Late to the Party: Sleepless in Seattle (1993)

Each week in Late to the Party, someone posts about an older piece of media that they’ve just experienced for the first time. Our focus this week is Sleepless in Seattle, a 1993 romantic comedy directed and co-written by Nora Ephron and starring Meg Ryan and Tom Hanks.

“I Know Where That Houseboat Is!”

At least it’s not the Space Needle again

Thus goes the refrain. As a Seattlite, there are two facts that I seem to have picked up about this film via osmosis. One is that the diner Tom Hanks and Rob Reiner have lunch at in Pike Place Market is the Athenian, and they do pretty good happy hour.

Interjection from the Boyfriend: That happy hour is amazing, what are you talking about?

There’s plaque at the counter where they sat now. The other fact is the location of the gorgeous-ass, ridiculously-expensive-even-before-the-tech-boom houseboat where Tom Hanks’s Sam Baldwin and his son Jonah (Ross Malinger) live. It’s a point of pride–not many things are filmed in Seattle, so Sleepless in Seattle and the time they used hoses to make it look like it was raining even though there had been a drought that year and we were conserving water became a fairly popular bit of local lore, and lots of people know where that damn rich-person houseboat is. When the subject of “media you’ve never experienced before” was brought up, Sleepless came immediately to mind as a piece of media that was both ultra-popular in its day ($126,680,884 domestic gross box office). It possesses an enduring reputation as foundational for ’90s/’00s romantic comedy, and as a key transition point for the genre as a whole. And nonetheless, I’d never seen it.

Interjection from the Boyfriend: It’s my favorite smash-hit romance set in Seattle. That’s not because I like Sleepless in Seattle.

It’s the kind of movie I would have avoided like the plague while it was still in cultural conversation, as I was the kind of young boy who did such things, helping me remain ignorant that I was, in fact, the subject of this film’s teasing for doing such things. The film’s presentation of this joke, while refreshing for its unabashed female perspective, could be considered somewhat essentialist in ways that haven’t necessarily aged well. At the time, it had me nailed. Cultural discourse about gender is complicated.

With That Out of the Way

Let’s jump in! This film is directed by Nora Ephron. You may know her as the director of Julia and Julia, that Bewitched movie with Will Ferrell and Nicole Kidman, You’ve Got Mail (in which she reunited with stars Tom Hanks and Meg Ryan) and more, you may know her as the screenwriter of When Harry Met Sally…Silkwood and more, you may know her for her career as a journalist, cultural critic and novelist, you may know her for the class action lawsuit she participated in against Newsweek as chronicled in Good Girls Revolt, you may know her as the woman who used to be married to Carl Bernstein and allegedly went around telling people who Deep Throat was.

Point is, she’s kind of a big deal.

This movie also has a crazy stacked cast. Beyond Hanks and Ryan as Sam Baldwin and Annie WilkesReed in the second of their three films opposite one another, you’ve got:

