I will always- without fail- watch the 1951 version of Christmas Carol (Alistair Sim) on Christmas Eve. I also picked up the peculiar habit a few years ago of watching "Stephen King's IT" some time in the beginning of April. No real reason at all.
And I never miss a Friday the 13th where I don't watch at least one of those.
Since I'm a kid, I always try to watch Home Alone and Home Alone 2 around Christmas. :o Except for one or two years I watched it every year. Just because they didn't show it on TV those years.
But now I'm prepared. I have the BluRay copy on my HDD.
My family has almost always put that god awful A Christmas Story movie on for Christmas. Yuck. Luckily for me, I'll be spending Christmas this year in NY, just me and my guy, so none of that this time
Halloween every October The Manchurian Candidate and The Candidate every election (major or minor)
A Mel Brooksathon every April Fool's Day A Charlie Brown Christmas (duh) and Goodfellas every Christmas
National Lampoon's Christmas Vacation and Die Hard around Christmas (occasionally Lethal Weapon as well). Often I'll marathon horror movies around Halloween. :dunno: