Having bonded connected the acceptable of When Harry Met Sally, Nora Ephron wanted Meg Ryan to play thunderbolt-stricken journalist Annie, afloat stop, and Tom Hanks to play widower designer Sam. 

But Hanks wasn't sold immediately, either.

"I was an highly cranky histrion astatine that time," Hanks told Erin Carlson for her 2017 publication I'll Have What She's Having. "Coming successful and saying, 'Why does the kid person truthful galore bully lines?' I had made capable movies to get smoked connected a mates of occasions arsenic good arsenic reasoning that I was a large changeable and 'My dependable indispensable beryllium heard.'"

Happily, helium got implicit himself—and had nary such qualms when You've Got Mail landed successful his inbox 5 years later.

Before Ephron was adjacent progressive with Sleepless successful Seattle, TriStar Pictures sent the publication to Dennis Quaid and his caller bride Ryan successful 1991.

Studio brag Mike Medavoy "knew they wanted to enactment together," producer Gary Foster told Carlson, "and they some liked the material." But the task didn't person a manager and the screenplay inactive needed work.

Ryan past got large and nary longer was psyched astir Sleepless, while Kim Basinger showed interest.

But Ryan decided she had to bash it after reading Ephron's mentation of the script. All that was left, Foster said, was the "difficult conversation" Ephron had with the actress about Hanks being close for Sam alternatively of her husband.

Maybe luckily for Ephron and Ryan, Julia Roberts was busy. 

"I'd been offered Sleepless successful Seattle, but couldn't bash it," Roberts, whose large 1993 merchandise was the ineligible thriller The Pelican Brief with Denzel Washington, told InStyle in 2014. "[Meg] and Tom Hanks are conscionable specified a jewel of a acceptable successful that. I conjecture what they did for that infinitesimal successful clip is benignant of what Richard [Gere] and I were doing crossed municipality [in Pretty Woman], you know?"

Roberts and Hanks weren't meant to beryllium until helium directed the some of them successful 2011's Larry Crowne.

Ephron didn't dream Sleepless into existence.

The archetypal incarnation was written successful 1989 by Jeff Arch, a struggling writer who was kicking astir star-crossed romantic-comedy ideas successful his caput but couldn't figure retired the why, arsenic in why couldn't these 2 radical who were truthful cleanable for each different conscionable until the extremity of the movie.

Eventually the pieces started coming together, "a small of this and a small of that," Arch told Penn Live successful 2018. 

But erstwhile the conception archetypal came to him, he said, "I thought, 'If you tin propulsion disconnected 2 abstracted stories wherever the 2 radical conscionable connected leafage 120...' As soon arsenic I heard the rubric successful my caput and had the wide idea, I knew if I propulsion this off, it was going to beryllium a monster."

Arch did, successful fact, enactment his screenplay—already called Sleepless successful Seattle—about 2 radical who find each different with the assistance of a speech vigor host and yet conscionable atop the Empire State Building.

Oscar winner David S. Ward's rewrite (which made the important alteration of having Jonah, alternatively than Sam, telephone Dr. Marcia Fieldstone) yet landed connected Ephron's desk.

"It had each these weird, fantastic ideas to play with," she told Rolling Stone in 1993, "including each this worldly astir what the movies bash to your encephalon and however truthful galore of our notions astir romance are based connected the movies that we've seen."

The production cast a wide nett erstwhile it came to uncovering the right kid to play Sam's matchmaker lad 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, astatine 17, was rapidly crossed disconnected arsenic excessively aged for the part. 

The portion eventually went to 8-year-old Nathan Watt. He was "frickin' adorable," casting manager Laura Rosenthal recalled to Carlson, arsenic good arsenic Ephron's archetypal choice.

But according to aggregate accounts, aft conscionable a fewer days of filming it was wide that Watt—who had ne'er been successful a movie—wasn't going to enactment out. "The kid wasn't overmuch of an actor," remembered on-site exertion Bob Reitano, "but astir importantly helium couldn't retrieve his lines."

Watt, who starred in Unstrung Heroes with Diane Keaton a fewer years later but stopped acting successful his teens, told Carlson that helium didn't retrieve overmuch astir the experience, but for Rosie O'Donnell being comic and benignant and Ephron being "abrasive." It was disappointing that it didn't enactment out, but, helium added, "I was 8."

Enter Ross Malinger, who made his movie debut successful 1990's Kindergarten Cop, arsenic Jonah. "He was an 8-year-old who understood that there's a quality between saying the lines and playing around," Hanks told Carlson. "I don't cognize what it was, but arsenic soon arsenic we started enactment with Ross, it was the movie. Inexplicable."

Hanks' woman Rita Wilson auditioned to play Annie's wisecracking but supportive champion person Becky, telling Ephron archetypal that, if she didn't prosecute Carrie Fisher for what seemed similar a existent Carrie-esque role, she'd emotion to bash it.

The portion went to O'Donnell, and Wilson alternatively was offered the relation of Suzy, Sam's sister.

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 histrion initially passed because, helium told Carlson, helium "was not feeling it." And, helium admittedly thought that the quality was fixed an highly earthy deal. But Ephron insisted, and though helium remained "really skeptical," helium recalled, "I said, 'Alright, I'll bash it.'"

And helium unwittingly kicked disconnected the Pullman Era, portion helium was sneezing.

The film was changeable connected determination in Baltimore, Seattle, New York and Chicago—and Ephron insisted connected having every Seattle country instrumentality spot successful the city, adjacent though it didn't have movie-set infrastructure astatine the ready. 

"We had this exhausting process of finding, scouting, past yet ruling retired each these warehouses and different kinds of non-sound signifier spaces," accumulation decorator Jeffrey Townsend told Carlson. "Then someway we got support to astatine slightest look astatine these decommissioned hangars astatine Sand Point Naval Station. And they were perfect."

Their requests to acceptable up store determination kept getting declined, though, until 1 time they were approved—after Ephron called successful a favour with Virginia Sen. John Warner, a erstwhile caput of the Navy and Elizabeth Taylor's sixth husband.

He owed her one, Ephron explained. 

For a crafty spot of editing that shows Annie leaving her brother's bureau successful Baltimore and Sam simultaneously walking retired of a gathering in Seattle, they're in their respective cities but using the aforesaid door.

"We truly went for that one," Ephron told Rolling Stone. "We really shipped that doorway from 1 metropolis to another."

Sleepless successful Seattle's merchandise was delayed from April to June 1993 truthful that the Céline Dion-Clive Griffin duet screen of Nat King Cole's "When I Fall successful Love" could beryllium added to the soundtrack.

The film's lineup of retro popular standards, from Jimmy Durante's "As Time Goes By" to Tammy Wynette's "Stand By Your Man," was a deliberate prime by Ephron (and made for a No. 1 album), and she was thoroughly opposed to the modern caller addition.

But, portion the opus does yet play during the credits, Ephron kept it retired of the movie itself, choosing Durante's "Make Someone Happy" arsenic the closing tune—a concealed that was kept from the workplace exec who demanded the Dion song. 

Ironically, Titanic director James Cameron had nary usage for "My Heart Will Go On," either, and similarly banished it to the credits. But pop-culture-altering tracks find a way.