I also second the following:
Love Actually
Elf
Holiday Inn
The Holiday
A Christmas Story (although I have OD’d on this movie with the 24 hour marathons)
and would add Christmas Vacation.
Christmas in Connecticut with Barbara Stanwyck - we watch it every year. We also watch the Christmas Carol with Alastair Sim, Both usually get a few showings during the holiday season on TMC.
Miracle on 34th street, no doubt.
We like the oldies: It’s a Wonderful Life, Holiday Inn, White Christmas, Bishop’s Wife (original), Christmas in Connecticut, Christmas Carol (I’m with @kiddie the Alistair Sim version) Little Women (I actually prefer the newer one with Susan Sarandon and Winona Ryder)
We watched Christmas Vacation and Christmas Story over Thanksgiving while family was visiting. I love both movies, but I’ve had my fill. We own every single Christmas movie ever made and can recite them word for word which makes them tedious to me now. We need a break for a few years before trying again. My all time favorites though are It’s a Wonderful Life and White Christmas.
My brother reminded me of how many VHS versions of Christmas Vacation he went through before DVDs appeared. He would burn through the tapes watching and re-watching the cat electrocution and then howling at a still of of the fuming, splayed cat outline. For some reason, that struck him at the funniest thing on earth and worth a ruined tape.
A Christmas Story
Traditional viewing every year for H and D
This Jewish girl likes A Christmas Story, Rugrats Hanukah and a movie I just saw for the first time the other day - Christmas with the Kranks. I also like the movie with Arnold Schwarzenegger and Sinbad where they fight over the toy, but I can’t think of the its name.
One movie that’s hysterical for one viewing is “Santa Claus Conquers the Martians.” My kids loved it.
Thanks all. I have never seen some of these. Some I had seen but forgotten. Lots of ideas
Fang Jr and I are going to watch Netflix’s new A Christmas Prince. We expect it to be notably, aggressively bad, hilariously bad. We’ll enjoy it with hot cocoa and several tabs open.
Arnold and Sinbad fight over a toy in Jingle All The Way–HATE this movie–crass story of what Christmas ISN"T about.
Planes, Trains and Automobiles.
Technically a Thanksgiving movie but still in the holiday spirit…
Neal: Where is your other hand?
Del: Between two pillows…
Neal: Those aren’t pillows!
National Lampoon’s Christmas Vacation, and Bridget Jones’s Diary (2001)
A Christmas Carol with Patrick Stewart as Scrooge is almost as good as the Alistair Sims version.
Deck the Halls is a silly, fun Christmas comedy with Danny DeVito and Matthew Broderick. If you like Christmas Vacation, you’ll probably like this one.
Elf is my favorite.
The Tailor of Gloucester, animated version.
Love Actually , The Family Stone , The Holiday, Full Metal Jacket …ok, not the last one 
Muppet Christmas Carol
“Light the Lamp! Not the rat!”
A Christmas Carol hands down. I love any version, but the one with George C. Scott is my favorite. I even love the Mr. Magoo one. (Am I dating myself?) My husband and his brother will roll on the floor laughing every time they see A Christmas Story.
I also enjoy most of the classic Christmas movies – Miracle on 34th Street, It’s a Wonderful Life, Holiday Inn. I love them all.
For some reason the movie Moby Dick was shown on TV at Christmas in the UK every year back when I was a kid. It became a tradition for us to watch it.
Love them all, but also the oft-forgotten gem, The Ref with Judy Davis and (dare I say it?) Kevin Spacey. They are a bickering Connecticut couple on the verge of divorce who are taken prisoner in their own home on Christmas Eve by bank robbers. The robbers soon regret holing up with THAT couple when the whole crazy family comes over.
Netflix’s A Christmas Prince was worse than we expected (and we thought it would be terrible). Do not watch this movie. I expected beautiful scenery and lush costumes, but it looked like it was shot at a ski chalet in the Poconos.