The Best Christmas Movie of All Time (no, it’s not “Die Hard”)

Evolve Winter Competition

Anita Gallagher
Evolve
5 min readDec 20, 2021

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Photo credit: Warner Bros. Entertainment Inc.

Around this time of year, I always look forward to the perennial “Best Christmas Movie” debate. Whether it’s colleagues, friends, or family, everyone seems to have a passionate opinion on the subject. Some might even argue about the very criteria for what qualifies a film as a Christmas movie. But dear readers, I am here to definitively settle the debate.

The best Christmas movie of all time is not “Miracle on 34th Street”, “Elf”, and it certainly isn’t “Die Hard”. In fact, the crown belongs to “It Happened on 5th Avenue”.

Never heard of it? I hadn’t, either, until last year. As a self-professed fan of classic film, I’m embarrassed to admit I’d been ignorant of this masterpiece. I stumbled upon the movie while watching TCM on a cold winter’s day in December, and I’m so glad I did.

Released in 1947, “It Happened on 5th Avenue” tells the story of Aloysius McKeever, a portly, charismatic fellow who takes up residence in the homes of the wealthy while they winter in warmer locales. The only catch is that the rich people don’t know that Mr. McKeever is living in their homes. He enjoys all the finery each estate has to offer, wearing the owners’ clothes, smoking their cigars, and helping himself to the pantry.

One of the homes inhabited by Mr. McKeever belongs to Mike O’Connor, a Warren Buffett-type character who invests in real estate. The mansion is located on 5th Avenue in New York City. McKeever meets a handsome war veteran, Jim, who is out of work and just evicted from his apartment in a building owned by Mr. O’Connor. McKeever allows Jim and a few of his friends, also veterans who have lost their housing, to move into the O’Connor mansion while they get back on their feet.

In a bizarre coincidence that would only happen in a fairy tale, O’Connor’s beautiful daughter, Trudy, lands a job at a Manhattan music shop where she meets Jim. She soon discovers that Jim and the others are squatting in her family home, unbeknownst to her father. She falls in love with Jim and pretends to be a runaway from an abusive home so that McKeever will let her stay in the house, too, hoping Jim will return her affections.

Mr. O’Connor returns to New York, and miraculously, Trudy convinces him to not only allow this motley crew to stay in his home, but that he should also pretend to be homeless so that McKeever will take him in as yet another guest in the mansion. Trudy wants her father to meet Jim and understand that, while he’s currently down on his luck, he has a good head on his shoulders and would make a suitable husband.

Predictably, O’Connor struggles living as a poor person and things don’t go as planned. Trudy enlists the help of her mother, who is estranged from O’Connor but is willing to help her daughter sort out the situation. She disguises herself as a homeless woman and maneuvers her way into the growing crowd at the mansion.

Meanwhile, Jim and his friends develop a solid plan to pool their resources and purchase abandoned Army barracks to repurpose as housing for veterans and their families now that the war has ended. However, they face competition from another investor — you guessed it — Mike O’Connor.

To avoid the risk of completely spoiling the film for those of you who haven’t seen it, suffice to say that O’Connor’s charade only lasts so long, and he learns the time-honored lesson that family, not money, is the cornerstone of a meaningful life. Naturally, the Christmas holiday serves as the perfect backdrop for O’Connor to arrive at this realization.

“It Happened on 5th Avenue” is a comedy, outlandish at times. Suspension of disbelief is crucial to engaging with the plot’s twists and turns. But the film is compelling because the relationship dynamics — Jim and Trudy’s budding love, Jim’s camaraderie with his fellow servicemen, Trudy’s complicated relationship with her divorced parents, and McKeever serving as the wise guidance counselor who holds them all together — are evergreen.

The film challenges us to examine our choice as to who the hero is of this story. Objectively, the viewer knows that trespassing and living off of someone else’s resources without permission is wrong. But McKeever, with his calm demeanor and big heart, is the perfect juxtaposition to O’Connor, who is introduced as a greedy, rigid man who doesn’t listen to his daughter’s wishes. Of course, O’Connor learns and evolves during the course of the story, and at the film’s conclusion, his redemption could land him squarely in the hero category.

Further, while the social commentary is blunt, it’s just as relevant today as it was in 1947. In the New York City of the film, a few wealthy investors buy up so much land and housing developments that it becomes extremely difficult for the less fortunate to find affordable housing. O’Connor is oblivious to the homelessness and desperation caused by his business dealings. Watching the film for the first time, I was struck by how little has changed between then and now. A similar dynamic can be found in rental housing markets throughout America.

While the film works through themes such as poverty and homelessness, the story strikes a deft balance between treating these social conditions with the gravity warranted and allowing the viewer to share in the characters’ optimism. We want to see Trudy and Jim end up together, even if their relationship is built on a farce and they represent very different socioeconomic backgrounds. The housing plan hatched by Jim and his friends is such an inspiring display of post-war ingenuity, one can’t help but root for their success, even if it is the longest of long shots. Heck, we even hope for crotchety old O’Connor to reconcile with his wife.

There you have it, folks. “It Happened on 5th Avenue” delivers everything you could possibly need for Christmas entertainment — a love story for the young and not-so-young, characters changed by the power of human connection, and a happy ending.

You can find “It Happened on 5th Avenue” on a few streaming platforms, and I hope you check it out. It’s sure to warm your heart this holiday season.

Disclaimer: As a Jew, Christmas isn’t my holiday, but I tend to fall into the “Christmas-is-a-vibe” camp and I certainly don’t mind a little yuletide cheer.

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Anita Gallagher
Evolve
Writer for

Governmental affairs professional by day, aspiring writer by night. Classic film buff. Recovering Kanye West fan. Pacific Northwest.