The scene where Joe accidentally closes the door of Kathleen's shop on the balloons was unscripted. Tom Hanks actually did that, and ad libbed the line, "Good thing it wasn't the fish." Nora Ephron thought it was so funny that she kept it in.
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The children's bookstore scenes in the film were filmed at Maya Shaper's Cheese and Antique Shop on 103 West 69th Street. The film makers wanted to use the antique shop because it had the quaint, homey feel they were going for. They sent the owner of the antique shop on vacation for a few weeks and while she was gone they turned the store into a children's bookstore. After filming was finished, they put everything back the way they had left it, and it became an antique store once again.
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The location of Fox Books in the movie is the location of a real-life Barnes & Noble, on Broadway and 83rd Street on the Upper West Side. The Barnes and Noble generated considerable neighborhood opposition when it opened in the early 1990s, as many feared it would drive a local bookseller, Shakespeare & Co. on 81st Street, out of business. In 1996 they closed their doors, with their two other locations remaining open. In 2018 they announced their return to the Upper West Side, opening a store on Broadway between West 69th and 70th streets. Ironically, the big chain bookstores have been hammered by online retailers who offer even lower prices and greater convenience. Barnes & Nobel's main competitor, Borders, went under in 2014. With the rollback on huge downtown stores, which have to pay extravagant fees for their leases, smaller bookstores are reappearing in key locations.
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All of Joe and Kathleen's e-mails were put on the movie's official website which Warner Bros. has kept active.
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A remake of the 1940 film The Shop Around the Corner (1940) starring James Stewart and Margaret Sullavan. The original film involved two employees at a leather goods shop in Budapest. Other incarnations were In the Good Old Summertime (1949), which took place in a music store, and "She Loves Me," a 1963 stage adaptation that reverted the action back to a parfumerie, the setting of the original Hungarian source play. In each case, the protagonists cannot stand each other at work while they are unknowingly falling in love through the mail as anonymous pen pals.
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The New York City previews were shown in the exact same theater (same building, same "room") that Meg Ryan and Greg Kinnear go into to see their movie, the Sony Lincoln Square 13 and IMAX Theater.
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The movie's opening and ending titles make use of commonly seen computer images of the time, specifically Windows 95/98. The ending title song, which begins just after the words "The End" appear on the screen, starts with an adaptation of the "startup" sound from Windows 95.
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Joe Fox (Tom Hanks) is obsessed with The Godfather (1972), and frequently uses dialogue from it to shape his philosophy on life. In the Coppola Restoration Godfather DVDs, Alec Baldwin claims that Hanks and Rob Reiner are both Godfather aficionados, and have hosted viewing parties where the attendees play drinking games and quote famous lines while watching the film. The quotes are often used as funny pseudo wisdom responses to various oddball questions in an informal game that is sometimes referred to as the Tau of the Godfather.
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The extra who is playing the florist in the beginning of the movie is pregnant. Later, Kathleen is buying flowers at that same florist and there's a sign in the window saying "It's a girl".
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One thing that distinguishes this film from any prior source material (Hungarian play, Hollywood movie, Hollywood musical, Broadway musical) is that both protagonists are in relationships while they correspond with each other. The leads in all other versions are single. The idea of infidelity does come up in all but the Hollywood musical, but it's such a terrible transgression that the characters involved are duly punished for it.
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Nora Ephron arranged for Meg Ryan and Heather Burns to work in a real New York City bookstore in preparation of their roles prior to filming. The store was Books of Wonder in Manhattan, and the jobs lasted for about a week.
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The passage that we see Kathleen Kelly reading during her bookshop's story time to a group of kids (including Joe Fox's aunt and brother) is from "Boy: Tales of Childhood", an autobiographical children's novel written by Roald Dahl.
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Kathleen and Joe used AOL software to connect to the Internet. They were both using version 4.0 which was in beta testing mode when the film was being made.
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This is the third time that Meg Ryan and Tom Hanks act together, the previous two being Joe Versus the Volcano (1990) and Sleepless in Seattle (1993).
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Jean Stapleton's character's name is Birdie Conrad, a reverse of the character Conrad Birdie from the famous Broadway musical Bye Bye Birdie (1963).
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Meg Ryan got her very first computer during the filming.
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Kathleen Kelly's bookstore in the film was based largely on Manhattan's Books of Wonder in Chelsea on 18th Street. Meg Ryan worked the counter at Books of Wonder for a day as part of her preparation. Decorative props from the film can still be seen at the store.
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The store used for Fox Books is the old Barney's department store at 17th Street and 7th Avenue in Manhattan.
