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A Christmas story. Not every year though.
Every year my family and I watch:
Santa Claus is Coming to Town
Rudolph the Red Nosed Reindeer
Frosty the Snowman
A Christmas Story (this ones my personal favorite)
Emmet Otter's Jug-Band Christmas is a great Christmas story. Catchy songs, cute muppets, and even a bit of real emotion.
Lots of great suggestions so far but the Gremlings movies are missing.
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Lenny: ...but the Gremlings movies are missing.
Miss the first post?
For me, the main Christmas movies I enjoy,

A Christmas Story, this is simply a classic film, enjoyable no matter your age.
A Christmas Vacation, one of the best comedies of all time.
Rudolph, the Red-Nosed Reindeer - Classic stop-motion film, can't be beat.
Nightmare Before Christmas - Who can deny that this movie isn't awesome? Tho
Home Alone I/II - Loved them as a kid, still enjoy them today.

For a more recent movie I really enjoy on the Holidays now, The Family man. It just helps bring things back thing, makes you focus more on the things that matter in life.
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Lenny: ...but the Gremlings movies are missing.
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nondeplumage: Miss the first post?
I sure did. Anyways, Gremlins rock.
Braindead (AKA Dead Alive) - no Christmas is complete without it. "I kick arse for the Lord!"
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Navagon: Braindead (AKA Dead Alive) - no Christmas is complete without it. "I kick arse for the Lord!"
This calls for divine intervention!
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Navagon: Braindead (AKA Dead Alive) - no Christmas is complete without it. "I kick arse for the Lord!"
"Party's over!"
it's a wonderful life is the citizen kane of christmas movies
Santa Claus: The Movie Because it's Dudley Moore.