The Holiday Rewatch List: Movies People Return To Every Winter

For movie lovers, a handful of classic holiday films resurface every December. Sometimes, you watch them for family time, and sometimes, to simply to revisit characters and worlds that feel like old friends.

These are the movies you return to when the year slows down, when the evenings stretch longer. Some are explicit Christmas films, others just feel right when the weather turns cold. This list brings together titles that consistently resurface during the end of the year stretch, balancing nostalgia with an emotional reset.

1. Die Hard (1988)
   

   Yes, it’s a Christmas movie - the debate itself is part of the tradition now. Office party, one barefoot cop and a journey of escalating chaos. Every December, this movie quietly reloads itself into rotation. It is about competence under pressure and surviving life when everything goes sideways.
   
   

2. Rocky (1976)
   Cold streets and the heroic run. Rocky is not about boxing, it is about showing up when no one expects you to. Winter cinema at its purest, if you really think of it. The weather matches the grind, and the film quietly reminds you that effort counts.
   
   

3. The Lord of the Rings: The Fellowship of the Ring (2001)
   Long nights call for long journeys. This is the kind of winter rewatch that asks for time and rewards patience. This is comfort viewing on an epic scale, best enjoyed when the world outside feels suitably far away.
   
   

4. It’s a Wonderful Life (1946)
   This is the movie that quietly resets the season. People return to it year after year. George Bailey’s life-lesson arc hits the “what really matters” vibe, plus it’s a reminder that even the smallest sacrifices matter.
   
   

5. Home Alone (1990)
   Kevin McCallister’s holiday ingenuity never gets tired. Home Alone blends slapstick comedy with the cozy chaos of family Christmas, making it impossible not to laugh and relive childhood mischief. The tactical genius of young Kevin versus the bumbling burglars is pure holiday strategy in action.
   
   

6. Home Alone 2: Lost in New York (1992)
   More of everything that worked in the first film. Same chaotic energy, now in New York City. Bigger traps, bigger laughs, and the nostalgia factor hits even harder if you grew up watching it. A perfect combo of nostalgia and absurdity.
   
   

7. National Lampoon's Christmas Vacation (1989)
   Clark Griswold’s quest for the perfect family Christmas teeters between genius and total absurdity. The film is a masterclass in escalating holiday fever. A favourite for those who know that surviving Christmas is an achievement in itself.
   
   

8. Gremlins (1984)
   Christmas with teeth. Gremlins start sweet and then gleefully lose control. Mixing horror and comedy, this small-town story ends in chaos in a way that still feels rebellious. It is the holiday movie for people who like their sentiment to be slightly sinister.
   
   

9. Klaus (2019)
   Klaus wins you over with gorgeous hand-drawn animation and a story that believes small good deeds can snowball into something bigger. This is a story of a postman and a mysterious toymaker turning a frozen town around. It is the kind of movie you put on casually and end up watching properly, then returning to every December.
   
   

10. The Nightmare Before Christmas (1993)
    This one lives in its own strange, wonderful lane. Half Halloween, half Christmas. And entirely Tim Burton. The classic movie also has dark humor to keep it interesting. Jack Skellington’s curiosity and obsessive planning? Surprisingly relatable during the holiday madness.
    
    

11. How the Grinch Stole Christmas (2000)
    Jim Carrey’s over-the-top Grinch makes winter mischief unforgettable. The movie is a masterpiece. It is loud and quite frankly slightly unhinged. It is one of those rare Christmas movies that lets you be grumpy and yet, still end up oddly festive by the end.
    
    

12. Miracle on 34th Street (1947)
    A man claiming to be the real Santa Claus walks into a New York department store and refuses to play along with the commercial circus of Christmas. His insistence on honesty lands him in court, where belief itself is put on trial. What follows is a funny and unexpectedly sharp take on capitalism and trust.
    
    

13. A Christmas Story (1983)
    A small-town winter, a kid obsessed with getting a BB gun and adults who keep saying absolutely not. It’s funny because it’s honest and timeless because it remembers exactly how big small desires once felt.
    
    

14. The Polar Express (2004)
    Hop on for a magical train ride straight into your childhood imagination. The Polar Express mixes wonder and the Christmas spirit. This is the film people put on when they want to feel twelve again, in the best possible way.
    
    

15. The Christmas Chronicles (2018)
    Kurt Russell’s Santa has swagger and just enough chaos to keep things moving. It plays like a festive road movie, with small disasters and a modern edge that keeps it from feeling sugary.
    
    

16. A Christmas Carol (2009)
    Disney’s take on the Dickens classic brings old-school morality to life with stunning visuals. The motion-capture visuals make the ghosts genuinely eerie. The movie's message stays reassuringly clear: it’s never too late to change.
    
    

17. Four Weddings and a Funeral (1994)
    On the surface it is classic British rom-com energy: awkward jokes and bad timing. Underneath, it’s about commitment anxiety and the quiet fear of being left behind while everyone else pairs off. Hugh Grant is in his charming best and the movie is funny without being loud. Every time you revisit it, a different wedding hits closer to home.
    
    

18. Notting Hill (1999)
    A classic story of ordinary-meets-extraordinary romance. Men watching Notting Hill get that perfect British humour, all wrapped in the kind of love story that feels both aspirational and honest.
    
    

19. Love Actually (2003)
    Love Actually works because of its intersecting love stories and great criss-crosses through different lives that somehow still feels familiar. Hugh Grant, Colin Firth and Emma Thompson delivers moments that are fun and unexpectedly emotional.
    
    

20. When Harry Met Sally (1989)
    Classic rom-com energy, but with clever writing. Movie lovers actually appreciate it for the witty observations on relationships and the timeless question: “Can men and women just be friends?” Iconic scenes aside, it’s the movie that makes you root for timing and honesty in love.
    
    

21. Sleepless in Seattle (1993)
    A story about love and the small coincidences that change everything. Sleepless in Seattle remains a romantic favourite because of its witty banter. A millennial favourite, Tom Hanks's acting and clever writing brings alive the nostalgic feel of holiday romance.
    
    

22. You’ve Got Mail (1998)
    Before DMs and swipes, there was email flirtation. You’ve Got Mail is a slow-burn 90's romance that still feels charming today. Two people falling for each other through emails before they even realise they are rivals in real life.
    
    

23. Pride & Prejudice (2005)
    Watching Pride & Prejudice is a study in quiet admiration. There’s something satisfying about seeing Mr. Darcy wins hearts without theatrics. Cult classic for women and equally addictive for men with a romantic inclination.
    
    

24. Little Women (2019)
    This isn’t just a story about women, it is a universal story about ambition, family, and choices that resonate with everyone. Little Women often appeals because of the complexity of the characters. It is clever and timeless, making it a perfect slow-night watch during the holidays.
    
    

25. The Holiday (2006)
    A vacation swap that turns a messy heartbreak into a cosy, romantic renewal. Watching The Holiday is like slipping into a warm blanket: funny, sweet and just the right amount of sentiment. The star cast is a major plus.