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Winter Watchlist: 20 Must-Watch Films for Wintertime

This article is written by a student writer from the Her Campus at Pitt chapter.

It’s almost winter break, and for me, that means one thing: a movie marathon. Winter is the perfect time to watch a new movie or revisit an old favorite, so here are some of my favorite movies to watch in the winter.

The Holiday (2006)

One of the most criminally underrated Nancy Meyers movies, The Holiday is about two women who swap houses for the holidays and find love in the process. This movie is charming and cozy to its core and is truly perfect for the holidays. 

Perks of Being a Wallflower (2012)

An all-time favorite for me, Perks is the perfect watch when you’re back in your hometown, feeling a little nostalgic and need something that’s just the right mix of sadness and hope. 

Parasite (2019)

Parasite has, in my opinion, the best twist in cinema history. This movie is a kind of claustrophobic commentary, and is best watched in the dark, in a cold room, for the full experience. 

About Time (2013)

Another one of my all-time favorites, About Time is an incredible movie, a perfect inspection of what it means to love, that will leave you with the reminder to cherish every single day and every single person. 

Popstar: Never Stop Stopping (2016)

Popstar: Never Stop Stopping has absolutely nothing to do with winter, but is just simply so much fun, and would be the perfect lighthearted lift to a dreary winter day. 

Love Actually (2003)

This is not a perfect movie by any means, but I still really love it. With a star-studded cast, Emma Thompson’s incredible performance and Hugh Grant’s monologue about love actually being all around, this movie has a really special place in my heart and in my holiday viewing habits. 

The Half of It (2020)

A criminally underrated movie, The Half of It will break your heart and put it back together again. 

Are You There God? It’s Me Margaret (2023)

One of my absolute favorite releases from the past year, Are You There God? is moving, kind and full of incredibly wonderful performances, especially by Rachel McAdams. This is a great movie to watch when you need some comfort and hope. 

Little Women (1994)

I grew up watching this movie with my mom on repeat. The Christmas scenes, the ice scene and the iconic snowball fight are some of my favorite moments in the film. This movie is warm, cozy, and one of the best winter movies around. 

Portrait of a Lady on Fire (2019)

This is a movie to give your complete and undivided attention. One of the most beautiful, richly gorgeous films I’ve ever seen, Portrait of a Lady on Fire desires incredible attention and is best suited for the kind of quiet spaces and moments that winter often offers. 

A Christmas Story (1983)

One of my family’s favorite Christmas movies, featuring the iconic leg lamp, this movie is guaranteed to be some good holiday fun.

It Follows (2014)

It Follows is not set in the wintertime, but it has this kind of creepy icy undertone that makes it an excellent horror film to watch in the winter months. 

Cha Cha Real Smooth (2022)

I absolutely adore this movie (it’s even in my top 4 faves on Letterboxd!), this entire movie has a kind of lost-in-your-twenties vibe and feels so deeply human and genuine. I cannot recommend this enough, it’s the perfect movie to sit alongside you if you’re feeling a little lost.

Dash and Lily (2020)

Okay admittedly, this isn’t a movie, it’s a series, but it only has one season and it’s so wonderful that I couldn’t leave it off this list. Dash and Lily follows two teenagers, Dash and Lily, as they hide a notebook across New York city, pushing each other into adventure, friendship and eventually love. This is forever one of the things I’m saddest about that Netflix canceled, but I’ll keep on rewatching each holiday season. 

Aftersun (2022)

Okay, you’re probably wondering how a movie about a summer vacation belongs here but hear me out on this one. Aftersun is about the main character Sophie, looking back on her vacation with her father–this kind of reminiscing, of reconciliation, is something that quickly bubbles up during the holidays. And while Aftersun may not make you feel better, it will make you feel much less alone.

Love Rosie (2014)

If you’re reentering your Hunger Games era, as I know that I definitely am (I never really left), this is the movie for you. Starring Lily Collins and Sam Claflin, yes that’s right Finnick Odair; this friends-to-lovers, will they won’t they rom-com, is perfect to watch with some friends, a warm blanket and a sweet treat. 

The Nice Guys (2016)

If you loved Ryan Gosling as Ken in Barbie, you’ll love this movie. It’s as simple as that. 

Celeste and Jesse Forever (2012)

Another melancholy pick, Celeste and Jesse Forever is the story of high school sweethearts Celeste and Jesse as they set out to get a divorce. This movie is a heartbreaking, but beautiful look at love and love lost. It also stares the endlessly charming Andy Samberg and Rashida Jones. 

Die Hard (1988)

Top tier Christmas movie. I said what I said.

A Charlie Brown Christmas (1965)

A Winter Watchlist wouldn’t be complete without A Charlie Brown Christmas, the little film that my family and I watch every Christmas Eve, and that I’ve loved my entire life. This is a tender joyous Christmas celebration.

So, grab a cozy blanket, some hot cocoa and a friend or two and snuggle up for some great movies!

Lauren Deaton is a second-year student at the University of Pittsburgh, she is currently serving both as Chapter Chair and Writer. She most frequently writes about entertainment topics– including music recommendations, topics of representation, and anticipated movie lists. Lauren is double majoring in English Literature and Media and Professional Communications with a focus on Public and Professional Writing. She is also pursuing a Film and Media Studies minor and is a member of the Honors College. She recently completed a communications internship with the Fletcher Free Library and will be beginning a research position with the Language and Literacy Division at Pitt during the Fall 2023 semester. In the future, she hopes to work in publishing helping to increase access to representation. She is also a writer for Studio 412 a creative outlet on Pitt’s campus and is a member of Alpha Epsilon Phi Sorority. Lauren loves her dog, her friends, her family, and everything reading, coming of age and cold brew related.