Why the 'Sleepless in Seattle' script continues to delight audiences, 30 years later: 'It's like a warm bath'

Sleepless in Seattle should never have worked; It's a romantic comedy in which the two main characters don't even meet until the last scene. They're supposed to have been swooning over each other, or at least — according to a well-worn trope — hating each other so that, in the end, they can suddenly realize that they're meant to be together.

And yet, this movie, which was released June 25, 1993, clearly did work, earning more than $127 million at the domestic box office and $228 million internationally, on a budget of $25 million, according to the 2017 book I'll Have What She's Having.

Writer/director Nora Ephron, who overhauled the script originally penned by Jeff Arch and David S. Ward, and with an assist from her sister Delia Ephron, an associate producer on the film, was nominated for her third Oscar for it. Critics and fans alike continue to rank the movie among the greatest romantic comedies of all time.

The story of Tom Hanks's Sam, a man who was recently widowed struggling to recover from heartbreak while fathering his 8-year-old son, Jonah (Ross Malinger), connecting over the radio with Meg Ryan's Annie, a woman who's found a humdrum partnership but is seeking true love, continues to warm hearts.

Lynda Obst, who was an executive producer on the film and a good friend of Ephron, who died in 2012, tells Yahoo Entertainment her theory: "It holds because of its writing, obviously, because it's classically written." Notable exceptions are when Annie uses the computer pre-Google and references to the 1957 romance movie An Affair to Remember, in which the main characters are supposed to meet at the top of the Empire State Building on Valentine's Day.

"There are really no references to time and place, apart from An Affair to Remember," Obst says. "The clothes are even classic. There's nothing trendy about it. It works in all times. And the music [which includes standards such as "A Wink and a Smile" and "Make Someone Happy"] ... Nothing trendy about it. And [Nora Ephron] was in total control of that. And knew what she wanted to do from the outset. So it was the conception for the film, in terms of this being, like An Affair to Remember, a romance for all time. And of course we had two delicious stars, who were at their peak of adorableness, and were great together."

It all made for, as Annie says in the movie, "magic."

We put the question of why the Sleepless and Seattle script still works after all these years, to Obst, who's gone on to produce movies such as How to Lose a Guy in 10 Days, and to three screenwriters in the entertainment industry, people who've created some of the most fantastic romantic comedies to come along in the past few years. Here's what they said:

It bucks many of the typical rules of a rom-com

Dana Fox, whose writing credits include Debra Messing's The Wedding Date and 2022's The Lost City, with Sandra Bullock and Channing Tatum, rewatched the movie before her conversation with Yahoo Entertainment.

"What I was struck by when I watched this last time is how many things she does that theoretically should make the movie terrible but it's great," Fox says. "The idea that you have two of the biggest stars in the world, they aren't in any scenes together. He doesn't even know she exists for like an hour and 15 minutes into the movie! PS she's a stalker and doesn't talk to him for an additional 15 minutes."

Also, Bill Pullman's character of Walter, the allergy prone guy that Annie ends her engagement to in order to go to the top of the New York City landmark, on the chance that Sam has accepted her blind invitation to meet there, is not the kind of jerk we usually see. He's not having an affair or treating her badly, not even in the scene where she calls off their engagement.

"He's so good to her in that scene. It's amazing," Fox says. "The tendency would be to want to have him be a d*** to her, so that we and she knew that it was the right choice. But if you think about that, then there's nothing at stake in the next scene. I also loved the sort of positive messaging of she didn't know if the guy was gonna be there or not. She was like, it's pretty unlikely that he is gonna be there, but I still have to break up with you, whether that guy is there or not."

Peter Chiarelli, who wrote The Proposal and co-wrote Crazy Rich Asians, notes that Sleepless is also unusual in that it invites the audience to appreciate the male character just as much as the female character. He's seen the movie maybe 15 times since he saw it in theaters as a kid.

"It's a two-hander," Chiarelli says, "You're seeing both sides. And that was something with that movie, with When Harry Met Sally…. It's not that romantic comedy where, often, the guy is kind of extra. It's really about these two people."

Obst recalls that she and Ephron used to say "this is a chicks movie," until men who approached them at speaking engagements said otherwise.

"'No, this is a man's movie, It's about his heartache,'" Obst says she's been told. "And I think men really like this movie, and that's not common for a romantic movie."

We're so engrossed by both of these characters and their separate journeys that we sometimes overlook logic, something that does align with other rom-coms.

