Chill Out: 31 Movies & Specials to Warm You Up All December

By Cory Angeletti-Szasz ● November 27, 2017 09:00

Updated November 27, 2019: We're reprising this fun piece from 2017, as many of the classics below are ones you'll want to see again! 

December is full of different celebrations and holidays, home to the winter solstice, and officially kicks off The Canadian Winter – a bittersweet season that lasts half the year. It’s a cold, dark month (but oh so festive!), making it the perfect time for cozying up in flannel PJs and wool socks with a mug of hot chocolate (or mulled wine) to watch (and rewatch) some fan-favourite festive flicks.

We’ve compiled a list of 31 films, TV episodes and specials (one for every day of December!) to help launch you full tilt into the winter season, whether you celebrate Christmas, Hanukkah, Kwanzaa, everything, nothing, or are a nonsecular winterphile. You may be so inclined to watch some of the below picks to help commemorate a holiday, a snowfall, a snow day, a night in, a warm beverage, some comfort food, or really any reason you have to celebrate (hey, more excuses to watch movies!).

December 1: A Christmas Story (1983)

Why not kick off this month-long movie challenge with what is considered by many to be essential holiday viewing – Bob Clark's classic A Christmas Story, set in Cleveland, but also filmed in Toronto!

Where to watch: iTunesGoogle PlayAmazon

December 2: Die Hard (1988)

Hey, less traditional holiday enthusiasts! Our second film of the month might be more your speed.

While still full of festive flare, and taking place on Christmas Eve, this pick also delivers lots of action and adventure. If you’re feeling particularly merry, keep the festivities going with Die Hard 2 (1990), which also occurs on Christmas Eve, to make it a Saturday night double feature.

Where to watch: iTunesGoogle PlayYouTube

December 3: A Christmas Horror Story (2015)

This one’s for all you die-hard holiday fans who also happen to be die-hard horror fans. Helmed by CFC alumni Steve Hoban, Grant Harvey and Brett Sullivan (and co-written by alumni Pascal Trottier and Jason Filiatrault), these four interwoven stories of seasonal terror that take place on Christmas Eve will provide your holiday horror fill.

Where to watch: iTunesGoogle PlayYouTube

December 4: National Lampoon's Christmas Vacation (1989)

Need a little holiday humour after all that holiday horror? Clark Griswold’s misadventures should do the trick in the Christmas edition of the Griswold family vacations.

Where to watch: Amazon, Google PlayYouTube

December 5: Serendipity (2001)

A holiday pick for the hopeless romantics featuring a star-studded cast (Kate Beckinsale, Jeremy Piven, Bridget Moynaghan, John Corbett, and CFC Board Member and comedy great Eugene Levy), lots of beautiful wintry and festive NYC scenery, and of course, a love story to boot. Best enjoyed while drinking hot chocolate.

Where to watch: Amazon

December 6: Gremlins (1984)

A festive film for those who prefer unconventional holiday entertainment, this horror-comedy delivers seasonal content, but maybe not the warm and fuzzy kind you’re used to. Contrary to popular belief, this terrifying treat can be enjoyed before or after midnight.

Where to watch: iTunesGoogle PlayYouTube

December 7: Dreaming of a Jewish Christmas (2017)

If you’re a Christmas enthusiast who turns on the holiday tunes November 1 at 12:01 a.m., then you might be particularly interested in today’s selection. This one-hour irreverent musical documentary from director Larry Weinstein tells the story of a group of Jewish songwriters who wrote the soundtrack to Christmas – from songs like Rudolph The Red-Nosed Reindeer and Have A Holly Jolly Christmas to The Christmas Song (Chestnuts Roasting On An Open Fire).

Where to watch: CBC

December 8: Home Alone (1990) and Home Alone 2: Lost in New York (1992)

Since it’s a Friday night, we figure there’s room for a double feature. And the best way to watch these iconic holiday films is back-to-back while indulging on cheese pizza and ice cream sundaes.

Where to watch: they’re probably airing on at least one TV station, but if not you can find them on iTunes, YouTube and Google Play.

December 9: Fargo (1996)

By now, you’ve had a week to settle into December, and have hopefully come to terms with the loads of snow outside your window and are even, dare I say, ready to embrace it? Well, either way, you can start embracing it by launching yourself into the brutal cold and snow of the American Midwest with this pleasant comedy-crime from the Coen brothers. Alternatively, or in addition, you could (also) spend the day binging on the Fargo TV series.

Where to watch: AmazoniTunes (film); Netflix (TV series)

December 10: Rudolph the Red-Nosed Reindeer (1964)

Santa and Rudolph

More than 50 years after the original airing, this stop-motion animated special remains not only the longest-running holiday special in television history, but also a steadfast holiday tradition in many households, akin to putting out cookies for Santa and listening for reindeer on the roof.

Where to watch: Amazon (and it likely airs on CBC at some point in December!)

December 11: Black Christmas (1974)

Mondays are horror-fying at the best of times, so you may as well accept it with this holiday horror classic (and a Canadian one nonetheless!), helmed by the same Bob Clark from A Christmas Story.

Where to watch: Amazon, DVD/Blu-ray, iTunes

December 12: A Rugrats Chanukah (1996)

Celebrate the first night of the festival of lights with some latkes and a delightful episode of the much-loved ‘90s kids cartoon as the brave tots go on an adventure to learn the story behind the holiday and vanquish the “meany of Chanukah.”

Where to watch: iTunesAmazon

December 13: An American Tail (1986)

On the second night of Hanukkah, follow brave young Fievel Mousekewitz on his journey to America and watch as he receives his signature blue hat as a Hanukkah gift from his father.

