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The Most Perfect, Classic Christmas Films to Watch Every Year

What equates to classic Christmas films? There’s probably a universal definition, but to me, it’s the films you watch every year, the ones you can involve the whole family in, and ones you’ll never, ever tire of.

Classic Christmas films aren’t always critically acclaimed, but they do something special—they hit in all the right ways, they keep the magic of Christmas alive even during the gloomiest of years. I love my fair share of overly cheesy Hallmark/Lifetime holiday films and romantic comedies, but the classic Christmas films have it all—an excellent story, a fantastic cast, and the kind of story that holds up.

It’s A Wonderful Life

classic christmas films, It's A Wonderful Life
©RKO Radio Pictures
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No film in the history of cinema could ever compare to the gift of It’s A Wonderful Life. As far as Christmas traditions go, a constant in my life has always been ending the night with the Baileys. The idea that a single human being can see the profound impact they’ve made on those around them is otherworldly. It doesn’t matter how many times I watch it because I’ll cry my eyes out every single time.  

It’s A Wonderful Life isn’t just the most timeless Christmas film, but it’s the most timeless film of all time. There’s a love story, heartwarming friendships, tremendously beautiful performances, and the most meaningful message: “Remember, no man is a failure who has friends.” And at that moment, when the camera pans closer, allowing us to read the note from Clarence, all is right in the world with the potent reminder that failure is nearly impossible in a world where love surrounds a person. And love, being the very heart of Christmas, the very heart of Christ is what makes this idea of angels that much more beautiful to me. A perfect reminder of the fact that it will always get better. The one film where words truly cannot do justice for.

Meet Me in St. Louis

Meet Me in St. Louis movie poster for Classic Christmas films
©Metro-Goldwyn-Mayer Studios Inc

Judy Garland is a living, breathing doll as Esther Smith in Meet Me in St. Louis, and her version of Have Yourself a Merry Little Christmas” is easily (and will always be) my favorite one. Is there ever a dry eye when she sings it? Is it possible not to sob? It’s an absolute masterpiece of a classic—one of the most beautiful renditions of the hardships being behind us. The vulnerability and heart in Garland’s voice is utterly unparalleled.

It’s the kind of film that reminds us of the fact that wherever we are, Christmas can still be the most beautiful time of year. Wherever troubles appear, for a moment, everything will be okay. It’s never easy to move away, it’s never easy to feel like you don’t belong when things don’t go your way, but Meet Me in St. Louis is the kind of film that feels like a home away from home. The production is stunning, the performances are darling, and the story is undoubtedly moving. 

The Shop Around the Corner

A Shop Around the Corner movie poster for Classic Christmas Films
©Metro-Goldwyn-Mayer

Where I imagine many might disagree, my own conscience included as a tremendous fan of romantic comedies and Tom Hanks, but You’ve Got Mail will always pale in comparison to The Shop Around the Corner. As far as holiday classics go, the warmth this film exudes is the romance novel equivalent. Jimmy Stewart and Margaret Sullivan are astounding as Alfred and Keira. There’s at least one person every year who’s surprised this film even exists, so hopefully, this list spreads it a bit farther, and you all join me in celebrating the holidays at Matuscheck and Company!

Enemies to lovers, competitive coworkers, and pen pals? Perfection. It’s the kind of film that hits all the right marks, sets the stage for everything that’s extraordinary, and successfully manages to deliver a whirlwind of emotions. 

The Muppet Christmas Carol

The Muppet Christmas Carol poster for Classic Christmas films
©Disney

Everyone has a favorite version of Charles Dickens’ A Christmas Carol, and The Muppet Christmas Carol just so happens to be mine. The interesting thing is, I don’t necessarily remember if I was a fan of the Muppets when I was a kid, but as an adult, they can do no wrong. I’ve seen every version of A Christmas Carol that exists, yet nothing makes me as weepy as this version does. Perhaps, it’s Michael Caine’s remarkable portrayal of Scrooge. Perhaps, it’s the way the Muppets always exudes a sense of home. Perhaps, it’s the childhood memories, it’s been years, and yet, I still don’t have the words for how this film makes me feel. 

The Muppet Christmas Carol is, in short, perfect. There’s nothing about it I would change, there’s nothing about it that doesn’t hold up, and there’s nothing about it that doesn’t make me feel deeply. 

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Home Alone I and II

Home Alone movie poster for Classic Christmas movies
©20th Century Studios

Is there a single soul in the world that hasn’t seen the Home Alone films? I’m pretty confident the answer to the question is no. We’ve all seen it, and most of us probably love it. I’m also fairly sure that I don’t have to convince anyone to watch this film, which is fascinating all on its own. Comedies are hard to recommend because everyone prefers something distinct to make them laugh, but the magic of these films is that somehow, they work for so many of us. 

Home Alone is a tradition for my entire family (and for many). There’s not a person who doesn’t laugh until their stomach hurts, and we all have such different tastes in films/TV series that it’s a wonder we can all agree on this. The adventures of Kevin McCallister are something special, as is essentially fawning over what an icon Catherine O’Hara is. Merry Christmas, Ya Filthy Animals!

