Don’t know what kind of holiday fun you’re in the mood for? This guide has something for every type of fan.
The holiday season is the perfect time to slow down, get cozy, and press play on something comforting or festive. Whether it’s a timeless classic, a feel-good family favorite, or a movie that simply feels like winter, these picks are perfect for nights spent under blankets with a warm drink in hand. From heartwarming stories to holiday laughs, this list has something for every kind of mood.
It Happened on Fifth Avenue
It Happened on Fifth Avenue (1947): In this beloved feel-good Christmas classic, a New York homeless man moves into a mansion and along the way gathers friends to live in it with him. Before he knows it, he is living with the actual homeowners. It’s a heartwarming film that addresses still-relevant themes of class disparity and what really matters in life. Now streaming for free with ads on Plex.
The Family Stone
The Family Stone (2005): This star-studded film stars Sarah Jessica Parker as an uptight businesswoman accompanying her boyfriend to his eccentric and outgoing family’s annual Christmas celebration. She finds that she’s a fish out of water in their free-spirited way of life. The rest of the cast includes Diane Keaton (RIP!), Rachel McAdams, Dermot Mulroney, Clarie Danes and Luke Wilson and Craig T. Nelson! What else is there to say?!Now streaming on Prime Video.
Four Christmases
Four Christmases (2008): Reese Witherspoon and Vince Vaughn star in this comedy as a couple struggling to visit all four of their divorced parents on Christmas. Relatable! There are some very funny supporting cast members here too, including frequent Vaughn collaborator Jon Favreau. Now streaming on HBO Max until Dec. 31.
Serendipity
Serendipity (2001): This romantic and hopeful film takes place on a magical night when a couple in their 20s (Kate Beckinsale and John Cusack) meet. Will destiny bring them back together? Romance and ice skating ensue. Now streaming for free on Kanopy.
Metropolitan
Metropolitan (1990): This laugh-out-loud hilarious and droll Whit Stillman film is about a group of young upper-class Manhattanites blithely passing through the gala debutante season, when an unusual outsider joins them and stirs them up. It may seem pretentious, but it’s actually making fun of that pretension. It’s a perfect winter-in-New-York-City vibe! Now streaming on HBO Max and the Criterion Channel.
Just Friends
Just Friends (2005): This 20-year-old Ryan Reynolds-Amy Smart-Anna Faris comedy has just enough Christmas spirit to make it a perennial. While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush and best friend, a woman whose rejection of him has turned him into a ferocious womanizer. Rent or buy.
Hundreds of Beavers
Hundreds of Beavers (2022): This exudes more of a cozy winter vibe than anything particularly Christmas-y, but it’s such a treat I had to mention it. A drunken applejack salesman must go from zero to hero and become North America’s greatest fur trapper by defeating hundreds of beavers. It’s as inspired by Buster Keaton and silent films as it is by Looney Tunes and old-school platformer video games. It’s hilarious and impressive. Even as a one-joke premise, it never overstays its welcome due to constant inventiveness and creativity in both the visuals and the comedy. A no-budget goofy slapstick “how the hell did they do that?!” live-action cartoon. Now streaming for free with ads on The Roku Channel, Kanopy and Pluto.
Eyes Wide Shut
Eyes Wide Shut (1999): The final film from Stanley Kubrick recently made its debut in stunning 4K on Criterion. Tom Cruise and Nicole Kidman famously star in the film about a Manhattan doctor embarking on a bizarre, night-long sexual odyssey after his wife’s admission of unfulfilled longing. It’s set during the holiday season and has gorgeous festive imagery. Rent or buy.
Noelle
Noelle (2019): Anna Kendrick and Bill Hader star in this Christmas comedy, one of the first original films to debut on Disney’s streaming platform. Santa’s daughter must take over the family business when her father retires and her brother, who is supposed to inherit the Santa role, gets cold feet. It’s cute! Now streaming on Disney+.
Happiest Season
Happiest Season (2020): This straight-to-Hulu flick sports a truly insane cast: Kristen Stewart, Mackenzie Davis, Mary Steenburgen, Victor Garber, Alison Brie, Dan Levy and more! It’s a holiday romantic comedy that captures the range of emotions tied to wanting your family’s acceptance, being true to yourself and trying not to ruin Christmas. Now streaming on Hulu.
Spirited
Spirited (2022): This straight-to-Apple-TV film with Will Ferrell and Ryan Reynolds is a musical version of Charles Dickens’s story of a miserly misanthrope who is taken on a magical journey. It’s a clever update with enough of a hook to satisfy, even if the musical numbers are hit or miss. It’s cute and fun and funny enough to justify itself, even if at first it may appear like a crass attempt to replicate something like Elf’s success as a holiday rewatch. Now streaming on Apple TV.
A Christmas Story Christmas
A Christmas Story Christmas (2022): Did you know this existed?! Ralphie returns to give his kids a magical Christmas like the one he had as a child in this long-awaited follow-up to holiday classic A Christmas Story starring Peter Billingsley. It came out on streaming a few years ago and isn’t as bad as you might think. Now streaming on HBO Max.
The Baltimorons
The Baltimorons (2025): This warm and gentle and sad and wonderful indie gem really sneaks up on you. After cracking a tooth on Christmas Eve, newly sober Cliff embarks on an adventure through Baltimore with Didi, his emergency dentist who’s nearly twice his age. It’s a fantastic showcase for the two leads that’s unexpectedly affecting, moving and even life-affirming, making you laugh all the while. Now streaming on AMC+.
The Shop Around the Corner
The Shop Around the Corner (1940): You’ve probably seen the modern remake starring Tom Hanks and Meg Ryan, You’ve Got Mail, but this Ernst Lubitsch classic starring Jimmy Stewart is even better. 2 employees at a gift shop can barely stand each other, without realizing that they are falling in love through the mail as anonymous pen pals. It’s also very class-conscious, and quite charming. A perfect rom-com! Now streaming on HBO Max until Dec. 31.
We’re No Angels
We’re No Angels (1955): In this lovely Humphrey Bogart film directed by Casablanca‘s Michael Curtiz, 3 convicts escape from prison on Devil’s Island just before Christmas and arrive at a nearby French colonial town. There, they find a store that gives supplies on credit. They initially intend to take advantage of the family running it but have a change of heart after learning of the family’s financial troubles. Now streaming for free with ads on Pluto.
