9 Movies And TV Shows I Have To Watch Every Holiday Season

James Stewart, Donna Reed, and Karolyn Grimes in It's A Wonderful Life
(Image credit: RKO Radio Pictures)

I know almost everyone has a holiday TV and movie ritual. There are some Christmas movies that some of us have to watch during the holidays. This could include Christmas classics such as Home Alone or The Santa Clause. Usually, it includes at least one of the best Christmas movies of all time. It doesn’t feel like this joyful season without watching these films. I have plenty of must-watch TV shows and movies from December to January. 

Some people start their holiday viewing traditions in November. Personally, that’s a little too early for me. Once December hits, I speed ahead by watching a few of my favorite holiday movies. Of course, that includes some great romantic Christmas movies and ones that were vital to my childhood around the holidays. 

Let’s discuss the movies and TV shows that make the holidays feel truly special.

Peter Billingsley in A Christmas Story

(Image credit: MGM)

A Christmas Story 

As I age, I can kind of see that A Christmas Story isn’t the most perfect movie of all time. There are issues. However, nothing will stop it from being one of my favorite movies ever. This is probably because it’s the film that I have seen most in my lifetime. I never grow bored of it. A Christmas Story is that classic tale of really wanting one thing and everyone denying you it.

You finally get it, and spoiler alert, you shoot your eye out. What a classic metaphor for life. I don’t think that there has ever been a Christmas since I can remember Christmases that I haven’t watched A Christmas Story. I really enjoyed A Christmas Story Christmas but I am not sure it’s earned its place yet in my Christmas tradition. I may rewatch it occasionally but I am not sure if I’ll still be watching it 30 years from now. I definitely will continue to watch A Christmas Story many decades into the future. 

Sandra Bullock and Bill Pullman in While You Were Sleeping

(Image credit: Buena Vista Pictures)

While You Were Sleeping 

There are many holiday-based rom-coms that I love. I know some things about Love Actually didn’t age well, but I still sometimes rewatch it during the holidays. My holiday film tradition often includes holiday romantic comedies that I occasionally watch, but While You Were Sleeping has recently become a must-watch Christmas movie. I've always loved the movie. However, only in adulthood have I begun to make it part of my holiday custom.

Sandra Bullock is my favorite romantic comedy heroine and this film best exemplifies her on-screen charm. Additionally, the movie world failed us by not making Bill Pullman the romantic lead in more films. This film rectifies that error. While You Were Sleeping being a film set in Chicago also adds to its specialness. 

Jack Skellington in The Nightmare Before Christmas

(Image credit: Buena Vista Pictures)

The Nightmare Before Christmas

The Nightmare Before Christmas is also one of those films that I have seen a million times and would watch a billion more. I don’t watch it every Christmas but I try to watch it almost every Christmas (or Halloween). 

It’s just a comfort film that also happens to be done really well. It is a film that I appreciate more as I age because I notice new elements. I find new things to admire, especially when it comes to  The Nightmare Before Christmas’s technical precision.

Bill Murray and Carol Kane in Scrooged

(Image credit: Paramount Pictures)

A Version Of A Christmas Carol 

There are a lot of great Christmas Carol films, so I have plenty of options. Scrooged happens to be one of my favorite versions of the story. Therefore, I often watch it. However, I also enjoy watching new takes on the Charles Dickens tale. And I enjoy watching favorites from my childhood, such as A Flintstones Christmas Carol. Recently, I even added another layer to my Christmas Carol yearly habit by listening to an audiobook production of it.

The story doesn’t get old. Therefore, if the world keeps making versions of this story, I’ll keep watching (or listening) to them. 

James Stewart, Henry Travers, and Sheldon Leonard in It's A Wonderful Life

(Image credit: RKO Radio Pictures)

It’s A Wonderful Life 

Maybe I am misremembering, but I felt like every year, It’s A Wonderful Life used to air after the Macy’s Thanksgiving Day Parade. This would signify that the holiday season had begun. If I didn’t watch It’s A Wonderful Life, the holiday season wouldn’t officially begin. This still somewhat rings true.

The holidays don’t quite feel complete without at least one viewing of It’s A Wonderful Life. 

Levi Miller and Olivia DeJonge in Better Watch Out

(Image credit: Well Go USA)

An Unconventional Christmas Movie 

This is a newer viewing tradition that started with adulthood. I love all the wonderful joyful Christmas movies. However, I have to watch at least one unconventional Christmas movie. For some, this could mean an action movie like Die Hard or Batman Returns. For me, this means some form of holiday horror film. Some of my favorites are Gremlins and Better Watch Out. I usually watch at least one of my favorite holiday horror movies or a new one each year.

This year, I have already knocked this off my holiday film checklist with It’s A Wonderful Knife. However, I could always go for more holiday horror, which likely means quite a few more holiday horror films before January.

Jack Frost claymation special

(Image credit: NBC)

A Claymation Classic 

I like to believe having classic claymation holiday films playing in the background on Christmas is a universal childhood thing for millennials and Gen X. This includes Rudolph The Red-Nosed Reindeer, Santa Claus Is Comin' To Town, Jack Frost, and many other popular claymation Christmas films. I am a little too old to still enjoy the magic of them. However, I usually watch at least one of these films (if not several) during the holidays, just for nostalgia purposes and to remember the bills-free years.

Cora Kirk and Asa Butterfield in Your Christmas or Mine 2

(Image credit: Prime Video)

A New Christmas Movie 

Netflix, Hallmark, Lifetime, and now Peacock, Prime Video, and other streaming services and networks are getting into the yearly Christmas movies market. So many of my favorite Christmas and holiday movies tie into childhood. However, I am always looking for a new addition to my holiday TV shows and film rotation. 

This means that if any new Christmas or holiday movie sounds interesting, I watch it. I have enjoyed a few of the new holiday films that I’ve watched in the last few years. However, I haven’t found any permanent ones yet, but I enjoy the search.

Nicole Byer hosting Nailed It! Holiday

(Image credit: Netflix)

A Holiday Cooking Or Baking Series 

Cooking holiday meals has become part of my new tradition. Therefore, I enjoy watching holiday cooking shows for inspiration. Additionally, I just enjoy the simplicity of cooking and baking programs. Max has a wide catalog of this type of programming. Therefore, I don’t have a specific holiday cooking or baking show I watch every year, instead, I  just see what looks interesting on Max, Netflix, and similar streaming platforms. 

A big part of the magic of Christmas and other holidays is the traditions. For me, and many others, a major part of that involves Christmas movies. I just don’t completely immerse myself in the season without viewing the shows and movies mentioned above. I look forward to these annual holiday film and TV show marathons. 

Jerrica Tisdale
Freelance Writer

Spent most of my life in various parts of Illinois, including attending college in Evanston. I have been a life long lover of pop culture, especially television, turned that passion into writing about all things entertainment related. When I'm not writing about pop culture, I can be found channeling Gordon Ramsay by kicking people out the kitchen.