Some of these are holiday movies because they feature Christmas in them while some came out in late December and thus are tied to it in my mind. And all of them are ones that I love to watch during the holidays...and all year round.
Meet Me in St Louis
This 1944 classic is actually my favorite movie musical of all time. Not only is it a heartwarming story of a family of all girls growing up in turn-of-the-century America, it also features my favorite Christmas song of all time: "Have Yourself a Merry Little Christmas" as sung by Judy Garland. (And yes, it should always be sung by Judy Garland and no, I don't approve of anyone who uses the "hang a shining star upon the highest bough" line.)
When Harry Met Sally
In all fairness, When Harry Met Sally is actually my favorite New Year's Eve movie. Has any movie ever had a more iconic NYE scene than the one at the end of this film? It also happens to be my favorite film of all time and every time I see a Christmas tree stand on the streets of New York, I think of Meg Ryan dragging a tree along the sidewalk.
Frozen
This movie came out late November in 2013 so I kind of associate it with Christmastime. I unashamedly love Frozen (though I will fight anyone who says it's superior to Tangled) and it's such a great movie to watch with the family that doesn't require too much brain power.
Serendipity
This is a very underrated rom-com with John Cusack and Kate Beckinsale being brought together by fate. And it takes place during Christmastime in New York City. This is one of those movies that veers on being a Christmas movie, but I think it has enough of a plot apart from the holiday that it counts for this list.
Samantha: An American Girl Holiday
As you would expect of any young American woman who loves period dramas, I grew up obsessed with American Girl dolls. Samantha was always my favorite and her movie is an absolute delight, even now at the age of twenty-four. A turn-of-the-century movie about a beautiful rich girl who fights for a better life for her young orphaned friends? Throw in some wonderful performances by Anna Sophia Robb and Mia Farrow and a lovely Christmassy ending and you've got yourself a great film.
Harry Potter and the Sorcerer's Stone
Speaking of children's movie's, I always associate the first Harry Potter film with the holiday season. Maybe it's because the scene in which Ron chooses to stay at Hogwarts with Harry for Christmas was always so poignant to me or maybe it's brainwashing by ABC Family. Either way, it's a great one to watch in December.
While You Were Sleeping
While You Were Sleeping is another extremely underrated rom-com that takes place around the holiday season though this one is set in Chicago and features Sandra Bullock and Bill Pullman. Something about this movie just feels cozy to me and I love that it's not your traditional rom-com in the slightest.
Felicity: An American Girl Adventure
I'm not even mad that I'm featuring two American Girl movies on this list. How could I be when this one gives me a great performance by a tiny Shailene Woodley and a colonial Christmas ball? Add in some plots about rescuing a horse and navigating friendship as war threatens to break out and I'm hooked.
You've Got Mail
This movie is the reason that I used to dream about seeing New York during the holiday season. I think it shows NYC to its best advantage in all seasons but there's something dreamy about the winter part. Plus, it's the rom-com dream team of Nora Ephron, Tom Hanks, and Meg Ryan. Could it get any better than that?
Little Women
I think what writing this post revealed to me is that my favorite Christmassy films are all period ones. Little Women is an absolute beauty of a film and features one of my favorite ensembles of all time. While the film is a bit of an emotional rollercoaster, the holiday section is heartwarming.
What are your favorite Christmassy non-Christmas movies? Let me know in the comments or on Twitter. x