The Best Holiday Films to Watch This Year

by Chris Petry

Sing it with me, “It’s the most wonderful time of the yeeeeeeeeaaarrr!” Yes, the winter holiday season is upon us. It’s time to grate the nutmeg, hang the mistletoe, decorate the tree, light the menorah, and promise yourself that come January 1st, you’re going to get your diet and finances back on track. Or, maybe not.
 
Some of the time-honored traditions of the season undoubtedly include: building a gingerbread house, driving way too far to sit in bumper-to-bumper traffic for the chance to glimpse at an underwhelming light display, and of course, watching feel-good holiday movies. Below, we’ve compiled a list of 25 of the best holiday-themed movies that are sure to make you feel warm and tingly. Maybe.
 
It’s a Wonderful Life
No list would be complete without the 1946 Frank Capra Christmas classic, It’s a Wonderful Life. The film stars Indiana, Pennsylvania’s own Jimmy Stewart as George Bailey, a melancholic banker who sacrifices his own dreams for the good of his family and community. On Christmas Eve he’s visited by his guardian angel who proceeds to show him the impact he’s had on others by revisiting crucial moments throughout his storied life.
 
Rudolph the Red-Nosed Reindeer
Another perennial favorite, and all-time stop motion animation classic, Rudolph the Red-Nosed Reindeer is the timeless story of the energetic but outcasted little reindeer with a prominent glowing red nose and a heart of gold.
 
Frosty the Snowman
Yet another all-time animated classic, Frosty the Snowman is the tale of a magical snowman who unexpectedly roars to life on a cold snowy day, much to the delight of the local children. Of course, the kids realize that frosty will melt when the temperatures rise so they set out on a journey to whisk him away to the North Pole, where he can live year-round in icy bliss. Fun fact: the instantly-recognizable voice of Frosty was handled by standup comedian Jackie Vernon.
 
Die Hard
Yep, I said it. If you’ve been paying attention to online discourse over the last decade or so, there’s been an annual debate as to whether or not Die Hard is indeed a Christmas movie. The debate was even the subject of a memorable episode of the hit CBS sitcom, How I Met Your Mother. This humble columnist will be taking the position of the affirmative. Sure, at its roots it’s an action movie, anchored by the immortal wise-cracking Bruce Willis and the suave but insidious Alan Rickman. However, the action unfolds on Christmas Eve at a corporate Christmas party. Not sold? You can go to Amazon, right now, and buy a “Hans Gruber falling from Nakatomi Plaza” advent calendar.
 
Eight Crazy Nights
Without a doubt the most famous, gloriously over-the-top, animated Hanukkah musical in cinematic history; Adam Sandler’s Eight Crazy Nights is a delightful story of redemption, family, community, and the meaning of Hanukkah. The voice cast is a who’s who list of classic and contemporary comedic figures like Rob Schneider, Kevin Nealon, Jon Lovitz, and the late Norm Crosby.
 
A Christmas Story
Seemingly always on a loop on basic cable in the month of December is Bob Clark’s early 80s Christmas masterwork, A Christmas Story. You know what? It’s a great film. After 40 years we’re still talking about leg lamps, Red Ryder BB guns, and bunny rabbit pajamas. Some films just have a way of weaving their way into the public consciousness. Hollywood legends Darren McGavin and Melinda Dillon play the parents of the narrator, Ralphie, who recalls the events of a particularly meaningful holiday season in the early 1940s. Super fans can visit the original home, as featured in the movie, in Cleveland, OH where much of the movie was lensed.
 
Black Christmas
Here’s another one that might cause some debate but it’s certainly worth noting. After all, it was directed by Bob Clark, who also gave us the above-mentioned, undisputed classic A Christmas Story. The film is a proto slasher flick, starring Olivia Hussey (Romeo and Juliet), Margot Kidder (Superman, Sisters), and John Saxon (Enter the Dragon, A Nightmare on Elm Street) and centers on a group of gals in a suburban Toronto sorority, terrorized by a mysterious attic-dwelling killer over Christmas break. Some may be turned off by the idea of a holiday slasher flick but if you like a little something outside the ordinary, this is one of the absolute best films in the holiday horror subgenre. Oh, and stick with the 1974 original.
 
Home Alone
Macauley Culkin plays Kevin McCallister, a mischief-making young man left alone over Christmas vacation after his family departs for Paris without him. Two opportunistic burglars, rather memorably embodied by Joe Pesci (Casino, Goodfellas) and Daniel Stern (Breaking Away, City Slickers), soon learn they’ve chosen the wrong house when they fall victim to repeated booby traps laid by Kevin. In the end, the family is reunited just in time for Christmas.
 
The Grinch Who Stole Christmas
I wasn’t sure which cinematic adaption of this film to recommend, so how about both? First there’s the 1966 animated film, voiced and narrated by legendary horror film star Boris Karloff and finally, Ron Howard’s big-budget, Jim Carrey-starring, live action extravaganza, How the Grinch Stole Christmas (2000). Both are centered around the feared outcast The Grinch, who lives in a cave lair overlooking the joyous Christmas town of Whoville. He and his trusty dog set out one Christmas Eve to destroy Christmas once and for all, only to have a change of heart. Fun fact: the live action Cindy Lou Who, Taylor Momsen, would later star in the cult classic TV show Gossip Girl and is the frontwoman of the chart-topping Hard Rock band, The Pretty Reckless.
 
