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The TOP 10 Best Movies to Watch at Christmastime

The TOP 10 Best Movies to Watch at Christmastime

Entertainment | December 23, 2020
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Some of my best Christmas memories are about gathering around in the family room on Christmas Eve, watching movies while waiting for midnight to eat Noche Buena, and celebrating by exchanging gifts. We’re Filipino, we like watching TV, and we love movies! While there are movies made about Christmas, there are also movies whose spirit is about the joy, love, peace, giving, and forgiving nature of Yuletide. These are movies that we always come back to this time of the year. And these are mine. (No, Home Alone is not a part of my list. Sorry Macaulay.)

10. The Sound of Music (1965, Robert Wise)

For most of my childhood, my mother would dress me and my 4 siblings up in matching patterns inspired by the von Trapp children on The Sound of Music, Oscar Best Picture winner in 1965 starring Dame Julie Andrews and Christopher Plummer. It’s a story based on a 1949 memoir, The Story of the Trapp Family Singers, and adapted from the 1959 stage musical, The Sound of Music, about an Austrian nun, Maria, who is sent to become a governess of the seven children of a retired Naval Officer and widower. 

Maria teaches all seven very spoiled and mischievous children good and proper behavior through the joy of music. She eventually wins the Captain’s heart and he marries her making her the new mother of the children. From nun to governess to stepmother—it is a beautiful character journey that made Julie Andrews a memorable star. Before Jodi Sta Maria’s “Maya” married Sir Chief in ABS-CBN’s Be Careful with my Heart, Maria did it first.

Also, the music composed by Richard Rodgers with lyrics by Oscar Hammerstein are childhood classics we have hummed to for many, many decades. Among them are My Favorite ThingsSixteen Going on SeventeenDo-Re-Mi, and Climb Ev’ry Mountain, which are treasures in everyone’s songbook.

Dame Julie Andrews’ exceptional performance and the film’s musicality made this timeless classic a must-watch movie.

9. The Holiday (2006, Nancy Myers)

I am in love with Nancy Myers movies! There’s just something always very light and breezy about them. They’re also full of insight and meaningfulness especially through the eyes of a woman who is maturing.

2006’s The Holiday is about two lovelorn women who swap homes for the holidays in two faraway countries to escape heartbreak during Christmas. Kate Winslet plays Iris, a very meek society columnist in London, who flies from across the pond to Los Angeles to switch lives with Cameron Diaz who plays Amanda, a high-strung movie trailer producer, to get away from her ex-boyfriend Jasper (Rufus Sewell) who cheated on her.

Iris is overwhelmed by the fast-paced and frenzied life of Amanda and meets Miles, played by Jack Black, an unlikely match that she opens up to despite initially eyeing his colleague Ethan played by Edward Burns, Amanda’s ex-boyfriend, who also cheated on her.

Meanwhile, Amanda, staying at Iris’ warm and cozy cottage in the country, meets her brother Graham, who is a widower played by Jude Law, and they develop an instant attraction to each other. Their attraction reaches them deeper, as the always guarded Amanda surprisingly shows vulnerability to Graham, and Graham sees an innocence with her that she shared with his daughters.

The Holiday makes you feel some sort of hope, especially if you are heartbroken on Christmas. Makes you want to believe that falling in love is as easy as wishing to exchange lives with someone else and finding love as surprisingly finding a present beneath the tree. That’s Nancy Myers for you, just a feel-good kind of filmmaker.

Light-hearted, easy, and fun, The Holiday plays on the warm sentimentalities of the season.

8. Little Women (2019, Greta Gerwig)

The newest film on this list and the latest incarnation of the classic coming-of-age novel “Little Women” by Louisa May Alcott. Although I’ve always loved and grown up with the Winona Ryder version by Gillian Armstrong, Greta Gerwig’s Academy Award-nominated adaptation starring Saoirse Ronan who is also Oscar-nominated for the iconic role of Jo March is much more modern and joyful in its telling. Gerwig reaches a very fair and balanced accuracy and revisionism to the beloved novel.

Little Women is about Jo March, a woman author who dreams of publishing a book under her own name in a time when only male authors are given importance. She writes under an alias as she continues to push on with her dreams. Unlike her sisters, her dream is not to marry or become a wife (which are also valid dreams, as portrayed beautifully by Emma Watson’s character Meg). She forgoes love while she puts herself first—a real feminist movement in a time before its time.

The story’s moments are set at Christmastime and tell the struggles of a family and the strength of the bond of sisterhood. From selling her hair to caring for her ailing sister to accepting that her childhood sweetheart has married another sister, Jo lives through the many seasons of her life unwavering in the pursuit of her dreams of independence.

But the great thing about Gerwig’s version is that she gives Jo everything. If Armstrong’s version ended with Jo having a successful career, Gerwig’s sees one of my most favorite literary heroines a successful career and love. Because in 2019, shouldn’t women have both?

Saoirse Ronan’s Jo March shows how much has progressed with the feminist movement since the last adaptation.

