My tradition this time of year is rewatching my favorite holiday movies. Not all of them are technically about the holidays, but they fit this season perfectly.
These are the films I return to again and again. Some feel playful. Some lean whimsical or magical. Others hold sadness, awkwardness, or longing. But every one of them leaves me lighter than when I started. When the credits roll, I feel renewed, hopeful, and happy.
Over time, my relationship with Christmas has shifted. While I don’t personally connect with the religious framing of Christmas, I deeply appreciate the meaning it holds for others and the joy it brings them. For me, this season represents family, love, generosity, connection, and gratitude. Those feelings intensify this time of year; they feel amplified, close to the surface. I feel emotionally charged and so achingly grateful.
That perspective shapes the movies I’m drawn to this time of year. My list might feel a little unexpected. But they offer comfort, perspective, and a sense of renewal. And they always get to the heart of what matters, however silly or serious movies present them.
There’s also science behind why these familiar movies work so well. We aren’t imagining it when we say we feel better after watching them. Favorite movies light us up with happy endorphins, setting off a firework of satisfying emotional joy that makes us feel, well, happy.
Feeling happy, it turns out, is healthy.
Psychologists have found that rewatching films we know and love can genuinely help us feel better. Familiar stories demand less mental effort, which lowers stress and allows the mind to relax. Anticipating scenes we love can release dopamine—the feel-good chemical connected to pleasure and motivation. Familiar stories offer steadiness and emotional reassurance, especially welcome during a full, busy, emotionally-charged season.
So yes, I rewatch these movies intentionally. They’re part of my holiday rhythm. And truthfully, when I need a lift at other times of the year, I return to them then too. Endorphins, you know. But they mostly resonate now.
Here’s my list—and why each one earns its place.
About Time
This is a brilliant movie. At its heart is a piece of sage advice I genuinely try to live by: learn to live every day as if you don’t get a redo. Be mindful of the mundane. Notice it. Respect it. Even love it. What we think we loathe—bad workdays, family chaos, the everyday messiness—isn’t a distraction from life. It is life. This movie reminds me to embrace that truth. It’s magical without being gimmicky, deeply human, and it always leaves me feeling reset in the best way. Quite honestly, it’s a gem.
Addicted to Love
Pure fun. Unexpected. And I secretly—well, not anymore—want to do my makeup and hair exactly like Meg Ryan in this movie. It’s laugh-out-loud funny and delightfully unhinged in the best way. This is my favorite Matthew Broderick role—quirky, charming, and surprisingly tender. Beautiful. Fun. One of those movies that never takes itself too seriously, and that’s exactly why it works.
A Long Way Down
Okay—this one is out there. And a clear warning: this movie deals with suicide and drug use. But hear me out. This is not a bleak film. At its core, it’s about hope, connection, and the unexpected ways friendship can save us.
Pierce Brosnan, Toni Collette, Imogen Poots, and Aaron Paul play four desperate souls who find themselves on the brink—literally—meeting one another at the top of a tall building on the same night. Each has their own reasons for being there. What follows is an unlikely friendship rooted in shared vulnerability and dark humor. As they begin to care for one another, something shifts. They don’t magically fix their lives, but they do find a reason to keep going.
Sounds heavy? It isn’t. The film is playful, endearing, and surprisingly life-affirming. The seriousness is carried by clever writing, moments of comedy, and an upbeat, deeply human soundtrack—so much so that I bought it. You come to love these characters and root for them all the way through. Against expectations, this movie lands on hope.
The movie takes place between Christmas and New Year’s Eve, which feels especially meaningful. That in-between season can be tender and difficult—a time when reflection hits harder and loneliness can feel amplified. This film doesn’t shy away from that, but it doesn’t wallow in it either.
What surprised me most is how playful and endearing it is. There’s whimsy here. There’s heart. And there’s warmth that feels earned, not forced.
We come to care deeply about these characters. We root for them. And we watch them change as they learn to care for one another—discovering that connection, even imperfect connection, can be enough to keep going.
Including this movie in a holiday list might feel unexpected. But maybe that’s exactly why it belongs. Not all holiday movies are about glitter and cheer. Some are about reminding us that we’re not alone—and that hope can show up in the most unlikely places.
The Family Man
This movie feels like fantasy done right. Fantasy is tricky — done wrong and it’s cheesy — but this is a beautiful movie. Téa Leoni is irresistible, and there’s a line in this film that I come back to again and again: “If you need this, Jack, if you really need this, I will take these kids from a life they love and I’ll take myself from the only home we’ve ever shared together and I’ll move wherever you need to go… I love you, and that’s more important to me than our address. I choose us.” Fantasy sure, but that’s real gold there. It’s a reminder that love isn’t about comfort but about choice — and that choice is where the heart lives.
The Family Stone
This movie just works. The cinematography is snowy and bright, the music feels sing-song and fresh, and the family is delightfully unorthodox—which is exactly why I love it. Because really, who doesn’t have family drama? I don’t know a single family that doesn’t. This film manages to be fun, heartwarming, sad, unexpected, and yet traditional all at once. It’s real, and it has all the feels.
And that scene—
when Dermot Mulroney walks away from Claire Danes and the bus,
through the falling snow,
in slow motion—
honestly? Worth the entire watch just to relive that moment.
Be. Still. My. Heart.
How the Grinch Stole Christmas (2000)
Director Ron Howard and Jim Carrey make this movie nearly impossible to criticize. It’s pure fun, deeply feel-good, and absolutely fable-worthy. Beneath the spectacle, it carries real moral weight—gentle lessons about commercialism, belonging, generosity, and choosing people over things. Jim Carrey simply is the Grinch; no other version comes close, and frankly, no other one will do. The whole thing feels oddly flawless. You’ll leave giddy. And really—what more should a Christmas movie do than that?
