Backdoor Santa - Clarence Carter - Unfortunately this one doesn't have an actual video to go with it which is too bad because this is the funkiest Christmas song ever. It's even funkier than The New Kids on the Block Funky Funky Christmas which has the benefit of having the word "funky" appear twice in it's name. Those two funkys are also the only funky thing about that song.
BONUS - A horribly inappropriate performance of Backdoor Santa by the kids of PS22 wherever that is. I wonder if their music teacher ever really listened to the song.
Boys Town - When I was little and couldn't fall asleep on Christmas eve my parents used to put the little portable black and white TV in my bedroom to keep me from waking them up every hour asking them if it was time to open presents yet. For some reason, Boys Town was always on in the wee hours of the morning. It's not even really a Christmas movie although it does have a Christmas scene in it. Back in the early 90s, I found a copy on video and I've been watching it every Christmas Eve since.
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