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The Most Whimsical Holiday Movies Ever Created

December has hit. The weather is officially cold, the days are officially dark at increasingly unreasonable times, and the whole “cramming the rest of the year into the next four weeks” thing is becoming real. It can seem like the only solution is to bury yourself in the socially constructed illusions of comfort and joy that are holiday magic. There is absolutely no panacea that can rival a whimsical holiday movie. Without further ado, here are the very most whimsical ones.

The Polar Express (2004)

Based on the eponymous children’s book by Chris Van Allsburg, The Polar Express is all about celebrating the wonder of life. Following a young boy who harbors growing suspicions about the existence of Santa Claus, the story chronicles the adventure that ensues when he is whisked away by a mysterious North Pole-bound train and taken on a journey that restores his belief in magic. Featuring dance numbers, complimentary hot chocolate, and icons such as Know-It-All Kid — this movie is the perfect watch to bring out your inner newly-unjaded child.

Love, Actually (2003)

This season classic explores nine uniquely compelling manifestations of the most arguably whimsical emotion of all… love. Whether you resonate more with Sam’s romantic sprint through Heathrow Airport security or rock legend Billy Mack’s drunken Christmas with Joe, this movie always serves as a warm and lighthearted reminder of what unites us all.

Elf (2003)

Add a dash of maple syrup, chocolate syrup, and marshmallows to your spaghetti and embark on a fun-filled trip to a Christmas-light-laden New York City alongside Will Ferrell’s Buddy the Elf. This quintessential holiday watch combines humor and absurd hijinks with a heartwarming story about feeling different, finding oneself, and finding the magic in life amid a sea of the seemingly mundane.

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

Both iterations of this farcical subversion of the classic childhood dream of independence are absolutely dripping in whimsy. The first version sees 8-year-old Kevin McCallister abandoned at home over the holidays, only to find himself resorting to increasingly creative methods of warding off two burglars. The second takes things a step further, leaving Kevin abandoned in New York City, where he makes himself comfortable at the Plaza Hotel, only to encounter the same two thieves. Both versions are characterized by the pairing of exciting childhood fantasies and slapstick comedy with genuinely poignant messages about how we appreciate others.

The Santa Claus 3: The Escape Claus (2006)

Following the precedents set by The Santa Claus (1994) and The Santa Claus 2 (2002), this story is centered around divorced dad Scott’s exploits as the newly appointed Santa Clause after he accidentally kills a man in a Santa suit on Christmas Eve at the start of the first film. That said, the third addition to the franchise is undoubtedly the most whimsical. Featuring Martin Short as Jack Frost, a mischievous member of the legendary council with his sights set on rising above his station, this Disney Channel holiday staple blatantly averts anything resembling an attempt at seriousness and makes for a very…punny (sorry) hour and thirty-seven minutes of entertainment.

The Year Without a Santa Claus (1974)

This stop-motion animated television special sees Santa Clause himself become disillusioned with Christmas joy, prompting Mrs. Clause and the elves to set out on an adventure in an attempt to make sure that he changes his mind. Encountering memorable characters such as Snow Miser and Heat Miser (who had their own spin-off in 2008), this program is adorable and unnerving in the precise way that it needs to be to make it peak whimsy.

Shrek the Halls (2007)

Featuring Shrek and all of the most beloved accompanying characters, this thirty-minute animated special truly asks and answers the question: What does Shrek do on Christmas? The answer is basically what one would expect: He jokes around and celebrates with the rest of the Shrek characters. It is wonderful, and it really is moving to see the Gingerbread Man so at home.

Paddington (2014)

Though less explicitly festive than many other recommendations on this list, this story compensates through its beautiful animation and undeniably warm and affecting narrative. Following an adorable, marmalade-addicted bear who finds himself lost on the cold streets of London only to find a new home with the Browns, who help him evade a crazed taxidermist, Paddington undoubtedly earns its place among the most whimsical holiday films on record.

Rudolph the Red-Nosed Reindeer (1964)

Though Rudolph the Red-Nosed Reindeer was initially created by Robert L. May as part of a marketing campaign, cultural touchstones such as this animated musical television special are what keep the icon alive. By combining catchy songs against the backdrop of an adorable felt-capped winter wonderland, this movie has become a staple of holiday whimsy for good reason.


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