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The Best Holiday Movies To Watch, And Rewatch, This Season

From "Die Hard" (yes) to "Home Alone," these movies never disappoint.
Leigh Blickley
By 

Senior Entertainment Reporter, HuffPost

NBC, Rialto Pictures, RKO Pictures via Getty Images, 20th Century Fox

It's the most wonderful time of the year ... to be inside on your couch next to the fire with a snuggly blanket and TV/Netflix/On Demand (or even a DVD player, if you're old school like that).

Who doesn't love to tap into their holiday spirit and watch dozens of movies that remind us of how special this season really is? Hot cocoa. Mistletoe. Love. Ahhh, the holidays.

Here's a roundup of the best holiday movies to watch, and rewatch, this month, according to your favorite editors at HuffPost Entertainment.

"Home Alone" (1990)
The first time I watched “Home Alone,” I didn’t even know what aftershave was. In the years since, I’m pretty positive I burned my dimples off recreating Kevin’s scream. But who needs dimples anyway? Dimples are stupid. All you really need for the holidays is to watch inept burglars get severely burned and hit in the face with paint cans. That’s always a merry Christmas, ya filthy animals. -- Bill Bradley

("Home Alone" is now available to rent on Amazon Video.)
"It's a Wonderful Life" (1946)
RKO Pictures via Getty Images
I feel like we'd be remiss not to mention "It's a Wonderful Life," which is probably the quintessential holiday film (right up there with "Home Alone," duh). Good guy George Bailey is feeling extremely down on his life, all of which has taken place in the tiny town of Bedford Falls, New York. He's on the verge of throwing himself off a bridge after a major cash mishap, convinced everyone would be better off had he never been born -- a pretty dark premise for one of the most historically beloved films, no? Luckily, an angel shows up in his time of need to point out how much he's actually done for his fellow man. NBC is airing the film on Dec. 3, but really, the best way to watch it is with your dinner guests when you're overstuffed and have run out of things to say to each other. We'll be over here trying to figure out the physics of how to lasso the moon. -- Jill Capewell

(Airing Saturday, Dec. 3, and Saturday, Dec. 24, at 8 p.m. ET on NBC.)
"Rudolph the Red-Nosed Reindeer" (1964)
NBC
An ad man named Robert L. May created the red-nosed reindeer character of Rudolph in 1939, for American department store Montgomery Ward. Unlike other corporate mascots — such as child made of dough and man in a clown costume — that only get to fly at the Macy's Thanksgiving Day parade, Americans welcomed Rudolph to zoom to the rooftops of their very own homes. The crimson beacon became full-fledged folklore just as if the Hamburglar was an integral part of Easter.

But as the future is nearly upon us when our children are nestled all snug in their beds anxiously awaiting the Amazon drones that will usurp the need for Santa Claus, I want to remember the times growing up when I loved everything Rudolph flew for. Although the department stores may throw out their broken stock in reality, "Rudolph" the movie is all about appreciating misfits as being just like anything else. Rudolph proved that body positivity wasn't exclusive just to old white men and that's a simple Christmas message that you don't even need to be well-red to appreciate. -- Todd Van Luling

(Airing Tuesday, Nov. 29, at 8 p.m. ET on CBS.)
"A Christmas Story" (1983)
There's a reason this film plays for 24 straight hours on Christmas Eve/Christmas. It is the real experience of being a kid, and it perfectly highlights how weird and quirky your family and friends can be around the holidays. Even though, in the end, you still love them.

