Okay, clearly I'm the kind of person who likes a little quirk with her Christmas. There's a few facts about me you should know before you take any of my recommendations:
1) I hate Santa. Seriously. I'm convinced that the tradition, however kindly and warm-hearted it began, has become a tool for undermining the true faith and confidence of child-type persons everywhere. Santa=Satan. Just call me the grinch and get over it. I'm absolutely what the Grinch would be, if he had been raised Calvinist. The Grinch is also not on this list.
2) I have a severe distaste for Frank Capra. It's a Wonderful Life is NOT on this list.
3) I have never seen National Lampoon's Christmas Vacation, and I didn't see A Christmas Story until I was well too old to think it was funny, or develop any warm memories.
That's at least five Christmas Classics that aren't making this list. You're bound to think one of them is the shizzle. Are you still with me?
Let's get started. In No Particular Order, the Christmas films I rewatch as often as possible include:
Christmas in Connecticut (1945). I've seen the '92 version with Kris Kristofferson and Dyan Cannon. I only remember hating it. The '45 version, though, is a brilliant combination of sweet Dennis Morgan and wry Barbara Stanwyck. Also, "Cuddles" Sakall really makes it complete. Christmas doesn't exist for me without his practical wit. "Nobody needs a mink coat but the mink!" It's a flight of fancy. A romantic interlude. And the closest I'll ever get to admiring Americana.
A Christmas Carol (1951). Alastair Sim is the other man without whom my Christmas simply doesn't happen. Nobody else in any version of this classic Dickens story, as much as I admire them (Michael Caine especially, because he SINGS! With MUPPETS!) quite captures the giddy glee of real redemption. He's a genius actor, because I watch him, and I don't know if he's ever felt it before, but I know I have. That's what it feels like to get a second chance - to TAKE a second chance. Bless the man.
Mixed Nuts (1994). I discovered this little gem when I was a teenager, and it stuck. It's insane, with a side order of Madeline Kahn. I adore her, but she doesn't make this film. Only the director and a team of highly trained professionals could make this movie. Even Steve Martin doesn't carry the whole film, though he comes off quite deliciously throughout. I grew up in the American Southwest, so I especially liked seeing a Christmas that wasn't compulsorily white, though the cast was.
Snow (2004) Okay, Santa actually shows up in this one. It's actually Santa Fic. but I don't hate it, because although it has that evil "Santa is REAL!" theme, it's so ridiculously fantastic, that I don't care. Besides, although he does wear red (annoyed face), he isn't old, fat, or jolly. He's young, neurotic, and in love. I watch this one for the romance, and for that little fact that must seem like a plot hole just begging for a "HISHE" mock: the magic is there when you need it. If the film were touting a "Santa always wins!" thing, I would reject it entirely. But I identify with Nick. My life works that way. The magic always comes through. Rather than expecting the audience to believe in Santa, he becomes an allegory. I also enjoy Snow 2: Brainfreeze because Family.
The Hudsucker Proxy (1994). Just watched it. Again, the redemption/second-chance theme is heavy and real in a film that's pure invention. The lines are thick, and the acting heavy-handed, but the story is, again, a brilliant allegory with symbols wrapped in sight-gags. This might be my new holiday favorite. It's problematic from a feminist perspective, and not very romantic at all, but visually fascinating and thematically poignant.
The Nightmare Before Christmas (1993). I hate that Disney owns this. But between Skeleton Jack and Batman Returns (1992), Tim Burton really knows how to capture the quirky, subculture, hipster side of Christmas. No redemption allegories, but a lot of subtextual kink and black leather, decorated with Christmas lights. Also, he knows who to invite to his party. In Nightmare that's Catherine O'Hara, in Batman it's Michelle Pfeifer and Christopher Walken (I like Danny Devito too, but his character is a bit extreme for my sensibilities), and in both, Danny Elfman accompanies. Brilliant stuff.
While You Were Sleeping (1995). You don't actually have to watch this one, you just have to be able to quote it. At my house, that involves ironic comments that "these mashed potatoes are so creamy!" every time we start an argument at dinner.
MST3K: Santa Claus Conquers the Martians (1991). While this is technically a television episode revolving around a 1960s film, it's legitimately funny. Though I mention it mostly for my little brother John, who introduced me to it and now lives in the arctic wastes of North Dakota.