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Was You’ve Got Mail Trying to Warn Us About the Internet? (Or Telling Us to Give Up?)

Olivia Rutigliano on the Rise of Amazon.com, Corporate Homogenization, and the
90s Rom Com in the Middle of It All

It’s springtime again in New York City, which makes me think of You’ve Got Mail. “You don’t want to miss New York in the spring,” Joe Fox (Tom Hanks) advises Kathleen Kelly (Meg Ryan) late in the movie, and you don’t, it’s true.

Making good on its advice, the film’s third act captures the Upper West Side’s bustling farmer’s markets and the flowering gardens of Riverside Park, radiant in the glorious sunshine and lively breezes of spring. You also don’t want to miss New York in the fall, when, the film shows, it is full of stoop pumpkins and small street fairs. Joe says fall in New York makes him “want to buy school supplies” (in lieu of flowers, he wishes to send “bouquet[s] of newly sharpened pencils”) and how could it not? The world is quaint and crisp. And you don’t, by the way, want to miss New York in the winter, either. The film lingers on shop windows garlanded with twinkle lights and places its characters in snug cafes to drink tea and read books.

You’ve Got Mail is meticulous in its rendering of the many shifting scenes of New York City, specifically the Upper West Side of New York City—representing this setting throughout its seasonal shifts as cozy, local, and familiar, not at all as chaotic or impersonal as the city’s reputation might have us believe.

But the first shot of New York City in You’ve Got Mail is not of one of these idyllic quarters, one of these provincial and folksy avenues dotted with decorative gourds or blooming flower boxes, persistent details of a district so charming and precious that it might have been embroidered rather than built. The first shot is a stark computerized rendering of the city, not at all like the real thing.

This digital opening suggests—portends—the imminent digitization of everything in the world, and it is right.

The film opens on a digital image, a dark screen with a few swirls and floating loops moving about. The title appears over this animation, typed out with a blinking cursor, as if on a word processor. But this is not intended to simply evoke a computer, it is intended to evoke the internet (the script refers to it as a visualization of the term “cyberspace”); we can hear the wails and chugs of dial-up in the background.

The camera then pulls into this void, swooping around inside it until it flies into a computerized model of Manhattan. Sailing through the reconstructed city streets as they take on more detail, the camera glides along the Upper West Side, whose buildings are homogenized as pastel blocks. The camera then turns and arrives at Kathleen’s brownstone apartment, before a wipe transition turns the graphic model into an identical, real-life shot of the same spot.

This digital opening suggests—portends—the imminent digitization of everything in the world, and it is right. You’ve Got Mail premiered in 1998, capturing the last shreds of the once-prevailing analog universe right before it would be brought to ruins. Windows 98 was being launched. Jeff Bezos, CEO of Amazon, had just made his first billion dollars. Barnes & Noble had just sued Amazon for referring to itself as “the biggest bookstore in the world.” When You’ve Got Mail begins, it’s not going to be long before everything changes in the lives of its characters.

In You’ve Got Mail, if you’re in love, you’re in love with a machine.

The film is aware that the technological revolution, the Information Age, is nigh. Like Pompeii, it has borne a few early signs and now it waits for the blast, the rush, the wave that will engulf it and change everything. The film focuses on several intertwined worlds, all targets for the overwhelming socio-economic transformation to come. These myriad settings include the literal neighborhood of the Upper West Side, the book industry, the brick-and-mortar marketplace system, and the corporate world.

Indeed, not long after the digital image of Kathleen’s brownstone apartment fades and the camera climbs through the window of her apartment, Kathleen’s boyfriend Frank Navasky (peak 90s Greg Kinnear) wakes her up complaining about a news story he has read about how computers are negatively impacting productivity. “We’re seeing the end of Western Civilization as we know it,” he tells her. “You think this machine is your friend,” he adds, “but it’s not.”

*

Written by Nora Ephron and her playwright sister Delia Ephron, You’ve Got Mail is an adaptation of the 1940 Ernst Lubitsch film, The Shop Around the Corner, which starred Jimmy Stewart and Margaret Sullivan, as well as that film’s source material, the 1937 play Parfumerie, written by Hungarian playwright Miklós László. Lubitsch’s movie was also adapted into two musicals—The Good Old Summertime in 1949, and She Loves Me in 1963. The plot in all these early versions concerns two gift shop employees who fall in love as anonymous pen pals, without realizing they are the coworkers they each despise in life.

