Your Holiday Movie Streaming Guide for Winter Break 2020

We are literally days away from winter break. Some of us will be going home to celebrate the holidays, whereas others will be staying put in their dorms. Whatever your plans are, you’ll need some entertainment, which is why I decided to compile a list of some of the best holiday-themed films to watch during your winter break!

1. The New Release: Happiest Season

Image credit:

This brand new release looks actually amazing and the cast is stacked! Dan Levy? Check. Alison Brie? Check. Kristen Stewart? Check. Aubrey Plaza? Gang’s all here. Happiest Season is about a gay woman (Kristen Stewart) who goes to her girlfriend’s family’s house for Christmas. The only thing is…her girlfriend hasn’t come out yet. Cue the shenanigans! 

Happiest Season can be streamed on Prime Video.

2. The Nostalgic One: A Charlie Brown Christmas

I’m sure you’ve seen this Christmas Special, but I swear it gets better and better every time you watch it. The dead-pan humour is very reminiscent of the classic comic strip and the 70s-style animation is strangely calming to look at. 

A Charlie Brown Christmas can be streamed on Apple TV+ or watched for free on Youtube.

3. The Surprisingly Funny One: Happy Holidays from Madagascar

This Christmas series can be streamed on Netflix and is actually hilarious! It’s technically for kids but still funny enough for adults and features all your favorite Madagascar characters like King Julien, Melman and Gloria. I wouldn’t normally recommend a kid’s show, but this is just too good to miss. 

Happy Holidays from Madagascar can be streamed on Netflix.

4. The One You’ll Love To Hate-Watch: The Family Stone

Sometimes it’s fun to yell at the TV. The Family Stone is one of those movies that people love to hate. It has a dangerously low score on Rotten Tomatoes (53%) with most people saying the story is contrived and doesn’t really make sense. The movie is a bomb, but it might be exactly what you need to release all your pent up anger as you wonder “how was this actually made!?”

The Family Stone can be streamed on Prime Video and Crave.

5. The One That Will Give You The Feels: Love Actually

Love Actually is one of those movies that you can devote an entire afternoon to and feel fine about it. It features almost every famous British actor you’ve ever heard of and will inspire you to fall in love this holiday season. 

Love Actually can be streamed on Prime Video or Crave.

6. The Classic One: It’s A Wonderful Life

You can’t go wrong with a classic like this one. It’s a lot longer than you remembered, but who can deny Donna Reeve and James Stewart (who was basically the Ryan Reynolds of the 40s)? This is another one of those movies that can be watched over and over again without it getting old. 


It’s A Wonderful Life can be streamed on Prime Video


Hopefully these holiday movies will bring you a little bit of joy this winter break. Don’t forget the caramel corn!

Posted in Blog.

Jennifer Enchin is an RTA Media Production student, aspiring screenwriter and Youtube writer hailing from Toronto, Canada. Jennifer has worked as a script reader for Pomegranate Pictures as well as a critic for the popular theatre blog “Mooney On Theatre”. She also placed as a quarterfinalist in The Austin Film Festival’s 2020 Screenplay Competition for her feature script “Seabirds”. Her favourite topics to write about include entertainment, health and wellness, spirituality and general spooky stuff.