The list, “Top 10 Cocktails for Santa,” was part of a packet Colbert had submitted to the show in 1997 to be considered as a writer. By the time Letterman’s team reached out, however, Colbert was working on his Comedy Central series, “Strangers with Candy.”
“He doesn’t have the job yet,” Letterman joked when band leader Paul Shaffer performed the classic countdown bit’s opening number.
Colbert, as it turns out, has a rich history of almost working for Letterman. Before he was almost hired as a writer on CBS staple “The Late Show,” he was almost an intern for Letterman’s NBC show, “Late Night,” after beating out his college girlfriend for the gig.
“And then I did a foolish thing, and I did not take the internship,” Colbert said.
“Why’s that?” Letterman asked.
“Because you did not pay people. It’s an expensive city,” Colbert said. “The next job I’m taking here, that pays right? Because I already signed.”
Watch the video below: