Editing Sleepless in Seattle (section)

== Production ==

=== Origins and development ===
In 1989, ''Sleepless in Seattle'' was conceived by Jeff Arch, a struggling writer and former cinematographer,<ref name=":3" /><ref name=":45">{{Cite news |last=Kempley |first=Rita |date=June 25, 1993 |title=Movies |newspaper=[[The Washington Post]] |url=https://www.washingtonpost.com/archive/lifestyle/1993/06/25/movies/dc628e50-87a9-4a1b-9f70-8ede68fc682e/ |access-date=March 21, 2022}}</ref> whose work as a writer had experienced little to no success at the time .<ref name=":44">{{Cite news |last=Adams |first=Sean |date=November 30, 2018 |title='Sleepless in Seattle' screenwriter and Harrisburg native on the film's 25th anniversary screenings |work=[[The Patriot-News]] |url=https://www.pennlive.com/life-and-culture/erry-2018/11/71b2bd34041075/sleepless-in-seattle-screenwri.html |access-date=March 21, 2022 |id= |quote=But at the time I remember reading an article in the Washington Post about women who were hiring detectives to investigate the men they were dating. So [Meg Ryan's character Annie]'s friend Becky was going to hire a detective to check up on her boyfriend.}}</ref> ''Sleepless in Seattle'' was Arch's first script to be optioned as a film.<ref name=":39">{{Cite news |last=Perez |first=Lexy |date=January 23, 2021 |title='Attachments' Book Excerpt: 'Sleepless in Seattle' Screenwriter Pens Debut Novel (Exclusive) |work=[[The Hollywood Reporter]] |url=https://www.hollywoodreporter.com/lifestyle/lifestyle-news/attachments-book-excerpt-sleepless-in-seattle-screenwriter-pens-debut-novel-exclusive-4119990/ |access-date=March 18, 2022}}</ref> The story began as a play about two people falling in love over the telephone without meeting in person.<ref name=":44" /> Arch decided that, unlike typical romance plots in which the main characters bicker for most of the film after they "[[meet cute]]", his couple would not meet until the end of the film,<ref name=":44" /> feeling unprecedented confidence that ''Sleepless in Seattle'' would be successful as long as he "got these people to the top of the [[Empire State Building]] on [[Valentine's Day]]".<ref name=":45" /> The writer drew inspiration from several sources, including the [[French film]] ''[[And Now My Love]]'' (1974), a seminar by motivational speaker [[Tony Robbins]],<ref name=":7">{{Cite web |title=Sleepless in Seattle (1993) |url=https://catalog.afi.com/Catalog/moviedetails/59663 |access-date=March 14, 2022 |website=[[AFI Catalog of Feature Films]] |id=Despite [[An Affair to Remember]] being a favorite of his mother's, Arch himself was not particularly fond of the film. |quote=[[Nora Ephron]] credited Jeff Arch with the motif of the 1957 film, An Affair to Remember}}</ref> and a ''[[The Washington Post|Washington Post]]'' article he had read about women hiring [[private investigator]]s to uncover information about their romantic partners.<ref name=":44" />

Arch faced criticism about the unlikelihood of the film being made due to the lack of scenes shared by its lead couple.<ref name=":44" /> He pitched the film to at least six studios and executives, all of whom rejected it for similar reasons.<ref name=":45" /> Desperate, Arch's agent Dave Warden submitted the [[spec script]] to producer Gary Foster in 1990.<ref name=":4">{{Cite news |last=Foster |first=Gary |date=June 25, 2018 |title='Sleepless In Seattle' Hits 25: Producer Gary Foster Narrates Evolution From Spec Script To Seminal Romantic Comedy |work=[[Deadline Hollywood]] |url=https://deadline.com/2018/06/sleepless-in-seattle-25th-anniversary-tom-hanks-meg-ryan-producer-gary-foster-1202416746/ |access-date=March 14, 2022}}</ref> Although Foster typically discards new scripts that fail to captivate him within its first 25 pages, he claims to have read past the 25th page of Arch's script unnoticed,<ref name=":4" /> only to find he was crying by the last page.<ref name=":3" /> Immediately noticing the script's potential, Foster submitted the script to [[TriStar Pictures]] executive Richard Fischoff, whose studio had produced all of his previous films.<ref name=":4" /> At first, Fischoff's staff screened the script and passed on it.<ref name=":4" /> After pleading from Foster, Fischoff eventually relented and read the script, optioning it to TriStar a few days later.<ref name=":4" />

Eventually TriStar chairman [[Mike Medavoy]] heavily promoted the film,<ref name=":45" /> and Foster began interviewing potential directors shortly after.<ref name=":4" /> [[Nick Castle]] had been slated to write and direct ''[[Hook (film)|Hook]]'' (1991), a big-budget adaptation of ''Peter Pan'' also for TriStar, but he was eventually removed from the film in favor of [[Steven Spielberg]].<ref name=":4" /> The studio reassigned Castle to ''Sleepless in Seattle'' as a consolation.<ref name=":4" /> [[Garry Marshall]] had also been considered to direct.<ref name=":7" /> While Foster retained sole producer credit, the film was co-executive produced by [[Lynda Obst]] and [[Patrick Crowley]].<ref>{{Cite news |last=Foster |first=Gary S. |date=October 15, 1995 |title=Female Producers;Whose 'Sleepless'? |work=[[The New York Times]] |url=https://www.nytimes.com/1995/10/15/movies/l-female-producers-whose-sleepless-060739.html |access-date=March 31, 2022}}</ref> Foster struggled to get the film made over the following two years.<ref name=":7" /><ref name=":4" /> After finally agreeing to maintain the idea of keeping the couple separated, TriStar insisted that the "wistful" script be re-written to make the film and each character edgier and quirkier, particularly Sam and Annie.<ref name=":45" /> Foster found the script lacked the sophistication and complexity required to elevate an emotional, sentimental story beyond merely treacle.<ref name=":4" /> Foster reluctantly informed Arch they were interested in changing writers in order to "sharpen" his script.<ref name=":4" /> Although Arch submitted a re-write himself, he soon found he was essentially "kicked off my own movie", and replaced by a writer with whose work he was not pleased, such as relocating the entire film to New York without including the Empire State Building.<ref name=":45" /> Arch begged Foster and director [[Nick Castle]] to hire a better writer "who's going to take this way up to the next level".<ref name=":45" />

=== Writing ===
[[File:Nora Ephron.jpg|thumb|260x260px|Originally hired to improve ''Sleepless in Seattle''<nowiki/>'s script, [[Nora Ephron]] was eventually promoted to director, replacing [[Nick Castle]].  ]]
Several writers and directors were involved with ''Sleepless in Seattle'' at various stages of development,<ref name=":3" /> with Arch's script being re-written approximately five times.<ref name=":45" /> Arch's original concept was more akin to a [[Romantic Drama|romantic drama]] than a romantic comedy.<ref name=":34">{{Cite news |last=Siede |first=Caroline |date=June 22, 2018 |title=25 years ago, Sleepless In Seattle found the romantic hiding in the cynic |work=[[The A.V. Club]] |url=https://www.avclub.com/25-years-ago-sleepless-in-seattle-found-the-romantic-h-1826855118 |access-date=January 5, 2025}}</ref> Despite already featuring several of the film's major elements, such as a central father-son relationship and references to the romance film ''[[An Affair to Remember]]'' (1957),<ref name=":3" /><ref name=":7" /> Arch admitted his script was not funny enough.<ref name=":3" /> Dramatist [[Larry Atlas]] attempted some revisions, most of which were discarded.<ref name=":7" /> Foster interviewed at least 10 potential writers before hiring [[David S. Ward]] to re-write Arch's script.<ref name=":4" /> Among the most significant changes, Ward decided to have Jonah call the radio station on Sam's behalf.<ref name=":4" /> Insisting that no self-respecting man would deliberately call a radio show to share his emotional grievances,<ref name=":4" /> Ward suggested that Sam be coerced by Jonah into revealing how he feels about his late wife to several single women throughout the country, including Annie.<ref name=":3" /> Arch credits Ward with convincing the studio to not give up on the film, believing the latter's Academy Award for writing ''[[The Sting]]'' (1973) helped them take him seriously as a filmmaker.<ref name=":44" /> However, the studio constantly pushed for an edgier and quirkier film.<ref name=":45" /> Despite acknowledging Ward's work as "a big step forward for the script", Foster was not entirely satisfied with the revisions and forwarded them to writer [[Nora Ephron]], having been a fan of her work on ''[[When Harry Met Sally...]]'' (1989).<ref name=":3" /> Ephron had been Foster's first choice, hoping she could offer the script "a cynical layer to justify the organic sweetness", but she was unavailable when first approached to re-write.<ref name=":4" />

