Just watched Krampus for the first time last night. Not something that will become annual viewing, but it's worth a watch for sure.
My annual picks are Scrooged and Gremlins. My family always watches Christmas Vacation.
My tier two which I will do every year or two are It's a Wonderful Life, Silent Night Deadly Night, Home Alone, Ernest Saves Christmas, Jack Frost, Christmas Story, and Black Christmas.