10 Unexpectedly Great Movies to Watch During the Holidays

This weekend we watched our favorite Christmas movie, Elf. It doesn’t matter how many times we watch it, we always laugh. It was especially fun watching with Theo this year who was old enough to get a kick out of, well, pretty much everything.

An “Elf” themed Christmas display from the lights we saw this weekend.

For me, though, there are plenty of movies that I love to watch around the holidays that aren’t “Christmas movies.” These are movies that either have classic holiday scenes, personal holiday memories for me, or simply have story lines (snow!) that get me all warm and fuzzy feeling and make me nostalgic for the holidays.

1. When Harry Met Sally

Because the movie takes place during countless seasons in New York, but the holiday scenes are some of the most memorable. But mostly because it has perhaps the greatest declaration of love scene ever. “Because when you realize you want to spend the rest of your life with someone, you want the rest of your life to start as soon as possible.”

2. Chitty Chitty Bang Bang

Because it’s about toys. And candy. And love.

3. Lady and the Tramp.

Because it starts and ends with Christmas!

4. The Lemon Drop Kid

Because I first watched this classic on New Years Eve, so it will always remind me of the holidays. But also because the movie takes place during Christmas, and Bob Hope and Christmas go together like, well I don’t know what like..but they go together really well.

5. We’re No Angels

Because this is one of my favorite, most underrated Bogie (Humphrey Bogart) movies. And because it also takes place at Christmas.

6. While You Were Sleeping

Because it has one of the sweetest love stories that begins at Christmas, but it’s not with who you’d think…

7. Sleepless in Seattle

Because who can forget that phone call, made by a little boy on behalf of his dad, one lonely Christmas?

8. The Chronicles of Narnia

Because of the snow, and the magic, and the allegory that is Christmas.

9. Serendipity

(Mike’s contribution) Because when it snows in New York, you can’t help but feel festive.

10. Little Women

Because it’s about love, and family, and because every scene looks like it belongs on a Christmas card.


What about you? Do you have any nontraditional holiday movies that you love to watch this time of year? I’d love to see your movie list!

11 thoughts on “10 Unexpectedly Great Movies to Watch During the Holidays

  1. Yes! When Harry Met Sally, Serendipity, Sleepless, While You Were Sleeping and Little Women are all on my list! I’ve never seen We’re No Angels – but I love Bogie’s lesser known movies too. Thanks for the recommendation! 🙂

      1. Also, I have to know – which version of “Little Women” do you prefer? The b&w version with Elizabeth Taylor, or the new version with Susan Sarandon and Winona Ryder?

  2. My favorite Christmas movie is the Ingrid Bergman Bing Crosby classic called “The Bells of St Mary”. It’s in black and white, and Bing sings, and Ingrid is fantastic as a feisty nun who teaches a kid who was bullied how to box. Tear jerker at the end.

  3. Elf is just the best, isn’t it? It’s a favorite for us too. I completely forgot about Serendipity…what a good one. I am all about the first two Home Alone movies, too. I used to watch them all the time as a kid.

  4. Meet Me In St. Louis. Judy Garland and the origination of “I’ll be Home for Christmas.” Not a typical Christmas movie but great all the same!

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