At least four writers attempted to rework ''Sleepless in Seattle'' before Ephron was recruited to "polish" the fifth and final draft.<ref name=":45" /><ref name=":9">{{Cite web |date=June 21, 2007 |title=Nora Ephron Interview |url=http://www.achievement.org/autodoc/page/eph0int-2 |archive-url=https://web.archive.org/web/20150701023133/http://www.achievement.org/autodoc/page/eph0int-2 |archive-date=July 1, 2015 |access-date=March 15, 2022 |website=[[Academy of Achievement]]}}</ref><ref name=":58">{{Cite book |last=Ephron |first=Nora |url=https://books.google.com/books?id=SZ8mCgAAQBAJ&dq=Delia+ephron+sleepless+in+seattle+interview&pg=PT35 |title=Nora Ephron: The Last Interview: and Other Conversations |publisher=[[Melville House Publishing]] |year=2015 |isbn=9781612195254 |location=United States |author-link=Nora Ephron |via=[[Google Books]]}}</ref> Ephron had been searching for [[script doctor]]ing jobs shortly after her directorial debut ''[[This Is My Life (1992 film)|This Is My Life]]'' (1992) proved unprofitable at the box office.<ref name=":9" /><ref name=":1">{{Cite magazine |last=Frascella |first=Lawrence |date=July 8, 1993 |title=On the Front Lines With Nora Ephron |magazine=[[Rolling Stone]] |url=https://www.rollingstone.com/movies/movie-news/on-the-front-lines-with-nora-ephron-61704/ |access-date=March 14, 2022}}</ref><ref name=":63">{{Cite web |last=Looney |first=Deborah |title=Sleepless in Seattle |url=https://www.tcm.com/watchtcm/titles/18873 |access-date=March 22, 2022 |website=[[Turner Classic Movies|Watch TCM]] |id=Click the "more" sub-menu under the "ARTICLES" heading, for the entire article.}}</ref> Admitting that she never would have conceived the film herself,<ref name=":56" /> Ephron initially accepted ''Sleepless in Seattle'' as a fun, easy writing project from which she could quickly earn money.<ref name=":7" /><ref name=":59" /> Although she found Arch's version simple and unfunny, Ephron particularly liked his romantic ending involving the Empire State Building,<ref name=":9" /> and was interested in several ideas discussed in Ward's second draft,<ref name=":1" /> particularly how movies affect people's perception about romance.<ref name=":63" /> Ephron assured Foster that she could re-write the script within three weeks,<ref name=":2">{{Cite web |date=May 18, 2020 |title=AFI Movie Club: Sleepless in Seattle |url=https://www.afi.com/afi-movie-club-sleepless-in-seattle/ |access-date=March 14, 2022 |website=[[American Film Institute]]}}</ref> adapting it into a funnier version of itself without entirely making it a comedy.<ref name=":9" /> She specifically improved Annie and Jonah's roles.<ref name=":58" /> In an early draft, the character of Annie was in the midst of ending an unhappy relationship; Ephron wrote this out of the film because she found Annie's original backstory inconsequential in comparison to Sam's loss of his wife.<ref name=":22" /> Annie was also relocated from Lancaster, Pennsylvania, to Baltimore, Maryland, as the character had originally been conceived as a Lancaster-based reporter.<ref name=":59" /> Foster credits Ephron with contributing most of the film's dialogue, while de-emphasizing much of Arch's sentimentality.<ref name=":8">{{Cite news |last=Hartl |first=John |date=June 20, 1993 |title=Sleeping In Seattle |work=[[The Seattle Times]] |url=https://archive.seattletimes.com/archive/?date=19930620&slug=1707282 |access-date=March 15, 2022 |quote=Early reviews have been encouraging.}}</ref> While crediting Ephron with providing her trademark wit and snark the studio felt the original script lacked, Arch does not think all of Ephron's ideas particularly elevated the film.<ref name=":44" /> Describing themselves as quite different as writers, Arch likened their working relationship to "a parent and a step-parent of the same kid".<ref name=":44" /> However, they shared a strong love for [[Classical Hollywood cinema|classic films]],<ref name=":44" /> with Ephron admitting she herself once considered ''An Affair to Remember'' to be "the greatest movie I'd ever seen".<ref name=":1" /> Ephron said the final film turned out funnier than she had imagined.<ref name=":56" />

Castle left the project over disagreements with Ephron's edgier, less sentimental script,<ref name=":8" /> accusing her of stripping the film of emotion.<ref name=":45" /> Ephron claims virtually everyone liked the final script she submitted, apart from Castle.<ref name=":58" /><ref name=":59">{{Cite news |last=Hunter |first=Stephen |author-link=Stephen Hunter |date=June 25, 1993 |title=Ephron balked at Pennsylvania, so . . . Baltimore! Long-distance love has 'em 'Sleepless' |work=[[The Baltimore Sun]] |url=https://www.baltimoresun.com/news/bs-xpm-1993-06-25-1993176137-story.html |access-date=March 30, 2022 |quote=Coming from print, I had overestimated the idea how important it was to say my lines. I saw how great it was when people brought their own presents to the party. The great thing for a director is to have an atmosphere where anyone can bring something. You end up with something better than your own script.}}</ref> Impressed by Ephron's swiftness and dedication, Foster invited her to direct.<ref name=":3" /> Although Ephron protested the film was not quite ready to be directed, feeling it warranted at least one more rewrite, she eventually accepted and recruited her sister [[Delia Ephron|Delia]] to help improve several scenes.<ref name=":9" /><ref name=":22" /> One such moment was the final scene in which Annie meets Sam and Jonah atop the Empire State building; Delia suggested that the father and son should be returning to the observation deck just as Annie is readying to leave, instead of having already exited the building.<ref name=":22" /> Despite serving as an associate producer alongside Arch,<ref name=":3" /> [[Delia Ephron|Delia]] remains uncredited for her script contributions,<ref name=":56">{{Cite news |last=Simon |first=Jeff |date=June 27, 1993 |title=Breakthrough: Ephron Laughs her Way into 'Sleepless' Romance |work=[[The Buffalo News]] |url=https://buffalonews.com/news/breakthrough-ephron-laughs-her-way-into-sleepless-romance/article_ddcfb867-8e7e-5504-9637-0aa329d43d6d.html |access-date=March 28, 2022}}</ref><ref name=":6">{{Cite web |last=Cormier |first=Roger |date=June 27, 2015 |title=15 Heartfelt Facts About Sleepless in Seattle |url=https://www.mentalfloss.com/article/65469/15-heartfelt-facts-about-sleepless-seattle |access-date=March 14, 2022 |website=[[Mental Floss]]}}</ref> although a script dated March 10, 1992, is credited to Arch with re-writes by Nora and Delia Ephron.<ref>{{Cite web |last1=Arch |first1=Jeff |last2=Ephron |first2=Nora |author-link2=Nora Ephron |last3=Ephron |first3=Delia |author-link3=Delia Ephron |date=March 10, 1992 |title=Sleepless in Seattle by Jeff Arch |url=https://www.scriptslug.com/assets/scripts/sleepless-in-seatlle-1993.pdf |access-date=March 31, 2022 |website=Script Slug}}</ref> Ephron considers ''Sleepless in Seattle'' a "secret present" to their late parents, who were also screenwriters, as well as classic Hollywood movies.<ref name=":56" /> As "a movie about love that was also about movies about love", Ephron aimed to direct a "timeless" film audiences could watch for several years, without it feeling like it was made in 1993.<ref name=":59" />