The Holiday
This is a beautiful movie. I think of it as a Sunday afternoon kind of film—the one you snuggle up to, step into, and leave the real world behind for a while. It’s a joy ride from start to finish. The people—Jude Law, Cameron Diaz, Kate Winslet, and Jack Black—are as beautiful as the scenery itself: sparkly, inviting, and seriously perfect. This movie deserves to be immortalized as one of the great Christmas films. What a fun romp.
Home Alone & Home Alone II
What continues to intrigue me about these movies is how director Chris Columbus makes the entire premise work. You don’t spend the film questioning how a child could realistically be left behind — somehow, he pulls it off. The result is fun, unexpected, and genuinely heartwarming. And the music, composed by John Williams, simply is Christmas to me. The score carries so much wonder and warmth that the movies feel inseparable from the season itself.
Love Actually
Imperfect, sprawling, and unapologetically emotional. I don’t watch this movie for realism—I watch it for connection. There’s something deeply comforting about all those intersecting stories finding their way toward hope. And that scene—Emma Thompson realizing she didn’t get the necklace, Joni Mitchell playing as she gathers herself alone in the bedroom—gets me every time. It’s restrained, human, and quietly devastating. Followed by that final airport scene of people greeting the ones they love? Holiday magic.
In Her Shoes
This movie is about an imperfect family—misunderstandings, old wounds, and the slow, sometimes awkward work of forgiveness. Watching Cameron Diaz’s character grow into her own confidence is the true heart of the story. It’s subtle, earned, and deeply satisfying. And that scene—when she reads poetry to the blind patient—straight to the heart. It moved me enough to go searching for the poem afterward: Elizabeth Bishop’s One Art. That moment captures everything the film does so well—unexpected tenderness, emotional intelligence, and the uplifting power of being truly seen. It’s a beautiful movie, grounded and humane, and it stays with me long after it ends.
The Other Sister
This movie isn’t without its leaps. Most families can’t simply afford a corner apartment in San Francisco for their child, and pretending otherwise would miss the point. But once you set that aside, the film opens the heart in an important way. It asks us to reconsider how easily we limit the independence of those we may not deem capable—and who gets to decide that in the first place. What it shows, beautifully, is that what we want for someone else isn’t the point. Love is love as defined by both the one who gives it and the one who receives it. Diane Keaton and Tom Skerritt shine as parents learning to let go, but the true stars are Juliette Lewis and Giovanni Ribisi. Their performances are fearless, tender, and deeply human—each deserving far more recognition than they received. This movie should be required viewing for its lessons in inclusion, independence, and love on its own terms.
Prancer
I might be a little embarrassed that I watch this every year. Sam Elliott stars in it, so my taste can’t be that questionable. This is a fantasy tale (or is it?) but it’s done in a way that inspires you to believe in Santa and his reindeer. In any case, little Jessica has her reasons to believe in Santa, and her journey makes us root for her with all our might. Who says we need to grow up, anyway? Along the way, she brightens an entire community and makes us believe in the magic of the season. Cloris Leachman’s endearing turn adds so much warmth and heart, grounding the story with humor and humanity. If you’re feeling even a hint of bah humbug about the holidays, this is the remedy. It’s a staple holiday film for me.
The Ref
This one is just plain fun. A total romp. Kevin Spacey and Judy Davis play a married couple who bicker like it’s an Olympic sport, and somehow it all feels completely recognizable. Sometimes the holidays have a way of forcing our true feelings to the surface—and while that can be uncomfortable, it can also be clarifying. In this movie, it takes being held hostage for that clarity to arrive. Denis Leary plays the ref, and honestly, this might be my favorite role of his. He’s sharp, funny, and oddly insightful, calling everyone out while stuck in the middle of their mess. It’s very Christmasy in its own irreverent way, hilarious, and oddly satisfying. Fun, funny, and proof that not all holiday movies need to be sweet to be worth watching.
The Snowman
An absolute joy to watch—an animated film with no dialogue, carried entirely by its music and imagery. I’m usually not one for fantasy, or even animation at this stage of my life, but I fell in love with this film when it came out, and it’s stayed with me ever since. I only watch it once this time of year, which somehow makes it feel more special. Maybe it’s because I still crave the feeling it evokes, which is hard to explain. It’s magical without trying too hard, and simply beautiful. Watching it feels like returning to a piece of art you’ve always loved—familiar, moving, and quietly transporting. What a joy.
With Honors
Brendan Fraser carries this movie, with Patrick Dempsey providing just the right touch of comic relief. At its core, this is a story about dignity—an important theme—but it delivers that message in a clever, approachable way. Joe Pesci plays a homeless man, and the bond that forms between his character and Fraser’s unfolds for unexpected reasons and in unexpected ways. Watching Fraser’s character arc emerge is part of the pleasure; it’s gradual and genuinely satisfying. Set against a snowy winter backdrop, this film is thoughtful without being heavy-handed—and ultimately, a tale with heart.
Endings matter. Familiar stories can be comforting. And feeling lighter at the end of a movie—especially this time of year—feels like a small gift.
These movies always do that for me.
Hope you find one here that does the same for you. Enjoy.
2 comments
My favorite movies this time of year are Elf, and the classic Christmas claymation ones!
Ooh! I will watch Elf and see what all the hullabaloo is about. It’s extremely popular and so you are in good and ample company. I wonder where I can see the claymation ones?