Home Alone
Why was it the movie for '90s kids? It might have something to do with eight-year-old Kevin McAllister (Macaulay Culkin). Sure, being left home alone is kind of scary—but truth be told, it's also every child's dream to have free rein in his home. Defeating a pair of silly burglars is just icing on the cake, of course. If you want to make a day of it, watch Home Alone 2 and Home Alone 3.
Elf
Will Ferrell could do no wrong in the eyes of America in 2003 when this silly tale of a giant man in an elf costume hit theaters. If you want to laugh for an hour and a half straight (and admire Zooey Deschanel's perfect bangs), then this is the movie for you. Bonus points if you scream out "You sit on a throne of lies!" at the same time Buddy the elf does it to a department-store Santa.
It's a Wonderful Life
If you're in the mood to ugly-cry in front of your parents, pop in this holiday classic. I've watched this movie more times than I can count, and I've cried every single time thanks to its moving, universal message about how everyone's life is valuable. And there's no better person to convey that than the quintessential everyman actor Jimmy Stewart, who makes you feel his despair and his joy when he triumphs at the end.
Bridget Jones's Diary
First of all, this movie stars not one but two of my fantasy boos (Hugh Grant and Colin Firth). Secondly, it features Renée Zellweger at her most charming. As the title character, she perfectly captures being a rough-around-the-edges and quirky singleton who has to deal with family members trying to set her up on dates—and an ill-advised relationship with her piggish boss (Grant). If you're still not convinced, you'll surely be won over by the perfect kiss a pantless Jones and Mark Darcy (Firth) share on the snowy streets of London. I'm swooning just thinking about it.
A Charlie Brown Christmas
This movie aired in 1965 and is still shown on TV every holiday season. Not many other holiday films have those bragging rights. But this movie isn't popular because of luck—it has just the right blend of melancholy (Cheer up, Charlie!), whimsicality, and a childlike sense of wonder that makes it a favorite for everyone.
Planes, Trains, and Automobiles
OK, so this movie takes place during Thanksgiving, but let me break the rules. Why? Because it touches my heart thanks to John Candy's complex portrayal of Del, a slightly hot mess of a man without a family. Sure, he makes Neal's (Steve Martin) trip a disaster by causing a fiery car situation and that "pillows" incident (just watch it), but it doesn't matter in the end because a lifelong friendship is forged.
The Nightmare Before Christmas
Freaky. Weird. Unexpected. That pretty much sums up this anti-holiday holiday movie from the fascinating mind of director Tim Burton. This stop-motion animated tale is probably the most original and visually stunning film on the list. There's no way you can watch this movie and not get sucked into the story of the Pumpkin King, who is bored with his job and life in Pumpkinland and takes a trip to Christmastown.
Trading Places
This movie packs in three holidays in one: It takes place during Thanksgiving, Christmas, and New Year's Eve. It also deals with a timeless fable—money is not important—in a dark comedy way. Throw in Eddie Murphy as a con man, Dan Aykroyd as a banker, and the awesome Jamie Lee Curtis and you've got one of the funniest holiday movies around.
The Bishop's Wife
I'm taking it back with another old-school entry: the Cary Grant classic The Bishop's Wife. Grant stars as Dudley, an angel who is called upon by a bishop (David Niven), who has been praying for guidance about how to raise funds for a new cathedral. Dudley has other plans—namely getting the bishop to realize that the guidance needed is not about money. It's a sweet, magical, and feel-good-all-over movie. If only we all had Dudleys in our lives.
Bad Santa
By far the raunchiest movie on the list, Bad Santa is still heartwarming (and really funny). Billy Bob Thorton stars as a con man, who, along with his partner in crime, pose as Santa and his little helper and rob department stores on Christmas Eve. Their plan hits a snag when they befriend a kid with a troubled life. Yeah, yeah, you know how the movie is going to end, but there's enough here to keep you interested, promise.
National Lampoon's Christmas Vacation
The Griswolds are a cursed family. No matter how many trips they take, they have never managed to have a successful vacation thanks to a series of unfortunate events. Of course, their Christmas holiday is no different. Cousin Eddie (Randy Quaid) is the perfect disaster (maybe your family has its own cousin Eddie?).
A Christmas Story
This movie is simply iconic. From the leg lamp to Ralphie's tongue getting stuck on a frozen pole to that BB-gun incident, A Christmas Story has left its mark on all our brains, so much so that it sometimes feels like this story is our own.
Love Actually
This year marks the 10th anniversary of this beloved modern holiday rom-com—and whether you adore it or hate it, you can't deny that this movie, which follows the ups and downs of eight very different couples, is the go-to flick for feel-good moments. Plus, if you don't adore little Sam (Thomas Sangster), then you could potentially be lacking a soul.
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