Advent Calendar Movies: 25 Days of the Best Christmas Films to Watch
What if you created an advent calendar, but for MOVIES!
Who is a movie advent calendar for?
If you’re a person who loves spending quality time together, and quality time is your love language then movie nights are one way to create that special moment with your friends or family.
On the other hand, if your love language is physical touch and you feel especially fulfilled after cuddles and snuggles, just think how awesome 25 days of watching movies will be!
Or maybe you’re a big movie buff and you love to revisit the classics each year, but like to add new ones to the mix. Knowing you won’t miss out on the traditional Christmas films you love while incorporating some hidden gems, adds variety to your list.
An advent calendar of movies is a fun, and inexpensive way of ringing in the Christmas season by enjoying the magic of the holidays through laughs, tears, music, great quotes, and all those memorable characters who make the holidays come alive. An advent season filled with these classics (and some not so classic) ‘holiday’ movies, can be an enjoyable way for friends and family to ring in the season – knowing you haven’t missed anything from your yearly must-watch list!
How to create a Holiday Movie Advent Calendar
Setting up a holiday viewing calendar might sound like a strange thing to do given the instant on-demand access to movies we have nowadays. But there is a kind of throwback nostalgia to planning what you’ll watch in advance.
Cable made a lot of decisions for you back in the day, while simultaneously causing a lot of disputes if two or more shows/events were airing at the same time and some family wanted to watch the game while others wanted to watch a holiday special. Remotes to the face anyone?
Since you likely didn’t purchase a whole library of holiday movies on DVD or VHS, you had to wait until the TV gods deemed it time to release these seasonal classics, usually around mid November.
In a sense the whole experience of movie night was simpler when the choice was made for you. Movie night was a special treat, one you anticipated and made time for in your week (you literally circled it in the TV Guide) and much like today movie watching still involves getting the popcorn and snacks together, jumping in your pjs, and basking in the glow of the analog experience. Just no more annoying commercials.
Although movie nights haven’t gone by the wayside like the beloved TV Guide (1953 – 2006), the splintered streaming services have meant the experience is far more reactive and less anticipatory. Hence the reason for creating an advent calendar of holiday movies – to bring back some of the excitement of family movie night.
Below you’ll find a real mish-mash of holiday films, some more appropriate for certain ages than others. There should be a little bit of something for everyone, if not just rewatch Home Alone on repeat!
Advent Calendar 25 Days of Holiday Movies
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Poster illustration by Robert Tanenbaum
A Christmas Story (1983)
“Ohhhh… fudge”
There are more than a few memorable scenes and more than enough one liners to make this an all time favourite movie to see during the holidays. Ralphie’s quest to get his Red Ryder BB gun is such a relatable story for any child who has wished for something different at Christmas. A sleeper film (released on Mickey Mouse’s 55th birthday) that has become a true holiday classic.
PG 1h 33m
Arthur Christmas (2011)
This animated film is a great movie for kids or adults. The movie features the voices of James McAvoy, Hugh Laurie, Jim Broadbent and Bill Nighy (Love Actually’s “Christmas is All Around” singer) with an ultra high-tech take on the operations of the North Pole. It’s witty, and different, and endearing.
PG 1h 40m
Batman Returns (1992)
Directed by Tim Burton (The Nightmare Before Christmas, 1993), this is the sequel to the 1989 film Batman, and the second of roughly 14 different Batman or Batman related films. The movie is set during the Christmas season and has lots of glittery glam to highlight the darkside of Christmas. An amazing cast, over the top settings, memorable villains – its a classic superhero movie and Batman Returns brings it all around.
PG 2h 6m
Catch Me If You Can (2002)
Not exactly a “Christmas movie” even though the opening scene takes place during Christmas Eve in Marseille, France right in the midst of a grande game of cat and mouse that is based on a true story of Frank Abagnale, a con man that forged millions of dollars of checks, without being caught. Starring none other than Tom Hanks (see article about why he’s the most universally perfect actor to have on in the background), Leonardo DiCaprio, Amy Adams, and of course Christopher Walken. This movie has action, suspense, comedy, intrigue, and mystery – it’s highly entertaining and because three of its most important scenes take place during Christmas Eve, it qualifies as an “un-Christmas” Christmas movie.
PG-13 2h 20m
Die Hard (1988)
“Welcome to the Party, Pal.” This is a classic only true Die Hards watch each and every Christmas. Not your sappy, feel-good, candy coated Christmas movie, it’s theme is redemption through violence and one that delivers. It is non-stop action with charisma. It could pass as a thriller, it’s definitely an action film and as for Christmas movie… you just have to believe.
R 2h 11m
Poster design by BLT Communications, LLC
Photography by Peter Tangen
Elf (2003)
This sugary sweet movie is over the top Christmas everything. It’s feel-good all the way, funny, and entertaining for both kids and parents. If you need a film to inspire your decorating, the scenes in this film do not disappoint. Starring Will Ferrell, James Caan, Bob Newhart, Mary Steenburgen, Zooey Deschanel, Peter Dinklage, Andy Richter, and Ed Asner as Santa – it has a top notch cast with a number of memorable scenes that quickly became classic holiday pop culture.
