In addition to Bill Pullman, Ross Malinger, and Rob Reiner, the film features Rosie O'Donnell, Gaby Hoffmann, Victor Garber, Rita Wilson, Barbara Garrick, and Carey Lowell.

Several of its most pivotal scenes were filmed on a former naval base due to the city's lack of sound stages, including a recreation of the Empire State Building's observation deck when the New York skyscraper was not available.

[4] The writer drew inspiration from several sources, including the French film And Now My Love (1974), a seminar by motivational speaker Tony Robbins,[7] and a Washington Post article he had read about women hiring private investigators to uncover information about their romantic partners.

[7][8] 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.

[8] 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.

[8] Insisting that no self-respecting man would deliberately call a radio show to share his emotional grievances,[8] 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.

[7][16] Although she found Arch's version simple and unfunny, Ephron particularly liked his romantic ending involving the Empire State Building,[11] and was interested in several ideas discussed in Ward's second draft,[13] particularly how movies affect people's perception about romance.

[32] 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 (1940),[20] envisioning himself as the James Stewart character to Hanks' Cary Grant and Ryan's Katharine Hepburn.

[34] Nathan Watt was originally cast as Sam's son Jonah,[31] 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.

[27] Inspired by Whoopie Goldberg's Academy Award-winning performance in Ghost (1990), Ephron felt hiring a comedian in a funny supporting role would similarly benefit Sleepless in Seattle.

[27] O'Donnell based her performance on singer and actress Bette Midler,[39] 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.

[19] Specific Seattle landmarks featured in the film include the Pike Place Market, the Sorrento Hotel, Alki Beach, the Fremont Bridge, SeaTac Airport, the Dahlia Lounge, and several 1st Avenue shops.

[19] 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.

[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.

Peter Guber, head of Sony Studios, wanted to use Celine Dion and Clive Griffin's duet "When I Fall in Love" in the final scene, but Ephron insisted on using "Make Someone Happy" by Jimmy Durante.

[69][70] The Baltimore Sun's Stephen Hunter described the film as a "shameless romantic fantasy" and its heroine as "a sort of icon of nearly pure '50s innocence", with Ephron herself dressing Ryan's character to resemble a Breck girl.

[71] Calling the film "a throwback to the great romantic comedies of the '30s and '40s", Common Sense Media described Sleepless in Seattle as "a fairy tale that encourages viewers to believe that true love and destiny will conquer all obstacles".

[77][78][74][79] Film and media studies professor Michele Schreiber said the quote is "meant to elicit a sense of recognition among Sleepless in Seattle's audience because the text assumes that by nature of the fact that they are watching the film, its spectators must empathize with, if not share, Annie's desire to fall in love in a way that is completely removed from the mundane realities of everyday life" while "assum[ing] that the audience will find equally familiar Becky's pointed critique of Annie's misguided preoccupation".

[33] The critic noted that while Annie initially dismisses the concepts of fate and soul mates, trying to convince herself that her relationship with Walter is more practical than romantic,[10] Sam openly likens his feelings for his late wife to magic, which ultimately prompts her "to embark on a philosophical journey of sorts to find out whether attraction is something otherworldly after all".

[85] He also maintains that the decision to advertise during the telecast was business-driven as opposed to political, explaining that the studio saw anticipated the gala's expected high ratings would promote Sleepless in Seattle to a significantly larger audience.

[87] Senior vice president of publicity Ed Russell arranged several word of mouth screenings for the film, including a conference held for romance novel and magazine editors on May 16, 1993, in San Diego.

[87] Tri-Star theorized the romantic comedy would attract women who were not particularly interested in watching the year's action films,[19] serving as "counter-programming" to the roster of more traditional summer blockbuster fare.

Meg Ryan, who is one of the most likable actresses around and has a certain ineffable Doris Day innocence, is able to convince us of the magical quality of her sudden love for a radio voice, without letting the device seem like the gimmick it assuredly is.

In a mixed review, Owen Gleiberman of Entertainment Weekly lauded Hanks performance for anchoring but found Sleepless in Seattle itself to be too contrived, writing, "it feels programmed to make you fall in love with it".

Criticizing Ephron's reliance on clichés, Gleiberman said the director "mixes old ones from Hollywood with new ones from pop-psych therapy", describing the film as "a '50s tearjerker synthesized by microchip" which lacks the "delicately sexy sparkle" of its predecessors.

[79] The Guardian's Luke Walpole, who had avoided watching the film until 2020 in fear that it had aged poorly, ultimately found Ephron's screenplay to be a gorgeous "balance of melancholy and fizzing optimism", but criticized Sleepless in Seattle's "narrowly middle class and privileged" characters.

[10] R. Eric Thomas of Elle noted that "in terms of rom-com hijinks and poor decisions that turn out great, nothing beats [Annie's behavior] in Sleepless in Seattle", but relented that the film remains "a jewel".

[3] Philip Sledge of Cinema Blend hailed the ending as one of the greatest in the romantic comedy genre,[18] while Jessica Brajer of MovieWeb called it "one of the most emotional scenes in all of movie history".

[147][149] According to Good Morning America contributor Luchina Fisher, Sleepless in Seattle is one of three Ephron films that "breathed new life into the" romantic comedy genre, alongside its predecessor When Harry Met Sally... and successor You've Got Mail.

[161] In 2013, co-executive producer Lynda Obst released a book named after the film, Sleepless in Hollywood: Tales from the New Abnormal in the Movie Business,[162] which explores the decline of romantic comedies during the 2010s.