The older I get, the more I enjoy Christmas. The mood, the family, the decorations, the weather, etc. It helps that I associate fond memories of my grandparents to this holiday. I'm quite old-fashioned, corny and quite into it, so I'll give an exhaustive list here:
Christmas Vacation - typically 2-3 times
Elf - several times
Home Alone - several times
A Christmas Carol - every version. Yes, even the Zemeckis one. I've never liked Scrooged, however.
Prep & Landing (new addition!)
Arthur Christmas (new addition!)
White Christmas - my wife loves this. I hate it. It's barely a Christmas movie.
Holiday Inn - the Bing musical I vastly prefer.
How the Grinch Stole Christmas - not the Ron Howard one
A Midnight Clear
Nightmare Before Christmas
I don't think I am missing anything. Christmas Story is played out, but I still manage to watch it as it reruns 7 thousand times over December. I've never seen It's A Wonderful Life. Shocking I know, but everything I understand about it leads me to believe I wouldn't be a fan - half because George seems like a prick, half because it's so hyped. Miracle on 34th Street comes out every once in a while, but that's not required viewing for me.
Straight No Chaser
Harry Connick, Jr.
Yes, I'm a damn dork. I don't care. It's the most wonderful time of the year. :)