In You’ve Got Mail, things are a bit different—more modern for the inclusion of email and online messaging, but also more doomed because of it. Joe is the third-generation mogul behind the superstore chain Fox Books, whose new Upper West Side location threatens to put Kathleen’s own nearby store, a historic children’s bookstore called The Shop Around the Corner that was opened by her late mother, out of business. Joe and Kathleen hate one another, locked in a kind of turf war for the bookselling primacy of the Upper West Side. But they are also, coincidentally, and unbeknownst to one another, online pen pals: “ShopGirl” and “NY152.”

The specific enemy of Kathleen’s quaint bookstore is not Joe Fox or his corporate chain, but the nascent internet itself—the very invention that kindles her big romance.

This is how Joe tells Kathleen how much he wishes he could send her a “bouquet of newly sharpened pencils… if he knew her name and address.” Online, he is a poet. In life, he’s a sardonic villain who cackles and draws finger-guns when he learns that he’s put a local bookstore out of business.

In the opening scene, right after Frank warns her about the treacherousness of the computer, Kathleen waits for him to leave and immediately logs on to AOL.com. She brightens when she hears the computer announce she has mail—an email from NY152. She reads it and writes back eagerly, beginning her letter with the phrase “Dear friend.” The internet might not be her friend, but it’s already being associated with one: entwined in her relationship, already shaping how she interacts with others and the rest of the world.

Literally, though, the central conflict in the film is not between analog culture and digital culture, but between small business and corporatization. The film’s opening, in which the computerized New York subsumes the real one, predicts imminent digitization of everything and that this will affect the fabrics of real, physical places. And yet, for now, the only man-made agent of change we’re supposed to worry about coming for New York City is the corporate pirate Joe Fox.

While the film focuses on the more tangible encroachment of Fox Books on The Shop Around the Corner, and homogenized, impersonal bookstores on the local neighborhood and the literary culture at large, this insinuation—that the internet will render this battle obsolete—hangs over the entire film. Watching this film in 2022, in which numerous “mom-and-pop shops” dotting the UWS have long since shuttered (including Maya Schaper’s Cheese and Antiques, the storefront on W. 69th that stood there for fourteen years and served as the set for The Shop Around the Corner), it becomes a kind of a time capsule, a movie preserving a version of the pre-millennium world that would never exist again. Joe Fox waxes on to Kathleen about how much he hates chain stores like Starbucks and loves the small shops of the Upper West Side, and yet he is the embodiment of the chain store, the antithesis of the small shop.

For a while, Fox Books has no greater challenger than Frank Navasky. Technology is all he talks about, but not favorably. He’s a writer, a columnist for The New York Observer. That he’s a print journalist and a devoted typewriter enthusiast (a short way through the film, he adoringly buys his third identical machine) sets him up to be our Diogenes, the stick-in-the-mud cynic, or our analog Cassandra, the eccentric prophet doomed to be ignored. “Name me one thing, one, that we’ve gained from technology,” he dares Kathleen. When she says “electricity,” he says “that’s one.”

When Frank is asked if he’s interested in doing a book, he offers to write about “something really relevant for today, like the Luddite movement in 19th-century England.” Like the textile-factory-machine-destroying faction of which he speaks, he is defined by suspicion of and resistance to technology. He reminds us of the weirdness, the strangeness of technology encroaching into our lives more and more—railing against the internet all day long, just as much as he does about Fox Books. He’s the only character who knits together the threats of the big chain store and the internet—but even when he crows in his column that Kathleen’s store should be preserved (“save The Shop Around the Corner and you will save your soul”), he can’t do anything much to forestall their approach.

The film’s opening scene, in which Frank warns Kathleen about the advancing internet, is staged as if Kathleen is having an affair with her computer. She waits for him to leave before creeping over to her laptop, logging on to AOL while still wearing her pajama set. Frank is in a similar situation, but with his typewriter. He has written a column all about how he appreciates it, he’s known for being “so in love with his typewriter.” In You’ve Got Mail, if you’re in love, you’re in love with a machine. The dividing line, for a while anyway, is which machine you fall for.

Except for Frank, the film allows the internet to seem like a bastion from the stressors of real life; Joe Fox might be the robber baron about to destroy Kathleen’s store, but NY152 is her gentle and witty confidante. And yet the film lays a trail between Fox Books and the internet all the same. The arrival of Fox Books (which mirrors the real-life, unwelcome construction of a Barnes & Noble outpost on the Upper West Side) also symbolizes, as Kathleen articulates often, the dwindling of customer service and personal relationships at the hands of commerce and consumerism. The impacts of the “personal” and the “impersonal” are debated throughout the film’s two hours.

