I was going to recommend The Nightmare Before Christmas too! I also like Joan Baez' and Harry Belafonte's Christmas albums - some old (and possible too full of associations) standbys, but also several I-never-heard-this-anywhere-else ones. You can make yourself a tape of just the strange ones to play in the background...

I find that the most soothing and uplifting "use" of Christmas music is while I am wrapping and ribboning presents. For some reason I don't really like to have it playing unless I am actively DOING something Christmasy, although I generally like the music. I don't mind all the associations then, for some reason.

Also, the British do something, I think, and I think on Boxing Day, with a cake with little somethings baked into it, and whoever gets the (thimble?) gets to be King/Queen For The Day and have everybody else kowtow (no abuses, obviously), wear a paper crown, and so on... And I believe the lesser prizes all do something too, none of which are the chit for the visit to the dentist after you forgot to chew carefully looking for little coins and other things. Perhaps a single walnut in an entire cake might be better, but what if you swallow it?

Other things my family does whenever we get together (which is when the Absence is Felt Most Strongly) is play silly games - Charades (which I assume you know how to play), In The Manner of the Adverb (kinda like charades except you have an adverb, like Sleepily or something, and then the other players give you things to do In The Manner of the Adverb, and you do them till someone guesses the adverb), and so on. If just the 2 of you, I recommend Jotto, which is kind of like MasterMind with words (you each have a, say, 6-letter word, no repeated letters; I guess a 6-letter word, you tell me if any of the letters in my guess are in your word, and if they are in the right place in the word; so if your word is MUDCAT and I guess COVERT, I have 1 letter that is both right and in the right place, the T, and one that is right but in the wrong place, the C; use logic to proceed till you get the word; start with 3-letter words and work up). After the second time of doing anything, it is the New Tradition, and when he's got a kid of his own, he'll be teaching'm to play Jotto at holiday time...