Ephron was also determined to give each character a "moment", such as when the minor mailman character has an inconsequential conversation about hiccups with Sam's son Jonah.<ref name=":2" /> At one point, the script mentioned that Sam and Annie had once both lived in Chicago at the same time, but this was edited out of the final film.<ref name=":6" /> ''Sleepless in Seattle'' became Ephron's second directorial effort.<ref>{{Cite web |last=Durling |first=Roger |title=Sleepless in Seattle |url=https://sbiff.org/sleepless-in-seattle/ |access-date=March 14, 2022 |website=[[Santa Barbara International Film Festival]]}}</ref> ''[[Premiere (magazine)|Premiere]]'' reported that, once Ephron became involved, the film "changed ... from a script that almost everyone had turned down into one that almost everyone wanted to be involved with".<ref name=":45" /> Although Arch did not necessarily agree that Ephron saved the film, he understood that "sometimes, you're not the star but that if you keep doing your job right, you will be the star", and maintains that several scenes ultimately remained almost exactly how he had envisioned them in his first draft, despite several re-writes.<ref name=":45" />

=== Casting ===
Ephron promised Foster that her revised screenplay would be deserving of actors [[Tom Hanks]] and [[Meg Ryan]],<ref name=":2" />{{Efn|Tom Hanks and Meg Ryan were considered to be two of the most popular and successful actors of the 1990s.<ref>{{cite web |last1=Dirks |first1=Tim |title=The History of Film The 1990s |url=https://www.filmsite.org/90sintro.html |website=[[Filmsite]] |access-date=March 30, 2022}}</ref>|name=Hanks and Ryan popularity}} the latter being the actress Ephron had in mind for the character Annie.<ref name=":22">{{Cite news |last=Sledge |first=Philip |date=January 14, 2021 |title=Sleepless In Seattle: 11 Behind-The-Scenes Facts About The Tom Hanks And Meg Ryan Movie |work=[[CinemaBlend]] |url=https://www.cinemablend.com/news/2561270/sleepless-in-seattle-behind-the-scenes-facts-about-the-tom-hanks-and-meg-ryan-movie |access-date=March 15, 2022}}</ref> While Arch had also written the female role for Ryan due to her performance in ''When Harry Met Sally'', he had envisioned [[Kevin Costner]] in the role of Sam.<ref name=":44" /> A different pair of actors had originally been envisioned in the lead roles, but departed because they were deemed not funny enough for Ephron's material.<ref name=":9" /><ref name=":58" /> Several actresses pursued the role of Annie once they learned of Ephron's involvement, including [[Julia Roberts]],<ref name=":2" /><ref>{{Cite news |last=Singh |first=Rishi |date=October 12, 2008 |title=Pretty facts |work=[[The Himalayan Times]] |url=https://thehimalayantimes.com/entertainment/pretty-facts |access-date=March 18, 2022}}</ref><ref>{{Cite news |last=Willis |first=Jackie |date=August 11, 2014 |title=Julia Roberts Turned Down 'Sleepless In Seattle'! |work=[[Entertainment Tonight]] |url=https://www.etonline.com/movies/149634_julia_roberts_sleepless_in_seattle_instyle |access-date=March 14, 2022}}</ref>{{Efn|[[Meg Ryan]] had previously turned down the lead role of Vivian Ward in Gary Marshall's "Pretty Woman", which ultimately starred [[Julia Roberts]].<ref>{{cite news |last1=Vollum |first1=Terry |title=The first choice is not always the best choice |url=https://www.trentonian.ca/opinion/columnists/the-first-choice-is-not-always-the-best-choice |access-date=March 18, 2022 |work=[[Trenton Trentonian]] |date=September 19, 2021}}</ref>|name=Meg Ryan "Pretty Woman"}} [[Kim Basinger]], [[Michelle Pfeiffer]],<ref name=":26" /> [[Sharon Stone]],<ref name=":8" /> [[Jodie Foster]],<ref>{{Cite news |last=Gibbs |first=Lynn |date=September 20, 2020 |title=10 Things Fans Didn't Know About Sleepless In Seattle |work=[[Screen Rant]] |url=https://screenrant.com/things-fans-didnt-know-about-sleepless-in-seattle/ |access-date=March 18, 2022}}</ref> [[Demi Moore]] and [[Madonna]],<ref name=":17" /><ref name=":37">{{Cite news |last=Tanabe |first=Karin |author-link=Karin Tanabe |date=August 21, 2017 |title=The most famous orgasm in romantic comedy history |newspaper=[[The Washington Post]] |url=https://www.washingtonpost.com/entertainment/books/the-most-famous-orgasm-in-romantic-comedy-history/2017/08/17/899f8e82-7c56-11e7-9d08-b79f191668ed_story.html |access-date=March 18, 2022}}</ref> but Ephron was determined to cast Ryan, having enjoyed working with her on ''When Harry Met Sally''...<ref name=":17" /> Ryan initially expected to star in the film with her then-husband [[Dennis Quaid]],<ref name=":3" /> who had been looking for a film to star in together.<ref name=":4" /> The couple had also been close friends with Medavoy at the time.<ref name=":4" /> However, Ephron felt Quaid was not funny enough to play Sam, a role she and the studio decided was more suitable for Hanks.<ref name=":17">{{Cite news |last=Fisher |first=Luchina |date=June 25, 2018 |title=How 'Sleepless in Seattle' and Nora Ephron changed romantic comedies 25 years ago |work=[[Good Morning America]] |url=https://www.goodmorningamerica.com/culture/story/sleepless-seattle-nora-ephron-changed-romantic-comedies-25-56092785 |access-date=March 15, 2022 |quote=the 1993 film was both a critical and commercial hit}}</ref><ref name=":5">{{Cite news |last=Connelly |first=Sherryl |date=August 12, 2017 |title=How Nora Ephron 'Saved the Romantic Comedy' despite a cranky Tom Hanks and a difficult Meg Ryan |work=[[New York Daily News]] |url=https://www.nydailynews.com/entertainment/nora-ephron-saved-romantic-comedy-cranky-tom-hanks-article-1.3406009 |access-date=March 14, 2022}}</ref> Having grown weary of playing goofy, immature characters by this point in his career,<ref name=":17" /> Hanks initially turned down the role because he was unhappy with its original script, but was drawn towards Ephron's revisions because he felt her version of Sam was more serious than previous roles he had played.<ref name=":0">{{Cite web |last=Catcher |first=Jess |date=February 28, 2017 |title='Sleepless In Seattle': 11 Surprising Facts About This Romantic Movie |url=https://littlethings.com/lifestyle/sleepless-in-seattle-facts/2868646-1 |access-date=March 14, 2022 |website=[[LittleThings]]}}</ref> Despite her interest in Hanks, Ephron was not entirely convinced the actor could play a romantic leading man in the vein of [[Cary Grant]] until she met him for the first time.<ref name=":17" /> Hanks and Ryan had previously starred as a couple in the film ''[[Joe Versus the Volcano]]'' (1990).<ref name=":7" /><ref name=":9" /> Despite being the film's romantic leads, the co-stars share only two scenes together,<ref name=":32">{{Cite news |last=Coates |first=Tyler |date=June 25, 2013 |title=The Underrated Brilliance of Nora Ephron's Meta-Romantic Comedy 'Sleepless in Seattle' |work=[[Flavorwire]] |url=https://www.flavorwire.com/400386/the-underrated-brilliance-of-nora-ephrons-meta-romantic-comedy-sleepless-in-seattle |access-date=March 17, 2022}}</ref> approximately two minutes of screen time.<ref name=":0" />