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In this film, which is written by Nora and Delia Ephron, Meg Ryan plays a woman who falls in love with a man she has never met. At the same time, she befriends the same man in real life while believing him to be a different person. This is a similar plot to the Fred Astaire-Leslie Caron musical Daddy Long Legs (1955), which was written by Nora and Delia's parents, Henry and Phoebe Ephron.
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One of Nora Ephron's signature filmmaking quirks was her use of songs to accentuate plot points (one of the chief elements that led her films to be termed 'chick flicks'). When Ryan's and Hanks' characters finally meet in person, with both knowing that they've been e-mailing each other, the song "Over the Rainbow" plays on the film's soundtrack. The duo shared a scene set to the same song in Sleepless in Seattle (1993).
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In the opening lines of the movie, Frank is describing how the state of Virginia had to have solitaire removed from their computers "because that hadn't gotten any work done in six weeks." This line is actually based on fact. In December of 1994, Governor George Allen of Virginia did in fact order that all video games (specifically minesweeper, hearts and solitaire), be removed from all state computers, because of a concern that state employees were playing these games during office hours and wasting tax payer dollars.
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The book that can be seen on Kathleen's bed during the scene when Joe unexpectedly shows up at her apartment is "The Scarecrow of Oz", the ninth book in the Land of Oz series written by L. Frank Baum.
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First film allowed to be filmed inside the classic grocery store on Broadway and West 80th Street - Zabar's
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Kathleen - the feisty, independent representative for what might be called the book store "for the rest of us" - uses a Macintosh which, at the time of this movie, had lost its lead to the Windows PC. Joe - the representative of the massive, impersonal big business bookstore - uses a Windows PC. At the time, Windows and PC makers were flooding the media with massive and highly successful marketing campaigns, with the average home viewer seeing approximately thirty Windows PC commercials every evening. Apple at the time was running virtually no commercials whatsoever. While Windows PCs were primarily used for business, the focus of the Macintosh at that time was more on creativity, education and children, and depending on repeat business and referrals. The parallels with You've Got Mail (1998) are quite prominent.
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The film invokes several literary and cinematic references to The Wizard of Oz (1939): a full shelf of Oz books on the shelf behind Kathleen when she opens the door for Jessica and Maya; the ruby slippers ornament that Kathleen is placing on the Christmas tree; the Scarecrow of Oz book opened on Kathleen's bed when Joe visits her apartment; and "Over the Rainbow" playing in the closing scene.
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When Tom Hanks is meeting Meg Ryan for a date but doesn't reveal his identity, Ryan pokes fun at Hanks' name 'Joe' and makes nasty references to young women with names like 'Kimberly.' In When Harry Met Sally (1989), Ryan's character's boyfriend, Joe, gets engaged to a girl in his office named Kimberly.
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For opening credits, Ephron wanted an animated version of Broadway's Boogie-Woogie, a representation of New York City by Piet Mondrian. When animator Mirko Ilic and his staff animated Mondrian's painting, Ephron wanted something more "realistic or romantic" so they photographed all of the buildings along Broadway on the Upper West Side, from 72nd Street to the brownstone where the film begins, as a guide for the computer graphic animation.
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When Kathleen is decorating her shop's Christmas tree, she places an ornament of Dorothy's ruby slippers from The Wizard of Oz (1939). Judy Garland, who played Dorothy Gale in that film, also played the main character in In the Good Old Summertime (1949), which like You've Got Mail (1998), was based on The Shop Around the Corner (1940).
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Kathleen's bookstore is The Shop Around The Corner, an homage to the movie this is based on.
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Since the movie, Heather Burns has actually petitioned for local New York City bookstores.
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In later interviews, Meg Ryan said the film was "not any kind of stretch for me. I can't have that kind of experience again. I'm just not interested in it".
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The original source material for this plot, the 1937 play "Illatszertár" (in English, titled "Parfumerie") by the Hungarian writer Miklós László, has been adapted into numerous other movies and plays. The first film adaptation was The Shop Around the Corner (1940) starring Margaret Sullavan and James Stewart. The first musical adaptation was In the Good Old Summertime (1949), which starred Judy Garland and Van Johnson. In 1963, a second musical adaptation, "She Loves Me," premiered on Broadway; its first production, which starred Daniel Massey and Barbara Cook, was a critical success but a box-office disappointment. A 1993 Broadway revival (starring Boyd Gaines and Judy Kuhn) was more successful, and another Broadway revival (with Laura Benanti, Zachary Levi, and Jane Krakowski) opened in 2016.
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Meg Ryan's character, Kathleen Kelly, uses a Macintosh PowerBook G3 "Kanga", (introduced 11/97), or a Macintosh PowerBook 3400c, (introduced 2/97) in the movie. The exact model she used can't be determined from looking at the outer plastic case, as both machines used the same plastic case.
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The film was shot primarily in New York City's Upper West Side.
