It Happened One Night with Claudette Colbert and company.

Bad Santa will set the spirit. In my mind Die Hard (the first one) is the ultimate xmas movie. It has it all, a hero, a bad guy, explosions etc. 

I love Home Alone 1&2 and the Santa Clause (Tim Allen).

Good Christmas Specials:

Planes Trains and Automobiles- Steve Martin and John Candy. Amazing.

A Christmas Story- Showed it to my wife last year and she loved it. She even thought that last bit when they are in the Chinese restaurant to be one of the funniest things that she'd ever seen. I was a little bit surprised because they do come off as Chinese Stereo types. 

It's a Wonderful Life- Timeless classic really. A lot of the movies made during the Great Depression are just morbidly sad, but this one pulls back at the last moment to give a satisfying, yet fully earned ending.

A Charlie Brown Christmas- Another Christmas movie that could have been just incredibly sad had it ended a minute or two before where it does. Contrary to popular opinion, Linus's biblical explanation of the true meaning of Christmas is not what directly produces a happy ending for Charlie Brown. After Linus's speech, Charlie Brown gather's his Christmas tree and returns to his home. Upon his arrival, he finds that Snoopy has won a cash prize for decoration his dog house with Christmas lights. Although he is momentarily shaken, he resolves not to let his even his dog's seasonal greed ruin his holiday spirit. Instead he removes a bulb from Snoopy's dog house and affixes it to his tree. However, the sapling cannot support the bulbs weight and Charlie Brown, his spirit finally broken after years of missed footballs, denudating line drives, and rejection from the little red haired girl, exits the scene to do god knows what. It's only then that his peers, inspired by Linus's monolog, return and welcome Charlie Brown back into the group.  Like It's a Wonderful Life disaster is ultimately avoided, disaster being explicit or implied suicide, through the saving power of the collective, all be it with the assistance of the the devine.    

Honorable mentions:

Rudolph the Red Nosed Reindeer (the Rankin Bass Claymation one) 

Frosty the Snowman (again, by Rankin Bass)

How the Grinch Stole Christmas (The cartoon by Chuck Jones and narrated by Frankenstein himself, Boris Karloff)

Simpson's Roasting on an Open Fire (Season 1 episode 1 of The Simpsons)

Bad Christmas Movies:

Jack Frost- The good news; Micheal Keaton's your dad and a snowman! This is gunna be awesome! The bad news; your dad is dead. 

The Family Stone- It's just terrible.

Dr. Suess's How the Grinch Stole Christmas- Late period Jim Carrey mugging while under a mound of make-up, facial prosthetics, and fake fur.

The Santa Clause- Tim Allen mugging in a fat suit. Nuff said.

Reindeer Games- If you've forgotten about it, lucky you.

Elf- I know it makes me history's greatest monster, but I hate Elf. Will Farrell can work in small doses, but for over an hour is a little too long.

Santa Claus: the Movie- *Spoilers* It was all just a dream. Santa Claus really froze to death at the start of the movie. Surprise!  

So-Bad-It's-Good:

Santa Claus Versus the Martians- It's exactly what you'd expect. Only with the worst production values imaginable.

I like Lampoons Christmas Vacation,, Christmas Vacation II sucks.

The Ref, National Lampoon's Christmas Vacation, A Christmas Story, Home Alone.