Will Ferrell in Elf

Photo: New Line Productions

Elf
Will Ferrell's enthusiasm is contagious—no matter the role—so his ability to spread holiday cheer to even the most skeptical scrooge is no surprise. In Elf, Ferrell plays Buddy, a human living as one of Santa's helpers. He landed on the North Pole as a boy after getting whisked away in Santa's sack, but as he continues to grow in a land of perpetual children, he starts to literally stand out. So Buddy leaves Santa's mystical home for a much scarier place: New York City. His exploits in the Big Apple—falling in love with a department store elf, turning his half-brother into a believer, seeking the approval of his Grinch of a father—are saturated with silliness and are the perfect vehicle for Ferrell to do what he does best: make his audience, young and old, feel like kids on Christmas. 
Jimmy Stewart in It's a Wonderful Life

Photo: Paramount Home Entertainment

It's a Wonderful Life
If we had to pick only one film that encapsulates the holiday spirit, it would be this timeless classic. When Jimmy Stewart's George Bailey contemplates suicide on Christmas Eve, his guardian angel, Clarence, appears to show him what his town of Bedford Falls would have been if he'd never been born—a sinful slum full of angry, depressed residents. After catching a glimpse of just how wonderful a life it really has been, George begs Clarence to let him live and return to his family. In the end, everybody wins—George returns to the love of his family and Clarence, an Angel Second Class, gets his wings. Director Frank Capra's 1946 film was deemed a box office flop in its day, but has emerged as a Christmas staple of the stocking and ham variety. 
A Christmas Story

Photo: Warner Bros. Home Entertainment

A Christmas Story
The ultimate Christmas cult classic introduced the Triple Dog Dare, the leg lamp and "fudge" (only he didn't say fudge) into the pop culture lexicon. The 1983 film takes us back to the 1940s, where little Ralphie Parker is hoping and praying to find only one thing under the tree: an official Daisy Red Ryder Carbine-Action 200-Shot Range Model Air Rifle. In layman's terms, the boy wants a BB gun. But no matter who he asks—his mother, his teacher, even the mall Santa Claus—he's continually told one thing: "You'll shoot your eye out." Despite its campy slant, A Christmas Story ends warm and fuzzily enough—Ralphie's very last gift is the gun he's been dreaming of. And then he almost shoots his eye out. 
Eight Crazy Nights

Photo: Columbia Pictures

Eight Crazy Nights
From the man who brought us "The Chanukah Song" comes this animated comedy about the festival of lights. Adam Sandler voices Davey Stone, a drunk party animal who, after getting into trouble with the law, is spared from jail and sentenced instead to referee a youth basketball league. A child of Sandler's Happy Madison productions, Eight Crazy Nights is rife with the potty humor you'd expect from the people behind Billy Madison and Happy Gilmore. But if you can look past the poop jokes, you'll see a holiday film with the traditional messages of appreciating the underappreciated and the importance of family.
Miracle on 34th Street

Photo: Fox Home Entertainment

Miracle on 34th Street
A young Natalie Wood shines as skeptical 9-year-old Susan Walker, daughter of the no-nonsense director of the Macy's Thanksgiving Day Parade. When a man claiming to be Kris Kringle shows up in town, first as the new Macy's Santa and then the subject of a sanity hearing, Susan tests his claim by requesting the thing she wants most: the house of her dreams. The perennial Christmas favorite steals our hearts because it takes us back to a time when we, too, had faith. Miracle on 34th Street is a perfect holiday reminder that we're never too old to believe in Santa Claus and that there is such a thing as a Christmas miracle. 
Love Actually

Photo: Universal

Love Actually
Most Christmastime romantic comedies are sappy, the kind of movies you watch with a pint of ice cream and not a man in sight. Love Actually has the marked distinction of being a chick flick that appeals to both genders. It's full of touching holiday-perfect moments—a young boy's crush singing "All I Want for Christmas Is You" certainly spreads cheer—but it also provides plenty of chuckles. While it's sweet, it's not saccharine, and it proves that romantic comedies don't have to follow a boy-meets-girl, boy-loses-girl, boy-wins-girl-back formula. The touching new classic is a mosaic of love stories in every form—familial, forbidden, brotherly and true—and is the perfect seasonal reminder that, as the adorable Hugh Grant tells us, "Love actually is all around." 
The Nightmare Before Christmas

Photo: Touchstone Pictures

The Nightmare Before Christmas
If you take your holiday cheer dark, this anti-Christmas movie is just for you. With a nod to a spookier holiday, Tim Burton's stop-motion cult hit is filled with the quirk and imagination we've come to expect from the singular producer. Jack Skellington is the king of Halloween Town. When he happens upon a portal to Christmas, he introduces the holiday to the ghosts and goblins in his residence. But Jack's take on the holiday spirit is a bit twisted, and after convincing some children to abduct the real Santa, he takes to the sky in his coffin-sleigh and delivers the likes of shrunken heads to the world's little boys and girls. Everything turns out okay—it's Christmas, after all—but if your family is looking for an alternative to the typical seasonal fare, this creepy flick is just the ticket. 
Home Alone

Photo: Fox Home Entertainment

Home Alone
Left behind by his family, now en route to Paris, Kevin McCallister must fend for himself and defend his suburban Illinois home against two dimwitted burglars. In the process, he learns that his terrifying neighbor is in fact just a sad and lonely man who, like Kevin, is yearning for the love of family during the holiday season. In case you forget the true popularity of the modern Christmas classic, consider this: It was the highest-grossing film of the year and topped the box office for three straight months. Perhaps that was because of Kevin's child-pleasing antics and don't-try-this-at-home safety strategies. Or, just maybe, it was because at its core, this Macaulay Culkin star-making vehicle sends the message that while fancy vacations are great, the only thing we want surrounding us on Christmas morning is family.
The Santa Clause

Photo: Disney

The Santa Clause
What if Santa lived among us in the working world? This Disney favorite gives a glimpse of what that might be like when Tim Allen becomes the man in the red suit. On Christmas Eve, the real Kris Kringle takes a nasty spill off Scott Calvin's roof. Scott follows orders, climbs into the Santa suit and is suddenly delivering gifts to children around the world. Once he arrives in the North Pole, the new Father Christmas is presented with the "Santa Clause": If something happens to the man himself, the next person to sport the outfit assumes the role of Santa and all the official duties that come with it. Suddenly, Scott finds himself with an ever-growing belly and white beard, the ability to see who's been naughty or nice and a serious case of the holiday munchies. True, the family comedy—which spawned two sequels—follows your typical feel-good seasonal formula. But sometimes Christmas is about the comfort of the same-old thing in bright and shiny new packaging.