[[Bill Pullman]] originally assumed he would have a larger role in the film as Annie's fiancé Walter, since ''Sleepless in Seattle'' had been pitched to him as a [[love triangle]] similar to ''[[The Philadelphia Story (film)|The Philadelphia Story]]'' (1940),<ref name=":6" /> envisioning himself as the [[James Stewart]] character to Hanks's [[Cary Grant]] and Ryan's [[Katharine Hepburn]].<ref name=":47">{{Cite news |last=Natale |first=Richard |date=April 20, 1995 |title=Now He's the One Who Has the Edge : From 'Sleepless' to 'Sleeping,' Bill Pullman Wakes Up in a Lead Role |work=[[Los Angeles Times]] |url=https://www.latimes.com/archives/la-xpm-1995-04-20-ca-56935-story.html |access-date=March 15, 2022 |archive-url=https://web.archive.org/web/20200427134148/https://www.latimes.com/archives/la-xpm-1995-04-20-ca-56935-story.html |archive-date=April 27, 2020}}</ref> Nathan Watt was originally cast as Sam's son Jonah,<ref name=":5" /> but after working together for a few days, Hanks found the child actor to be disruptive on set while trying to film scenes he was not involved in.<ref name=":5" /> Watt was ultimately replaced with Ross Malinger,<ref name=":5" /> an actor Ephron remembered from earlier auditions,<ref name=":17" /> although Ephron did not like some aspects of his appearance.<ref>{{Cite news |last=Armitage |first=Hugh |date=August 21, 2017 |title=Tom Hanks admits he was an arse on the Sleepless in Seattle set |work=[[Digital Spy]] |url=https://www.digitalspy.com/movies/a836148/tom-hanks-sleepless-in-seattle-cranky/ |access-date=March 17, 2022}}</ref> [[Jason Schwartzman]] had also auditioned for the role.<ref>{{Cite web |last=Hayes |first=Britt |date=November 30, 2013 |title=See the Cast of 'Sleepless in Seattle' Then and Now |url=https://screencrush.com/sleepless-in-seattle-then-and-now/ |access-date=March 15, 2022 |website=[[ScreenCrush]]}}</ref> Comedian [[Rosie O'Donnell]] was cast as Becky, Annie's best friend and coworker.<ref name=":26">{{Cite news |last=Jacobs |first=Matthew |title=Rosie O'Donnell Answers Every Question We Have About Sleepless in Seattle |work=[[Vulture (magazine)|Vulture]] |url=https://www.vulture.com/2021/08/rosie-odonnell-answers-every-sleepless-in-seattle-question.html |access-date=March 16, 2022 |archive-url=https://web.archive.org/web/20210826160649/https://www.vulture.com/2021/08/rosie-odonnell-answers-every-sleepless-in-seattle-question.html |archive-date=August 26, 2021 |id=Although Sleepless in Seattle was the fourth highest-grossing film according to Vulture, sources vary in terms of the film's placement as one of the highest-grossing films of 1993. Outlets agree that the film finished within the top-10.}}</ref><ref name=":24">{{Cite news |last=Guerrasio |first=Jason |date=August 27, 2021 |title=Rosie O'Donnell said a 'Sleepless in Seattle' crew member taped her lines to his leg because she couldn't get the scene |work=[[Insider.com|Insider]] |url=https://www.insider.com/rosie-odonnell-sleepless-in-seattle-line-crew-help-2021-8 |access-date=March 15, 2022}}</ref> O'Donnell had made her film debut in ''[[A League of Their Own]]'' (1992) the previous year, appearing alongside both Hanks and Pullman.<ref name=":9" /><ref name=":25">{{Cite news |last=Boucher |first=Ashley |date=August 26, 2021 |title=Rosie O'Donnell Recalls Forgetting Lines in Front of Nora Ephron While Filming Sleepless in Seattle |work=[[People (magazine)|People]] |url=https://people.com/movies/rosie-odonnell-recalls-forgetting-lines-in-front-of-nora-ephron-while-filming-sleepless-in-seattle/ |access-date=March 16, 2022}}</ref> O'Donnell credits Ephron's son Jacob Bernstein with helping her secure the role, as he was a fan of her friend Madonna, with whom the comedian had also starred in ''A League of Their Own''.<ref name=":26" /> Inspired by [[Whoopi Goldberg|Whoopie Goldberg]]'s Academy Award-winning performance in ''[[Ghost (1990 film)|Ghost]]'' (1990), Ephron felt hiring a comedian in a funny supporting role would similarly benefit ''Sleepless in Seattle''.<ref name=":26" /> O'Donnell based her performance on singer and actress [[Bette Midler]],<ref>{{Cite news |last=White |first=Abbey |date=August 28, 2021 |title=Rosie O'Donnell on Getting More Roles as She Ages and the Bette Midler Connection to Her 'Sleepless in Seattle' Character |work=[[The Hollywood Reporter]] |url=https://www.hollywoodreporter.com/movies/movie-news/rosie-odonnell-aging-hollywood-bette-midler-sleepless-in-seattle-1235004669/ |access-date=April 1, 2022}}</ref> specifically emulating the way she walks and talks in order to convey "the funny, caustic best friend with a heart of gold" role she had wanted to play since deciding to become an actor.<ref name=":26" /> Eventually reduced from two-pages, the speech was the longest of O'Donnell's career at that point.<ref>{{Cite news |last=Moore |first=Sam |date=August 28, 2021 |title=Rosie O'Donnell reveals how she remembered her lines for Sleepless in Seattle |work=[[The Independent]] |url=https://www.independent.co.uk/arts-entertainment/films/news/rosie-o-donnell-remember-lines-b1910194.html |access-date=March 16, 2022}}</ref> She noted her experience was particularly different from ''A League of Their Own'', which had been largely improvisational compared to Ephron's organized directorial style.<ref name=":25" /> O'Donnell and Ephron lived in the same apartment building while filming ''Sleepless in Seattle'', which Ephron had obtained for her.<ref name=":26" /> Hanks' wife Rita Wilson originally auditioned for the role of Becky, but Ephron preferred her for the role of Sam's sister Suzy, which the director found particularly convenient because Wilson was already in Seattle with her husband.<ref name=":22" /> Ephron cast [[Rob Reiner]], who directed ''When Harry Met Sally''..., as Sam's friend in the film, with Reiner contributing to many of the film's laughs.<ref name=":44" />

