1. Elf (2003)
2. Mixed Nuts (1994)
This is a bit of a lesser known holiday movie, but an excellent one, nonetheless. For an indie-style film, it actually has an awesome cast. The cast includes Steve Martin, Rita Wilson, Juliette Lewis, and Adam Sandler among others. It's been a holiday movie staple in our house for quite a while. I find it really cool that it has all my favorite people, and I just feel drawn to it. I have to also mention that Liev Schreiber's portrayal of Chris is wonderful.
3. National Lampoon's Christmas Vacation (1989)
This is another big one in our household, and it's one of the few holiday movies we actually watch more than once during the season. It's another one with a great cast of people, including one of my favorites William Hickey as Uncle Louis. It's one of those films that really gets you into the holiday spirit, because of how Clark always go overboard. It strangely reminds us not to forget about the holidays.
4. Jingle All The Way (1996)
This is another overlooked Christmas gem, with another bizarre cast, but a great movie to get into the spirit of the holidays, and an actual depiction of the hustle and bustle of the holidays. I always associate this one with my childhood, because I remember seeing it when I was really young and it's one of our many holiday favorites.
5. How The Grinch Stole Christmas (2003)
This movie is seriously marvelous, and Jim Carrey's portrayal of the Grinch is honestly excellent. All the cinematography has such a great look to it too!! The story of the Grinch has this awesome dark, holiday vibe to it, which really makes it stand out in comparison to other holiday movies.
6. Home Alone (1990)
I'm counting the first and second movies because both of these are great. Kevin McCallister is an insanely talented kid when it comes to having a master plan. I love the cinematography in these two, especially that one scene in Lost In New York when they show the twin towers when they were still standing. It's cool to see that preserved on film. All the cinematography is great in the second film, because it really captures Christmas in New York at that time, and it just looks lovely.
7. Scrooged (1988)
This is another childhood favorite, and actually a movie we only have on VHS. For whatever reason, it began my fascination with David Johansen, because that's how I was introduced to him. I always thought he was cool after seeing Scrooged, and he still remains as one of my favorites. Anyway, this is another lovely holiday film that follows that dark, holiday vibe like The Grinch does, which is a lesser explored holiday movie type.
8. March Of The Wooden Soldiers (1934)
This one's always been a tradition from when we were young, but we watch it every year since they play it on Christmas day. We always watch it, after we open our gifts when we're just hanging out for the rest of the holiday. We also watch "Little Spirit: Christmas In New York" and "The Muppets: Letters To Santa" before our dinner too. We also have a tradition, that we get the newest Simpsons season on DVD (since it comes out in December) and we open it and watch it during our breakfast on Christmas morning.
9. The Polar Express (2004)
I can't talk about this movie with discussing the hot chocolate scene because it's one of the greatest things I've ever seen. I just love hot chocolate, and that song always goes through my mind when I have it this time of year. Anyway, this is another lovely Christmas story, all aboard the Polar Express, in a tale of holiday spirit and friendship.
10. Planes Trains and Automobiles (1987)
I actually consider this to be a Thanksgiving movie, but it is holiday themed, so I'm throwing it in any way. We actually watch it every Thanksgiving, and it's always the start of our holiday movie season. It's a beautiful blend of comedy and heartfelt bonding between Neal and Del, despite their arguments. It's one of the best holiday films, period.