White Christmas is a classic and I love it! But NL Christmas Vac is a must watch every holiday as well. Anything with Bing Crosby and Sinatra and the like are classic movies! I wish we had movies like that nowadays instead of the same ole crap hollywood keeps pumping out
2nd would probably be Home Alone, only because I've seen it about 20 times. A kid I used to babysit would watch it over and over again. I like the music, the movie is just so-so.
My wife made me (no, really, she mad me) watch Love Actually with her when it first came. She bought it, it takes place at xmas, and after watching time and again around the holidays it's really not too bad. I kinda even like it now.
Watched CV a couple weeks ago along with Its a Wonderful Life.
My wife and I watch White Christmas every year. We will watch A Christmas Story tomorrow night after we open gifts.
My favorite though is Elf. Watched it several times this year and it is on in the DVD player when we head to the grandparents.