According to some of the main cast, Ephron typically insisted that the actors recite their lines almost exactly as-written,<ref name=":3" /><ref name=":24" /> although Ephron herself said she was open to the cast improvising and re-writing dialogue they felt was unfunny.<ref name=":34" /><ref name=":59" /><ref name=":26" /> Hanks and [[Victor Garber]] improvised the scene in which their characters feign tears while recounting the film ''[[The Dirty Dozen]]'' (1967),<ref name=":3" /> mocking Suzy who has been brought to tears by summarizing the plot of ''An Affair to Remember''.<ref name=":0" /> Hanks and Ephron agreed that his character was underwritten.<ref name=":58" /> Ephron invited the actor to help rewrite his character, which ultimately resulted in "a grumpier, funnier Sam".<ref name=":17" /> Hanks did not truly commit to the role until he, Ephron and Delia reviewed his character scene by scene, ultimately improving his part.<ref name=":58" /> Hanks and Ephron sometimes disagreed over his character's actions, with Hanks accusing the director of making Sam too "wimpy" by writing him from a woman's perspective.<ref name=":17" /><ref name=":10" /> He also complained that better lines had been written for his character's son,<ref name=":17" /> and lobbied for Sam and Jonah's relationship to be more paternal than maternal.<ref name=":26" /> In the original screenplay, Sam decides not to spend a weekend away with his new girlfriend Victoria in fear of upsetting Jonah.<ref name=":10" /> Hanks found this unconvincing for a grown man, suggesting to Ephron that, despite his son's feelings, his character would most likely be absolutely determined to sleep with Victoria after having been single for several years by that point.<ref name=":6" /> Ephron re-wrote the scene so Sam only relents once he learns Jonah has taken a plane to New York.<ref name=":6" />  Hanks believes the film's drama ultimately benefited from being rooted in logic and "true, human behaviour".<ref name=":10" /> Arch explained that, despite some resistance from the actor, Hanks ultimately "rode that boundary, between being a man and having feelings he's able to express", which was rare for a male character during the 1990s.<ref name=":44" /> Ephron described Hanks as "manly in a part that requires him to be tender -and a lot of other things", calling him "one of the few actors around ... who can do tender and irritable and angry all at the same time".<ref name=":50">{{Cite magazine |last=Schwarzbaum |first=Lisa |author-link=Lisa Schwarzbaum |date=July 9, 1993 |title=The Nice Man Cometh |magazine=[[Entertainment Weekly]] |url=https://ew.com/article/1993/07/09/nice-man-cometh/ |access-date=March 23, 2022}}</ref> She credits Hanks with teaching her that writers should always provide the main actor with something to play off of, so they are never passive or idle during a scene.<ref name=":58" />