G 1h 37m
The Family Stone (2005)
A deeply memorable, likable movie about what a family looks like to an outsider. It’s casting is as diverse as its characters, with Diane Keaton, Craig T. Nelson, Sarah Jessica Parker, Dermot Mulroney, and Luke Wilson. It rambles on at times, but hopefully one leaves more empathetic and sympathetic after viewing this family during the holidays. This is a quirky film with a lot going on, but it’s worth a watch. Just have a tissue box nearby.
PG-13 1h 44m
Four Christmases (2008)
A deeply memorable, likable movie about what a family looks like to an outsider. It’s casting is as diverse as its Balancing the holidays with all the in-laws, ex-laws, siblings, and step-parents can be a physically and mentally exhausting adventure that is hilariously portrayed by Reese Witherspoon and Vince Vaughan. A movie about escaping the holidays turns into a movie about confronting all the drama that the holidays bring. A funny film with many relatable scenes, and an excellent supporting cast.
PG-13 1h 28m
The Holiday (2006)
A home swap during the holidays with delightful results. Kate Winslet and Cameron Diaz change their holiday plans and stay in one another’s homes in different countries in order to escape the same old, miserable, Christmas alone. It’s a feel good film that will have you dreaming of spending Christmas doing something new. Nothing like a little perspective during the holidays to keep you connected with who you are and that love is all around us.
PG-13 2h 12m
Holidate (2020)
Sometimes predictable is good. There is safety in this film and an endearing chemistry between the characters that make this a pretty good romantic comedy. Have a laugh, have a cry, and remember to reach out to someone who is alone this holiday season. Connection is good for the soul.
TV-MA 1h 43m
Home Alone (1990)
This 30 year old film has been a classic for more than one generation. Macaulay Culkin may well be 41 in real years, but for many he will always be 10 year old Kevin McAllister. There are so many classic lines, memorable scenes, and unbelievable scenarios, not least of which is the total lack of airport security (and also how Kevin’s dad could afford to take 15 people on a trip to Paris for Christmas – like seriously? See here for theories as to his profession ). Ring in the holiday season with this film or save it until closer to Christmas Day, either way it’s a gem.
PG 1h 42m
The How the Grinch Stole Christmas (1966)
The made-for-TV Christmas special is the only Grinch in this calendar for a reason. It’s vibrant, simple, and filled with emotion and memorable dialogue. It’s tough to find a better Christmas movie out there, and as has been shown, it’s even harder to remake it. A seasonal must see for sure.
G 26m
How to Marry a Millionaire (1953)
If diamonds are a girl’s best-friend, then this is your best Christmas movie. Why Christmas? Because what better time of year to get diamonds. This is a funny, clever, highly-entertaining movie about three young New York models hoping to find themselves wedded to millionaires, I mean how hard can it be? Turns out there is a lot more involved in just looking pretty and going on dates. You’ll see.
G 1h 35m
It’s A Wonderful Life (1946)
“I’m the richest man in town”. An angel is sent from Heaven to help a desperately frustrated businessman by showing him what life would have been like if he had never existed. It’s not officially Christmas until this movie is played. This film has a great message and an exceptional cast to bring it to life. It almost gets better every year you watch it. A superb film to feel connected to the spirit of the season and I bet you’ll never listen to bells the same way again.
PG 2h 10m
Jingle All the Way (1996)
A home swap during the holidays with If you want a laugh watching other parents hunt down the hottest gift of the season, this is the film for you. Starring the actor Arnold Schwarzenegger, Sinbad, and Rita Wilson, it is a fun satirical film and has been on Christmas watch lists for years.
PG 1h 28m
Kiss Kiss Bang Bang (2005)
Starring Robert Downey Jr, Val Kilmar and Michelle Monaghan in a murder mystery that brings together a private detective, struggling actress and a thief pretending to be an actor. This dark comedy fits in with the holiday themes of redemption, forgiveness, and rebirth. It’s got great dialogue, lots of plot twists and if you’re into a bit of crime fiction neo-noir, this is your kind of film.
R 1h 42m
L.A. Confidential (1997)
The Christmas references are sprinkled throughout this film noir, linking together some of the movie’s most poignant scenes; all while shining a light on the tailend of Hollywood’s most powerful era. It’s a highly stylized vision of a corrupt Los Angeles coming out of the Golden Age of Hollywood with nostalgia and old fashioned glamour that is “just off the record, on the QT, and very hush-hush…” Crime, Scandal, Love, Lust, and Gossip. Merry Christmas.
R 2h 18m
Love Actually (2003)
A vignette of holiday romance, humor, heartache, and irony. Originally intended to be two different films, one for Hugh Grant’s character, the second for Colin Firth’s story, Richard Curtis (writer and director) melded it into one that has become a cult classic. There are more than a few heartbreaking and heartwarming scenes woven together, making this an easy pick every year in order to relieve all the memories. To make it even more memorable add a drinking game for each time the word “Actually” is said in the film. (Spoiler see below:).
R 2h 15m
Miracle on 34th Street (1947 or 1994)
Either version of this holiday classic is sure to be enjoyable. Set in Macy’s department store in New York City (hence the 34th street), it delivers a warm holiday message about believing in yourself.
