1. It’s A Wonderful Life
Spoiler-Free Synopsis: A down-on-his-luck man get’s a glimpse of what the world would have been like if he hadn’t been born.
The holiday movie of the last few generations and the King until about 8 years ago or so. So much so that it was usually shown about a dozen times per holiday season, until NBC bought the exclusive rights. Now it pops up once or twice per year. It’s still a classic, and still my favorite. It’s been spoofed, mocked and re-imagined so many times over the years that people have lost count. It’s also nearly impossible not to get choked up at the end.
Because of it’s significance as one of the all-time holiday classics, this one is probably must see, but I suspect many younger people would leave disappointed. Still must see in my opinion.
2. Bad Santa
Spoiler-Free Synopsis: Two thieves befriend a loserish kid while working as a mall Santa Claus and elf before attempting a Christmas Eve robbery
Although I could never make it #1, if nothing else because it’s so offensive, Bad Santa is the only movie on this list that I could watch any time of the year. Billy Bob Thornton plays a raunchy, trashy guy like no one else can. The swearing, puking, pants-peeing and drunkenness bring out the holiday cheer in everyone! It’s also John Ritter’s last movie and has a great performance by the late Bernie Mac.
Well deserving of it’s R-rating, this one is not for kids. But if you like raunchy comedies, this is as good of Christmas movie as you can get. Not worth watching on cable, definitely Netflix or borrow from someone.
3. A Christmas Story
Spoiler-Free Synopsis: A man retells the story of his Christmas quest for a BB gun in 1940s.
If It’s A Wonderful Life is the holiday movie of the last generation, A Christmas Story is the movie for the current generation. Part of this has to do with TNT’s decision to run this movie for 24 straight hours every Christmas. The amount of things I saw in stores this year related to this movie was very surprising. The leg lamp and the bunny suit have become iconic parts of Christmas, and more kids know about sticking your tongue to cold things because of this movie. The fact that this movie is 28 years old, but only seems to be gaining steam still blows my mind
I thought it was impossible for people between the ages of 15-55 to have not seen this movie, but I was recently proved wrong. A must watch for anyone who celebrates Christmas. Because of TNT’s 24-hour marathon, anyone with cable should have no problem seeing it.
4. The Family Man
Spoiler-Free Synopsis: A wealthy, successful man gets dropped in an alternate universe where he is married to an old girlfriend he always regretted leaving.
A controversial pick undoubtedly, and also a re-imagining of It’s A Wonderful Life, The Family Man is another movie that I have seen 10 times for sure. Of course it’s cheesy, and Nicholas Cage isn’t Jimmy Stewart, but I still enjoy it. It aims to deliver a message about what is really important in life and whether or not money is the answer to lifelong happiness, but not in a deep way.
Pops up on TV here and there. Enough funny moments in my mind to be worth your time, including his fictitious daughter figuring out that something isn’t right with her dad.
5. Home Alone
Spoiler-Free Synopsis: A boy is accidentally left home alone when his family goes to France for Christmas, and he must fend off cat burglars intent on robbing his parents’ lavish home.
Macaulay Culkin deserves a lot more credit for this command performance than he ever receives. He was not even 10 years old when this movie was filmed and he just owns it. The funniest thing about Home Alone, for me, is that this is where I first met Joe Pesci. I knew nothing about him before this, and looking back, it’s so weird to think of him in this movie. I enjoy this movie for personal nostalgia as much as anything, and like I have said about The Goonies not being good upon first viewing as an adult, I am sure this movie would be the same.
There’s enough of a feel-good story in this one to make worthwhile to show kids nowadays. Also, it doesn’t feel all that dated. The fact that internet and cellphones would have made the plot easier to fix, it’s so implausible already that it doesn’t really matter.
National Lampoons Christmas Vacation – Funny, but overrated. The Christmas lights remain iconic, but much of this movie could be ignored.
The Santa Clause – Tim Allen at the peak of his popularity. This one is a clever, original story that has it’s moments, but wouldn’t be on my list of must see.
Home Alone 2: Lost In New York – Included only because my sister insists it’s a package deal with the original. Blatant cookie cutter move from the first one, where Kevin basically learns the same lessons again.
How The Grinch Stole Christmas (the original) – Must see for anyone who grew up with Dr. Seuss. I have to be in the right mood for this one.