What are the Best Christmas Holiday Movies of All Time?

‘Tis the season, and a holiday movie marathon could be an excellent way to slow down and savor this time of year. After all, one of the best micro-luxuries of the holidays is an evening of heartwarming movies, hot chocolate and chill. So what are the best Christmas holiday movies of all time? Our expert on all things cinematic, Abbie Martin Greenbaum, has curated a list of the best movies set on or around the winter holidays.

our winter holiday and Christmas movie marathon

It’s the most wonderful time of the year. If we’re lucky, the air around us smells like cinnamon and nutmeg, fresh pine and clean snow. We give and receive beautiful and meaningful gifts, snuggle up with loved ones in front of a roaring fire, and if we’re very lucky, we see miracles come true.

While they can sometimes be goofy, overly sentimental or contrived, we shouldn’t underestimate the cultural significance of Christmas and holiday films. Movies are the meta way we learn How to Holiday.

Not only are they a great holiday activity – who doesn’t want to spend their vacation watching a beloved classic film from childhood? – but they are the way we learn how to be during this time, how we learn what to want from it. These films teach us the lessons that the holidays themselves are supposed to teach us: how to feel grateful for what we have, and hopeful that, just this once, we might get some of the things that we don’t have yet, but that we desperately want.

the best movies set around the winter holidays

On that note, here are our top picks of Christmas and holiday movies that will make for cozy, happy watching this season. They are mostly classics – what holiday movies aren’t? – but they are so tried and true, sweet and sincere, they are worth an annual revisit this time of year.

1. While you were sleeping

Sandra Bullock and Bill Pullman star in While You Were Sleeping, the romantic comedy that is certainly someone’s wacky, impossible fantasy. A woman watches the man she has a crush on (played by Peter Gallagher) fall onto the train tracks and saves his life, only to become embroiled in a complicated web of lies about her relationship to him.

There is something extra sweet about the wish fulfillment of watching Lucy befriend Peter’s family and accidentally fall in love with his brother (there are no spoilers; this movie came out in 1995). This is a movie set at Christmas-time rather than an out-and-out Christmas movie, but it has all the feel good elements: changed self; found family; dreams come true. 

2. Scrooged

Scrooged, the comedic retelling of A Christmas Carol, never gets old. Bill Murray is perfect as Frank Cross, a modern interpretation of Ebenezer. Like the original Scrooge, he has to go on a journey of self-improvement, meeting retooled versions of the three Ghosts (Past, Present and Future) as he learns to re-think his cruel behavior.

The movie is over the top in many ways, but Murray makes it a timeless gem. And its underlying message allows this one to stand the test of time and remain a permanent favorite in the Christmas movie marathon rotation.

3. Elf

Will Ferrell’s Buddy the Elf won our hearts when he first walked onto the big screen in Elf in 2003, sporting a bright green outfit and a sunny disposition.

Most of the movie is ostensibly about Buddy’s experience coming to our world from the North Pole to find his father. But underneath, it’s really about someone who is just a little bit different – and whose differences may help to inspire Christmas (and general) cheer in those around him. This is one that has more moments of humor than anything else, and it’s perfect for anyone looking for a light Christmas film.

Alamo Drafthouse Cinemas will be showing this fan favorite on the big screen one night only nationwide in December, for a full rush of holiday nostalgia.

4. The Family Stone

The Family Stone is a Christmas movie, but of all the movies on the list, it is the one that is most appropriate to watch any time of year. It has everything (and seemingly, everyone). Both emotional and funny, and it’s nuanced in a way that is so unexpected that it makes for a really special viewing experience. 

After all, who wouldn’t want to be a Stone? Your siblings are Rachel McAdams, Dermot Mulroney and Luke Wilson – and your parents are Craig T. Nelson and Diane Keaton?

There is something irresistible about watching Meredith (played by Sarah Jessica Parker), who is the fiancé of one of the Stone sons, interact with the disapproving family. Maybe because the secondhand embarrassment and mutual dislike is simultaneously so relatable and so uncomfortable. The movie swings from a committed chaos to a committed sincerity, and pulls both off with a flair that must be the cause of some holiday magic.

5. This Christmas

A favorite of many, This Christmas is the story of Ma’Dere (Loretta Devine), the matriarch of the Whitfield family. She assembles her six children at Christmas for their first reunion in four years. Various secrets come to light, and ties are strained. The all-star cast includes Regina King as the eldest daughter Lisa and Delroy Lindo as Ma’Dere’s live-in boyfriend. 

The film takes its name and its beating heart from the beloved, iconic Christmas song first released as a single by Donny Hathaway in 1970. Further proof that when it comes to the holidays, there’s no school like the old school.

6. Love Actually

In Love Actually, eight intertwined stories about love play out across London at holiday time. It’s a classic, with a star-studded cast of predominantly British actors, including Hugh Grant, Keira Knightley, Chiwetel Ejiofor, Colin Firth, Bill Nighy, Laura Linney and Emma Thompson.  

