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I'll vote for "It's a Wonderful Life".
It's fairly hardcore. I mean it takes on multiple serious issues (social justice, suicide, self-sacrifice), with some very intense scenes. But it still also funny and lighthearted too; with an effective romance as well.
I'm not really sure why it's become a film traditionally played during the Holidays, but it certainly has. It has some well timed Christmas tie-ins, not to mention the over-all feel.
Grinch would be my next choice. Simple and artistic. Basically a reworking of the Bible story Job. Grinch takes all their Christmas stuff (and more), but they still celebrate Christmas without the stuff. The sight of it brings on redemption for the Grinch.
I'm really fond of lots of The Nightmare Before Christmas. I think the "What is This?" song and sequence is particularly fine. But the over all message (and every film has one) seems to be don't try something new, or don't mess with Christmas tradition, or you can't change. Which seems a bit bleak for a December holiday film.
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