We don’t do it anymore, but we used to watch the Charlie Brown Christmas special when I was growing up. Nowadays we don’t have a tradition like that, but I’ll always do my best to watch The Santa Clause because it’s one of my favorite holiday moves.
I rewatch the Blade Runner movies every year on Boxing Day. Sometimes I do different cuts, but mostly final cut. Then BR2049 turned out good enough to add to the tradition, so I watch that next.
My favorite movie to watch at this time of year, or any time of the year for that matter, has to be the multiple Golden Globe nominated sensation of 2023, Barbie, which, coincidentally, is also available on Blu-Ray and select streaming services.
Home Alone I: Kevin is alone in the house
Home Alone II: Kevin is alone in the house in New York
Home Alone III: Dennis the Menace
Home Alone IIII: Fake Kevin is alone in the house
Home Alone IIIII: Heeeeiiiiist
Home Alone IIIIII: Kevin and New Kevin alone in the house (not New York)
I tend to watch the whole Marvel lineup to this day starting early December and my wife and I watch the whole shebang of Harry Potter on Christmas eve and day.
March/April I tend to rewatch Boston Legal and the cliffnotes of Dragon Ball OG to Super. Rest of the shows I rewatch aren't as tied to time of year.