Christmas Classics to Watch Over Winter Break

By Ryan Crawley

Now that we are arriving towards our winter break, us teachers finally have a bit of time on our hands. Of course, we will use most of this time for holiday matters and catching up on things we have been putting off lately. 

Still, there are certain traditions we all have around the holidays. We put up the tree a day after Thanksgiving and hang up all the lights around the house. Perhaps we do all of our shopping on a certain weekend. Possibly we all meet at the same relative’s house on Christmas Eve. These are things we do every year, year in and year out.

For quite a few of us, watching movies about Christmas has become part of that tradition. Every year I lie down and absorb these films into my soul. These holiday classics are as big a part of Christmas tradition now as opening gifts and seeing family. At the end of the article, I would love to hear about some of the holiday films that hold a special place in your heart as well.

White Christmas
I’ll watch Bing Crosby sing, act, or even brush his teeth. He was an entertaining fellow. Even though he died in 1977, he was the best selling recording artist of the 20th century. He was cool hanging out with the Rat Pack, playing singing neighbors with David Bowie, and narrating the spooky The Legend of Sleepy Hollow. In fact, his song White Christmas is the best selling single of all time.

Without ruining much of the film (incase you have not seen it), the movie White Christmas is about Bing and a buddy (Danny Kaye) doing a good deed for someone they are fond of. At the same time, Bing falls in love with a girl (Rosemary Clooney) that is young enough to be his daughter. One of my favorite scenes is when they sing Snow while they are on the train. Interestingly enough, quite a bit of White Christmas was improvised on the spot.

12 Dates of Christmas
Yes, I am a guy. But I still enjoy watching this Family Channel-like movie with Amy Smart and Mark Paul Gosselaar. Of course, Gosselaar is famous for his time spent as Zack on Saved by the Bell. It’s a simple film that borrows a bit from Groundhog Day. It is available on Netflix if you are interested in checking it out.

Home Alone
Home Alone stars Macaulay Culkin as a young boy accidentally being left behind at his house on Christmas as his large family cluelessly does not notice until a couple days later. I think I enjoy this film because my large family would often leave me behind in various places as well. Either that or they were just trying to get rid of me.

It’s a Wonderful Life
Jimmy Stewart just never made a bad movie. He was the everyman that most of us could identify with. It’s a Wonderful Life has become the ultimate Christmas classic, and they couldn’t have chosen a better actor to star in it than Stewart.

All of us at one point or another think that everyone would be much better off if we were never born. As teachers, we often consider if we are actually shaping anyone’s life at all. George Bailey, the main character, gets to see what exactly would happen if he was not around. It’s extremely interesting that although this film is considered the go-to Christmas classic, it struggled when it first came out in theaters on December 20, 1946. It didn’t make much money and was initially considered a failure.

Yogi’s First Christmas
Yogi’s First Christmas is hardly ever shown around the holidays anymore. It came out in 1980 and is a who’s who of the characters created by Hanna-Barbera. I remember as a kid watching it every time it was on. It was finally released in 2009 on DVD. I had to go on Amazon and order myself a copy just so I could continue my tradition of watching it every year. The film is definitely one of my favorites!

A Very Brady Christmas
I believe A Very Brady Christmas should be recognized with the other holiday classics like White Christmas and It’s a Wonderful Life. It should be shown every day on television between Thanksgiving and Christmas. I could be a bit bias, though, since I loved the Brady Bunch growing up.

Much of the premise of the movie is a bit preposterous, much like the old Brady Bunch episodes themselves, but it is nice to catch up with all the characters. Spoiler alert, Bobby is now a college dropout and a secret racecar driver. Alice and Sam finally got married, then separated, and Alice came back to work for the Bradys at 97 years old to be a maid again. And Mike and Carol Brady, for some reason, redesigned their house using the worst colors possible. Still, whenever I hear O Come, All Ye Faithful whether in church or on the street, I expect to see Mike Brady emerging from a collapsed building.

A Christmas Story
I think every kid can identify with the main character Ralphie. He wants something for Christmas that he feels he just never will have regardless of how many hints he leaves behind for his mom, dad, and teacher. As a teacher, I think it is quite funny that his teacher wrote a warning on his essay about why he shouldn’t get that BB gun for Christmas. It is definitely something a lot of us have probably done without thinking. But to him, it is heartbreaking.

Holiday Inn
Holiday Inn is another Bing Crosby film centered around Christmas. In fact, Holiday Inn came out before the film White Christmas. In addition, Bing sings the song White Christmas in the film. This time he is joined by Fred Astaire, so you know there is going to be some fancy dancing routines involved. Plus, Bing’s character is pursuing a lady 15 years older than him this time. She might be just a bit too old for him. Once again, Bing Crosby and the holidays are a perfect match!


Ryan Crawley is a writer/educator from Illinois. Born into a family of eleven, he spent most of his childhood watching old reruns of Three's Company and Happy Days. He has his Masters in Reading and Literacy, and is a certified Reading Specialist. He spends his free time writing, working out, and hanging with his two dogs Flair and Smoosh Face.