You’ve Got Mail and the power of the written (well, typed) word

Nora Ephron loved words. Her parents were an old Hollywood screenwriting duo who raised their four daughters with the ethos “Everything is copy.” Ephron started out as a journalist and columnist before transitioning into novels and screenplays, including the smash-hit romantic comedy classics When Harry Met Sally and Sleepless In Seattle. So it’s perhaps no surprise that back in the late ’90s, Ephron was able to see the rise of the internet for what it was: a bold leap into the future that was also poised to return us to the epistolary nature of the past. Despite the dated dial-up modems and AOL interfaces, 1998’s You’ve Got Mail is remarkably prescient about the fact that the World Wide Web was soon going to have us all writing to each other more than ever before.

The film is anchored by the anonymous email correspondence of optimistic Kathleen Kelly (Meg Ryan) and cynical Joe Fox (Tom Hanks), who meet in an “over 30” chat room. Little do they know that he owns the Barnes & Noble-esque superstore Fox Books, which is trying to put her small independent children’s bookstore out of business. As the trailer intones, “In life, they’re at odds. Online, they’re in love.” But You’ve Got Mail isn’t really about online dating or the anonymity of the internet. It’s about the ways in which putting our thoughts down on paper (or screen) changes how we understand ourselves.

“Do you ever feel you’ve become the worst version of yourself?” Joe asks his online pen pal after butting heads with Kathleen at a dinner party. “That a Pandora’s box of all the secret, hateful parts—your arrogance, your spite, your condescension—has sprung open? Someone provokes you, and instead of smiling and moving on, you zing them? ‘Hello, it’s Mr. Nasty.’” It’s a confession he wouldn’t or even couldn’t make it real life, precisely because his hotheadedness would get in the way. In Kathleen’s much-discussed favorite book, Pride And Prejudice, Mr. Darcy botches his initial proposal to Elizabeth Bennet only to write her a long letter explaining all the things he couldn’t figure out how to say in the moment. Ephron recognizes that email has brought back that reflective, vulnerable form of written communication.

While You’ve Got Mail has devoted fans ranging from Mindy Kaling to Quentin Tarantino, I have to admit, I’ve always struggled a bit with its central romance. Not only does Joe succeed at gleefully putting Kathleen’s bookstore out of business (the one she inherited from her beloved dead mom, no less!), he spends the second half of the film rather creepily manipulating her after he finds out about their email identities long before she does. Yet if there’s one thing you could say about Ephron—a director who once weighed in on the specific type of avocados that should be on the table during a dinner party scene—it’s that nothing in her films was ever unintentional. Love it or hate it, Joe’s problematic qualities are a feature, not a bug.

Although You’ve Got Mail is based on the 1940 Ernst Lubitsch romantic comedy The Shop Around The Corner (which was itself based on Miklós László’s 1937 Hungarian play Parfumerie), Ephron and her co-writer/sister Delia Ephron purposefully gave their film a far thornier setup. In The Shop Around The Corner, Jimmy Stewart and Margaret Sullavan are bickering co-workers whose animosity mostly stems from not knowing how to express a crush. There’s no business rivalry or class divide to keep them apart, just their own stubbornness and pride, which melts away easily enough after their letter writing identities are revealed.

For the Ephron sisters’ updated take on the material (which they also saw as a spiritual sequel to Sleepless In Seattle), they wanted to do something more complex. As Nora Ephron put it on the DVD commentary: “Sleepless is a movie that’s about, ‘Is there one perfect person out there for you?’… This movie is all about, ‘Can you fall in love with the person who isn’t the perfect person for you?’ Or as Delia and I used to say, ‘Can you fall in love with a Republican?’”

You’ve Got Mail refuses to take the easy route of having Joe reform his capitalistic ways or swoop in at the last minute to save Kathleen’s store (which, in a nod to the original film, is named The Shop Around The Corner.) Instead, Ephron is interested in the way sadness runs alongside happiness, and compromise co-exists with fulfillment. Being forced to close her shop allows Kathleen to finally step outside her mother’s outsized shadow and forge her own path as a children’s book writer. But that doesn’t undo the pain of the loss either. As she writes in one of her emails:

My store is closing this week… Soon we’ll just be a memory. In fact, some foolish person will probably think it’s a tribute to this city. The way it keeps changing on you, or the way you can never count on it. I know because that’s the sort of thing I’d say. But the truth is, I’m heartbroken. I feel as if a part of me has died and my mother has died all over again. And no one can ever make it right.