As a small-business owner and a modern robber-baron, Kathleen and Joe have diametrically opposite principles, and so their love story feels bittersweet, wrong, when it ends successfully.

“Do you want the Upper West Side to become one giant strip mall?” Kathleen cries about the encroachment of Fox Books, during a rally she holds to save her shop. She recognizes that the point of the city is its personality—which is to say, that its personality is made by just how very personal it is. Her neighborhood is local despite being ostensibly metropolitan. The giant new Fox Books location is, she calls it to a friend, “impersonal” because it does not provide meaningful customer service and specialization and it is not a scion of the neighborhood.

And at the start of the film’s third act, when Joe Fox comes to her apartment to tell her that his destruction of her shop was “not personal” (because it was “just business”) Kathleen retorts, “All that means is that it wasn’t personal to you.” She adds, “And what’s so wrong with being personal, anyway? …Whatever else anything is, it ought to begin by being personal.”

This tenet, of any, is the principle Kathleen is readiest to defend. She snarls at Joe on an accidental blind date with him earlier in the film, “You, with your theme park, multi-level, homogenize-the-world mochaccino-land. You’ve deluded yourself into thinking that you’re some sort of benefactor, bringing books to the masses… no one will ever remember you, Joe Fox… but plenty of people remember my mother.”

Later, when the store closes, she tells NY152, about her shop. “It’s a lovely store, and in a week it will be something really depressing, like a Baby Gap. Soon, it’ll just be a memory. In fact, someone, some foolish person, will probably think it’s a tribute to this city, the way it keeps changing on you, the way you can never count on it, or something. I know because that’s the sort of thing I’m always saying. But the truth is… 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.” The film’s entwining The Shop Around the Corner with Kathleen’s own mother’s legacy is its most literal paean to the “mom-and-pop” store, and that the increased corporatization not only drains some of the personality, but also the personal-ness (and even some of the personnel) from it.

But her preoccupation with the notion of being “personal,” as well as Joe’s inability to be anything but impersonal in person, offers a handy vernacular to handle the film’s largest question, about what happens when the agent of change is more impersonal than even Joe Fox and his cruel marketplace capitalism. What happens, the film asks, when the agent of change is not simply a one-size-fits-all corporation, threatening to swap out the little storefronts in a neighborhood, but when it is the internet, a non-personal entity which gains power precisely by trying to seem personal?

*

In 1999, one year after You’ve Got Mail, Jeff Bezos, the founder of Amazon.com (then originally a bookselling forum), would be named TIME’s Person of the Year. The fight between Barnes & Noble and Amazon had only intensified, with Barnes & Noble launching its own online bookselling platform with its own funds, as well as, a year later, $300 million total from Bertelsmann, the German publishing house.

In 1998, barnesandnoble.com made $62 million. In 2002, the number was up to $422 million. For a blip, in the early 90s, Amazon had been the underdog, a small start-up taking on the corporate booksellers that were putting small ones out of business. History is clear that Amazon has posed just as much, if not more, of a threat as these chain stores once did.

You’ve Got Mail makes no mention of online bookselling, but it clearly grapples with questions about how the internet will specifically (and already does) play a role in these imminent large-scale changes—foregrounding how Fox Books is a precursor to the widespread multi-structural transformation that the internet will ultimately control. The film contains the idea that the specific enemy of Kathleen’s quaint bookstore is not Joe Fox or his corporate chain, Fox Books, but is the nascent internet itself—the very invention that kindles her big romance.

In You’ve Got Mail, going back on one’s principles seems to be the only way to find interpersonal happiness.

Kathleen’s inevitable falling in love with Joe, the man who represents everything she is against and who literally poses a threat to her entire livelihood, is an unsettling, uncomfortable undercurrent of the film, and I think this is partially the point. You’ve Got Mail (a film about a small business that is also full of product placement) is in a little way about the ways we surrender to capitalism and convenience, and that the internet is the intermediary by which this disquieting capitulation has occurred.

The pessimistic reading of You’ve Got Mail says that this bitterness is rather the point; that the romance has been compromised since it started. As a small-business owner and a modern robber-baron, Kathleen and Joe have diametrically opposite principles, and so their love story feels bittersweet, wrong, when it ends successfully. This is part of how You’ve Got Mail might offer a critique of the internet—something that facilitates convenience and even social-ness but which creates something inauthentic and precarious when it tries to function in lieu of pure humanity.

The film knows that books will soon be sold to us via robot instead of in a chain store, but in warning us about the dangers of trusting, of using the internet too much to replace our normal habits, it chooses for its cautionary tale a plot more extreme than shopping: love.

