The '90s were a great movie decade that saw us introduced to lots of different characters and worlds. But one genre really thrived in the '90s and delivered some all-time classics: the romantic comedy.
'90s rom-coms will always have a special place in my heart, because they're the love stories I've been raised on, and they all mark sort of seminal moments in my life when I saw them.
There is a specific kind of magic that only existed in the late 1990s that's etched in my brain. It was a time of beige desktop computers, the screeching symphony of dial-up internet, and the undisputed reign of Meg Ryan and Tom Hanks, who seemed to fall in love every few years for our viewing pleasure.
While Sleepless in Seattle is my favorite of those iterations, I think you can't deny the behemoth that was You've Got Mail.
Released in December 1998, the movie earned over $250 million worldwide.
But nearly three decades later, we’re realizing something new about this Nora Ephron classic: it’s actually one of the best "sneaky" Christmas movies ever made.
Let's dive in.
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The Ultimate Comfort Watch
I think there's some sort of phenomenon of people having nostalgia for the simplicity of the '90s. We didn't have cell phones, we had to make plans, people could only access us via email if we were in front of a computer, and chatting was brief and direct.
When I think about You've Got Mail, I know it captured all those romantic feelings of someone you can fall in love with without ever seeing them, but also the fun of how big the internet is and how it could be someone terrifying on the other end.
While many categorize it strictly as a romantic comedy, the film’s DNA is woven with holiday spirit. It follows the professional rivalry and digital romance between Kathleen Kelly (Ryan), the owner of a charming independent children’s bookstore, and Joe Fox (Hanks), the mogul behind a corporate book giant.
Why This Movie Still Works
Whenever I watch the movie now, I think about how both Kathleen Kelly and Joe Fox are probably unemployed thanks to Amazon.
But then you get lost in the charming story about finding the right person and not being with the wrong one. There's this honesty in this movie where these two people need to grow independently before they meet.
And then when you hit the midpoint twist of Joe knowing about Kathleen but her not knowing about him, I really love how the movie then spends extra effort getting them to fall in real love.
Here are a few other things I dig:
- The Atmospheric Evolution: The film spans the seasons, but the climax and the most emotional beats happen against the backdrop of a crisp, twinkling New York City winter. Is this a Christmas movie? Kinda!
- The "Shop Around the Corner" Aesthetic: Kathleen’s bookstore is the physical embodiment of "cozy." When she decorates that small space for the holidays, you can almost smell the pine and old paper through the screen.
- The Human Connection: At its core, it’s a movie about loneliness and the search for a kindred spirit—themes that resonate deeply during the holiday season.
Is it Actually a Christmas Movie?
If we consider Die Hard a Christmas movie, You’ve Got Mail earns its spot on the shelf with ease. Here is how the holiday plays a pivotal role in the narrative.
The soundtrack has Joni Mitchell’s "River" and Harry Nilsson, perfectly capturing that bittersweet holiday nostalgia, and we get scenes with the Macy’s Thanksgiving Day Parade to the Christmas trees being hauled through the Upper West Side.
The heartbreak of Kathleen closing her shop happens right as the holiday season peaks, making Joe’s eventual redemption even more poignant.
Sure, the movie ends in summer, but this is a film you want to watch with a hot beverage and someone you care about, with twinkly lights in the background.
'You've Got Mail' Credit: Warner Bros.
Why the $250M Success Matters
In today’s landscape of superheroes and streaming, it’s hard to imagine a mid-budget movie about two people emailing each other becoming a global phenomenon.
But this movie changed the cultural lexicon at the time.
Its success was a testament to Nora Ephron’s sharp writing and the undeniable chemistry of its leads.
It captured a moment when the internet felt like a place of "enchantment" rather than "doom-scrolling."
When I think about this movie, I come back to this quote, which I think embodies its ethos.
"I lead a small life - well, not small, but sometimes I wonder do I do it because I like it, or because I haven't been brave? So much of what I see reminds me of something I read in a book, when shouldn't it be the other way around?" — Kathleen Kelly
The small life she's talking about is one she dares to let us all into, and those feelings perfectly mirror Joe Fox's feelings. It makes the theme of their movie pop and brings us all together.
Summing It All Up
If you’re tired of the usual high-gloss holiday tropes, revisit the Upper West Side this week and watch You’ve Got Mail.
It's the perfect cozy watch this season, and a movie I don't think gets enough credit for touching people for almost 30 years and making the internet and online dating seem much more inviting.
Let me know what you think in the comments.
