3 Films To Watch This Holiday Season
3 Films To Watch This Holiday Season
By Campbell Bensley — December 23. 2025
As the weather turns colder and the days spent inside grow longer, winter becomes the perfect opportunity to sit back and experience a new film or revisit a classic. While these picks aren’t traditional holiday movies, each offers a cozy, distinct feeling that makes them perfect for anyone looking to stay entertained throughout the season.
1. The Holdovers
Academy Award-winning director Alexander Payne delivers a modern holiday classic with The Holdovers. An ode to the films of the 1970s, The Holdovers feels like a warm hug, despite an overwhelmingly bittersweet story. A cast full of beautifully written and emotionally grounded characters, led by Paul Giamatti and Da’Vine Joy Randolph, gives award-winning performances that give the film a timeless feeling. A perfect balance of melancholy humor and gut-wrenching heartbreak, the film captures the comfort of finding family where you least expect it, creating one of the most enjoyable holiday films of recent memory.
2. The Grand Budapest Hotel
Filled with the highly stylized visuals and deadpan humor Wes Anderson has become known for, The Grand Budapest Hotel is as meticulously written as it is visually stunning. Set in the snow-covered European Alps, the film follows a famed concierge and his devoted lobby boy sidekick through a fast-paced, intricately crafted murder mystery. The film easily holds your attention and offers the kind of dream-like storytelling that Anderson’s cult-like following has come to expect from his work.
3. Dead Poets Society
A classic winter film for many, Dead Poets Society delivers a heart-warming story about an English teacher and his journey to inspire his elite boarding school students through poetry. The film explores themes of boyhood, self-discovery, and the value of human connection, making it a classic that still holds up more than 35 years after its release. Robin Williams gives one of his most iconic performances, creating an inspiring and quietly beautiful film that continues to resonate across generations.
For more 25 Days of Square articles like this one, keep reading at umsquaremagazine.com and follow us on Instagram @um.squaremagazine.
All images belong to their respective owners.