Ho ho ho! I’ve been combing the internet looking for what I consider to be the best overlooked Christmas specials of the past 30 years. While I couldn’t find absolutely everything, I was very happy with what I turned up. This assembly of programs deconstruct the traditional holiday special in hilarious and inventive ways. Collectively they are hosted by a Late Night icon, an insult comic dog, a Kid in the Hall, two lunatics, a drunk, and Pee-Wee Herman! Here now, are some of my favorite, oft-forgotten Christmas specials. Happy Holidays!
Christmas with the Lettermans • Late Night with David Letterman
A one-hour send-up of countless corny Christmas specials featuring Letterman’s pretend family and memorable numbers like “Smells Like Christmas Time”.
The Triumph Family Christmas Special • Late Night with Conan O’Brien
The insult comic dog hosted a mini special on Late Night with Conan O’Brien in 1998 where we meet his uncooperative son and his poodle mistress. Featuring an appearance from Triumph’s College All-American Football Team
Pee-Wee’s Playhouse Christmas Special • Pee-Wee’s Playhouse
This 1988 special features appearances from Little Richard, Magic Johnson, Frankie Avalon and Annette Funicello, Charo, k.d. lang, and Dinah Shore. Pee-Wee pokes gentle fun at the holiday special while maintaining a genuine sweetness.
Dave Foley’s The True Meaning of Christmas Specials • CBC Television Special
Considered by many to be the holy grail of Christmas specials as it was once very difficult to find. This 2002 CBC special is hosted by Kids in The Hall and NewRadio’s Dave Foley and features a long list of celebrity guests including Dick Dale, Joe Flaherty, Tom Green, Mike Myers, Andy Richter, Jason Priestly, and Dave Thomas.
Kenny vs. Spenny’s Christmas Special
This freewheeling Christmas special was also the series finale for the popular Canadian show. For the uninitiated, two friends named Kenny and Spenny dedicate each episode of their quasi reality show to a series of competitions. The loser typically performs some act of humiliation of the loser’s choosing. In this episode, Kenny and Spenny compete to see who can create the best Christmas themed variety show.
Drunk History Christmas • Drunk History
In this special edition of Derek Waters’ Drunk History, Allan McLeod drinks a bottle of whiskey and recites a famous Christmas poem. Jim Carrey, Ryan Gosling, and Eva Mendes perform the reenactment.