14 Behind-the-Scenes Facts You Never Knew About ‘You’ve Got Mail’

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

When people talk about the heyday of romantic comedies, there’s one movie in particular that’s guaranteed to get a shout-out every time: 1998’s You’ve Got Mail. Directed by Nora Ephron, the film — about a small bookstore owner’s online romance with her corporate rival — was both a major box office success and a critical darling, and in the years since, it’s become nothing short of a classic. Now, 25 years after its release, the film is more beloved than ever, with countless viewers revisiting its charm and very-’90s lingo whenever they need a mood-boosting love story.

From Meg Ryan’s and Tom Hanks’ winning lead performances to the always witty script to the tear-jerking soundtrack, there’s so much to love about You’ve Got Mail, even two and half decades later. But even if you consider yourself one of the film’s many superfans, there’s probably a lot about its behind-the-scenes making that you don’t know. In honor of the film’s 25th anniversary this month, read on for some You’ve Got Mail fun facts — starting with the Jane Austen classic that acted as inspiration.

It’s Seemingly a Modern Retelling of Pride and Prejudice

Many fans of You’ve Got Mail know that it was based on the 1940 movie The Shop Around the Corner (which, in turn, was based on a 1937 Hungarian play). But what you may not realize is that the film was also likely heavily inspired by Jane Austen’s classic Pride and Prejudice. Not only do Kathleen (Ryan) and Joe (Hanks) have similar traits as Elizabeth and Mr. Darcy, but the movie’s plot largely follows the same path as the novel, with the characters eventually falling in love despite their different views and mutual dislike.

And in a meta twist, co-screenwriters Nora and Delia Ephron leaned into the comparison, with Kathleen revealing that Pride and Prejudice is her favorite book and even encouraging Joe to read it on his own.

Meg Ryan and Tom Hanks Both Almost Turned Down the Movie

It’s impossible to imagine You’ve Got Mail without Ryan and Hanks at the center. But both stars have revealed that they had serious qualms about signing on, and nearly said no. At the time, Hanks was earning frequent comparisons to old Hollywood actor Jimmy Stewart (who starred in The Shop Around the Corner), and he wasn’t keen on stepping into his shoes so literally. Hanks eventually “decided to disregard that concern,” as he told Entertainment Weekly in 1998, reasoning that the character of Joe would be very different from Stewart’s Alfred.

Ryan, meanwhile, had begun feeling typecast in romantic comedies and was itching to move to another genre. “I was getting locked into that. It was starting to get irritating,” she told EW. Thankfully, she ended up saying yes, and we’re all thankful for it.

Ryan and Heather Burns Worked in a Real Bookstore for a Week to Prepare

To convincingly take on the roles of employees of a children’s bookstore, Ryan and co-star Heather Burns (who played Christina) actually worked in a real kids’ bookshop — Manhattan’s Books of Wonder — for a week before filming. “We’d go and just kind of hang out with the staff and learn what we would be doing from moment to moment,” Burns told HuffPost in 2015. “How to work the cash register and things like that.”

Two Future TV Stars Made Blink-and-You-Miss-It Cameos

If you rewatch You’ve Got Mail, you might spot two familiar faces: future Grey’s Anatomy and And Just Like That star Sara Ramírez (as a cashier) and The Mindy Project’s Chris Messina (as a Fox Books salesclerk). “I think I had, like, four lines in You’ve Got Mail, and Nora Ephron was one of the only people who ever cast me on the spot, in the room, which doesn’t really happen that much,” Messina told HuffPost in 2012.

A Cheese Store Was Transformed Into Kathleen’s Bookshop

To create the cozy, welcoming world of the Shop Around the Corner, the movie’s crew took over a real New York cheese and antique shop and totally transformed the space while the owner was out of town. According to a 2018 interview with the film’s location manager Randy Sokol Sweeney, Ephron wanted the fake bookstore to be “as real as it could be,” so the filmmakers “emptied [the cheese shop] and redressed it into the bookstore.”

Barnes & Noble Wouldn’t Allow the Movie to Be Filmed in It

It’s meant to be obvious that Fox Books is based on bookselling mega-chain Barnes & Noble, but the retailer wouldn’t allow the You’ve Got Mail filmmakers to shoot scenes inside one of its real locations. The reason? They didn’t want to have to shut down the store to customers during the film shoot. So instead, Ephron and company used a just-closed Barney’s department store and built the entirety of Fox Books within those walls. More than 25,000 books were carted in to fill the shelves, per the 2017 book I’ll Have What She’s Having: How Nora Ephron’s Three Iconic Films Saved the Romantic Comedy. There was even a real coffee bar built for the cast and crew to use!

