The holiday season is officially here, and depending on where you live, you’re probably surrounded by snow and cold weather! Fear not, because there’s no better way to embrace the season than curling up with a cozy blanket, a warm drink, and of course, a classic holiday film or TV show.
With literally thousands of classic films and shows to choose from, how do you land on the best ones? Well, hopefully this list will help! Keep in mind that these are obviously a matter of personal preference, but if you’re looking for something fun and lighthearted to watch with the family, you can’t go wrong with any of these picks.
But hang on! Before we get to the list, we need to share some HUGE news with you. Here at iCash, we have a holiday contest every year. This year, we’re going all out! This is literally the biggest contest we’ve had, with over $5,500 in prizes up for grabs. Want to know how to win? Keep reading!
Enter Our 12 Days of Giveaways with Over $5,500 in Prizes!
From December 1st through December 16th, iCash is hosting The 12 Days of Giveaways, featuring 12 different prizes with a combined value of over $5,500!
Here's how it works: each day brings a brand new prize reveal and a fresh chance to win. Simply visit our giveaway page, fill out the entry form with your name, email, and province of residence, and you're automatically entered for that day's prize. The best part? You can come back every single day for new opportunities to win throughout the contest period.
8 Must-See Holiday Films and TV Episodes
Now, let's get to what you came here for! We've curated a little diverse mix of classic favorites that we think capture the magic, warmth (and occasional chaos) of the holiday season.
1. Home Alone (1990)
No holiday movie list would be complete without this absolute classic. I probably don’t even need to give you the synopsis because everyone knows this film, but just in case.
This absolute classic follows eight-year-old Kevin McCallister, who's accidentally left behind when his family rushes off to Paris for Christmas. What follows is pure comedic, slapstick gold as Kevin defends his home from two burglars using creative booby traps.
The iconic performances from Macaulay Culkin, Joe Pesci and Daniel Stern, along with the film’s balance of humor with genuine heart make it a movie that brings together multiple generations, year after year after year.
2. Elf (2003)
Will Ferrell is Buddy, a human raised by elves at the North Pole who travels to New York City to find his biological father. This modern film became an almost instant classic and has become one of the most watched holiday movies of all time.
So, why is the movie perfect for the whole family? Buddy's childlike wonder and belief in Christmas spirit provide endless laughs. Kids love the physical comedy parts, while adults appreciate the clever writing and touching family dynamics.
3. The Holiday (2006)
Kate Winslet and Cameron Diaz star as two women who swap homes for Christmas. One from snowy England, the other from sunny California. And (shocker) both find unexpected romance.
With outstanding chemistry between all four leads (Jude Law and Jack Black round out the cast), beautiful cinematography, and a sweet message about opening yourself up to new possibilities, it's the perfect choice for anyone craving romance and gorgeous holiday aesthetics.
4. A Charlie Brown Christmas (1965)
This 25-minute television special deserves a spot on any holiday viewing list. Charles M. Schulz's beloved Peanuts gang tackles “the commercialization of Christmas” in this surprisingly deep and meaningful story.
Charlie Brown's search for the true spirit of Christmas, his selection of the small scraggly tree, and Linus's famous speech about “what Christmas is all about” have resonated with audiences for nearly six decades. One of my personal favorites about this special is the perfectly subtle and iconic jazzy score by Vince Guaraldi, which just works perfectly with the entire episode.
5. Love Actually (2003)
Love Actually might be one of the most famous romantic comedies of all time. The audience witnesses multiple interconnected love stories, all in the weeks leading up to Christmas. You’ve got a seriously all-star cast with this one. Hugh Grant, Emma Thompson, Keira Knightley, Andrew Lincoln, Colin Firth, and Liam Neeson are just some of the names you’ll recognize.
The iconic cue card scene has been referenced countless times in pop culture, and its message that "love actually is all around" continues to resonate year after year, especially during the holidays.
6. The Muppet Christmas Carol (1992)
Most of us are probably familiar with the original “A Christmas Carol” by Charles Dickens. It’s a story that has been retold over and over again, but the most iconic version might just be the one starring everyone’s favourite Muppets!
Michael Caine plays Ebenezer Scrooge, surrounded by beloved Muppet characters like Kermit and Miss Piggy, who bring humor and heart to every scene. With catchy musical numbers, it’s an entertaining introduction to Dickens for younger viewers and a thoroughly enjoyable watch for Muppet-loving adults.
7. Merry Christmas, Mr. Bean (1992)
Rowan Atkinson is one of the greatest slapstick comedians of our generation and underrated genius (in my humble opinion). You just need to watch any episode of Mr. Bean to see that. But none are more iconic than the classic Christmas episode.
The episode follows Mr. Bean's disastrous approach to holiday celebrations, which ultimately leads to a catastrophic Christmas dinner preparation scene where Mr. Bean gets his head stuck in a turkey.
What makes this special so endearing is the purely physical, visual comedy that has virtually no dialogue, making it accessible to all ages. Mr. Bean's childlike wonder mixed, paired with the absolute mayhem he creates, results in genuinely funny moments that have held up remarkably well.
8. Jingle All the Way (1996)
Most of us probably know Arnold Schwarzenegger as the Terminator, Conan the Barbarian, or Dutch from Predator. And while there’s no shortage of fantastic action films to see Arnold in, when Christmas comes around, it’s time to turn on “Jingle All the Way.”
In this film, Arnold plays a workaholic father desperately hunting for the sold-out “Turbo-Man” action figure his son wants for Christmas. The film takes that concept and goes overboard with it, as his character goes through chaotic malls, warehouses, and holiday parades, competing with other frantic parents, including Sinbad's memorable postal worker character. It’s funny, heartwarming, and also features the legendary Phil Hartman in one of his last few roles.
Making the Most of Your Holiday Season
These eight picks are all guaranteed to have you and your family smiling during the holidays. You’ll get some laughter, tears, romance, adventure, etc. Even if you just have these on in the background while you prep Christmas dinner, they create an undeniably cheery atmosphere that just makes things feel “Christmas-y.”
The beauty of the streaming era is that you can likely find all of these on a streaming service, or even digitally rent them for a small fee. So, this holiday season, treat yourself to cozy movie nights, enter our 12 Days of Giveaways for a chance to win amazing prizes, and remember that iCash has your back if you need a little financial support to make your celebrations special. From our team to yours, happy holidays and happy watching!