For this reason, the romance in You’ve Got Mail is a bit unfulfilling; the whole time, it feels a bit like Kathleen might be selling out or giving up. Nearly everyone in the film ends up making similar concessions. George (Steve Zahn), one of The Shop Around the Corner’s expert booksellers, winds up working in the Children’s Department of Fox Books, after he is laid off. “He’s revolutionizing the place,” Joe tells Kathleen, later. “You can’t work in his department unless you’ve got a PhD in children’s literature.”

When Frank meets Joe Fox and excoriates him for threatening The Shop Around the Corner, he drops his defenses entirely when Joe’s then-girlfriend Patricia Eden (Parker Posey), head of her own publishing house, compliments his work and offers him the chance to talk about a book deal. Frank ends up falling in love with a TV journalist named Sidney-Ann who has him on her show, even though he doesn’t like television. “Yours is the only show I do watch,” he tells her. Later, after he tells Kathleen he’s fallen in love with Sidney-Ann, Kathleen asks, stunned, if it’s true that she’s a Republican. Frank, the closest thing the show has had to a Marxist critic, informs her, “I can’t help myself.”

In You’ve Got Mail, which depicts a society in late capitalism, going back on one’s principles seems to be the only way to find interpersonal happiness. Technological assimilation and corporate patronage alike are unavoidable and can often lead to happiness. Just as Kathleen’s former customers and even authors relocate to Fox Books with little resistance, Kathleen herself buys coffee at Starbucks more times than she is seen visiting the UWS’s European coffee shop and patisserie, Café Lalo, where she has her blind date with Joe. Birdie (Jean Stapleton), Kathleen’s beloved surrogate mother, is revealed to be independently wealthy for having “bought Intel at 6” years before.

All of these developments don’t make the film’s circumstances any less painful. Kathleen, who adores children’s books, weeps, heartbroken, when she walks into the colossal kid’s section of Fox Books and tells a mother about a classic book series to get for her daughter. What does it mean, then, that Kathleen genuinely feels Pride and Prejudice-esque sparks with Joe? Their overlapping similarities and divergent differences perfectly turn up the heat of their already-simmering chemical connection. How can she love the man who, in another aspect of his life, has proved so destructive towards everything she holds dear?

Like many of its viewers, for years I’ve struggled with how to answer this question—long before I pitched this very essay, about the film’s technological and cosmopolitan anxieties, to Lit Hub in my application for employment in the summer of 2019. I think the answer is that this is, ultimately, a pointless question because Joe Fox will likely be in Kathleen’s commercial straits in the not-too-distant future. The film doesn’t seem to know how she can forgive him, except to say that he is also her best friend and this is enough: for Kathleen, Joe Fox has become so personal that he is almost impossible for her not to love.

As much as You’ve Got Mail is a film full of whimsy and love, all it can do with these sentiments is capture the last days of a world in which they were able to thrive.

When the film brings its two characters together at last, on a warm spring day in the 91st St Garden in Riverside Park, they greet each other almost wearily, collapsing into a kiss that is, for them, both surprising and inevitable, but most importantly, the end of their months-long struggle. The camera pans upward over their embrace into a sky so pale it’s hardly noticeable when the screen transitions to a matte blue color and the blinking cursor of a word processing platform appears to type out “The End,” drawing the fable, and its beautiful New York scenery, into the sheathe of the internet for good.

As much as You’ve Got Mail is a film full of whimsy and love—full of books and friendship and long walks through droll, historic, tree-lined urban streets—all it can do with these sentiments is capture the last days of a world in which they were able to thrive.

I said earlier that You’ve Got Mail is a time capsule, and it is. This is the film’s greatest achievement—even more than designing a squirming, fascinating, compelling, highly allegorical bit of folklore criticizing the drawbacks of commerce and technology. It takes a camera to a time and place that won’t be around much longer and—alongside the impressive feat of identifying its killer—fights to do what its characters can’t and save a little bit of its soul.

Olivia Rutigliano
Olivia Rutigliano
Olivia Rutigliano is the Associate Editor of LitHub's CrimeReads vertical and the Senior Film Writer at LitHub. In addition to Lit Hub and CrimeReads, her work appears in Vanity Fair, Lapham's Quarterly, Public Books, The Baffler, Bright Wall/Dark Room, Politics/Letters, The Toast, Truly Adventurous, PBS Television, and elsewhere. She is a PhD candidate and the Marion E. Ponsford fellow in the departments of English/comparative literature and theatre at Columbia University, where she specializes in nineteenth and early twentieth-century literature and entertainment.





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