There's No Crying in Seattle
Having bonded on the set of When Harry Met Sally, Nora Ephron wanted Meg Ryan to play thunderbolt-stricken journalist Annie, full stop, and Tom Hanks to play widower architect Sam.
But Hanks wasn't sold immediately, either.
"I was an extremely cranky actor at that time," Hanks told Erin Carlson for her 2017 book I'll Have What She's Having. "Coming in and saying, 'Why does the kid have so many good lines?' I had made enough movies to get smoked on a couple of occasions as well as thinking that I was a big shot and 'My voice must be heard.'"
Happily, he got over himself—and had no such qualms when You've Got Mail landed in his inbox five years later.
Sam and Annie in an Alternate Universe
Before Ephron was even involved with Sleepless in Seattle, TriStar Pictures sent the script to Dennis Quaid and his new bride Ryan in 1991.
Studio boss Mike Medavoy "knew they wanted to work together," producer Gary Foster told Carlson, "and they both liked the material." But the project didn't have a director and the screenplay still needed work.
Ryan then got pregnant and no longer was psyched about Sleepless, while Kim Basinger showed interest.
But Ryan decided she had to do it after reading Ephron's version of the script. All that was left, Foster said, was the "difficult conversation" Ephron had with the actress about Hanks being right for Sam instead of her husband.
Another Pretty Woman
Maybe luckily for Ephron and Ryan, Julia Roberts was busy.
"I'd been offered Sleepless in Seattle, but couldn't do it," Roberts, whose big 1993 release was the legal thriller The Pelican Brief with Denzel Washington, told InStyle in 2014. "[Meg] and Tom Hanks are just such a jewel of a fit in that. I guess what they did for that moment in time is sort of what Richard [Gere] and I were doing across town [in Pretty Woman], you know?"
Roberts and Hanks weren't meant to be until he directed the both of them in 2011's Larry Crowne.
The Dawn of Sleepless in Seattle
Ephron didn't dream Sleepless into existence.
The first incarnation was written in 1989 by Jeff Arch, a struggling writer who was kicking around star-crossed romantic-comedy ideas in his head but couldn't figure out the why, as in why couldn't these two people who were so perfect for each other meet until the end of the movie.
Eventually the pieces started coming together, "a little of this and a little of that," Arch told Penn Live in 2018.
But when the concept first came to him, he said, "I thought, 'If you can pull off two separate stories where the two people meet on page 120...' As soon as I heard the title in my head and had the general idea, I knew if I pull this off, it was going to be a monster."
Keeping Sleepless Awake
Arch did, in fact, option his screenplay—already called Sleepless in Seattle—about two people who find each other with the help of a talk radio host and eventually meet atop the Empire State Building.
Oscar winner David S. Ward's rewrite (which made the significant change of having Jonah, rather than Sam, call Dr. Marcia Fieldstone) eventually landed on Ephron's desk.
"It had all these weird, wonderful ideas to play with," she told Rolling Stone in 1993, "including all this stuff about what the movies do to your brain and how so many of our notions about romance are based on the movies that we've seen."
H&G
The production cast a wide net when it came to finding the right kid to play Sam's matchmaker son Jonah, and the young actors who came up during the search, per Carlson, included Elijah Wood, Joseph Gordon-Levitt, Ben Savage and Rider Strong, Jason Schwartzman and Joaquin (still going by Leaf) Phoenix—who, at 17, was quickly crossed off as too old for the part.
The part eventually went to 8-year-old Nathan Watt. He was "frickin' adorable," casting director Laura Rosenthal recalled to Carlson, as well as Ephron's first choice.
But according to multiple accounts, after just a few days of filming it was clear that Watt—who had never been in a movie—wasn't going to work out. "The kid wasn't much of an actor," remembered on-site editor Bob Reitano, "but most importantly he couldn't remember his lines."
Watt, who starred in Unstrung Heroes with Diane Keaton a few years later but stopped acting in his teens, told Carlson that he didn't remember much about the experience, except for Rosie O'Donnell being funny and kind and Ephron being "abrasive." It was disappointing that it didn't work out, but, he added, "I was 8."
Enter Ross Malinger, who made his movie debut in 1990's Kindergarten Cop, as Jonah. "He was an 8-year-old who understood that there's a difference between saying the lines and playing around," Hanks told Carlson. "I don't know what it was, but as soon as we started work with Ross, it was the movie. Inexplicable."
Moving Parts
Hanks' wife Rita Wilson auditioned to play Annie's wisecracking but supportive best friend Becky, telling Ephron first that, if she didn't hire Carrie Fisher for what seemed like a real Carrie-esque role, she'd love to do it.
The part went to O'Donnell, and Wilson instead was offered the role of Suzy, Sam's sister.
And He's Such a Wonderful Athlete...
Pre-Ace Ventura Jim Carrey, Griffin Dunne, Peter MacNicol and Kyle MacLachlan were among the names floated to play Annie's allergy-plagued fiancé Walter—but Ephron and Ryan wanted Bill Pullman.
Incidentally, the actor initially passed because, he told Carlson, he "was not feeling it." And, he admittedly thought that the character was given an extremely raw deal. But Ephron insisted, and though he remained "really skeptical," he recalled, "I said, 'Alright, I'll do it.'"
And he unwittingly kicked off the Pullman Era, while he was sneezing.
Team Ephron
Gaby Hoffman, who shined in Ephron's directorial debut This Is My Life, was happy to reunite and play Jonah's precocious, acronym-loving friend Jessica. And When Harry Met Sally director Rob Reiner said yes to the role of Sam's contractor buddy Jay without even reading the script.
Space Needling
The film was shot on location in Baltimore, Seattle, New York and Chicago—and Ephron insisted on having every Seattle scene take place in the city, even though it didn't have movie-set infrastructure at the ready.
"We had this exhausting process of finding, scouting, then ultimately ruling out all these warehouses and other kinds of non-sound stage spaces," production designer Jeffrey Townsend told Carlson. "Then somehow we got permission to at least look at these decommissioned hangars at Sand Point Naval Station. And they were perfect."
Their requests to set up shop there kept getting declined, though, until one day they were approved—after Ephron called in a favor with Virginia Sen. John Warner, a former secretary of the Navy and Elizabeth Taylor's sixth husband.
He owed her one, Ephron explained.
When One Door Closes...
For a crafty bit of editing that shows Annie leaving her brother's office in Baltimore and Sam simultaneously walking out of a building in Seattle, they're in their respective cities but using the same door.
"We really went for that one," Ephron told Rolling Stone. "We actually shipped that door from one city to another."
Empire State of Mind
There were no pullable strings when it came to filming atop the Empire State Building. Unable to get permission, they built a replica of the skyscraper's observation deck inside Sand Point's Hangar 27 for Annie and Sam's climactic meeting.
Not Exactly the Heart of the Movie
Sleepless in Seattle's release was delayed from April to June 1993 so that the Céline Dion-Clive Griffin duet cover of Nat King Cole's "When I Fall in Love" could be added to the soundtrack.
The film's lineup of retro pop standards, from Jimmy Durante's "As Time Goes By" to Tammy Wynette's "Stand By Your Man," was a deliberate choice by Ephron (and made for a No. 1 album), and she was thoroughly opposed to the contemporary new addition.
But, while the song does eventually play during the credits, Ephron kept it out of the movie itself, choosing Durante's "Make Someone Happy" as the closing tune—a secret that was kept from the studio exec who demanded the Dion song.
Ironically, Titanic director James Cameron had no use for "My Heart Will Go On," either, and similarly banished it to the credits. But pop-culture-altering tracks find a way.