And who doesn't want a narrator in their life to say things like, "Only one thing in the world could've dragged me away from the soft glow of electric sex gleaming in the window" or "My father worked in profanity the way other artists might work in oils or clay. It was his true medium, a master"? Sorry, everyone else on this list. This is the best Christmas movie ever made. -- Andy McDonald

(TBS is airing "A Christmas Story" marathon starting at 8 p.m. ET on Saturday, Dec. 24.)
"Metropolitan" (1990)
Rialto Pictures
If we include Christmas-adjacent movies, a whole world of holiday films suddenly opens up. You can watch "Gremlins" or "The Apartment" or "Sleepless in Seattle" in honor of Old Saint Nick. Imagine that! You can also watch "Metropolitan," which should be on your must-see list year-round. Whit Stillman's 1990 cult classic follows a middle-class Princeton student returning home to Manhattan for his first winter break. There, he encounters a group of well-to-do socialites near his age who invite him into their "urban haute bourgeoisie" circle. Together, the entitled aristocrats carouse through 1960s New York, mourning the loss of elitist values that has set in with the rise of the counterculture. Sound festive and jolly? It's no "Christmas with the Kranks," but "Metropolitan" is a humorous portrait of changing generational tides and the oddities of returning home after being away. Stillman's script was nominated for an Oscar, and the movie enjoyed a nice bout of attention for its 25th anniversary rerelease earlier this year. Curl up with eggnog and save the schmaltz for another night because this sharp satire is exactly what you need. -- Matthew Jacobs

(Available to rent on Amazon Video.)
"Love Actually" (2003)
Even if you hate cheesy romantic comedies with hundreds of celebrities, this one will find a place in your cold, dead heart. From Emma Thompson's heart-wrenching Joni Mitchell sing-along to a deliciously shirtless Rodrigo Santoro to the iconic airport scene at the end, Love Actually is a film that highlights some of the best (and worst) parts of love in all of its raw, uncomfortable glory. -- Jenna Amatulli

("Love Actually" is now on Netflix.)
"Die Hard" (1988)
Twentieth Century Fox
When I dream of Christmas, I dream of many things. I dream of a grotesquely buff Bruce Willis in a wife-beater, bleeding profusely from his feet while making cute banter. I dream of Karl, that poor Eurotrash Ken doll, slung over a wheelie chair in a Santa Hat covered in cryptic bloody messages. Of young professor Snape hurtling through space. Of '80s office buildings that look like flattened rainbow sherbet. Of estranged spouses making out after a near death experience. I dream of "Die Hard." -- Priscilla Frank

(Airing Saturday, Nov. 26, at 7 p.m. ET on IFC.)
"Christmas Vacation" (1989)
Giphy
Clark Griswold (Chevy Chase) is clearly the star of the movie. His crazy eyes, terrible driving, love of Christmas lights and tendency to do the absurd -- like grease a sled or saw of a part of the banister -- make "Christmas Vacation" absolutely hilarious. But the best parts of the movie (the cat chewing on an electrical cord and blowing up, Ruby Sue cursing, Aunt Bethany saying "the blessing" and the Griswold's TERRIBLE neighbors) make the movie a unforgettable classic that will ~hopefully~ live on forever. -- Carly Ledbetter

(Airing on Freeform throughout December.)
"Just Friends" (2005)
This movie rests on a very simple plot: Chris (Ryan Reynolds) liked Jamie (Amy Smart) in high school, but Jamie -- considerably more popular and conventionally beautiful -- kept Chris in the friend zone. (Sidebar: Let's all agree to hate that term, but this film is from 2005, so...) Fast forward 10 years post-graduation and Chris, newly svelte and successful, finds himself serendipitously in his hometown for Christmas. This is the time, he figures, to finally break out of the friend zone. Alas, the rules of rom-com-dom dictate that things will not go smoothly. And they don't. For example, Anna Faris as a deranged pop star ends up eating toothpaste on Chris' brother's bedroom floor, concussed but still horny, in a moment that pretty accurately captures how shockingly hilarious this movie is.

Many of my millennial acquaintances harbor intense feelings about this movie, that boasts a whopping 42 percent on Rotten Tomatoes. (I was once part of a high school-era Secret Santa group in which three of the seven gifts given were DVD copies of "Just Friends.") For me, it's just not the holiday season unless I've watched an inflated Ryan Reynolds sing "I Swear" into the mirror at least three times.

("Just Friends" is now on Netflix.)
"Snow Day" (2000)
Nickelodeon Films
If you're a kid of the '90s, then "Snow Day" is one of those movies that makes you smile. Plus, it has holiday actor galore Chevy Chase in it, and he always makes things more entertaining.

