The Greatest Holiday Movies of All Time

Hyperbole? I think not.

Gillian Armstrong could not stop crying.

The director, on location in Vancouver filming 1994’s Little Women, the greatest holiday movie of all time, sat behind the camera, stunned, as 14-year-old Claire Danes, her Beth March, burst into spontaneous sobs. The scene involved Marmee (Susan Sarandon) helping frail, sickly Beth walk down the stairs on Christmas Eve. She steers her daughter into a cozy, candlelit room where family and friends pull back a curtain and reveal a charming wooden piano, a gift from a neighbor, Mr. Laurence (John Neville). “I should have given it to you long ago,” the old man declares. “It belonged to my little girl, who had to leave us when she was very young. But now, it will make music again.”

Beth, a gifted pianist, begins to weep viscerally, overcome by the gesture. Sitting down at the instrument, she smiles through tears while playing “Hark! The Herald Angels Sing” for the festive occasion. It’s a joyful performance that pierces the heart — Beth, you see, is not long for this world, an unspoken truth, and until then she bravely muddles through somehow.

Danes, always prepared, knew what was coming, yet she hadn’t anticipated her reaction to Mr. Laurence’s generosity. The waterworks were contagious.

“She was meant to be affected by this present but actually, she just started sobbing — these deep, deep sobs and it was shocking,” Armstrong recalled when I interviewed her for my Jo March tribute in Vanity Fair. (Many of her memories, including this one, hit the cutting-room floor.) “We all started crying. I was crying. Her sobs were so deep and heart-wrenching. People know these sobs now because of Homeland. They know Claire very well, but the way her face just crinkled — that was unexpected. When I realized it, it was a wonderful, very real moment, and my greatest panic as director was to quickly get the camera around on the rest of the family because they all started tearing up and I wanted to catch that while it was fresh.”

Armstrong added, “I could hardly call ‘Cut.’ I was sobbing as much as anyone.”

Her timeless adaptation of the Louisa May Alcott classic is a handcrafted celluloid valentine, and it wrecks me, my friends. At once epic and intimate, it boasts unforgettable performances from Danes, Winona Ryder, Kirsten Dunst and Trini Alvarado as the iconic sisterhood, Sarandon as the wise matriarch and Peak Christian Bale as the swoony boy next door, Laurie, an adorable fop. The picture, more comforting than a limited-edition Starbucks peppermint mocha (oh, you love it), evokes all the best Christmas songs: It’s happy, sad and hopeful, awash in childhood memories, yearning for home. Thirty years ago, when Armstrong presented her director’s cut to the studio brass at Columbia Pictures, male cynics entered the screening with great reluctance. They commiserated beforehand, groaning, bracing for the worst. Why had they let their pushy female colleague, Amy Pascal, green-light a PG-rated, coming-of-age drama that dared center a bunch of wassailing, Civil War-era brats?! Amazingly, as the end credits rolled, “They all cried,” Armstrong told me. “That was my best audience screening ever: a room full of men in suits who cried for women.”

As you may have read, I have this thing with movie soundtracks, and had I owned the soundtrack to Little Women in middle school, I’d have glued it to myself, so core was that nostalgic, heart-tugging story, that cast, that wintry Thomas Newman score, to my tweenage identity. I had never, ever seen anything like Armstrong’s masterpiece on the big screen. It showed girls in all their glory and messy contradictions; Jo and Beth and Meg and Amy were funny and serious, loud and soft, ambitious and vulnerable, even annoying. I couldn’t believe it! They mirrored my whole existence. They made 19th-century Concord, Massachusetts seem like the place to be, and as Laurie had, I imagined myself as the fifth March sister, since I had no sisters of my own. Little Women, available for rent on most streaming platforms, remains permanently atop my evolving holiday watchlist. Runners-up include streamable vintage and modern classics, and a sparkly new favorite:

• Holiday (1938): Cary Grant and Katharine Hepburn banter and make sparks in George Cukor’s brainy romantic comedy uniting a self-made dreamer (Grant, fine as hell) and an heiress with a rebellious streak (Hepburn, electric, her cheekbones as sharp as her tongue). Obviously, they’re M.F.E.O., or Made For Each Other. The problem: He’s dating her sister! Will the soulmates ever get together? (Hmmmm, I don’t know.) The dialogue, reflective of the class warfare that existed in society amid the Great Depression, feels fresh and contemporary, as though it were written yesterday. Hepburn: “Do you realize that you are trying to marry into one of America’s 60 families?” Grant: “When I find myself in a position like this, I ask myself, what would General Motors do?”

• Meet Me in St. Louis (1944): When Judy Garland croons “Have Yourself a Merry Little Christmas,” forget it. You’re in her thrall. She owns you, and her once-in-a-lifetime talent anchors the beloved musical, which follows the ups and downs of an affluent Missouri family in the year leading up to the 1904 World’s Fair.

• It’s a Wonderful Life (1946): Duh!