"When the son gets on a plane to go to New York, and the dad realizes, 'Oh my god! Where's my son?' The dad, Tom Hanks, does not pick up the phone and call the airline and say, 'Hey! My kid's on that plane for the next four hours. Would you stop him at the gate? And I'm gonna find him at the airport.' And I don't mean that as a criticism," Chiarelli says. "I mean, you are so invested in that place and you want him to end up at the top of the Empire State Building so bad. That's how good the movie is."

He says he's referenced this when executives give him notes about logic in his scripts: "'You ever seen Sleepless in Seattle? Yeah, so answer me this. Why?'" he asks. "Cause we were so invested in it, and we don't want to slow it down. And we don't have a movie if he calls the airport and does it. So it's OK. We're along for the ride."

The characters, period

Harper Dill, who co-wrote 2022's Jennifer Lopez-Owen Wilson movie Marry Me and two dozen episodes of The Mindy Project, estimates that she's seen Sleepless in Seattle 50 times. The first was in a theater, when she was a child.

"It's like a warm bath," she says. "Like, there are certain movies that you have playing just like on loop in the background of life, and that's definitely one of them."

Her answer to why the movie still resonates is simple.

"I think she writes incredibly likable human characters," Dill says of Ephron. "Specifically flawed but still people you wanna hang out with, and I think there's like a normalcy to everyone in her movies, and it's normal people taking these bigger risks, and there's something really invigorating about that, because it makes you feel like maybe you could do that too. So there's like this grounded wish fulfillment to everything she does. The fact that she makes Annie and Sam — and Harry and Sally, and everybody — so self-aware and working through their stuff and kind of wearing it on their sleeve, it just makes everything so accessible."

Everyone understands what it feels like to fall in love and for it not to work out. We also know the feeling of talking with co-workers about newspaper headlines, like a study that says women over 40 are more like likely to be killed by a terrorist than to get married, or ask where a word comes from. Why don't we say widowered?

"It's just approachable, accessible writing. She makes you feel cozy… and so it just feels like you're part of it or something," Dill says. "Obviously, her observations are so universal — they remain universal — they're things that kind of stand the test of time. And the way she weaves in humor."

Dill notes that she's heard banter close to that Ephron wrote in her regular life, and she jokes that she'd like to be able to do what seems so simple but is actually difficult to master one day.

That 'perfect' An Affair to Remember scene kills

Obst was on the set for every moment of filming, she says, including the delightful scene in which Rita Wilson, Hanks's real-life wife portraying his sister and the wife of Victor Garber, gets emotional over her love of An Affair to Remember. This causes Hanks and Garber to mock Wilson, in the funniest way, and she ends up laughing it off.

Obst says it was the only scene in which the actors did not stick precisely to the script.

"The lines for Rita were the same, and Nora gave her a lot of line readings in that scene because in her heart she knew exactly how it would be funny. And then when she got it, when Rita got it, she nailed it so brilliantly," Obst says. "Nora jumped and clapped. And Rita felt that that was it. Telling her what word to emphasize got it. And then the guys were having so much fun with this conversation. They just went off on the Dirty Dozen. And Nora let it roll."

She laughs and adds, "I think that Tom was so desperate for male company and adult company at that point. But he was just so happy to be on set with his wife and his buddy that he was having a day."

Fox appreciates the way it makes fun of both sexes.

"You make fun of the stereotypical male/female stuff. But you keep your arms around everyone," she says. "So there's a way for men to laugh at that moment, a way for women to laugh at that moment. Men are laughing at themselves as well as at women. Women are laughing at themselves as well as at men. It's the perfect, perfect joke."

Count Dill, too, among the fans of that scene. She also enjoys the moment when the story cuts to Ryan and her friend Becky (Rosie O'Donnell) weeping as they watch the exact film being discussed.

"It's perfect why in this movie, men are not understanding women, and women are not understanding men, but really the gap is not that huge," Dill explains. "There's something so sweet about those scenes."

The optimism it displays — it's rom-com-ness

Is that a word? It means that even though it breaks the rules of its genre, Sleepless in Seattle holds onto the heart, that coziness of a romantic comedy that Dill mentioned.

"Kind of like an unabashed optimism. There's no cynicism in it, and I wonder if that's a product of the time. The world's OK, we're not plunging into darkness in the '90s like we are now," Dill says. "There's something that's so wonderful, and I think that's why it really remains relevant and beloved is that there’s a levity to it that you need in stories about relationships and love. And I think that the ones that really remain everyone's favorites have that quality. There's that aspiration, there's that hope, there's that optimism.

Fox echos that.

"I absolutely love that the last line of the movie is 'It's nice to meet you,'" she says. "Just fantastic."