Ephron had envisioned the role of Clarisse, Jonah's babysitter, as a [[Shelley Duvall]]-type role.<ref name=":8" /> They ultimately cast Amanda Maher in the role, a waitress they had discovered at the Gravity Bar in Seattle, citing her as a natural.<ref name=":8" /> Ephron herself voices "Disappointed In Denver", a depressed character who calls into the radio show Annie is listening to in the middle of the night.<ref name=":0" /> Actress [[Parker Posey]] was cast in a minor role that was ultimately cut from the film.<ref name=":0" /> The director wrote Posey an apologetic letter assuring her that the removal from the film was not her own fault.<ref>{{Cite news |last=Peele |first=Anna |date=July 27, 2012 |title=Louie: The Parker Posey Recap, Part Two |work=[[Esquire (magazine)|Esquire]] |url=https://www.esquire.com/entertainment/tv/reviews/a15092/louie-season-3-episode-5-11083134/ |access-date=March 15, 2022}}</ref> Ephron eventually cast her in a larger role in the romantic comedy ''[[You've Got Mail]]'' (1998), also starring Hanks and Ryan.<ref name=":0" /> Foster appears as an extra in the restaurant scene, during which Sam and Victoria attend their first date.<ref name=":16" /> Hanks accused Foster of being too loud during the scene.<ref name=":16" />

=== Filming ===
Although Seattle had always been the film's main setting, the filmmakers only realized how significant the location was upon seeing it for themselves.<ref name=":8" /> Arch was inspired to have Sam live in a [[houseboat]] after watching a Seattle-based episode of ''[[This Old House]]'' that featured host [[Bob Vila]] visiting a similar home.<ref name=":44" /> Ephron initially believed that during the 1990s young Americans prioritized [[Work–life interface|their careers over their personal lives]].<ref name=":0" /> However, upon visiting Seattle, she discovered it as a city where "people have chosen lifestyle over work", and decided to set the film there.<ref name=":0" /> Ephron explained that this is one of the reasons why Sam moves to Seattle from the work-focused Chicago.<ref name=":1" /> Vancouver, British Columbia, which film studios typically use as an affordable Seattle stand-in, was briefly considered an option, but Foster ultimately found the Canadian city to be less diverse than Seattle, hardly distinguishable from other large cities and too Canadian-looking.<ref name=":8" /> Principal photography began in July 1992.<ref name=":7" /> Once she submitted the final draft in March 1992, Ephron described the film's filming schedule as almost instant, recalling that they were scouting locations in June and filming by August that same year.<ref name=":9" /> The film had a production budget of $25 million, with ''The Seattle Times'' reporting that the studio spent approximately $4 million on Seattle-based labor, hotels, meals and local vendors.<ref name=":8" /> Foster explained that they decided to primarily use resources local to save money on necessities such as crew, import labor and airfare.<ref name=":8" /> Specific Seattle landmarks featured in the film include the [[Pike Place Market]], the [[Sorrento Hotel]], [[Alki Beach Park|Alki Beach]], the [[Fremont Bridge (Seattle)|Fremont Bridge]], [[Seatac Airport|SeaTac Airport]], the [[Dahlia Lounge]], and several [[1st Avenue (Seattle)|1st Avenue]] shops.<ref name=":8" />

