20 of the Saddest Christmas Movies of All Time
Reading Time: 8 minutesThe holidays are a time for big emotions. The weather’s extreme (in many places), there’s too much to do, and family gatherings offer up wild swings of intense feeling: joy, excitement, apprehension, annoyance, exhaustion. The movies (and life) teach us that any holiday meal with a sufficient number of guests must involve drama of some sort: somebody’s pregnant, somebody’s getting married or divorced, someone’s coming out of the closet, someone’s dying. The season truly has it all.
The movies offer us the opportunity to escape from all that by watching other people deal with their drama—and we’re not so much interested in subtlety and nuance, because that’s not what’s in the air. Is it even a Christmas movie if you’re not bawling into your eggnog? Many of the saddest Christmas movies share very similar plot beats (it’s Dickens’ world; we’re just living in it), but it’s in the execution that they rise or fall. The most successful of them take big swings and hit us right where we live.
Obviously. It’s easy to dismiss It’s a Wonderful Life as over-played holiday schmaltz; constant public-domain airings resurrected it from near-obscurity, but also turned it into seasonal wallpaper. It’s always playing in the background, but nobody’s paying all that much attention—which is too bad, given that it’s a much weirder and more nuanced film than the bit about angels and bell-ringing would suggest. We can only watch as George Bailey compromise his dreams over and over again, only to find that what little he has built rests on a house of cards. America, amirite? There’s real emotion in George’s breakdown, and a (mostly) satisfying catharsis in the ending, which is harder won than in many other gentler, cozier Christmas classics.
Where to stream: Prime Video, Plex
Holiday gatherings always offer great potential for comedy and drama, with The Family Stone landing a bit of each. The setup involves Dermot Mulroney bringing home his new girlfriend, played by a fearlessly brittle Sarah Jessica Parker, for Christmas. That doesn’t go great, with the visitor constantly feeling out of place and embarrassed amid the insular, tight-knit, standoffish clan—which, relatable. But, in the background, strong-willed matriarch Sybil Stone (Diane Keaton) is also looking for an opportunity, amidst the holiday chaos, to reveal a terminal medical diagnosis. The subtle final shot lands like a sledgehammer every time.
Where to stream: Starz
The chemistry between Rooney Mara’s Therese and Cate Blanchett’s Carol is palpable from the moment their eyes meet across a crowded department store—but it’s the 1950s, and theirs is a love that dare not speak its name, even to one another. Queerphobia was, as we all know, entirely eradicated decades ago, so it might seem odd that a gay romance would raise eyebrows…but that’s just how things were back then. The women suffer for their love, but the tears come less when things are going bad as when it starts to feel like they might just possibly start to go a little right.
Where to stream: Tubi, Pluto, Vudu, Hoopla, Freevee
The sequel to 2013’s The Best Man, this one quickly updates us on the fallout from that earlier film before moving into new territory (it’s not strictly necessary to have seen the original if you’re looking to dive straight into the holiday festivities). Morris Chestnut, Taye Diggs, Regina Hall, Terrence Howard, and Sanaa Lathan lead the sequel, which offers a bold blend of off-color humor, hot shirtless guys, sincere religious themes, and shamelessly heartbreaking plot twists. It all somehow mostly holds together. It’s a well-acted soap opera with over-the-top moments of comedy, family drama, and tragedy, hitting every emotional beat you’d want from a holiday movie.
Where to stream: Peacock
A fictionalized version of a true story, this Academy Award nominee deals with an unusual moment during the first year of World War I, when, at several points along the front lines, French, German, and British soldiers called a series of informal truces, often mingling to celebrate Christmas Eve and Christmas Day. The German Crown Prince even sent the lead singer of the Berlin opera to perform along the front lines, entertaining both sides. In dramatizing the event, the filmmakers understand that the truce was both glorious and absurd—after all, if soldiers could stop fighting for an evening, why not forever? Those complicated feelings, and the knowledge that what we’re seeing represents a momentary lull in a war that would continue for years, make for powerful emotional moments.
