Divided by loosely defined categories:
Classic - Been around forever, will be around forever
It's a Wonderful LifeOddly, most of the movie isn't set at Christmas, and the moral seems to be that abandoning your dreams is okay as long as everybody else is happy. No wonder it was once considered a Communist propaganda threat by the US government.
Miracle on 34th StreetSanta ends up in Bellevue. Makes me wonder where kids send their wish lists now, in the age of e-mail.
A Christmas CarolStricly OG. Scrooge might be the character most identified with Christmas after Santa.
White ChristmasNever seen it. I believe Hollywood made this movie to cash in on the popularity of the song.
Cartoons - You still watch them as an adult
How the Grinch Stole ChristmasEven Jim Carrey and Ron Howard's pointless live-action film couldn't diminish the greatness of Chuck Jones collaborating with Boris Karloff and the Doc.
A Charlie Brown ChristmasIt wasn't until I was 24 that somebody pointed out to me how sad this cartoon is. I prefer bittersweet, which is what Christmas often is.
Frosty the SnowmanHappy Birthday!
Mickey's Christmas CarolCome on, give it a chance. Yeah, I know it's "Disney" (in quotes to enhance the loathesomeness people attach to that name), but it's fun just to see how they cast the Disney mainstays in the various roles.
Comedy - Bringing the ha-ha to the holidays
National Lampoon's Christmas VacationThe second best of the Vacation movies, and one of the last good movies Chevy Chase made. We have all been Clark Griswold slowly breaking from sanity at one Christmas or another.
A Christmas StoryFor many, the single greatest Christmas movie of all time. Fudge, I won't argue.
Scrooged"Cross: (noun), something you nail people to."
Trading PlacesEddie Murphy in his prime. Dan Aykroyd drunk, in a Santa suit, putting a gun to his head on Christmas Eve in front of a bunch of asshole stock brokers. And Jamie Lee Curtis's jingle bells.
Family Comedy - Blame it on your kid for watching these
ElfCould probably be in the regular comedy category, except for the part at the very end with the singalong that reboots Santa's sleigh. Still great.
Home AloneAnother "give it a chance" movie. Ignore the fact that it's Culkin. It's all about the scene where the two crooks break into the house and the kid fights back. Classic Tom & Jerry action.
A Very Brady ChristmasPure cheese, but perfect Brady.
The Night They Saved ChristmasNorth Pole City is threatened by an oil company dynamiting nearby, so Santa kidnaps the lead geologist's wife and kids to convince them he's real. Obscure, and kinda lame, but it's also kinda quirky and endearing.
Puppets - Creepy!
Rudolph the Red-Nosed ReindeerWhat isn't awesome about this show? The elf who wants to be a dentist. The Island of Misfit Toys. Yukon Cornelius. And, if that's not enough for ya, there's an Abominable Snowman. This thing's got a friggin' Yeti!
The Year Without a Santa ClausFast forward to the song and dance revues by Heat Miser and Cold Miser.
Santa Claus Is Coming to TownThe bad guy is a German anus named Burgermeister Meisterburger who hates the sound of children laughing. Just like all Germans.
The Muppet Christmas CarolSee also
Mickey's Christmas Carol.
Strange Christmas - WTF?
GremlinsHer dad's corpse was cooking in the chimney! Dude, that's just messed up.
The Nightmare Before ChristmasMore puppets.
Tim Burton puppets.
Silent Night, Deadly NightA Santa Claus slasher movie made by Belgians. What else do you need to know?
Santa Claus Conquerors the MartiansI wish I had something clever to say about this movie like on one of those VH-1 clipshows, but this one is just too screwed for words.
Manly Christmas - To be watched while drinking one of those fruity holiday lambic beers your family gave you
Bad SantaIt's the caper we all wish we'd thought of. And it's got an angry midget. (Like there's another kind.)
The RefDenis M-F-in' Leary. He spends the entire movie crapping all over everything, and still somehow manages to reconcile a couple near divorce and reaffirm their relationship with their wayward son.
Die HardIt's like
Die Hard, but at Christmas.
Lethal WeaponI think most people forget that this movie is set at Christmas. That's really just sprinkles on the sugar cookie of this, the first installment of the greatest heterosexual man-on-man love story of all time. "Whadda ya say? Would you like a shot at the title?"