BY ALLYSON HEALEY

When I was a kid, choosing which VHS to watch was a careful and highly emotionally charged process. The film I chose had to complement my headspace like a cinematic wine pairing, because I knew I’d be thinking about it for the rest of the day even after it was over. My personal movie sommelier skills faced greater challenges as I got older and grew more tired of the same family films over and over, and frequently I’d find myself reaching for the upper shelves, where my parents kept their copies of movies that were for grown-ups. These included James Bond and Steve McQueen movies (my dad’s preferred viewing) as well as things like Funny Girl and a couple of Hallmark movies (my mom’s movies of choice). But there were a hallowed three movies that, no matter how earnestly I asked to watch them as a kid, I was never given permission to view. These were my mom’s trifecta of romantic movies: Sleepless in Seattle, While You Were Sleeping, and You’ve Got Mail.

These were the movies my mom watched when she really needed comfort. They were for her, and her alone. But I was a hopeless romantic even as a kid, and I’d look at the covers of the VHSs, read the blurbs on the back, and ask her if I could watch them with her, even though I knew she’d say no. I remember You’ve Got Mail intrigued me particularly, as it dealt with the Internet and email in particular—I greatly romanticized the idea of letter-writing and thought the added element of the World Wide Web made it all so much more intriguing. In addition to begging to watch grown-up movies, I also frequently begged my parents to let me have an e-mail account, or to install AOL Instant Messenger on the family computer. I thought the idea of an e-pen pal relationship was so dreamy, and I very much wanted to see the turtleneck-clad woman and trenchcoat-clad man on the You’ve Got Mail VHS fall in love in cyberspace.

There eventually came a point when my mom allowed me to watch her trifecta movies with her, and I felt like I’d been given a special privilege. You’ve Got Mail is the one of the three that we watched the most, and I fell just as in love with it as I had expected to. The image of Meg Ryan and Tom Hanks sitting at their respective desks, typing on their respective laptops, connecting with one another over cyberspace, was deeply imprinted on my brain as A Cool Thing, A Romantic Thing, An Intriguing Thing.

For the uninitiated, You’ve Got Mail is an Internet-age retelling of a story that originated in the form of a 1937 play by Miklós László and was first adapted for film in 1940 as The Shop Around the Corner, starring Jimmy Stewart and Margaret Sullavan as the main love interests. In 1949 it was remade once again as a musical titled In the Good Old Summertime, with Judy Garland and Van Johnson in the leading roles.The 1940, 1949, and 1998 film versions are pretty close in story—two people in the same industry who are at each others’ throats in real life are, unbeknownst to one another, corresponding anonymously (and romantically, though they tell their friends it’s an intellectual connection). Fundamentally, You’ve Got Mail is pretty close to its 40s forebears, but something about the addition of the email element makes it feel new, and not just because email itself is new. Romantic letter-writing or answering lonely hearts ads in the newspaper pop up in a lot of pre-Internet media—this was the most visceral and private way to express one’s innermost feelings to someone, especially if you were apart for some reason (think of the soldiers’ letters read aloud in Ken Burns’s Civil War documentary series).

But what is it about putting it in the e-mail context that makes the relationship-by-correspondence in You’ve Got Mail feel so different from similar stories that preceded it? Perhaps it’s the satisfaction of instantaneous communication—in one scene, Ryan’s Kathleen Kelly and Hanks’s Joe Fox use AIM to communicate, allowing them to have something like a normal conversation, rather than a protracted correspondence. Perhaps it’s the visibility of editing—both Kathleen and Joe visibly delete and rewrite parts of their emails before they send them, giving the audience a peek into their state of mind and what they feel they can’t or shouldn’t write to one another. Even over twenty years later, that glimpse into how Joe and Kathleen write their emails, the deleting and reconsidering, the talking back to one’s computer, the getting up and walking around before typing a reply, and the deliberate, emphatic pressing of the “send” button are all things we can recognize in how we write emails and texts now. The letters in In the Good Old Summertime, for instance, feel like they sprung fully formed from their respective authors’ heads, neatly written on stationery without any crossing-out or rewrites. You’ve Got Mail shows its characters going through the process of expressing themselves, connecting emotionally not just with one another but with the very medium by which they communicate, lip-syncing along to the robotic expression of the titular phrase and visibly taking joy in it. That was what drew me—and still draws me—to You’ve Got Mail, and probably why it became part of my mother’s Holy Trinity of rom-coms in the first place. This is not just an enemies-to-lovers story with the requisite farcical misunderstandings. This has heart, it has emotion, and it imbues emotion even into the coldest and most unemotional technologies, in the same way that actual people imbue their computers and phones with emotions and personalities. Few other pieces of media have been able to achieve that with quite the same grace and charm as You’ve Got Mail.

You can hear The Cutaway’s take on You’ve Got Mail here!

Allyson hosts a podcast called Art History for All that looks at art across time and cultures and how it’s relevant to us today. In addition to podcasting, Allyson works at a commercial art gallery researching a catalogue raisonné, and loves to go to museums and make jokes about the art. Allyson is @arthistory4all on Twitter and Instagram, and you can find the Art History for All podcast on all major podcatchers and on arthistoryforall.com, where you’ll also find episode transcripts.