17 Must-Watch Movies For the Holiday Season

Whether you celebrate Christmas, Hanukkah, Kwanzaa or Yule, I am sure you agree that there is nothing better than curling up on the couch on a cold day with some hot cocoa to binge-watch your favorite holiday movies.  Although I tend to get hooked on Hallmark Holiday Movie Marathons (why are they so good even though they are so predictable?), there are many must watch movies in our household every year.  Enjoy this compiled list of holiday shorts, classics, and guilty pleasures.  Are there any movies you would add to the list?

Short Holiday Movies

Olaf’s Frozen Adventure (22 minutes):  We are big Frozen fans in our house, so it is to no surprise that this is number 1 on our watch list.  Olaf attempts to find Anna and Elsa a holiday tradition because they do not have one.  There are many surprises, wonderful ballads, and a heart warming ending.  

Trolls Holiday (26 minutes): Ever since the Bergens lost Troll Day, they have no holidays to celebrate.  Queen Poppy decides to find a holiday for the Bergens.  Filled with catchy songs and dance numbers, this will definitely be a favorite movie for your kids.  

How the Grinch Stole Christmas (26 minutes): This original animated cartoon made in 1966 is both a short and a holiday classic.  This movie teaches such a great lesson on love and friendship, and it is a good excuse to make these delicious themed cookies.

A Charlie Brown Christmas (30 minutes): Also a short and a classic, A Charlie Brown Christmas will make you sing “Christmastime is here” for the rest of the holiday season.  

Mickey’s Christmas Carol (26 minutes): There are many Mickey Christmas movies but this one is my favorite because it is a movie from my childhood.  Mickey’s Christmas Carol is the Disney take on A Christmas Carol, where Mickey is Mr. Cratchit and Scrooge McDuck is Ebenezer Scrooge! 

Classics

It’s A Wonderful Life I. LOVE. THIS. MOVIE! Honestly, this is my favorite movie of the season.  This black and white classic teaches us that life without our existence would be very different – it is important to appreciate what you have and know that love will help you conquer all.  “Every time a bell rings, an angel gets his wings…” 

White Christmas:  Bing Crosby and Danny Kaye woo us all with song and dance in this 1954 classic.  Watch this film for romance, friendship, and Vermont Christmas beauty.  

A Christmas Story: “You’re going to shoot your eye out, kid.”  This hilarious classic gets us rolling on the floor laughing every time.  It’s hard to pick a favorite part, but it is definitely on our must watch list every year.  

Home Alone: Oh, how I love this series. Although there are scary robbers in these films, it is awesome to see a child combat them and find the true meaning of Christmas.  

Elf:  You are now wondering, is this a classic? I think this movie will stand the test of time.  Everyone falls in love with Buddy the Elf as he ventures to meet his father who is on the naughty list.  With the help of his friends, Buddy saves Christmas.   

Die Hard:  My husband and I get in a heated discussion every year on whether this movie is a “holiday classic” or not, but because I am a 9 enneagram I will put this little film on this list to avoid any argument (..for now..).  Do not watch this one with the kids.  

National Lampoon’s Christmas Vacation:  Clark Griswold is at it again and runs into many challenges during the Christmas Celebration at his house.  Cringe-worthy and comical disasters strike, but it doesn’t ruin Christmas.  

Guilty Pleasure

Love Actually:  This romantic film makes my heart soar. It follows eight different people around during the holiday season, and it is so fun to see how all of their lives interconnect.  Definitely a guilty pleasure I watch every year (along with my many Hallmark Films). 

The Holiday: I’m not going to lie, I do watch this rom-com year round. I love Kate Winslet’s character, and I love to see how both couples fall in love again after experiencing heartache during the holiday season.  

The Grinch Who Stole Christmas :  This live action movie brings Dr. Seuss’s characters to life. Jim Carrey’s Grinch is hilarious, and you can’t help but feel sorry for him when realizing why he hated Christmas so much.  

The Santa Clause: The first Santa Clause is a guilty pleasure we can all enjoy over the holiday season. Tim Allen is forced to become the new Santa after the original fell off his roof, causing a rift in his family relations.  

Jingle All The Way:  Arnold Schwarzenegger plays a dad who vowed to buy his son a specific action figure for Christmas, however, he could not find it.  This silly movie shares his struggles to obtain the hottest gift of the season.  

Jillian Henry
Born and raised in Wisconsin, Jillian has called many states home since she left the beer and cheese state five years ago. Currently, she resides in Derby with her husband, one-year-old daughter, and four-year-old “Boshih” (Boston Terrier Shih-Tzu mix). Jillian has a bachelor’s degree in Education and a Master’s Degree in Psychology, but her favorite role is taking care of her daughter as a stay-at-home mom. When Jillian is not moving across the continental United States, she enjoys spending time with her family, traveling, singing the Moana soundtrack in its entirety, exploring nature, catching up with friends, and eating any gluten-free dessert she can get her hands on. Jillian is looking forward to learning more about Wichita while experiencing life on the plains.