Christmas in Connecticut. These movies are in no particular order, except this one, which happens to be my absolute favorite Christmas movie. It's basically a 1940s romantic comedy set during the holiday season. While there are aspects of it that require a suspension of disbelief (like the whole baby situation), it's hilarious and charming. Barbara Stanwyck is spot-on with her comedic timing, and Felix is an awesome character. This movie doesn't get near the attention it deserves! (Review here.)
The Shop Around the Corner, In the Good Old Summertime, and You've Got Mail. I'm tying these all together, because while they're basically the same movie, they're all worth watching. :) The Shop Around the Corner was the first film adaptation of a play, made in 1940 and starring Jimmy Stewart and Margaret Sullavan. It's such a sweet movie, and while it's essentially a romantic comedy, part of the story line is a bit darker than the next two. (Review here.) Nine years later, the story was remade into a musical: In the Good Old Summertime. (Despite the title, all but the first and last minutes are set during Christmas time.) This one has Judy Garland and Van Johnson, and it's probably one of my favorite musicals. It's very similar to the first film in basics, though it's lighter and much more of a comedy. (Review here.) And then there's You've Got Mail, one of my favorite chick flicks. It's a loose modern remake, though there are some references to the original if you pay attention. I watch this movie year round, of course, but parts of it are set during Christmas.
A Charlie Brown Christmas. I've watched this every Christmas for as long as I can remember, and you probably have, too. So I don't think much of an explanation is required. :) It's charming and classic and the soundtrack is perfect. (Review here.)
Holiday Inn. I might actually prefer Holiday Inn a tiny bit more than White Christmas. It's a classy musical starring Bing Crosby and Fred Astaire, with lots of clever holiday songs (for Christmas and more obscure holidays) and good humor. And of course you get Bing Crosby singing and Fred Astaire dancing. (Review here.)
White Christmas. While Holiday Inn is classy, White Christmas feels a little tacky at times, but that's okay. I love about half of the musical numbers in this one and really dislike the other half, but the cast is great and I love the military aspect of the plot. (Review here.)
Elf. Elf is definitely my favorite modern Christmas movie. It also makes me laugh more than any other movie on this list. No matter how many times I see it, Buddy's antics always crack me up. I love the references to classic Christmas movies, all of Buddy's quotable lines, the soundtrack, everything. It's a lovely film. (Review here.)
The Santa Clause. I grew up watching this one, so my affection for it might be largely because of how nostalgic it makes me feel. I have a soft spot for cheesy 90s films. :) But honestly, it's a cute movie that's quite funny. I don't really like the sequels, though. (Review here.)
It's a Wonderful Life. This seems to be most people's favorite Christmas movie. It's not mine, but I definitely get the appeal. It's a timeless classic. I just have a hard time with Jimmy Stewart sort-of being an unlikable jerk for a big chunk of this film...he usually plays nice guys. (Review here.)
Miracle on 34th Street. I don't love this movie, but it's charming and I like it enough to watch it every year. It's a sweet, fluffy, Santa-themed Christmas film. (Review here.)
The Bishop's Wife. The best thing about this film is Cary Grant, by far. It's a quiet, slow sort of movie, and while it's not an absolute favorite, I always like it more than I remember. (Review here.)
And a few honorable mentions...I use Christmas as an excuse to watch While You Were Sleeping again. :) It's one of my favorite movies and I've seen it more times than I'd like to admit. Since it's mostly set during Christmas, it has that cozy feeling. (Review here.) I also watch Sleepless in Seattle in December, because it takes place between Christmas and Valentine's Day. And because I grew up watching them, I usually check out the classic Rudolph the Red-Nosed Reindeer and Frosty the Snowman TV specials at some point during the month.
Which Christmas films do you watch every year? Are there any "classic" ones that you don't actually like?