While my wife is fine watching whatever Holiday movie the Hallmark Channel happens to be showing, she does make a point to watch Christmas Vacation every year. For me I try to squeeze in viewings of It’s a Wonderful Life and Die Hard. I also like to watch Planes, Trains and Automobiles this time of year as it's one of the few movies that takes place at Thanksgiving.
Not at all a holiday film; but the first big blizzard of the Winter I like to bundle up and watch John Carpenters The Thing.
I know I will sound like a spoil sport, but I rarely watch things twice. I love to have the tv on and would dearly miss it if it wasn't around, but I don't watch much anymore. I would prefer to read or knit. So shows that don't require a lot of attention are my favorites. Christmas music or having the shows on in the background is most likely what will happen. My husband is the big softie and will watch all the tear jerkers through the season. Have you all seen the one about "my mamma's red shoes", oh boy get out the Kleenex. He watches that and I go sit in the other room, too much for me lol.