7. Bridget Jones’s Diary (2001, Sharon Maguire)

Who can forget the scene where Renée Zellweger was running in her animal panties on the street in the snow on New Year’s to chase after a man? I mean, we should all be so confident!

I remember loving this book by Helen Fielding because it was so witty and wickedly funny. I would laugh under the covers or during breaktime at work. Bridget Jones was such a beautifully crafted, overweight and beautiful British woman who embodied most of us and represented all of us in our desire to find the perfect man and have him fall madly in love with us.

And so, the casting of the lead role for the film adaptation was crucial. When Renée Zellweger was cast, there was so much resistance and controversy surrounding that choice, firstly because she was American, and not British. Secondly, because she was thin.

But she proved everyone wrong when she literally beefed up for the role and nailed that British accent, all the while remaining her charming and lovable self. Renée’s role as Bridget Jones fetched her her first Oscar nomination for Best Actress and spawned two sequels.

Bridget Jones is about a single, aspiring 32-year old professional working at a publishing company who fell in love with her boss, sexy, womanizing Daniel Cleaver played to perfection by Hugh Grant, and begins a torrid affair with him. 

When he dumps her for a waif of an American, she spirals into self-pity and morbid thoughts of her cat eating her dead body. But throughout the Christmases and holiday parties her mother would force her to go to, there would always be family friend Mark Darcy. Presumably, an ode to Mr. Darcy of Jane Austen’s Pride and Prejudice played by Colin Firth, who has, unbeknownst to her has always been in love with her.

Bridget Jones is delightful to watch at Christmas because of the modern way it empowers a woman who is less than perfect. And that if someone as delightfully imperfect as Bridget Jones can find a perfect man, so can we!

Renée Zellweger’s character reflected many women’s deep thoughts and insecurities, making her very relatable and inspiring.

6. Eyes Wide Shut (1999, Stanley Kubrick)

Although not really your usual Christmas movie, this erotic thriller by famed master filmmaker Stanley Kubrick is set at Christmastime in sexy, mysterious New York City starring (at the time) real-life husband and wife superstars Tom Cruise and Nicole Kidman.

It’s about a seemingly quiet and boring rich couple that thrives in secrecy and moves around the holidays with sexually charged adventures.

Tom and Nicole play Drs Bill and Alice Harford, who play around with fire around each other flirting and seducing high-class prostitutes and dirty old wealthy men, maybe to make each other jealous. And then they make love like animals. There is so much A-list nudity for both actors, and the air of mystery Kubrick creates around them both is so thick and engaging it makes you want to have a kind of Christmas that is not always homey, wholesome, and safe. 

This movie is filled with innuendo, sexual tension, and mystery. And it will get you in the mood to play a role different than what you’re used to, especially if you are a couple with many Christmases together in your books.

In the end, Eyes Wide Shut is about the gratitude of a kind of relationship that survives the monotony of having everything.

Kubrick directs this passionate play of lovers (his last movie) starred by then husband-and-wife, Tom Cruise and Nicole Kidman.

5. When Harry Met Sally (1989, Rob Reiner)

If you wanna talk about iconic scenes, you can never leave out Meg Ryan’s “fake orgasm” scene at the diner in front of Billy Crystal. It was both shocking and comedic at the same time because you would never expect it from such a wholesome actress like Meg Ryan and such a platonic pairing like Meg Ryan and Billy Crystal. It was so ahead of its time in a way that wakes all men up to the fact that they are not always good lovers because women, for generations now, have perfected the art of faking an orgasm. Feminism, I say.

But yes, even as you would think they are an unlikely couple, at the end of this movie when they kiss at a New Year’s party, it’s impossible that you do not fall in love with them.

For many decades, this movie has been a top staple in the Romantic Comedy genre department and rightfully so because it follows the relationship of two unwitting stranger who would be in each other’s lives for years to be there for each other through breakups and engagements only to realize eventually that they have been in love with each other for years.

Meg Ryan and Billy Crystal play Harry Burns and Sally Albright, who share a long drive from Chicago to New York City discussing their differences in beliefs about relationships. They part in disagreement, never thinking they would see each other again. But as fate would have it, the two would meet over and over again on the same flight and at parties, eventually becoming friends. But one drunken night, Harry and Sally have sex, and that changes everything.

Friends crossing the line still wanting to be friends are brought back together by the sentimentality of the season, eventually making them realize who and what each other is in their life. And that is the enduring magic of this movie.

That best friends always make the best lovers.

The relationship that Harry and Sally had was peculiar but familiar to many of the film’s audiences.

4. The Family Stone (2005, Thomas Bezucha)

Imagine meeting the family of your fiancé for the first time over the holidays and then falling in love with his brother. Yep. That, in a nutshell, is The Family Stone.

Who really has the right to get a guy’s mother’s engagement ring? What or who do you have to be worthy of the family stone?

Fresh from her success as Carrie Bradshaw in Sex and the City, Sarah Jessica Parker plays Meredith Morton, a successful Manhattan executive… from New York City. But she does a good job of distinguishing the two New Yorkers by playing this one with so much conservatism and an uptight way that annoys the heck out of the Stone family at first.