The 2000 film tells the story of brother-sister pair Hal and Natalie, who get into all kinds of mischief on a day off from school. Hal tries to impress his crush (Emmanuelle Chriqui) while his little sister Natalie and her friends do everything they can to prevent a snowplow driver (Chris Elliott) from plowing the streets. Such fun! -- Leigh Blickley

("Snow Day" is now on Netflix.)
"The Muppet Christmas Carol" (1992)
Giphy
This movie has everything: ghosts, children living in poverty, a bitter old miser, the Christmas spirit, a bunch of Muppets. And it's a musical! Happily, the story doesn't stray too far from the classic Dickens tale we all know. Ebenezer Scrooge, who still claims one of the greatest bad-guy names in children's literature, is a mean old human money-lender who begrudgingly gives his puppet employees a day off for Christmas. To show him the error of his coldhearted ways, three ghosts visit Scrooge on Christmas Eve. One reminds him that he wasn't always such a jerk, one shows him how his actions hurt the people around him, and the last, most terrifying ghost shows him that if he doesn't soon change his ways, he'll have the blood of Tiny Tim on his hands. All the while, a big cast of Muppets sings beloved holiday carols, and Miss Piggy continues to harass Kermit the Frog. It's great. -- Sara Boboltz

(Airing Sunday, Nov. 27, at 3:55 p.m. ET on HBO Family.)
"The Nightmare Before Christmas" (1993)
What's not to love about a movie that mixes Halloween and Christmas (aka, the best holidays of the year)? "The Nightmare Before Christmas" gives you everything you could ask for in a holiday movie -- presents, Santa Claus, singing, romance (Sally and Jack forever!) -- with an added dose of darkness. (Shout out to all the people who were terrified of Oogie Boogie in their childhood!)

I really can't express how much I love this movie in one simple blurb. It's strange, creative, original, and in my humble opinion, a classic. Plus, as a kid/teen, my obsession with Jack Skellington made me feel so ~edgy~ and undeniably cooler than everyone else. -- Julia Brucculieri

(Airing on Freeform throughout December.)
"Jingle All the Way" (1996)
Giphy
I first saw this movie in theaters with my mom and, almost 20 years later, we still watch it for the holidays! (Yes, I have it on DVD). The entire movie sort of celebrates being ultra campy -- it never takes itself too seriously. It also feels somewhat accurate in capturing the hysteria of trying to get a silly trendy toy like "Turbo-Man." The slapstick is unreal -- it's really shocking that these characters survive some scenes?! There's even a scene where there's an actual bomb that's set off.
But this movie isn't about the plot -- it's about the wonderfully '90s cast. I mean, just the simple fact that a movie exists starring Sinbad, Arnold Schwarzenegger, Rita Wilson, and Phil Hartman should compel anyone to watch this. Plus, you also get to see Phil in one of his last film performances, which is very bittersweet. -- Melissa Radzimski

(Airing on Freeform throughout December.)
“I’ll Be Home for Christmas” (1998)
Giphy
If “Planes, Trains and Automobiles” meets “Home Improvement” doesn’t sound like the sort of laugh-track-fueled story sure to put you in the Christmas spirit, well, you’re wrong. If you weren’t a sentient being in 1998, or on the off-chance that you’ve forgotten this total gem, here’s the rundown: Jonathan Taylor Thomas (or, “Jake,” but let’s be real, no matter who Jonathan Taylor Thomas is playing, he’s still Jonathan Taylor Thomas) doesn’t want to go home for Christmas. He’s got a good reason for it -- his dad remarried shortly after the death of his mother, and he’s still coping with his grief. But when his dad says he’ll gift him his vintage car in exchange for his mere presence, JTT reconsiders. In what can only be considered a totally reasonable request, JTT’s dad asks him to come home no later than 6 p.m. on Christmas Eve. (Why the specificity, JTT’s dad? Did you perhaps know that your son would struggle in a gaffe-filled race against the clock?) A ridiculous string of roadblocks later -- including a stealthy ride inside a dog kennel on an airplane -- and JTT finally makes it home for Christmas. OR DOES HE? You’ve gotta watch to find out! -- Maddie Crum

