die hard.
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Not really a movie, but In Germany there is a weird tradition to watch Dinner for One every new years eve.
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Nightmare Before Christmas
Has anyone said Die Hard yet?
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Home Alone 1 and 2
The Big Lebowski, although there's not often a season where I don't revisit.
Cannibal: The Musical for me, my wife hates it
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Groundhog Day every February 2nd
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National Lampoon's Christmas Vacation and A Christmas Story
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I’m a huge horror fan and I watch those based on the season. So throughout winter I watch all of these:
The Thing
The Shining
The Frankenstein Theory
Frozen
Devil’s Pass
We Are Still Here
Wrong Turn 4
30 Days of Night
The Blackcoat’s Daughter
Pontypool
Wind Chill
Paranormal Activity: Next of Kin
No Exit
Curse of Aurore
The Last Winter
Brazil
MST3K's Sants Claus Conquers the Martian on Christmas Eve
Winter in general: Storm of the Century, and I don't care how cheesy it is
Christmas: Gremlins
Anything that basically isn't from 2005 onwards
Jingle all the way and not a movie but SAO Abridged
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