Where to stream: Tubi
For a musical that’s perhaps best known for Judy Garland’s epic ode to old-timey streetcars, there’s a surprising bit of emotional depth here. Following the upper-class Smith family for a year starting in the summer of 1903, the movie tracks changing times and changing circumstances—nothing excessively dramatic, unless you’re Margaret O’Brien’s joyfully morbid Tootie, who suddenly finds that the things that she expected never to change are more precarious than she thought possible. The key moment is Judy Garland’s heartbreaking performance of ‘Have Yourself a Merry Little Christmas,’ a song that was later brightened up for radio but that, here, implores us to enjoy what we have while we have it—because the future is uncertain.
Where to stream: Digital rental
Blending inspirational sports-movie stuff with a bit of holiday magic, this seasonal staple finds the young teens at Philadelphia Hebrew Academy struggling build up their basketball team in spite of their truly awful coach. A struggling outsider enters the picture, and might be the one who can put them on the right track…if only the students and faculty will put their trust in him. The moment when the local rabbi relates the story of Hanukkah in relation to the kids’ basketball game is honestly pretty darned effective.
Where to stream: Disney+
Writer/director Kenneth Branagh’s indie isn’t nearly as dour (or bleak) as its title might suggest, being more of a black comedy about a depressed, out-of-work actor who gets talked into staging a Christmas production of Hamlet (very Branagh, that) in an effort to save his sister’s church from greedy land developers (aren’t they always). The let’s-put-on-a-show-to-save-whatever premise has been done, but sharp performances and the director’s clear affection for Shakespeare lend the film added emotional resonance, even if you’re not a sucker for stories about finding the true spirit of the season in connecting with others—but who isn’t, really?
Where to stream: Digital rental
The Grainger family could be forgiven for giving up on the holiday spirit entirely: Jack is out of work, and Ginnie’s job at the grocery store isn’t enough to save the family home—which doesn’t matter much, as she’s about to lose that gig too. That’s all before a botched bank robbery leaves their two kids with only one parent. Fortunately, there’s an angel waiting in the wings, but he’s played by Harry Dean Stanton, so definitely not the cheerful sort. Daughter Abbie winds up being the family’s only hope for something resembling a happy ending, but there are a lot of reasons to shed tears before the final act.
Where to stream: Disney+
We can’t get enough to alternate timelines and glimpses into roads not taken, and Family Man represents a slightly more modern, fully Nicholas Cage-ized, and therefore more extreme, version of the trope. Here, a boring (but successful) corporate drudge gets sucked into an alternate timeline where he married Tea Leoni (the one who got away in his native timeline) but is also jobless and stressed by his inability to provide for his family. No life is ever perfect, I guess. When returned to his own timeline, he takes the opportunity to reconnect with the old girlfriend that might have become his wife…except that, even with lessons learned, there’s no way to get back the time they lost or the children they had in the other timeline. (It’s all very that-one-episode-of-Star Trek: The Next Generation.)
Where to stream: Peacock
With a bit of the ol’ Christmas spirit, otherwise tough New York District Attorney John Sargent (Fred MacMurray) agrees to let shoplifter Lee Leander (Barbara Stanwyck) out on bail, and even offers her a ride to her mother’s house in Indiana on the way to his own family gathering. The trip naturally includes moments of comedy and hints of romance, but it’s the ambiguous, not entirely happy ending that really packs a punch—suggesting that the manipulative Lee might have been genuinely moved by her time with John.
Where to stream: Digital rental
Emilia Clarke and America’s sweetheart Henry Golding have tremendous chemistry as a down-on-her-luck aspiring singer and the slightly mysterious man with whom she shares a lovely and inspiring holiday season. The twist ending here will either work for you, or it really won’t (either way, it’s hilarious on paper), but in the context? I was prepared to chuckle, but it still got me in the end.
Where to stream: Fubo
I have yet to find a Muppet movie that won’t leave me in a puddle, so this one’s an easy addition. It’s more true now than ever, though—Disney+ has finally made available a musical segment that was cut shortly after release and that, while sporadically available in various home releases, hasn’t been part of the movie for quite some time. It’s a moment between Scrooge (both present and past), and Belle, whose love he cast aside before giving in to a life focused on money. The Muppet goofiness stops for just a few moments that make the emotional stakes for Scrooge clear, and for Sir Michael Caine to warble a tune.
