For Christmas, if I go for anything, I deem it a good time to re-watch all the Harry Potter and LOTR movies. My husband’s #1 movie at that time is Die Hard, followed by National Lampoon’s Christmas Vacation. At Halloween time, I’ll watch anything remotely scary (but not gorey).
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Some Halloweens we’ll go for Beetlejuice or Ghostbusters. Christmas Vacation is a Thanksgiving weekend tradition to kick off the season, followed by most any other Christmas stuff. We’ll have to try Emmet Otter and Muppets Christmas Carol this year.
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I’d highly recommend that you give A Muppet Christmas Carol a chance. It’s so well done, and the music is absolutely wonderful.
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Only second to Muppet treasure Island
Always start with the original Miracle on 34th Street on Thanksgiving weekend. Then all of the Rankin Bass specials plus Charlie Brown Christmas and the original animated How the Grinch Stole Christmas. Scrooge with Albert Finney. And Elf, usually.
Halloween favorites are The Nightmare Before Christmas, Arsenic and Old Lace, The Addams Family, Young Frankenstein, and of course Rocky Horror.
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I am ashamed to admit I have never seen miracle on 34th st. Or its a wonderful life for that matter. I don’t know how I forgot Elf all these years though.
My kids were finally old enough to add Gremlins in last year but we are a ways off from die hard.
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Back in 2016, my son and I began a tradition of going out to a theater to see one or more Korean films. Couldn’t do that in 2020, alas.
So I started a new tradition of finding more obscure Christmas things to watch:
The Shop Around The Corner
Holiday Inn
The Bishop’s Wife
The Holly and the Ivy
White Christmas
“The Tick” episode “The Tick Loves Santa!”
Joyeux Noel
In Bruges
Rare Exports
Krampus
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Takes place on Halloween.
Taped it off Showtime’s Cinemax equivalent, The Movie Channel, about 13 years go.
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Growing up, my house didn’t really watch anything for Halloween but sometimes I’d watch this:
For Thanksgiving, gorging on food was always followed with the adults putting this on:
… because 
.
Xmas, every year after it came out:
And then I grew up, moved away, got into movies that my parents would never watch in a million years, lost any love for the holidays. Halloween now involves watching this at some point:
For Thanksgiving time:
And an admittedly weird one for Xmas day:
On this last one, it became an “tradition” by way of habit. I’ve had to work on Xmas day for several years now and it just sorta became a thing to sit down with Troll 2 to burn the final hours on the clock. I’ll usually whip up something silly as a late lunch beforehand (last year was spaghetti tacos; haven’t decided on this year but there is plenty of time left to figure it out).
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My roommate and I have a very set order of holiday movies, beginning the day after Thanksgiving:
The Nightmare Before Christmas
Elf
The Polar Express (always with hot chocolate)
Frosty the Snowman (Rankin/Bass)
He-Man & She-Ra Christmas Special
The Muppets Christmas Carol
Love Actually
National Lampoon’s Christmas Vacation
Occasionally something like Home Alone or the Christmas That Almost Wasn’t riff slips in there!
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I have two holiday movie traditions: Life of Brian every Easter and The Star Wars Holiday Special every November 17 (its original air date).
I need to mix in “The Tick Loves Santa” somewhere now that @moviegique mentioned it. I watched Holiday Inn every Christmas for probably 30 years and can pretty much quote it, but that has fallen by the wayside recently.
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It’s a yule tide!
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Mine are little still, so the holidays are more about running around than sitting down to watch something. That said, we do like Nature Cat: A Nature Carol from PBS–a simple telling of the Dickens classic with an Earth friendly element. Ronald’s song is my favorite part:
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Favorite Halloween and Xmas movie is The Nightmare Before Christmas
For Halloween, The Haunting (the original, accept no substitutions)
For Xmas, I’m pretty traditional. It’s Muppet Christmas Carol, Alistair Sims’s Christmas Carol, and It’s a Wonderful Life
I guess I should stipulate that I’m my own family, so I’m not subjecting small children to The Haunting
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Bruce Campbell and Tom Atkins usually show up on my tv around Halloween, but which particular films are subjective to mood. Simpsons and Regular Show halloween episodes are great, too.
Around December usually Batman Returns, Empire Strikes Back, The Thing, or Gremlins will show up. We also usually run some rifftrax cheer, with one of the holiday mst3ks, too.