(Available to rent on Amazon Video.)
"Annie" (1999)
No screen adaptation has come as close to capturing the spirit of the classic musical than Disney’s Rob Marshall-helmed “Annie.” It may have been made for TV, but the talents of Broadway legends Victor Garber, Audra McDonald, Alan Cumming, Kathy Bates and Kristin Chenoweth (seriously, that cast though) elevated the material to new heights. Nothing screams the holidays more than President Franklin D. Roosevelt promising the orphans of New York a happy ending under Daddy Warbucks’ towering Christmas tree. Whatever you do, do not -- we repeat do NOT -- mistake this version with 2014’s “Annie.” Sorry, Quvenzhané. -- Cole Delbyck

(Available to rent on Amazon Video.)
"The Family Stone" (2005)
When I look back on the last 10 years, it's become clear to me that I have watched "The Family Stone" way too many times. But hey, let a girl live. Sure there are other Christmas movies out there to watch, but something about Carrie Bradshaw meeting the family of Michael O'Neal ("My Best Friend's Wedding, anyone?) gets me every time. Plus, what's a holiday flick if Diane Keaton isn't in it?

Not to mention the sibling love-swap is too great to believe ... no one saw that coming, right? -- Leigh Blickley

(Available to rent on Amazon Video.)
"A Christmas Kiss" (2011)
Atmospheric Pictures
I grew up on the truly classic Christmas movies -- "Christmas Vacation," "A Christmas Story," "It's a Wonderful Life" -- all of which I still love. But now that I have cable, and more control over movie selection, I have a soft spot in my heart for the truly ridiculous, cheeseball made-for-TV Christmas romantic comedies that play endlessly on the Hallmark Channel and its ilk throughout December. "A Christmas Kiss," starring Laura Breckenridge and Brendan Fehr, has it all: It's overly devoted to the holiday theme, littered with two-dimensional characters, and lacks any narrative logic, yet despite all of this, it's full of winning charm instead of being mind-numbingly dull. (I credit Breckenridge, who is a fresh and delightful presence; though in the interest of full disclosure I should mention that we were classmates, if not exactly personally acquainted, in college.) Breckenridge plays Wendy, an aspiring designer whose successful but difficult boss also happens to be engaged to a handsome heir. When Wendy and her boss' fiancé are set to work planning a holiday ball together, little holiday lights twinkle between them.

What better way to celebrate a girls' night in around the holidays than with aromatic cocktails and a made-for-TV movie in which two devastatingly attractive people fall in love, despite all obstacles, because they both just love Christmas so damn much? There is no better way. If you really love Christmas or at least like watching cold-hearted, holiday-hating fiancées get what they deserve, don't miss this "Kiss." -- Claire Fallon

(Available on Netflix.)
"A Charlie Brown Christmas" (1965)
"A Charlie Brown Christmas" never gets old no matter what age you are or how many times you've watched it. The 1965 TV special, based on Charles M. Schulz’s “Peanuts” comic strip, follows Charlie Brown as he tries to uncover the true meaning of Christmas. And who could forget the tree? "I guess you were right, Linus," Charlie Brown says after choosing a small wilted tree for the school play. "I shouldn't have picked this little tree. Everything I do turns into a disaster. I guess I really don't know what Christmas is all about." Melancholy, yet hopeful, the animated special touches upon materialism and commercialism. Along the way, the Peanuts characters learn about the importance of friendship, and maybe, just maybe, the meaning of the holiday. Backed by a classic soundtrack that includes “Christmas Time Is Here” and “Hark! The Herald Angels Sing,” this long-running TV special is a pop culture tradition that keeps on giving. -- Lauren Moraski

(Airs Thursday, Dec. 1, at 8 p.m. ET on ABC.)

Also on HuffPost:

It's A Wonderful Life

The Best Family Christmas Movies

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