• Scrooged (1988): I was 7 years old when the Bill Murray horror comedy hit theaters, and I’m pretty sure my cinephile parents took me to see it the opening weekend. I know for sure that it scared the living daylights out of me. It still does. Who needs CGI monsters so long as you’ve got a lunatic, taxi-driving Ghost of Christmas Past? I shudder. And yet it’s a treat to witness Murray’s amoral television executive awaken to his misdeeds and rediscover his humanity — in this clever, antic, unexpectedly poignant spin on A Christmas Carol, Murray proves that it is possible to change for the better, and it’s never too late.

• When Harry Met Sally (1989): Because Nora Ephron was a mastermind (cue Midnights), the writer understood that holidays were the ideal backdrop to stage a high-stakes romantic comedy. December, for many, is an emotional month. It heightens heartache and brings loneliness to the fore. It compels intrusive but well-meaning aunts and grandmothers to ask an outdated question: “Why are you still single?” As if flying solo were a character flaw! And if you long for romantic partnership, the lead-up to New Year’s Eve, the biggest Date Night of them all, can be a real nail-biter as time runs out to secure plans in advance. I know. I’ve been there. So have Sally Albright and Harry Burns, whose heart-pounding midnight countdown remains the most famous in cinematic history. (Watch this space: In the next few weeks, I’ll post a Harry-and-Sally-centric outtake from I’ll Have What She’s Having.)

• Love Actually (2003): I want to hate this movie. I really do. It’s a Christmas-themed rom-com through the male gaze, and I find its internalized misogyny insufferable and downright insulting. I saw it at an AMC multiplex in Oakbrook, Illinois, with my friend Kate McDonough, and vividly remember that we looked at each other during the end credits, asking, “What about Laura Linney?” Sadly, I don’t believe that Richard Curtis, its shortsighted writer-director, intends to make a sequel that would provide such closure. While Curtis’ major female characters wind up dateless (Linney), stalked (Keira Knightley) or cheated on (Emma Thompson), his leading men (Hugh Grant, Colin Firth and Liam Neeson) land the women of their dreams. Love Actually is male wish fulfillment on steroids, and, ugh ugh UGH, I hate that I love it anyway. (Ah, those messy contradictions.) The MVP: Olivia Olson belting “All I Want for Christmas Is You” at her school talent show. I strongly suspect that the child’s stirring homage to Mariah helped elevate the five-octave diva, now the unofficial Queen of Christmas, onto her rightful throne. And that alone is worth placement on this (definitive) lineup.

• The Family Stone (2005): Though critics dismissed this irresistibly sappy dramedy in its time, it has aged like a fine, full-bodied wine, deepening in flavor and richness with each watch. Sarah Jessica Parker is fabulously brittle as an uptight city slicker engaged to Dermot Mulroney, or is it Dylan McDermott? Anyway, she struggles without much luck to earn the approval of her fiancé’s withholding relatives, an aspirational WASP nightmare collective fronted by Diane Keaton (brilliant) and Rachel McAdams (terrifying). Only one Stone makes SJP feel at home, and that’s Luke Wilson, brother to DermotDylan MulroneyMcDermott and the laid-back, groovy yin to her type-A, pointy-heels yang. In my favorite vignette, a buzzed Wilson and SJP sing “Joy to the World,” a thrilling, romantically charged duet that gives me intense butterflies.

• The Holiday (2006): Nancy Meyers, unlike Richard Curtis, gives marquee actresses the happy endings they truly deserve. The filmmaker’s satisfying romp offers a dream scenario to women jilted at Christmastime: The vicarious thrill of watching Cameron Diaz escape the hustle culture of Los Angeles and her dumb industry ex-boyfriend and take temporary refuge in a sweet cottage in the English countryside, where she meet-cutes Jude Law, a hot widowed dad, and has the grandest, sexiest, Champagne-soaked time. I shan’t tell you how much I’ve replayed the scene in which those two hotties, who somehow look exactly alike, meet up in that cute little pub as Imogen Heap’s ethereal “Let Go” plays in the background. That Nancy Meyers, with her white turtlenecks, bright copper kettles and impeccable casting. She knew exactly what she was doing, and I love her for it.

• Spirited (2022): This one surprised me. I must admit that I didn’t have high hopes for the Apple TV musical comedy co-starring Will Ferrell and Ryan Reynolds. I thought it would be tedious. I thought it would be bland. I thought it would be the Dickensian riff that nobody wanted, that had been done a zillion times, and better. I was so, so wrong. If you give it a chance, and look past the slick marketing and inorganic, in-your-face production design, you’ll find a sharp-witted bromance filled with captivating ideas — about internet clickbait, the fear of change, and yes, the true meaning of Christmas. Things get really interesting the minute Reynolds, the irredeemable villain, graces the screen, chewing up scenery in a stunning song-and-dance number that rivals Hugh Jackman in The Music Man. (So, Reynolds can’t sing. So what? He’s still got range, baby.) I imagine his pitch meeting with Ferrell, the pair telling Tim Cook or whomever, “We have an idea! Elf meets Scrooged meets BROADWAY.” And you know what? It works. Here they are, rehearsing together. Take it away, boys: