Love, Actually: I can count on one hand the number of people I've met who don't like this movie (I'm actually having a debate with a friend who just saw this movie for the first time and claims to not have liked it). My parents and I watch this every year (luckily, we're over the awkward-to-watch-with-family parts), and my wireless password is based on a line from the movie (which my dad set up, a sign he's given this movie a thumbs up). Even with the storylines I don't care for (blasphemy, but I don't like Colin Firth's storyline at all), this movie still captures my heart each time I watch it. "I hate Uncle Jamie!"
The Family Stone: so unlike Love, Actually's mass appeal, this movie is very polarizing. Most people complain that SJP is really annoying in the movie (um, she's supposed to be), but I honestly don't focus on that part of the movie. I love stories about big families who are crazy but still get together for the holidays and are there for each other. I love that Thad Stone is deaf, gay, and in a biracial relationship yet that's not at all his defining storyline. I love that they call each other out on their, um, crap. That their house looks magical. That Susannah watches Meet Me in St. Louis on Christmas Eve. Note how I haven't mentioned SJP? Yeah, don't care about that part of the movie at all. Just plop me down in the middle of The Family Stone and I'm a happy camper.
The Holiday: I'm not a big fan of Jude Law as a person, but he is literally perfect in this movie. Mr. Napkinhead continues to crack me up, and his children are my ideal kiddos (I really want to speak in a British accent while my kids are learning to talk so they'll have British accents). I'll let Buzzfeed tell the rest.
While You Were Sleeping: When I was younger, we sometimes had a tradition to watch a video that one of us had gotten for Christmas on Christmas night. One year it was Muppets Christmas Carol, and the next was this gem. Like The Family Stone, it includes a big family that doesn't always get along, but sticks together. Also, the 90s fashions are pretty clutch. And Sandra Bullock is such an endearing person in the movie. Since the movie starts on Christmas Day and ends in January or February, we always watch it between Christmas and New Years.
Of course, there are many chick flick Christmas movies, but these four are actually in my Christmas collection (as in I own the DVD). Now that's saying something. . . .