On December 19, 1984, after devoting entire episodes to a bar mitzvah and an intermediate school's election night, and before their episodes from an airplane and a hotel room, Late Night with David Letterman presented Christmas with the Lettermans, a one hour send-up of every single cheesy Christmas special that had ever run on television. The special, which ran unsuspectingly on a Wednesday during Letterman's usual 12:35am time slot, won Late Night the Emmy for outstanding writing in a variety or music program for the second year in a row.
The special began with NBC's classic "brought to you in living color" identification that welcomed viewers to countless peacock network shows until 1975, only to be used again for significant events (Conan O'Brien's Tonight Show debut being the most recent). The audience was then thrust into a Winter Wonderland scored by none other than the Doodletown Pipers, an actual "easy listening vocal group" from the 60's and 70's that wikipedia claims were "considered by some to be the epitome of bland, squeaky-clean, 'white-bread' popular music". They sang "Smells Like Christmas Time" accompanied at times by an as-yet unidentified group of somewhat bratty children, their folksy mother, a bearded man that reminds one of David Ogden Stiers, and Gospel Music Hall of Famer Pat Boone. The last person you would expect after such a wholesome display would be David Letterman, and therefore David Letterman is the next person to appear. Following announcer Bill Wendell's introductions, the host, eschewing his usual suit for a sweater vest over a flannel shirt, welcomed the audience, wondered out loud where exactly Doodletown is and quickly tossed it over to Paul Schaffer. Schaffer at that point in his late night talk show bandleader career could match David snark to snark, who said with not a straight face that the cheer that's experienced during the holiday season is a cheer that permeates show business all year round. "That's right," Letterman added. "Three hundred and sixty five days a year."
Letterman introduced his "family." First to be presented was his wife, Audrey Daniels-Letterman, a woman straight out of a Norman Rockwell painting. Dave bragged that she was a cast member of the TV show Mission: Impossible, a fact that Audrey quickly shot down as being inaccurate. "Oh," Letterman said, unconvincingly claiming that that fact wasn't disappointing. Daniels then introduced their two sons Hank and Terry, one of which looks like a slightly older version of Ralphie from A Christmas Story, Daniels' "favorite" child Melissa, and the youngest kid, Kyle, accompanied by the David Ogden Steirs look-alike, Letterman's older brother Darryl. When Darryl is told he is kind for joining the group he retorted that he figured Kyle should have some adult supervision for a change. When Letterman implored his brother to promote his home insulation company, Darryl countered that Dave's lawyers made him change the name of his company from "Letterman's Home Insulation" due to a "conflict of interest." Darryl is the only fake family member that you believe has any actual blood affiliation with Letterman.
The horrible family dynamic is further exhibited when Dave showed that Melissa is also his favorite child. After letting Hank and Terry take a candy cane from the candy cane tree, Melissa is asked what her one wish is. "I wish I had fifty dollars." Without blinking, Letterman counted out fifty dollars and handed it to the eight year old, with a disappointed Hank and Terry looking on. The worst (and funniest) action of all, and the set-up to the runner of this episode, is Dave explaining to the audience that Kyle, who is probably five years old, as per Letterman family Christmas tradition has to procure a Christmas tree alone. The reward for coming back with a tree that is over seven feet tall is a solid gold coin of indeterminate value. Throughout the show before and after commercial breaks, the viewers were shown updates on Kyle's adventures alone on a cold and unforgiving winter New York night.
While Kyle is away, the rest of the family got to sit in the studio throughout the show. (In fact, Audrey Daniels-Letterman is seen during every traditional two shot with David and his guest sitting by the window behind Letterman, which for the special displayed a light snowfall.) Letterman's staff must have been feeling confident in their creativity that night; since they already had the running gag with Kyle's tree and a few segments featuring the dysfunctional phony family, only two guests were booked for the one hour episode, neither of whom were household names. The first was Pat Boone, who appeared on his own Christmas special on the Christian Broadcast Network a few days later. Boone was surprisingly aware of his surroundings, although his repeated sarcasm over the reality of the family ("Your son looks so much like you") was a sign that he was making sure he wasn't going to be considered an unsuspecting fool. At first Boone's interview wa played straight. Boone told a story about the time when he sang one of his many gospel tunes "Wonderful Time Up There" on The Tonight Show and forgot the lyrics. Letterman was guest hosting for Johnny Carson that night and quipped following the performance: "Folks now we have these auditions every Friday night…" The guest then promoted his upcoming special, Pat Boone's Old Fashioned Christmas, with a clip of the kind of mundane and cookie-cutter holiday show Late Night was parodying. Three years later Late Night would air another Christmas special titled Dave Letterman's Old Fashioned Christmas. (Ted Nugent had a cameo.)
