I have a somewhat atypical relationship to holiday movies. Well, we say 'holiday', but in America, 'holiday' means Christmas with some vague penumbra of collateral jollity (Thanksgiving, Khanike, Kwanzaa) to be read in.
Anyway, though I grew up within pretty mainstream American culture, I generally avoided watching 'Holiday' movies. I hated the Charlie Brown holiday special. Never saw It's a Wonderful Life or A Christmas Story. Not because my parents forbade it or frowned particularly on non-Jewish content.... I just wasn't that interested in Christmas. One thing I knew for sure, it didn't include me.
Last year I decided to see a couple Holiday movies. For example, I watched Scrooged based on many recommendations. I re-watched The Nightmare Before Christmas which was just as disappointing as I remembered it. I watched the Mr. Magoo Christmas movie which just, no.
Anyway, I have a list of three 'Holiday' movies I approve of, for 100% idiosyncratic reasons.
1. Scrooged. It's the perfect piece of '80s nostalgia and a just right satire on the entertainment industry. Bill Murray, David Johansen, Carol Kane, the whole cast is perfect. A great compromise movie to put on when the whole family is awkwardly sitting around and can't think of anything else to talk about.
2. Sint. If you catch this Dutch movie on Netflix you'll find that it's been dubbed into English. That may be a plus or a minus in your book, but it didn't bother me too much. Sint (Saint) is probably the most timely of these movies, as St. Nicolas day is December 5. The night before, Dutch kids traditionally leave out a boot to be filled with toys by Sinterklaas and his not at all racist helper, Black Pete. Black Pete may or may not be based on Spanish Moors and/or may or may not be based on chimney sweeps with blackened faces.
You may have seen pictures of contemporary Dutch Black Petes here or there in recent discussions about cultural appropriation and racist costumes. It was worth it to watch the movie just to understand the context for Black Pete. Doesn't make it ok, but it's good to understand what's actually being discussed.
Anyway, the premise for the movie (which by the way, is quite gory) is that Sinterklaas is a murderer who visits mayhem every time St. Nicolas day eve falls on a full moon. Since I can't say when the last time was I watched a Dutch movie, I thought that alone was worth the price of admission. (Which, to be honest, was $0. Available for streaming on Netflix)
3. Rare Exports: A Christmas Tale. io9 calls Rare Exports "the most disturbingly awesome Christmas movie ever." And even though (or maybe because) I haven't seen that many Christmas movies, I have to agree. I watched this with my family without knowing anything about it, which made the experience much more enjoyable. It's also Finnish, which obviously makes it even better. Don't read too much about it, just watch.
Those are my picks, what are yours?