1Holiday Inn
Paramount Pictures Set during the WWII era, the movie follows a love triangle that unfurls at a hotel over the holidays. Bing Crosby and Fred Astaire's characters sing their way through various crushes. Irving Berlin wrote 12 original songs for the movie—including the iconic "White Christmas," which ended up inspiring a movie of its own in 1954, also starring Crosby.
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2White Christmas
John Swope//Getty Images Why there are two snowy Irving Berlin tales that each star Bing Crosby and the General Waverly’s Inn—White Christmas (1954) and Holiday Inn (1942)—we’ll never really know. We just look at it as though it’s a gift from cine-Santa and a good reason to cue up a double feature. Our favorite of the two, though, has to be the one where Crosby and Danny Kaye sing and dance to save their inn from closing.
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3Christmas in Connecticut
LMPC//Getty Images This is a comedy about a food writer (Barbara Stanwyck) whose perfectly latticed persona as a housewife with supreme cooking skills gets exposed as the sham over one traditional Christmas she never agreed to host. It's the holiday rom-com you never knew you needed.
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4Jingle All the Way
Murray Close//Getty Images This classic 1996 film will make you grin from ear to ear every year, and stars Arnold Schwarzenegger, Rita Wilson, Sinbad, and Phil Hartman. Workaholic father Howard (Schwarzenegger) constantly lets his family down, but when his young son Jamie (played by Jake Lloyd) begs for a super popular action figure for Christmas, he goes on an epic mission to make his son's dream come true.
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5The Shop Around the Corner
LMPC//Getty Images You’ve Got Mail borrowed its tech-age narrative from this 1940 gem about a pair of shop workers whose feud grows with every holiday sale, and whose love blooms with every letter of written correspondence. Yep, it’s pen pal mystery love all the way with this one. And though there may not be a Santa cameo, it does star the season’s other most iconic presence: James Stewart.
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6It’s a Wonderful Life
IMDb Whichever version you choose, Frank Capra’s classic is an exercise in depicting “the grass is always greener” proverb. Although, should you prefer the black-and-white original, “the grass is always grayer” might be more appropriate. A seminal holiday classic, it stars James Stewart as a man who gets a glimpse at what life would look like without him.
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7Miracle on 34th Street (1947)
IMDb Maureen O’Hara and John Payne star in the original film about that time New York City authorities committed a man to a mental facility because he thought he was Santa Claus. And though it can be debated which version of the classic film—this one or the John Hughes contribution starring Mara Wilson—is your favorite, there simply would be no miracle without the George Seaton 1947 prototype.
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8Dr. Seuss' How the Grinch Stole Christmas
Universal Pictures Jim Carrey was the Grinch in this 2000 adaptation of Dr. Seuss's iconic children's book, about the ultimate holiday grump—well, right up there with Scrooge. Don't worry: The green-hued, mountain-dwelling loner's heart ends up "growing a size" thanks to Cindy Lou Who (Taylor Momsen), one of the cheery Whos from Whoville.
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9A Christmas Story
IMDb If Ralphie Parker didn’t rattle off his desire for an “official Red Ryder, carbine action, 200-shot, range model air rifle, with a compass in the stock and this thing that tells time,” did Christmas even happen? It’s become an unofficial rule—thanks in part to 24-hour airings on cable networks—that every year, we all watch the Bob Clark tale about a kid in the ‘40s try and convince Santa to gift him with a BB gun.
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10Rudolph the Red-Nosed Reindeer
IMDb Good for little drummers and little drummers at heart, this animated Claymation gem is arguably the best of the Videocraft classics. About a toymaker elf who wants to be a dentist, an illuminated reindeer who wants to be accepted, and all their misfit friends in between, it’s iconography of the 1960s that is just as quintessential 58 years later.
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11The Preacher's Wife
Walt Disney Studios Motion Pictures The Preacher's Wife isn't the first Christmas movie to feature an emissary from heaven helping a human with his quest to be a better person (see: It's a Wonderful Life). But it is the only version of this story to do so with Denzel Washington and Whitney Houston. Washington plays a heavenly guest who, during his stay on Earth helping a preacher, ends up falling for—you guessed it—his wife.
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12The Man Who Invented Christmas
Bleecker Street If you've already seen every single Christmas Carol adaptation—and there are many, including a few on this list—then check out this movie about the man who created so many Christmas tropes: Charles Dickens himself. Dan Stevens (Downton Abbey) plays the successful author as his life intersects with one of his most famous stories.
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13The Holiday
Universal The Holiday is essentially two Nancy Meyers rom-coms for the price of one. Cameron Diaz and Kate Winslet play women who decide to swap homes over the holiday season—changing scenery between a gorgeous home in L.A. and a charming English cottage. Under the twinkling lights and dropping temperatures, they each find transatlantic beaus.
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14The Polar Express
Warner Bros This whimsical story is best served by the movie's animation style, which brings the cold of the North Pole and the magic of a train headed to the North Pole to life. The Polar Express is based on Chris Van Allsburg's picture book of the same name.
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15Scrooged
Paramount Pictures Charles Dickens's "A Christmas Carol" has been told over and over, in Muppet form to dark miniseries on FX. But Scrooged, a satire starring Bill Murray, is one of the most memorable and unique interpretations of the classic morality tale. Bill Murray's version of the troubled protagonist is a crass television executive who has lost his way. A series of over-the-top ghosts help reorient his priorities.
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16A Christmas Carol (1951)
IMDb Watching the time-honored Charles Dickens classic about a miser who changes his tune after visits from three ghosts is a no-brainer. But choosing which version from an abundance of adaptations can actually make your head hurt. No worries; we got you.
If you’re after satire, you want the Richard Donner/Bill Murray comedy Scrooged. If it’s animation you’re after, you want Mickey’s Christmas Carol. But if you’re a stickler for tradition, go with the Brian Desmond Hurst/Alistair Sim crowd-pleaser, A Christmas Carol.
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17Home Alone
IMDb The McCallisters head from Chicago to Paris for Christmas, accidentally leaving their 8-year-old troublemaker son at home, where he finds himself defending their three-story house against a pair of bumbling bandits. It’s the film that turned Macaulay Culkin into a household name and John Hughes’s box-office beast into a household holiday classic.
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18Love Actually
IMDb We’re not sure which part of Richard Curtis’s gloriously British Christmas ensemble film we love most: Bill Nighy as a pelvis-swiveling rock star, Colin Firth getting lost in translation, or Hugh Grant cold-knocking on residents’ doors to find his one true love. In a romp that is as funny and heartwarming as it is sad and heart-wrenching, Curtis delivers a holiday film that “To us, it is perfect.”
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19National Lampoon’s Christmas Vacation
IMDb Though the word vacation appears in the title of this 1989 classic, the only place the Griswolds, led by patriarch Clark, are going is to Crazy Town. Preparing to host a big family get-together at their home in Chicago, Clark (Chevy Chase) and Ellen (Beverly D’Angelo) brace for the dysfunction that inevitably comes along with Cousin Eddie, Aunt Bethany, and a Rottweiler named Snots.
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20A Charlie Brown Christmas
IMDb Snoopy, Lucy, Linus, those iconic Peanuts dance moves: It’s beginning to look a lot like A Charlie Brown Christmas. Relive the animated special you grew up watching, as your favorite shy and dispirited comic strip character wades through the holiday’s trademark commercialism to unearth the true meaning of Christmas.
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