Meg Ryan Got Her First Computer While Filming

Although director Ephron was already a computer pro in the late ’90s, espousing the virtues of email and the internet, Ryan was a bit slower to catch on. In a 2015 Vanity Fair retrospective, the actress revealed that she got her first computer while filming You’ve Got Mail, courtesy of Warner Bros. (Whether she used it to send flirty emails about books and New York, though, isn’t known.)

And Future Marvel Head Kevin Feige Taught Her How to Use It

Years before becoming the president of Marvel Studios and producing superhero blockbusters, Kevin Feige was just a production assistant on You’ve Got Mail. One of his responsibilities entailed teaching Ryan, Hanks, and even Ephron how to use AOL and send emails. According to I’ll Have What She’s Having, Feige was starstruck by Ryan in particular. “I just thought it was very exciting to be in a movie star’s house teaching them how to use email,” he said, adding that he was elated when Ryan said hi and remembered his name a few days later.

Tom Hanks Improvised One Memorable Line

Many You’ve Got Mail cast members have said that Ephron encouraged them to improvise on set, including in the scene in which the Shop Around the Corner employees talk about their online dating experiences. But one of the movie’s most memorable improvised lines came courtesy of Hanks, who — in the scene when Joe accidentally closes the bookshop door on balloons — looks at the fish he’s holding in his other hand and said, “Good thing it wasn’t the fish.” Per E!, Ephron reportedly liked the line so much that she kept it in the movie’s final cut.

Hanks Helped Get Dave Chappelle a Role

In You’ve Got Mail, then-on-the-rise comedian and actor Dave Chappelle played Kevin, best friend to Hanks’ Joe. The duo had nearly starred together in 1994’s Forrest Gump, but Chappelle (as he later revealed in a stand-up show) had turned down the role of Bubba over concerns it’d be a racist stereotype.

When Forrest Gump became an Oscar-winning blockbuster, though, Chappelle reportedly had regrets. A few years later, Hanks, wanting another chance to work with the comedian, suggested to Ephron that she cast Chappelle as Kevin, leading the two men to finally star side-by-side.

The Child Actors Didn’t Even Know They Were Filming a Movie

Some of You’ve Got Mail’s cutest scenes come courtesy of Hallee Hirsh and Jeffrey Scaperrotta, who played Joe’s young aunt and half brother, respectively. As they recalled in a 2018 interview with Today, the kids had such a blast filming scenes with Hanks that they didn’t always realize it wasn’t real life. “I didn’t know I was actually filming just because of how friendly he was with me,” said Scaperrotta. “Like, I was on his shoulders for basically the whole entire time. Even after shooting, I was, like, still hanging on his shoulders, eating cotton candy, playing with the carnival games.”

Ryan Found the Movie to Not Be Enough of a Challenge

Despite You’ve Got Mail making her an even bigger movie star than she already was, Ryan didn’t seem to love the filming experience. “I have to say that You’ve Got Mail was not any kind of stretch for me,” she told Vanity Fair in 1999. “And I can’t have that experience again. I’m just not that interested in it.” It’s no surprise, then, that Ryan started moving away from romantic comedies only a few years later, eventually taking a 14-year break before returning to the genre with this year’s What Happens Later.

Some Fans Believe There’s an Alternative Ending That Doesn’t Exist

You’ve Got Mail famously ends with Kathleen and Joe embracing each other in Riverside Park while “Over the Rainbow” plays in the background. Yet for whatever reason, many viewers have taken to Reddit and Twitter over the years to swear that the movie ended differently: specifically, with a scene of Kathleen setting up a small version of her bookstore inside Fox Books and reading stories to children. Yet when Lainey Gossip reached out to Delia Ephron in 2021 to ask about the existence of an alternate ending, the screenwriter shot down the rumor. “The movie always ended in Riverside Park. And no one has messed with the movie since it was released,” Ephron said. Turns out this one’s just a classic case of the Mandela effect.

You Could Read Joe’s and Kathleen’s Emails Until Just a Few Years Ago

Amusingly, Warner Bros. kept the original website for You’ve Got Mail fully alive and accessible, complete with its very-’90s design and features, all the way up until 2019. And on that site, you could relive the film’s romance by reading the actual emails that Joe and Kathleen sent each other in the movie (albeit in hilariously inconvenient pop-up form). Sadly, the site is no longer accessible, but you can take a tour through its highlights in this piece. And if you really want some You’ve Got Mail nostalgia, you can always rewatch the movie on one of the many streaming platforms it exists on today.

Rachel Simon is a writer with work in The New York Times, Glamour, NBC News, Marie Claire, and many other outlets. Follow her on Twitter @rachel_simon.

Get Shondaland directly in your inbox: SUBSCRIBE TODAY

You Might Also Like

• 30 Anti-Aging Foods for Women That'll Keep You Feeling Young

• A Definitive Ranking of Popular Potato Chip Brands