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Five Movies to Watch This Holiday Season

Sophia Calvillo Student Contributor, Vassar College
This article is written by a student writer from the Her Campus at Vassar chapter and does not reflect the views of Her Campus.

We have finally reached the last month of the year, which means the dread of finals week is officially upon us. If you are anything like me, you are already looking forward to traveling home after writing that final paper or taking that last exam, and cozying up on your couch with a cup of hot cocoa in hand. As a movie lover, I cannot wait to revisit some of my favorite holiday films and watch some new movies I have yet to see! Of course, the Christmas season wouldn’t be complete without classics like “Elf”, “The Polar Express”, and “Home Alone”, but I wanted to branch out a bit and share some films you may—or may not—have seen before. If you are in need of recommendations, then look no further because here are my top five picks for your Christmas movie marathon.

  1. The Family Stone (2005)

This classic might just be the best Christmas movie to ever grace my screen. You will fall in love with every member of the Stone family, in-laws included, while you follow them through a particularly intense holiday as the oldest Everett (Dermot Mulroney) brings home his very serious girlfriend Meredith (Sarah Jessica Parker), to meet his unconventional (and shall we say, judgy?) family. As tensions rise between Meredith and the Stone clan, unlikely relationships begin to form as the days inch closer to Christmas morning. Diane Keaton is the heart of the film, delivering a heartwarming performance as the family matriarch, while Rachel McAdams and Luke Wilson add perfect comedic balance. I assure you, there will not be a dry eye at the end of this film as it hits you right in the feels. 

  1. The Holiday (2006)

Nancy Meyers, the woman that you are! “The Holiday” radiates that mid-2000s rom-com charm we all miss, elevated by Meyers’ signature Old Hollywood sensibilities—warm lighting and classic meet-cutes. The film’s mise-en-scène is so memorable that its sets and houses still circulate online every December as the blueprint for cozy holiday aesthetics.

The story follows Amanda Woods (Cameron Diaz), a high-powered movie trailer editor whose seemingly perfect life unravels after a breakup. Seeking an escape, she stumbles onto a home-exchange site and decides to swap her huge LA mansion for Iris’s (Kate Winslet) charming English countryside cottage. As both women are looking to get away from their past romances, love ends up finding its way into their lives anyway. Amanda finds herself in an unexpected relationship abroad, while Iris befriends Arthur (Eli Wallach), a retired screenwriter straight out of Hollywood’s Golden Age. His wisdom—and their deeply sweet friendship—guides her toward rediscovering her worth. And of course, Hans Zimmer’s perfect musical score ties it all together.

  1. It’s a Wonderful Life (1946) 

Frank Capra’s “It’s a Wonderful Life” endures as one of the most profound and timeless films ever made. It is a movie that shifts your perspective on what it means to live a meaningful life. Jimmy Stewart delivers an unforgettable performance as George Bailey, a man whose quiet sacrifices shape his community in ways he never fully realizes. As the film traces his life from childhood dreams to unexpected detours, we witness how every choice, setback, and small act of kindness shapes it. When George reaches his breaking point and believes the world would be better off without him, his guardian angel Clarence intervenes, showing him an alternate reality of Bedford Falls where he never existed. What follows is a deeply moving reminder that no life is insignificant and that our impact on others often goes unseen. If you are a fan of “A Christmas Carol”, you will really like this film. 

  1. The Holdovers (2023)

It is not every year Hollywood delivers a great Christmas movie that feels genuinely crafted rather than a corny, unoriginal story that was rushed to a streaming service with a Hallmark-style script. However, “The Holdovers” achieves just that. I would say this film has cemented itself as a classic, and its run during awards season proves it. The cast was honored for their performances, and rightfully so. Paul Giamatti won a Golden Globe for Best Actor, and Da’Vine Joy Randolph won an Academy Award for Best Actress in a Supporting Role. The soundtrack offers an authentic 1970s vibe, featuring classic rock, folk, soul, and Christmas carols. The soundtrack, combined with the snowy New England landscape, creates such an intense feeling of nostalgia. It is a perfect blend of films like Dead Poets Society (1989), With Honors (1994), and The Breakfast Club (1985), with a generous sprinkling of the Christmas spirit. 

The story centers on Mr. Hunham (Paul Giamatti), a cranky and widely unlikable teacher at Barton Academy, who is assigned to supervise the students stuck on campus over winter break. Among them is Angus Tully (Dominic Sessa), a smart but troubled teen, and Mary (Da’Vine Joy Randolph), the school’s grieving cafeteria cook who lost her son in the Vietnam War. What begins as an uncomfortable holiday turns into an unexpected makeshift family as the three navigate loss and loneliness. 

  1. Love the Coopers (2015)

Nothing screams the holidays quite like returning home to your big, dysfunctional family. The message of the story, of course, is like most Christmas movies, but it’s still worth watching. I love this film because you start to fall in love with each character, despite the many storylines, as they tackle their own internal struggles and overcome them. Not to mention, the cast is stacked, and the film’s narration, delivered by Steve Martin, guides us through the Cooper family’s complicated emotional history and ends with the cutest narrator reveal.

For their annual Christmas Eve dinner with their entire extended family coming over, Sam Cooper (John Goodman) and his wife Charlotte (Diane Keaton) pretend that everything is fine while they secretly contemplate divorce after 40 years of marriage. Their son Hank (Ed Helms) is dealing with the aftermath of his own divorce as he navigates unemployment while parenting his angsty teen son Charlie, played by a young Timothée Chalamet. Meanwhile, Sam and Charlotte’s daughter Eleanor (Olivia Wilde)—the rebellious, cynical daughter—brings home a U.S. soldier she just met at the airport to pose as her boyfriend, leading to a cute, romantic story arc. As secrets spill and tensions rise, each character confronts what’s really missing in their lives, ultimately rediscovering the imperfect but undeniable love at the center of their family. 

These movies are sure to get you in the Christmas spirit! Whether you watch one a night or watch them all in one night, they’re the perfect way to enjoy the Christmas season. Happy watching, and happy holidays!

Sophia Calvillo is a Political Science major and Film Studies minor from Long Beach, California. She is a member of the Varsity Women’s Golf team and a copy editor for The Miscellany News. Sophia has a deep passion for film, entertainment, media, and sports. She hopes to bring this passion to law school, where she plans to specialize in entertainment and sports law. In her free time, she enjoys baking, watching movies with her family, going to the beach with friends, and spending time with her dog, Duke.