The film has become deeply embedded in the lives of some fans. So if you happen to live in LA, you might want to catch the stage show “Love Actually Live.” It returns to the Wallis Annenberg Center for the Performing Arts in Beverly Hills from November 27 – December 29, 2019.

Or see it again on the big screen at Alamo Drafthouse Cinemas nationwide. 

7. Meet me in St. Louis

Meet Me in St. Louis spans the entire year – so it could also be valid summer watching, or fall – but its most pivotal, memorable scenes happen during Christmas time, as the Smith family prepares to leave their beloved home in St. Louis.

Thanks to the beautiful music and Judy Garland’s amazing voice, this nostalgic musical from the 40’s will absolutely sweep you away with it. The film will take you on a ride that is equal parts happiness and sadness, but that will ultimately leave you feeling full of joy.

8. An American Tail

The animated classic An American Tail is a story about a Russian-Jewish family who immigrates to New York after a flood of anti-Jewish sentiment. The family just happens to be the Mousekewitzes, a Jewish family of mice.

The movie opens with a Hanukkah celebration, making it apt for wintertime viewing, but it is also the exact mix of sweet – adorable mice! – and emotional – a dramatic story about the difficulties of immigration! – that makes for the perfect holiday watch.

9. The Holiday

Everyone knows that love and the holidays go hand-in-hand. Romantic Christmas movies are their own beloved genre-within-the-genre, pairing tender plots with attractive actors for movies that play like sections of our high school diaries. And why not? This is the best time of the year to watch dreams come true on screen. 

 The beloved Nancy Meyers film The Holiday starring Kate Winslet, Cameron Diaz, Jude Law and Jack Black is the best of the best. Two women participate in a house exchange, one of them in sunny California and one of them in England. But of course, when they switch, they both end up finding their true loves – and making important changes for themselves along the way.

This is a fluffy love story but with plenty of substance, and that is why we come back to it year after year. In fact,  you can catch it on the big screen over brunch at Alamo Drafthouse Cinemas nationwide during the holiday season.

10. Almost Christmas

 Almost Christmas tells the festive story of a beloved patriarch who asks his family for one gift this holiday season: to get along. If they can honor that wish and spend five days under the same roof without killing one another, it will be a Christmas miracle. Share the holiday love, laughs, and charm with an all-star cast including Danny Glover, Mo’Nique, JB Smoove, Gabrielle Union, Jessie T. Usher, and Omar Epps.

11. The Santa Clause

Thanks to the presence of family tradition, the end of the year, and a lot of time off from work with which to reflect, December is often the best month for looking back – and for nostalgia. It is a time to remember the best, worst and most magical times of childhood.

The Santa Clause is the perfect vehicle for these feelings, since it is both a movie many of us watched as children. And a movie about an adult who needs to see the world through a child’s eyes in order to, yes, become the Santa Clause. This is a movie that really asks both you and its main character to suspend your disbelief – and there’s no better time of the year to give that a try.

12. Home Alone

Another childhood favorite, thanks to Home Alone it was every 90’s kid’s dream to end up stranded in their family’s house and have to set a series of elaborate traps for a pair of robbers. Macaulay Culkin as Kevin McCallister is every child’s role model, as he seems smarter, more creative and more fun than any other child ever.

But what Home Alone does so well is walk the line between a wild, whimsical, flippant adventure and our much-loved holiday sincerity about the unexpected people who come to save us. This is another one that never gets old.

13. It’s a wonderful life

There is no holiday movie list that is complete without It’s A Wonderful Life, the movie that defines what the holidays should be all about: generosity, family, introspection – and of course, miracles.

Watching George Bailey (a young Jimmy Stewart) come to understand his own impact on his community is enough to make even the most jaded viewer feel grateful for what they have, and maybe even believe that wishes can come true. If there is only one movie on this list you have time to watch this year, make it this one. 

And if you want to see it on a proper big screen, IFC Center in Greenwich Village in New York will be screening the film throughout December.

14. The Polar Express

Based on the 1985 children’s book of the same name by Chris Van Allsburg, the film version of The Polar Express is a visual feast. And a boost for the spirit.

When a doubting young boy takes a ride on the Polar Express train to the North Pole on Christmas Eve, he embarks on a journey of self-discovery. The film celebrates bravery, friendship, and the wonders of life that never fade with just a little belief in magic.

The Cinépolis luxury theater in Chelsea in Manhattan will be showing The Polar Express on the big screen in mid-December.

the best holiday movies of all time

That’s our list of the best movies set during Christmas or the winter holidays. What’s your favorite? Enjoy the season!

join our community

For access to insider ideas and information on the world of luxury, sign up for our Dandelion Chandelier newsletter here. And see luxury in a new light.

Abbie Martin Greenbaum grew up in New York City and currently lives in Brooklyn, where she drinks a lot of coffee and matches roommates together for a living. At Oberlin College, she studied English and Cinema, which are still two of her favorite things, along with dessert and musical theater. She believes in magic.

Forward This Article