The challenge was to make this character as lovable as Carrie, which Parker does gradually throughout the movie. She is misunderstood, judged, and to some degree, maltreated by her fiancé Everett’s (Dermot Mulroney) family, which makes her retreat even more into her shell. But a series of family misadventures and colorful characters in this very well-casted ensemble superstar cast makes her rightfully the leading lady of the film. And that’s so hard to do when you have an actress as legendary as Diane Keaton in the fold. 

But everyone in the cast does a remarkable job to make each of their roles stand out and shine through. The most lovable, of course, is Luke Wilson who plays Everett’s brother Ben who turns out to be the right fit for Meredith.

Because isn’t that what family is about? Sharing and caring? Even fiancés? Just kidding. 

But yes, the beauty of Christmas is always found in the acceptance of family. It is a love set in stone.

Also starring Claire Danes, Rachel McAdams, and Craig T. Nelson.

Sarah Jessica’s crazy misfortunes are hilarious to a point that these make you want to root for her even more.

3. Love Actually (2003, Richard Curtis)

This Christmas-themed British Romantic Comedy is everyone’s favorite. All with its powerhouse ensemble cast and multi-layered intersecting storylines seamlessly weaving into each other is a well-drawn out masterpiece filled with delight, emotion, and love, actually.

Hugh Grant leads the star-studded cast that includes Liam Neeson, Emma Thompson, Colin Firth, Keira Knightley, Laura Linney, Bill Nighy, Alan Rickman, Andrew Lincoln, Chiwetel Ejiofor, Rowan Atkinson, and the delicious Rodrigo Santoro.

The ensemble movie that started ensemble movies is about 10 separate stories linked by love in terms of friendships and family relations. It is about the many definitions, kinds of love, including unrequited love, forbidden love, and of course, romantic love and the themes of fate, forgiveness, and sacrifice.

It is a beautiful coming together of emotions we feel at Christmas, whether it is a time to let go, a time to start, or a time to be true to your heart.

Love is the best felt at Christmas. Actually.

This famous scene by Andrew Lincoln has served as inspiration for many romantic proposals.

2. Serendipity (2001, Peter Chelsom)

Why are so many Christmas movies set in New York?

Perhaps because it is a city of possibility. And that is why the characters of John Cusack and Kate Beckinsale meet in a New York department store fighting over the last pair of mittens to give as a very neutral Christmas present.

Feeling the Christmas rush and the rush of initial attraction, the two decide to split the pair of mittens and let fate decide if they should ever meet again, serendipitously. 

But before they part, Jonathan Trager (Cusack) and Sara Thomas (Beckinsale) spend a few hours together walking around snowy, dreamy New York City, planting seeds along the way that they will all eventually harvest in the quest of finding each other again.

The movie presupposes that destiny happens in real life and in the busiest city, and though it may seem small, the odds of ever encountering the same stranger again, ever is still pretty much against you.

But love finds a way. And the signs we ask become the spark that lights the way to true love.

Because what other time will you meet someone at their most loving but at Christmastime.

This movie is one of the most romantic I’ve watched, it is truly feel good and will make you want to believe in love on Christmas day. It’s a date with destiny.

The movie paints a wonderful picture of New York at Christmastime and makes you fall in love while doing it.

1. While You Were Sleeping (1995, Jon Turteltaub)

The movie that made Sandra Bullock a star.

She stars as Lucy, a lonely, orphaned, poor Chicago Transit token collector, probably one of the most overlooked professions ever, which makes her such an ideal underdog heroine that you’re almost set up to cheer for.

Every day, in her menial, monotonous life, her only joy is seeing handsome stranger Peter, played by Peter Gallagher, her fantasy man, a regular commuter who one day falls into the tracks and she saves his life.

A series of misunderstandings and mistaken identity ensues when Peter wakes up at the hospital with amnesia and Lucy is mistaken as his fiancé. Lucy plays along because of the love she feels from Peter’s very warm and welcoming down-to-earth family who takes her in as one of their own.

This little act of deception on Lucy’s part is something she wants to come clean about, at the same time the feeling of being welcome she gets from the family is something she has longed for all her life.

But the truth needs to be revealed when Lucy meets Peter’s brother Jack, played by Bill Pullman, who isn’t exactly the man of her dreams but quite obviously a man who is in love with her.

The whole movie will wake up every happy emotion inside you and make you believe that even when you are sleeping and as you are dreaming, the fates align to bring you someone who is meant to be in your life and spend every Christmas with you from then on.

All it takes is just a little courage. Because love truly saves a person’s life.

Sandra Bullock’s charming and adorably funny character made viewers fall in love with and root for her.

These 10 movies are the movies that remind me of Christmas because of the way they make me feel. Because Christmas isn’t just supposed to be merry. It’s supposed to be happy, sad, lonely, hopeful, mysterious, sexy, dreamy, real, true, and most of all, for you. 

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G3 San Diego is a Filipina writer, an entertainment journalist, a key opinion leader, an online talk show host, a third-generation farmer, and a modern-day romantic.
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