Where to watch: Amazon

December 14: The Hebrew Hammer (2003)

This cult-hit comedy, which follows Mordechai Jefferson Carver, a Jewish crime fighter known as the Hebrew Hammer (played by Adam Goldberg) as he saves Hanukkah from the evil son of Santa Claus (played by Andy Dick), is an excellent choice for the third night of Hanukkah. What’s more, it’s the Hanukkah gift that keeps on giving! The filmmakers behind the film have launched a crowdfunding campaign for the sequel, The Hebrew Hammer vs. Hitler.

Where to watch: Amazon, DVD

December 15: Kiss Kiss Bang Bang (2005)

A perfect Friday night flick for those of you looking for an alternative to the more saccharine holiday hits (like tomorrow’s pick!). This irreverent noir crime-comedy set to a backdrop of holiday cheer and imagery is sure to please.

Where to watch: Amazon, iTunes

December 16: Love Actually (2003)

If you’re experiencing a little mid-month slump, watching this holiday staple is sure to give you the warm and fuzzies and bring the festive cheer back into even the Scroogiest of hearts. Which brings us to our next pick …

Where to watch: AmazonCRAVE/HBOGoogle Play

December 17: The Muppet Christmas Carol (1992)

Gather with some family and friends to enjoy the Muppets’ version of the classic tale of an old and bitter miser’s Christmas Eve redemption in this now 25-year-old take on the Charles Dickens tale.

Where to watch: iTunes, Google PlayAmazon

December 18: The Magic Hockey Skates (2012)

Animated image of a boy in a sports store holding a hockey skate

Insert a little Canadiana into your holiday viewing with this feel-good Canadian animated special about – what else – the national winter sport of Canada.

Where to watch: CBC Gem

December 19: The Shining (1980)

This masterpiece of horror is an excellent cinematic selection all year round, but why not enjoy it on a particularly cold, dark, stormy December night to match the winter weather in the film’s Colorado Rockies?

Where to watch: iTunesGoogle PlayAmazon

December 20: Elf (2003)

Son of a nutcracker! You didn’t think we would leave this gem off the list, did you? Some might say that the holiday season isn’t complete without watching this beloved, syrup-soaked film at least once.

Where to watch: AmazoniTunesGoogle Play

December 21: The Nightmare Before Christmas (1993)

On the darkest day of the year, you may find that you have a yearning to watch a darker holiday tale, like this Halloween-Christmas mashup, where the merry and the macabre, the festive and the frightening collide.

Where to watch: iTunesGoogle PlayAmazon

December 22: Jingle All the Way (1996)

Have you been too busy watching the movies and specials on this list to pick up your holiday gifts? Fear not, there’s still time! Arnold Schwarzenegger will show you the way and maybe even uncover the real meaning of Christmas (hint: it’s not presents!).

Where to watch: Google PlayHuluCRAVE/HBOAmazon

December 23: Seinfeld, “The Strike” (1997)

On December 23, air your grievances, demonstrate your feats of strength and celebrate Festivus, the festival for the rest of us, with the episode of Seinfeld that ushered the “holiday” into mainstream popular consciousness.

Where to watch: DVD

December 24: It’s a Wonderful Life (1946)

Christmas Eve feels like an appropriate time to watch one of the most cherished and loved holiday films. This Frank Capra classic is an emotional journey (good for a therapeutic cry!) filled with much-quoted lines and indelible moments, ultimately leaving you feeling full of merriment in time for Christmas Day.

Where to watch: iTunesGoogle PlayAmazon

December 25: Miracle on 34th Street (1947)

On Christmas Day, celebrate the 70th anniversary of the original Miracle on 34th Street – a tried-and-true Christmas classic.

Where to watch: iTunesGoogle PlayAmazon

December 26: The Black Candle (2008)

A vibrant documentary that uses Kwanzaa as a vehicle to celebrate the African-American experience, this film is a perfect fit for the first night of Kwanzaa – the evening that the black candle in the center of the candleholder is lit. It’s a great choice for those who observe the holiday and those who are curious about it.

Where to watch: iTunes

December 27: A Rugrats Kwanzaa (2001)

Animated image of babies sitting around and on the lap of a grandmother as she tells stories
On the second day of Kwanzaa, join Susie Carmichael, her family and her baby friends as they learn about and celebrate the cultural holiday.

Where to watch: iTunesAmazon

December 28: The Holiday (2006)

This light-hearted holiday house-swap is a great choice for when you’re already feeling nostalgic for Hanukkah and Christmas, but also excited about NYE. All three celebrations are featured in this festive favourite!

Where to watch: Google PlayYouTubeAmazon

December 29: The Thing (1982)

Another pick for horror and winter lovers alike, this cult horror classic (set to a background of Antarctic snow) is sure to keep you warm on a cold December night. Spoiler alert: You might not want to watch it with your dog snuggled up next to you.

Where to watch: Google PlayYouTube

December 30: March of the Penguins (2005)

Need some motivation to meet those New Year goals heading into January?

Watch the determined and resilient emperor penguins make their journey across the frozen tundra of the Antarctic in this Academy Award-winning feature documentary.

Where to watch: Amazon

December 31: When Harry Met Sally (1989)

It’s time for the final hurrah of this December holiday viewing list, so we’re signing off with a timeless rom-com – a perfect pick for snuggling up indoors on NYE. Grab a glass of champagne and let Harry and Sally help you ring in the New Year.

Where to watch: iTunesCRAVEGoogle Play

Cory Angeletti-Szasz

Interim Director, Marketing & Communications