David Letterman

Long before he was the Elder Statesman of Late Night Television, David Letterman was bringing a very new and unique version of comedy to television - a bizarre, absurdist vibe that flew in the face of classic late night conventions. He was the bridge between the traditional style of Johnny Carson and modern-day comedy anarchists like Conan O'Brian and Jimmy Fallon. His persona, influenced deeply by writers like Merrill Markoe and Chris Elliot, has mellowed with age, but back in the 80s he was like nothing else on television. And he also did some pretty awesome Christmas-related stuff.

Before he was America's crazy Republican uncle who you hope doesn't start to talk politics at Thanksgiving dinner, Ted Nugent was the Motor City Madman. Here he is doing a duet of "The Christmas Song" with Dave back in the late 80's - I could have gone with a better quality clip, but this one includes a bit at the end with a cigar-chomping Dave riding with some Christmas carolers in a sleigh driven by 1987 Indy 500 winner Bobby Rayhal.


In December of 1986, Darlene Love appeared on Late Night to perform her classic "Christmas (Baby Please Come Home)" with Paul Schafer and The World's Most Dangerous Band. Dave was so impressed that he invited her back to do the song again next year, and every year since that for the past 27 years. Below is footage of her original '86 performance, as well as a mashup of all of her performances from Dave's Late Show days ('93-present).




Perhaps Letterman and company's most memorable Christmas invention was 1984's "Christmas with the Lettermans", in which Dave and his fake family welcome Pat Boone, the Doodletown Pipers, and monologist and "standup tragedy" performer Brother Theodore to their annual holiday special. Along the way, Dave's youngest son is sent on a tragic journey through the streets of New York City to fetch a tree, we learn that, sadly, Dave's "wife" Audrey Daniels-Letterman, was not a regular on Mission: Impossible, and the whole gang treats us to a rendition of the incredibly dumb "It Smells Like Christmas".