G 1h 36m
Mickey’s Christmas Carol (1983)
Based on Charles Dickens “A Christmas Carol” this stars all your Disney favorites, with Uncle Scrooge McDuck playing Scrooge. A great film to introduce kids to larger Christmas lessons.
G 26m
National Lampoon’s Christmas Vacation (1989)
Hilarious to watch year after year despite knowing what disasters lay ahead. Chevy Chase, Beverly D’Angelo, Juliette Lewis, Randy Quaid and more star in a movie centered around the Griswolds family shenanigans. If you think your family is dysfunctional, this is the perfect film to add to your holiday list. In fact so many people enjoy this movie that one of the most expensive Hallmark ornaments ever sold is held by Cousin Eddie’s RV<link> Who knew?
PG-13 1h 37m
The Nightmare Before Christmas (1993)
An edgy film juxtaposing the scary side of Halloween with the cheer and happiness of Christmas. Tim Burton’s creative genius is creating a dark dream world that is a meticulously crafted claymation world. It is both a horror film and a musical, it is fantasy, seriousness, comedy and suspense. A hit with those who love it. Not entirely recommended for very young children.
PG 1h 15m
The Preacher’s Wife(1996)
A movie the whole family can enjoy. A romantic film that will uplift you and make you laugh. The casting and music is superb – Denzel Washington, Lionel Ritchie, Gregory Hines and the iconic Whitney Houston. This is an inspiring film about the power of miracles – something good when good is needed.
PG 2h 04m
The Polar Express (2004)
Another classic Tom Hanks film to have on during the holidays. It is based on the 1985 children’s book by Chris Van Allsburg and follows a skeptical child on a magical train ride to the North Pole on Christmas Eve. This is the first movie ever filmed entirely with motion capture (a process by which filmmakers animate characters using a recording of their real life movements). Because of this technique, not everyone is a fan. However, there is a glossy, shiny, lustre the film has that other animated films don’t have, which lends itself to the child-like wonder and magical quality of the movie. You have to see it to believe it.
G 1h 40m
The Santa Claus (1994)
“Seeing isn’t believing. Believing is seeing.” The essence of this film is getting out of your own way in order to feel and see what’s right in front of you. It’s full of witty one-liners, absolutely luxurious depictions of Santa’s workshop and home in the North Pole, I mean those red silk pajamas are ahh-mazing! This is the type of Christmas movie that adds to the magic and encourages you to see the season through a child’s eyes.
PG 1h 37m
That’s the list. You’ve opened the last door of your entertainment advent calendar.
To wrap up
If you’re looking for date night ideas, family traditions, or feeling festive you can cross that off your list when you choose one of these films. If you’re looking for a challenge and really want to watch a movie for 25 consecutive nights then this is the Advent calendar for you. Feel free to stretch it out over several weeks (Remembrance / Veterans’ Day to Christmas Day) or through the 12 days of Christmas, wrapping it up on January 6th. There are many wonderful holiday films to hunt down and some that aren’t holiday at all yet seem fun to watch this time of year. Whatever makes you merry happy!
Feeling extra? Here are a few holiday movies that didn’t make the cut
Poster design by Indika Entertainment Advertising
American Psycho (2000)
This is the kind of film that fits well between Halloween and the holidays, for obvious reasons? Starring Christian Bale, Jared Leto, William Dafoe, Chloe Sevigny and Reese Witherspoon this is a dark, wry comedy that is not at all family-friendly. The acting is excellent and the business card scene is absolutely priceless. Watch if you’re really feeling like you want a “holly-jolly Christmas”, or not.
R 1h 43m
Photography by Mark Seliger
The Best Man Holiday (2013)
This is a sequel to the entertaining and funny movie Best Man. Taking place around the holidays where a group of college friends reunite, it turns up the heat on past flames, quarrels and drama. A bit of everything is sprinkled into this movie with a great cast.
R 2h 2m
Goodfellas (1990)
This is a movie for the hardened Christmas viewers. Not a real family viewing piece – Goodfellas skirts the edge of the holidays by delivering a brilliantly acted, memorable and very funny film about hitmen and the mob. It’s often looked at as one of Martin Scorsese’s greatest works and credited as one of the best gangster films of all time.
R 2h 26m
Poster illustration by John Alvin
Gremlins (1984)
Why would a horror film be considered in a Christmas list? This is a dark take on Christmas and an annual must-watch for movie fans. The idyllic setting is a perfect small town turned upside down by these vicious monsters. It’s certainly not for everyone, especially little kids, but it’s an entertaining, suspenseful Christmas Horror (I guess that’s a thing).
PG 1h 46m
Surviving Christmas (2004)
Romantic comedy starring Ben Affleck, James Gandolfini, Christina Applegate, and Catherine O’Hara. It’s set in the home town of an annoying millionaire who is trying to find happiness by burning his grievances on the front lawn of his childhood home and then finding himself by reconnecting with his past. A movie to remind you that grudges aren’t worth holding on to.
PG 1h 30m
Actually is said 23 times. Happy Christmas!
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