Nell Scovell at Vulture:
In 33 years, more than 90 writers churned out countless monologue jokes, remotes, and desk pieces. Some stayed for decades. Others, like me, passed through briefly. But we all had one thing in common: the desire to get Dave’s approval. It wasn’t easy.
“I really wanted the people writing this show to be so much funnier and so much smarter than I was,” said Letterman a few weeks before the end of his run. “I think that’s exactly the way you’ve got to run a show like this.”
For every comedy bit produced, there were roughly a hundred pitches that didn’t make it. So I asked fellow Late Night and Late Show vets to recall their most memorable rejections. Then I ran some of those by Dave, who was happy to reminisce about former writers.
JILL A. DAVIS (1991–1997; author, Girls’ Poker Night)
Dave was actually quite uppity about choosing jokes. For example, he was adamant that jokes must be funny. Mildly amusing material was not okay. Neither were wigs. I learned this when I wrote a viewer mail response that answered the question: “How did you and Paul meet?” It involved a flashback to their meeting at Woodstock. We were set to shoot it at rehearsal, and Dave showed up ready to shoot. He took one look at the fringed vest and long wig and said, “I’m not doing this.”
Another pitch was “All Week Long William F. Buckley Rates the Mustard.” The idea was that Mr. Buckley would come in through the blue doors in the NBC studio, hold up a jar of mustard, and eat a teaspoonful. With great importance, he’d ponder the flavor and describe the mustard’s most pronounced qualities, then say something like, “That’s mama’s milk!” or “For intravenous use only!”
After the idea was shot down, I likely resubmitted it suggesting we replace Buckley with Manute Bol.
Letterman: Good lord. [Laughs.] Okay, I made a mistake there. Either way, that should’ve been on. Who knows what kind of day I was having, but, by God, that … in a heartbeat.