The filmmakers could not find a warehouse large enough to house one set; therefore, much of the film was shot on the [[Naval Station Puget Sound|Sand Point Naval Base]].<ref name=":8" /> Due to the lack of sound stages in Seattle at the time, the filmmakers sought to use the base as it was about to be shut down, but received little response from the federal bureaucracy until Ephron herself contacted Republican senator [[John Warner]], a former Secretary of the Navy.<ref name=":3" /> At times sets and parts of props were shipped between Seattle to Baltimore to ensure sets remained consistent,<ref name=":0" /> particularly a door that both Ryan's and Hanks' characters use in separate scenes.<ref name=":1" /> Ephron ensured the same door was used to demonstrate the connection between the characters,<ref name=":2" /> working with editor Robert M. Reitano to connect their stories via visual parallels, since otherwise the characters hardly share screen time.<ref name=":34" /> Because Seattle was experiencing a drought while filming, the filmmakers imported water trucks to simulate the rain scenes.<ref name=":2" /> The city was reportedly angry about what they perceived as a waste of water.<ref name=":9" /><ref name=":6" /> In addition to Seattle, scenes were shot in Chicago, Illinois; Baltimore, Maryland; and New York City.<ref name=":7" /> Ironically, Foster deemed a house located on Queen Anne Hill "Baltimore enough" to serve as the Baltimore-based home of Annie's parents.<ref name=":8" /> Ephron intended for the opening shot of the [[Chicago skyline]] at Maggie Baldwin's funeral to evoke artist [[Saul Steinberg]]'s 1976 ''[[The New Yorker]]'' cover ''[[View of the World from 9th Avenue]]''.<ref name=":6" /> A set designer reportedly found working with Ephron so difficult that they begged to be fired from the film.<ref>{{Cite news |last=Tanabe |first=Karin |author-link=Karin Tanabe |date=August 25, 2017 |title='I'll Have What She's Having' explores Ephron's rom-com trifecta |work=[[The Houston Chronicle]] |url=https://www.houstonchronicle.com/entertainment/books/article/I-ll-Have-What-She-s-Having-explores-Ephron-s-11959853.php |access-date=March 18, 2022 |archive-url=https://web.archive.org/web/20170828230839/https://www.houstonchronicle.com/entertainment/books/article/I-ll-Have-What-She-s-Having-explores-Ephron-s-11959853.php |archive-date=August 28, 2017}}</ref>

The studio was initially denied permission to shoot some of the film's final scenes at the Empire State Building,<ref name=":2" /> whose management refused to close the observation deck to tourists to allow filming.<ref name=":5" /> Ephron strongly believed that "you are two phone-calls away from anyone".<ref name=":16" /> Ephron knew the publicist who was representing building owner [[Leona Helmsley]], who was in prison for [[tax evasion]] at the time.<ref name=":3">{{Cite news |last=King |first=Susan |date=June 25, 2018 |title='Sleepless in Seattle' at 25: Inside the Making of Nora Ephron, Tom Hanks and Meg Ryan's Classic Rom-Com |work=[[Variety (magazine)|Variety]] |url=https://variety.com/2018/film/news/sleepless-in-seattle-25th-anniversary-meg-ryan-tom-hanks-1202851688/ |access-date=March 14, 2022}}</ref><ref name=":5" /> After discussing the matter with her publicist who visited her in jail,<ref name=":16" /> Helmsley granted them permission to use the building for only six hours.<ref name=":2" /> This allowed them to film the helicopter shot, Annie's lobby scene, and Jonah searching the observation deck for Annie.<ref name=":3" /> The observatory of the Empire State Building on which Sam and Annie finally meet during the film's climax was actually a replica built in Hangar 27 of the Sand Point Naval Base, instead of New York City.<ref name=":8" /> The building was digitally lit for the film.<ref name=":44" /> Ryan was physically uncomfortable while running towards the Empire State Building in order to meet Sam because her shoes were ill-fitting.<ref name=":33">{{Cite news |last=Dawn |first=Randee |date=December 5, 2018 |title=Meg Ryan reveals why she loved working with Tom Hanks on 'Sleepless in Seattle' |work=[[Today (American TV program)|Today]] |url=https://www.today.com/popculture/meg-ryan-reveals-why-she-loved-working-tom-hanks-sleepless-t144279 |access-date=March 17, 2022}}</ref>

The film's costumes were designed by Judy Ruskin, who designed most of Ryan's wardrobe.<ref name=":62">{{Cite news |last=Goodwin |first=Betty |date=June 25, 1993 |title=Simple Clothes, Complex Hairdos |work=[[Los Angeles Times]] |url=https://www.latimes.com/archives/la-xpm-1993-06-25-vw-7107-story.html |access-date=April 1, 2022}}</ref> Ruskin was careful to dress Ryan in modest, loose-fitting clothes to demonstrate Annie's "pure heart", as per Ephron's direction.<ref name=":62" /> Ephron hired [[Sven Nykvist]] as the film's cinematographer, as she was instructed to recruit "the world's best cinematographer".<ref name=":59" /> According to Ephron, he was typically able to light scenes in as little as six minutes.<ref>{{Cite news |last=Lee |first=Chris |date=September 21, 2006 |title=Sven Nykvist, 83; Cinematographer Won Oscars for Work With Bergman |work=[[Los Angeles Times]] |url=https://www.latimes.com/archives/la-xpm-2006-sep-21-me-nykvist21-story.html |access-date=March 31, 2022}}</ref> Ephron and production designer Jeffrey Townsend deliberately limited the use of the color red during the first hour of ''Sleepless in Seattle''. The color appears more frequently after Sam and Annie first pass each other at the airport in Seattle, and a soccer team wearing red uniforms spills into the crowd between them.<ref name=":22" /> Red gradually becomes more common throughout the rest of the film, representing the "passion shared by the pair as they finally meet and fall in love".<ref name=":22" /> The filmmakers also avoided using blue, a color Ephron particularly dislikes.<ref name=":22" /> Arch was surprised to find that certain shots matched what he had envisioned when writing the film, including the use of shooting stars in the title sequence.<ref name=":44" />