Miracle on 34th Street
Another stone cold classic from the golden age of Hollywood, Miracle on 34th Street is a 1947 comedy drama film about a department store Santa who just might be the real thing. Starring the “Queen of Technicolor,” Maureen O’Hara (The Hunchback of Notre Dame, The Quiet Man), John Payne (NBC’s The Restless Gun), and a young Natalie Wood (Rebel without a Cause, Splendor in the Grass).
 
Elf
“Santa, I know him!” Yes, the early 2000s absurdist Christmas comedy Elf has become a cult favorite in recent years. It’s easy to see why. First, the movie was one in a string of masterpieces released in what I like to refer to as the “Season of Will Ferrell.” Old School, Anchorman, Zoolander, Talladega Nights, Blades of Glory… Will was on fire. Now, put the 6’3 funnyman in green and yellow tights, have him convinced he’s just another elf, tell him his real father is James Caan, and send him to New York to look for him. It’s a classic fish out of water story, sprinkled with seasonal charm.
 
Batman Returns
Much like Die Hard, the movie’s status as a Christmas movie is heavily debated. Personally, I think people get hung up on the whole comic book superhero thing and neglect to notice all the wonderfully tacky Christmas kitsch, interpreted through the trademark neo-Gothic lens of Tim Burton. The movie opens on Gotham City’s light up night, which is of course ruined by the Penguin’s cronies who spring out of oversized packages to wreak havoc on unsuspecting spectators. It snows the entire film. Christmas trees are everywhere. Bruce Wayne and Selena attend a Christmas ball. The last lines of the film are, “Merry Christmas Master Bruce. Good will to all men… and women.” Come on people, it’s a Christmas movie! Starring Pittsburgh’s own Michael Keaton, Michelle Pfeiffer, Danny DeVito, and Christopher Walken. 
 
Fred Claus
What if Santa had a lesser known, slightly dysfunctional, older brother named Fred? Well, Fred Claus dares to answer that question and it’s just as funny, emotional, and heartfelt as you’d imagine. Vince Vaughn and Paul Giamatti, two of the most consistent thespians working today, deliver as always. The supporting cast includes Miranda Richardson, John Michael Higgins, Elizabeth Banks, Rachel Weisz, and Kathy Bates.
 
National Lampoon’s Christmas Vacation
Much like A Christmas Story, it seems National Lampoon’s Christmas Vacation is playing on loop on every channel on TV starting December 1st. Truth is, everyone, even if they don’t know it, is well aware of many of the holiday film tropes established in this particular movie. Not to mention, almost every commercial lighting display seems to play tribute to the movie’s classic holiday decorating-mayhem scene. Chevy Chase, Randy Quaid, and Beverly D’Angelo star.
 
A Charlie Brown Christmas
Leave it to Charlie Brown to deliver one of the most poignant commentaries on the true meaning of Christmas. The 1965 animated TV special is one of the most definitive inclusions in the annual holiday movie roster.  If you haven’t watched it since your youth, you might be surprised by how well it plays today, traditional hand-drawn animation and all. Who hasn’t owned one of those pitiful, iconic, stick Christmas trees?
 
The Santa Claus
There is a whole generation of young adults who rightfully considers the 1994 Tim Allen-starring The Santa Claus an all-timer. The plot centers around a recently divorced Dad who is unwittingly chosen to become the new Santa Claus. It’s a wonderfully touching movie that touches on the complexity of childhood and parenting, societal expectations, and the unifying nature of shared cultural traditions.
 
Christmas Evil
I haven’t forgotten about you my fellow gore hounds. If you ask me, Christmas Evil is THE holiday horror film. It’s the story of a disturbed Santa-obsessed man who’s put everyone on the naughty list. NOT fun for the whole family. Starring pop star Fionna Apple’s father Brandon Maggart and the shamefully underrated Jeffrey DeMunn (who Walking Dead fans will instantly recognize as Dave Horvath). Highly recommended for Christmas-loving horror fans.
 
A Christmas Carol
There have been so many different adaptions of the quintessential Charles Dickens Christmas Eve ghost story, it’s hard to single in on one particular version. A quick search shows that Alastair Sim, George C. Scott, Patrick Stewart, and Jim Carrey have all played the infamous Ebeneezer Scrooge over the decades. Then there’s 1988’s Scrooged, starring Bill Murray in a then-contemporary reimagining of the mid-19th century novella. The basic plot points are all the same. A cranky, less-than-generous, older man has a Christmas revelation after being visited by the Ghost of Christmas Past. Soon, he embraces the giving nature of the season and repairs his curmudgeonly reputation.
 
The Nightmare Before Christmas 
In this early-90s stop motion animation classic (directed by Henry Selick and produced by Tim Burton), Jack Skellington, King of Halloween Town, decides to invade Christmas Town and take over their most coveted celebration. It’s the movie that spawned a million Goth girls! There’s no denying it, it’s masterpiece of late 20th century animation with a killer Danny Elfman score. Plus, it’s the rare holiday film that makes sense at Halloween AND Christmas parties.
 
Bad Santa
Rounding off our list today is the outrageous adult Christmas comedy, Bad Santa, starring Billy Bob Thornton, Lauren Graham, Brett Kelly, Tony Cox, John Ritter, and Bernie Mac. Celebrating its 20th anniversary this year, it’s the kind of movie that has to be seen to be believed. Worst Mall Santa ever and that’s a compliment! Despite its crude raucous exterior, there’s a beautiful Christmas metaphor buried within. You’ll have to endure a lot of guilty laughter to get there though!