Serendipity

Serendipity movie poster
©Miramax Films

No, this movie isn’t everyone’s consideration for a classic Christmas-themed movie, but because Jonathan (John Cusack) and Sara (Kate Beckinsale) meet on Christmas eve, it’s always been one of my favorites to watch during the holidays. (And because I promised myself I’d only choose two romantic comedies for this feature, I needed to include this one.) 

Serendipity has several points to appreciate, but personally, it’s the idea of signs, the magic of the holidays, and the fact that believing in everything is somehow much easier this time of year. (Even the incomparable Ted Lasso is a fan of the film and he’s right to be!) Sara Thomas (Kate Beckinsale) is a firm believer in the fact that fortunate accidents give us the signs we need to make the decisions that’ll make us the happiest. And throughout the trajectory of the film, watching both Sara and Jonathan search for one another only to miss the chances by mere seconds continuously makes for the best kind of tension that’ll lead to an amazing reunion scene.

It’s all worth it when we’re back on the skating rink with them. There’s a perfect kind of happy ending, and if you’re a romance sap, it’s going to make you cry. Five dollar bills and the book and the gloves, in the end, they’ll all represent something even more prominent, something more beautiful. As will the shared frozen hot chocolate and Eugene Levy being a class act. 

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Miracle on 34th Street

Miracle on 34th Street Classic Christmas films feature
©20th Century Studios

Both versions of Miracle on 34th Street are darling (and while my memory of the 1994 version is fuzzy), for my personal taste, the 1947 version hits in all the right ways. I’m also not the biggest fan of live-action films about Santa Claus, and I typically prefer cartoons if this is the direction we’re going in. Still, everything about Miracle on 34th Street feels authentic and heartwarming. A true Christmas classic in what it attempts to achieve with a riveting screenplay and remarkable performances. 

The idea that belief can carry on towards kindness is the very reason I love films like this because the concept of belief and good deeds transcends even the most jaded hearts. And it’s right up my alley with its tropes, too—second chances at love, second chances at belief, and the type of grace that works to tell the story of why we want to believe in what Christmas represents as a holiday. It’s about the power of love above all things. 

While You Were Sleeping

While You Were Sleeping for Classic Christmas films
©Buena Vista Pictures

Again, while it’s tough to choose between the holiday romantic comedies, promising myself that I was only going to do two absolutely means While You Were Sleeping needs to be included in this list. You can never go wrong with Sandra Bullock, Bill Pullman, and Peter Gallagher. I tend to have mixed feelings about the “amnesia” and “unrequited love” trope together because it needs to be done correctly to work, yet While You Were Sleeping handles it flawlessly. 

While faking the engagement, Lucy falling in love with Peter’s brother, Jack, makes for the kind of meant-to-be, organic romance that I’ll always prefer. The budding friendship, the real heart behind their conversations, and the eventual realization of why it hadn’t worked out previously with others. Romantic comedy dreams. There’s something so innocent about the performances in this film, something so tender and honest that Bullock masters brilliantly in a way that’s always been captivating. And even Pullman because they’re divine as scene partners.

How the Grinch Stole Christmas

How the Grinch Stole Christmas movie poster
©Universal Pictures
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I debated adding this to the list or not, but what are classic Christmas films, if not the movies you re-watch every year? How the Grinch Stole Christmas (star-studded delight and the best version of Dr. Suess’ tale. Jim Carrey is perfect as the Grinch, and Christine Baranski in a film automatically makes it an ace. Plus, the set design of Whoville always floors me. 

The magic of Christmas and belief works so well in this version—it’s no wonder I love it the same way I did when I was 9. (Don’t think about the fact that the year 2000 is 21-years-ago.) But much like Elf and Home Alone, How the Grinch Stole Christmas is so easily quotable, it effortlessly lands itself into a classic Christmas films list without even really intending to. Did anyone realize just how glorious this adaptation would be when they made it? Inquiring minds would like to know. Also, the Grinch’s “help me I’m feeling!” scene acts as one of the best gif reactions to anything.

Elf

Elf movie poster
©Warner Bros. Pictures

Elf is undoubtedly the most quotable Christmas film and the last modern-day comedy that became an instant classic for me. There have been some great comedies to follow, but nothing has achieved what Elf managed to. Will Ferrell is at his best in embodying Buddy the Elf, and the screenplay is a gem. There’s not a single comedy that I’ll quote as much as it.

“OH MY GOD! SANTA’S COMING! I KNOW HIM! I KNOW HIM!” “I just love to smile. Smiling is my favorite!” “COTTON-HEADED NINNY MUGGIN!” And the amount of times I’ve said “you sit on a throne of lies” all throughout the year on random occasions is ridiculous. I call people angry elves all the time as a joke, and it’s entirely because of this movie. It’s a good time, fun for all, and the idea of belief and family encapsulates the magic of Christmas too.

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