls to bother their new corporate bosses. Not only did Letterman do that, but he also revealed General Electric’s secret corporate handshake.
Dave just set out to bother some McDonald’s employees, but he managed to get a pretty interesting interview. There has probably never been a more loyal employee than the woman who gave birth to her child in the McDonald’s bathroom and named her son in honor of the restaurant that didn’t give her time off.
Letterman decided to annoy customers at a Taco Bell drive-thru. “Medium relative to what?” is probably the funniest question ever asked.
Sometimes Dave would farm out the annoying people duties to Rupert Jee who owned the Hello Deli near the Ed Sullivan Theater. With Dave telling him what to say, Dave could annoy people without being recognized as a celebrity.