Although You’ve Got Mail ends with Joe and Kathleen kissing in an idyllic garden as “Somewhere Over The Rainbow” plays, the sting of those words doesn’t entirely go away. There’s a melancholic ambiguity to You’ve Got Mail, which isn’t something you often see in a studio romantic comedy. In his review, Roger Ebert praised the sophistication of refusing to turn Fox Books into a villain. (“Say what you will, those giant stores are fun to spend time in,” he admits, which feels doubly true now that Amazon has forced so many of them to close.) After describing the scene in which Kathleen ventures into the happy, bustling megastore only to quietly start crying when she’s able to answer a question the store clerk can’t, Ebert ends his review with a simple “Whoa.”

The best defense I’ve found for the romance of You’ve Got Mail comes from Sarah Raphael of Refinery29, who makes the case for Joe as an “anti-ghoster”—someone who commits rather than disappears when he discovers his online pen pal isn’t what he was expecting. Unlike in The Shop Around The Corner, where the letters are more of a plot device, Ephron is interested in the way Kathleen and Joe’s months-long communication changes them both for the better. It’s Joe’s advice that emboldens tongue-tied Kathleen to bravely fight for her store. And though she loses the battle, she maintains that bolder outlook. Joe, meanwhile, is able to bring the emotional vulnerability of their email exchanges into the real world. When a flu-ridden Kathleen asked why he stopped by to check on her, Joe answers, simply and honestly, “I wanted to be your friend.”

Still, for my money, the most romantic and least problematic version of this story is the 1963 musical She Loves Me, which gives the central relationship a better sense of equality. (The show got a lovely 2016 Broadway revival starring Zachary Levi, Laura Benanti, and Jane Krakowski, which is available to stream.) In comparison, You’ve Got Mail skates by largely on the cheat code of using Tom Hanks to soften Joe’s most questionable behavior. In the years between Sleepless In Seattle and You’ve Got Mail, Hanks had evolved from beloved movie star to America’s Dad. He won back-to-back Oscars for Philadelphia and Forrest Gump, and starred in films like Apollo 13, Toy Story, and Saving Private Ryan, which debuted just five months before You’ve Got Mail. Coupled with the meta comfort of seeing Hanks and Ryan reunited again after Sleepless and Joe Versus The Volcano, it’s easier than it might otherwise be to roll with the unbalanced dynamic of You’ve Got Mail’s love story.

It also helps that the romantic atmosphere of You’ve Got Mail stems as much from its world as from its central couple. The film was originally meant to be a larger ensemble piece, with bigger roles for the quirky employees of Kathleen’s store and for Kathleen’s and Joe’s right-on-paper, wrong-in-practice partners (Greg Kinnear and Parker Posey, respectively). Although You’ve Got Mail was streamlined to just the Ryan/Hanks story, there’s lingering specificity to its supporting players. Joe’s “American family” includes an aunt and a half-brother who look more like his two young kids—the result of both his father and grandfather having more children later in their lives. Hanks’ talent for physical comedy is put to great use in a sweet sequence where Joe takes his young relatives to a fall carnival.

Ephron’s world-building also includes some hilarious satirical jabs at Kinnear’s pompous left-wing columnist—a man who eagerly double-checks that Kathleen is taping the TV interview where he decries VCRs as the downfall of modern society. And Ephron knows not to mess with perfection. The café scene where Joe figures out that Kathleen is his pen pal is a nearly beat-for-beat re-creation of the same sequence from The Shop Around The Corner, with Dave Chappelle stepping into the best friend role originally played by Felix Bressart. It works just as well in 1990s New York City as it did in 1940s Budapest.

As cinematographer John Lindley explained in Vanity Fair’s oral history, Ephron wanted to convey the sense of New York as a bunch of little villages, not an intimidating monolith. If When Harry Met Sally is an ode to New York City in general, You’ve Got Mail is Ephron’s love letter to the Upper West Side in particular. She requested that the same extras be used repeatedly in the street scenes, so that as Kathleen and Joe walk their parallel paths to and from work, you get the sense that the other people in their neighborhood are doing the same. In the beginning of the film, Kathleen’s local florist is pregnant. The next time she’s buying flowers, there’s a sign in the window that says, “It’s a girl!” It’s that level of care and detail—not to mention all her crackling dialogue—that elevates Ephron’s work above that of her lesser rom-com imitators.

Ephron would go on to write and direct several more films before her death, including her final feature, 2009’s Julie & Julia. But You’ve Got Mail marked the culmination of her era-defining work in the romantic comedy genre. The rom-com as we know it today wouldn’t exist without Ephron and her ability to blend old Hollywood sensibilities with a modern feminist touch. When she died in 2012, Tom Hanks wrote, “Knowing and loving Nora meant her world—or her neighborhood—became yours.” For all its oddities and imperfections, You’ve Got Mail allowed Ephron to share her literal and metaphorical neighborhood with the world.

Next time: All is fair in Love & Basketball.