Pat Boone's job in his second segment is to set-up a bit. When Boone asked Letterman what Christmas means to him, the studio went dark and Dave walked off the stage deep in thought,with viewers able to hear his thoughts via voiceover. "What does Christmas mean to me?" Letterman asked himself, bathed in spotlight. The studio audience laughed immediately, recognizing they were watching a parody of the painfully schmaltzy television device used to show a character pensively considering not being such a self-centered asshole during the holidays. David quickly forgot the reason why he was wandering the hallways in the first place, even going as far as to park himself underneath the mistletoe for a few moments in the hopes of getting some action. (It didn't work out for him on this night, but apparently it might have on others.) Schaffer, also only speaking in voiceover, reminded Letterman that he left his family and Pat Boone behind in the studio, with all of the lights out.
All seemed to be resolved following the commercial break, as Letterman continued to exhibit how he is a terrible fake father. After Audrey yelled off-stage to Dave asking if he allowed Darryl to take the car, the children that were not preoccupied with finding a tree were each asked what they wanted to be when they were older. When Terry admitted he wants to be an astronaut, Dave immediately pointed out that he has "that inner ear problem." When Melissa said she wants to be a ballerina Hank laughs and says "Yeah, and maybe someday people will be tired of all those tall and thin ballerinas." Letterman has a long laugh at that comment, even sayingg it was a "good one" (the voiceover moment did absolutely nothing.) The actor portraying the oldest son Hank forgot Darryl's name and realized it halfway through his line, to the bemusement of the audience and Dave. Favorite child Melissa implored Letterman to sing "Have Yourself A Merry Little Christmas", to which the host acquiesced to, in full silhouette, with a voice that was clearly not his own.
The second guest, Brother Theodore, was introduced by Letterman as a "noted philosopher, metaphysician and podiatrist." He both resembled and spoke a bit like Scrooge, complaining that he was not in a holiday mood due to a painful visit to the dentist. Theodore was one of a few Late Night guests that was clearly the butt of a joke they only understood when it was too late for them to stop coming back, for fear of ending their sudden uptick in money. Theodore complained that Dave "invented" him and that women are suddenly interested in him just because he had appeared on television. To try and prove his point he asked Audrey Daniels-Letterman if she found him attractive. An embarrassed Daniels said "no." Theodore responded that that was fine and he didn't find her attractive either. Letterman threatened to "turn his lights out" as soon as the show was over, which wasn't enough for Theodore and claimed if Letterman was a man he would that right then and there. Dave deftly turned the tables and purposely poked the bear, commenting that Theodore didn't seem to be in a good mood this particular holiday season. "For me there is NEVER a good holiday season…You want to enrage me again as you always do…Each time I come here you know in some hidden way how to drive me OUT OF MY MIND."
"Which is a pretty short trip."
Theodore would end up appearing on Late Night sixteen times. He died in 2001. His headstone read: "As Long As There is Death, There Is Hope."
After Brother Theodore, little Kyle returned with a Christmas tree. The whole family looked on as Letterman put the tree in the stint and measured it to be just over seven feet. "Aren't you supposed to measure the tree before you measure the stint?" Melissa asked. Kyle would be doomed to spend the Christmas of 1984 without a shiny gold coin. "What happens to the gold coin now Kyle?" "Melissa gets it." As the audience gently booed at Melissa receiving the coin, Letterman offered that he never said it was "fair."
For the end of the program the entire cast appeared with Letterman to say goodbye. After thanking everybody else and saying who will appear on tomorrow's broadcast, Letterman remembered to thank Uncle Darryl, who had been behind Dave the entire time appearing disheveled. It is then when the audience remembered the seemingly throw-away line a few segments earlier about Darryl taking the car out for a spin. Poor Darryl. As the credits roll Schaffer and the band lead the cast to sing "We Wish You A Merry Christmas" before launching into the end of the show theme. Everyone seemed to dance along except for Letterman, who had wandered off, down a hallway to his office, no doubt thinking about everything that went wrong, finding some solace in letting himself imagine that tomorrow's interview with Michael Keaton is going to exceed his impossible expectations.
Two years later NBC would re-air Christmas With The Lettermans, with a new introduction. By 1986, Hank had become "Henry" and Dave divorced Audrey Daniels for Mioshi. 1987 would have the aforementioned Dave Letterman's Old-Fashioned Christmas, with Audrey back into the fold, but played by a different actress.
You can find Christmas With The Lettermans in its entirety – Michael J. Fox Pepsi commercials included – on YouTube.
Roger Cormier has been retweeted by Dan Harmon on two separate occasions.