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The computer graphics at the start of the film were considered to be extremely primitive at the time this movie came out. For example, the wireframe graphics followed by the animation of the terraforming of a planet in Star Trek II: The Wrath of Khan (1982) was done sixteen years before You've Got Mail (1998).
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In the party scene, Tom Hanks' character responds to Kathleen's comment "that caviar is a garnish!" by scooping up all the remaining caviar for himself. In the movie Big (1988), Hanks' character tries caviar at a party, which he hates; he spits it out & wipes his tongue with a napkin.
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Nick Castle was the original director before departing over "creative differences".
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The cast members actually e-mailed each other during filming.
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Katie Finneran, who plays the babysitter, is the second cast member in this movie to win Broadway's Antoinette Perry ("Tony") Award. The first was Sara Ramirez.
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Kathleen tells the brother of Hanks' character Joe that daisies are her favorite flower. In Sleepless in Seattle (1993) Ryan's character Annie tells Walter that the daisy engagement ring was exactly the one she would have chosen.
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When visiting Kathleen's bookstore, Joe Fox is interested in a first edition of Swiss Family Robinson, which is a castaway story. Tom Hanks would go on to do Cast Away, released two years later.
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The only song during the film that is not on the soundtrack is "Never Smile at a Crocodile," which plays as Joe and the kids are leaving Kathleen's store. It is performed by The Paulette Sisters.
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There is a Broadway musical adaptation of the original movie called, "She Loves Me".
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Joe's online name is "NY152" and Kathleen's name is "Shopgirl".
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When Tom Hanks reveals himself as the pen pal to Meg Ryan in the park, he uses a below the waist hand shrug. This is the same gesture his grade school character gives to Elizabeth Perkins when he says goodbye to her in the movie "Big", in both cases signifying "What can I say?"
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Brinkley the dog in the movie is a Golden Retriever. Joe Fox and Brinkley are best mates in the movie.
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In the children's section of the Fox Bookstore, there is a cardboard cutout of a fox playing a flute or recorder, much like the Pied Piper, as if to lure in customers.
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The movie references Muhammad Ali. When Kathleen Kelly is in the Shop Around The Corner, she prepares herself for the coming confrontation with the Fox Books store by quoting Ali's famous lines: "Float like a butterfly. Sting like a bee."
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At approx. 21:15 when Annabelle Fox (Hallee Hirsh) and Matt Fox (Jeffrey Scaperrotta) are running on to the marina Joe Fox (Tom Hanks) says to them "I know you, I know you". Chuck Nolan (Tom Hanks) says the same line to Wilson the volleyball in the movie Cast Away (2000) approx. 1:31:12.
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Could arguably be a modern re-telling of Jane Austen's "Pride and Prejudice," of which Kathleen is a fan. Joe Fox mimics the story's male protagonist Mr. Darcy (Pride), while Kathleen Kelly mirrors the female protagonist, Elizabeth Bennett (Prejudice.) Like the novel, the two meet under casual circumstances only to end up at odds with each other due to differing views and opinions. Like Elizabeth, Kathleen becomes determined to hate Joe Fox due to his proud disposition. But, their continued encounters lead them to eventually fall in love. The redeeming factor of the novel however, is inverted in this film. In the story Darcy finally "wins over" Elizabeth when she learns of the noble service he selflessly performs for her family. Joe Fox on the other hand, does Kathleen a great "disservice" by putting her out of business; making the story somewhat unique as the two fall in love in spite of this.
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The song at the end of the film when they are standing on the bridge is "Over the Rainbow". A clip of this song is played in the previous movie with Meg Ryan and Tom Hanks, Sleepless in Seattle (1993).
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Tom Hanks also collects typewriters, like the character Frank.
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This movie's screenplay is based loosely on The Shop Around the Corner (1940), starring James Stewart and Margaret Sullavan. Kathleen's store is named The Shop Around the Corner, the two main characters are latter day (mail) and present day (e-mail) "pen pals"; they both know they are falling in love with their respective pen pals; when the man realizes who the woman really is, he pursues her, but is not sure the love match will work; in the end, they find they belong together.
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Kathleen/Shopgirl arrives at Riverside Park to meet NY152 (revealed to be Joe) at 1 hour and 52 minutes into the film.
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Of the three movies where Tom Hanks and Meg Ryan star as the leads this is the only one where they start off disliking each other before eventually falling in love. In their first starring film Joe Versus the Volcano (1990) Meg Ryan's main character starts off being rude to Hanks but very quickly has a change of heart and declares her love for him, in their next film following Sleepless in Seattle (1993) Meg Ryan is in love with him for a majority of the movie but their characters don't meet until the very end of the film where it is implied during the climax that they begin a relationship.
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