Where to stream: Disney+
A Christmas Tale plays with some of the same ideas as does The Family Stone, even to the point of casting a legendary lead actress—in this case, Catherine Deneuve as the matriarch recently diagnosed with leukemia. This French comedy-drama goes a bit deeper and darker in its exploration of family dynamics around the holidays, but also approaches its central family with more empathy, acknowledging that, as we change, so do even our most stable relationships.
Where to stream: The Criterion Channel, AMC+, Pluto
A face familiar (and welcome) to American indie movie fans, Kentucker Audley stars as a Christmas-tree salesman returning home to New York, an act which only exacerbates the downward spiral of depression and a sense of failure he’s been mired in for years. He’s living in a trailer and just barely getting by before a mysterious woman enters his life, alongside some weird and eclectic customers who help him fight his self-destructive impulses. There are familiar beats here, but filmed with more realism and restraint (writer-director Charles Poekel partially financed the film with money from his own depressing Christmas-tree salesman job), so the darker moments hit a bit harder, while the moments of light feel very well earned.
Where to stream: Kanopy, Mubi
A charming, bespoke Santa origin story based on nothing in particular, Klaus finds the lazy son of a postmaster general in 19th century Norway forced to a distant island town where he’s tasked with delivering 6,000 letters within a year, otherwise he’ll be cut off from the family fortune. Arriving there, he discovers the two primary feuding families can’t be bothered to send letters for him to deliver, but that an elderly widower might be able to help him in a scheme he’s concocted to convince the town’s children to write letters in the hopes of receiving toys in return—toys crafted by old Klaus in hope of a family that never materialized. It’s all beautifully hand-animated, and the genuine emotion wrings tears with Pixar-like efficiency. I defy you not to cry during the final act.
Where to stream: Netflix
Will Smith plays an advertising executive who retreats from life following the death of his daughter. His friends and loved ones aren’t able to connect, and he tries to cope by writing letters to his conceptions of Love, Time, and Death—all of whom respond. It’s all a bit silly, but Smith leads a fabulous cast who very nearly sell the fantastical premise, and offer some genuinely weepy moments.
Where to stream: Netflix
Less an outright tearjerker than a quietly emotional coming-of-age story, this Québec-set story sees young Benoît helping his undertaker uncle on the day before Christmas in their rural town. The two bond, and fall out, while transporting the body of a teenager who’d died unexpectedly—though once Benoît’s hero, Antoine reveals, over the course of the day, that he hates his job and his life, and that drink has become his only escape. As a picture of growing up during troubling times, it’s an all-around great movie.
Where to stream: The Criterion Channel, Kanopy
Though, at moments, it looks a bit like a horror movie, the Michael Keaton-starring Jack Frost is surprisingly affecting, especially for a generation of kids who saw it at just the right age. A year after the Christmas-day death of his often-absent father, his young son Charlie finds that he’s been magically restored to life as a snowman on the lawn. On paper, the idea of a snowman possessed by the ghost of your dead dad must’ve been a tough sell, but as a story about the deep-rooted desire for just one more day with a lost loved one.
Where to stream: HBO Max
This grim seasonal drama is already depressing on its face—the plot follows a young girl who determinedly maintains her holiday spirit despite the recent death of her mother, her father’s depression, and the failure of the family business—but is somehow made all the worse for the stark realism with which director John Hancock treats the material; the movie is slowly paced, near-colorless, and nakedly unsentimental even when the girl rescues a wounded reindeer she is convinced fell off of Santa’s sleigh. THe ending refuses too be too happy; the most it can offer is a reconciliation between the girl and her depressed dad, who offers that even if their whole lives continue going to shit, at least they’ll still have each other. Merry Christmas!
Where to stream: HBO Max
The beautiful Oscar-nominated short film finds a young boy having a series of adventures with an especially well-crafted snowman. Suffice it to say that snow-people have all too short a season, and the lesson here winds up being a deeply poignant one about the bittersweet beauty of impermanence and change.
Where to stream: Prime Video, Vudu, Pluto (It’s also readily available on YouTube.)