Christmas Story...totally. Of course, my hubby's mom sent us old photos of hubby as a kid and HE LOOKED JUST LIKE RALPHIE! Ever since then I make hubby watch it with me every year.
I love The Holiday as well. FYI - did you know that the kid who played Ralphie in Christmas Story was in the movie Elf? He is friends with the director. He was one of the elves at the North Pole. See if you can find him!!
It's A Wonderful Life
A Christmas Carol (w/ George C. Scott)
The Family Man (Nicholas Cage & Tea Leoni)
Home Alone
National Lampoon's Christmas Vacation
Scrooged (Bill Murray)
And of course all the classic cartoon movies... Rudolph, Frosty the Snowman, The Year Without a Santa Claus, A Charlie Brown Christmas, How the Grinch Stole Christmas, etc.