MerryCarey
A Voice from the North
MMC Lifer
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Christmas Crew
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Santa's Elf
Kringle Radio DJ
My favorite off-season, holiday-flavored film is "Shop Around the Corner."I didn't realize those were movies that take place during Christmas. I'll have to check them out. I haven't even seen Die Hard which I also see on a lot of Christmas movie lists.
Another suggestion I have for you is Paul Blart: Mall Cop. It takes place during the Thanksgiving weekend and the main events occur inside a mall that is fully decorated for Christmas and has Christmas music playing. It's a good fun clean comedy and is definitely not a "holiday" movie in that traditional sense.
Also a lot of Christmas themed horror movies are fun to watch during the Christmas off season and especially during September and October when it's Halloween season but you might want a little bit of Christmas thrown in there.