  • Bill Pullman as Walter, Annie’s nice-but-boring fiance and the movie’s secret hero (check out a great piece on the movie from Walter’s perspective here. It also posits that he might be a superhero in his spare time, you don’t know, a theory which I heartily endorse). Bill Pullman was nervous to take the part, as he worried it might turn him into the Ralph Bellamy (that’s the James Marsden for the young folks in the audience). It did turn him into the Ralph Bellamy, at least for a time. Ephron gave books to the main cast as gifts to help them relate to their characters, and Pullman received a biography of Teddy Roosevelt, because great men can have allergies too.
  • Rosie O’Donnell as Becky, Annie’s wisecracking best friend. This was O’Donnell’s second film after A League Of Their Own, and she’s spoken very fondly of Ephron for being willing to cast her in a more feminine role, as otherwise it would have been easy for her to wind up with a difficult typecast to navigate after her debut.
  • Rob Reiner as Jay, an equivalent wisecracking friend of Sam’s. I don’t care about Jay.
  • Ross Malinger as Jonah Baldwin, Sam’s son. A precocious child who believes in fairy tale endings but who doesn’t believe in Barbara Garrick.
  • Victor Garber and Rita Wilson (married to Hanks in real life) as married friends of Sam’s, who exist so that Wilson can deliver a great monologue summarizing and describing the appeal of An Affair to Remember, and so that I can jump up and yell “Victor Garber!” almost immediately after the film opens.
  • Barbara Garrick as Victoria, a woman Sam dates who Jonah doesn’t like, for no apparent reason other than that she’s not one of the hundreds of women who sent letters to his dad because they heard him on the radio. Garrick was crushed by audience response to her character–George C. Wolfe told her “well, you did your job. You were completely obnoxious.” Another producer told her that the jury was still out on whether she was “the best actress in Hollywood or the worst, and no one’s decided yet.” She had not intended the character to be so, or ever thought of her as such. Bias alert: Barbara Garrick is one of my absolute favorites. If you want some peak Barbara Garrick, check out Tales of the City. She, Laura Linney, and Olympia Dukakis are the only actors to appear in every iteration of it, and Garrick is its secret weapon: the best fucking character who always gets stuck in the worst fucking plots.
  • Gaby Hoffmann, then 10-years-old, as Jessica, Jonah’s even more precocious friend, an amateur travel agent who makes up acronyms for literally everything because that’s what the kids do.

Interjection from the Boyfriend: No, she is the fucking future. Texting. Emojis.

  • Also there’s a terrifying scene at the start where Annie introduces Walter to her family and two of them are played by David Hyde Pierce and Frances Conroy.
Run, Walter. Run.

So What’s It About?

The elevator pitch for this movie, as conceived by original screenwriter Jeff Arch, is deceptively simple: it’s a romantic comedy in which the leads don’t meet until the film’s final moments. Ultimately, though, that’s a description of what the film isn’t, not what it is. If they don’t meet until the end, what exactly happens to fill the 105 minute runtime?

Well, it’s kind of two movies that are thematically linked: one, a dramedy starring Hanks about a grieving widower attempting to connect to his son, and the other an ecstatic romantic comedy starring Ryan as a woman deciding whether she should settle. It’s not so much about love as it is how we feel about love, and the way film media shapes our feelings about it in particular. The film opens with Sam and Jonah at Jonah’s mother’s funeral, and quickly sends the two of them off from Chicago to Seattle for a new start. About a year and a half later, on Christmas Eve, Jonah calls in to a radio talk-therapy show in response to a query about wishes and dreams, and tells host Dr. Marsha that his wish is for his dad to find someone new, or at least talk to him about what he’s feeling. She gets him to pass the phone to his dad, and after some cajoling, he winds up confessing his big, HSTGWIL (Holy Shit This Guy Was In Love) feelings to her over the radio.

Meanwhile, Annie Reed is on the other side of the country in Baltimore, about to introduce her somewhat nebbish fiance Walter to her WASPAF (WASPy As Fuck) family (Ephron’s primary note to Ryan on the character was, allegedly, “Just remember–you’re a Republican who’s never had an orgasm”). Allergies will be the primary topic of discussion and everyone involved will pointedly ignore a bunch of red flags from all corners. Listening to the radio while driving on Christmas Eve, she at first tunes past Sam’s call to Dr. Marsha in disgust at the sentimentality (put a pin in that), but after finding nothing else worth listening to, settles into it and becomes one of, apparently, many women across the country listening to this show and falling deeply in love with a man they know only as Sleepless in Seattle.

Worth noting, there’s a throughline in the film about how wild it is that, like, it’s 1993 and we’re all super connected in a global village now! People laugh at the same jokes, discuss the same news stories, and can feel attuned to one another across distances now. Because of phones and the radio and television, and what not. Like we’re all interlinked, somehow. Almost like some sort of web. There’s also a major theme about how men are all like this, while women are all like that, which pingpongs between incisive and irritating. Here, it’s sharp. When the subject of the Sleepless in Seattle Guy and the throng of women who’ve begun writing him letters comes up, the men are dismissive until a minor character pipes up to deliver the obvious truth of the matter: emotional availability is sexy.

Interjection from the Boyfriend: It’s weird that that character was framed so unlikably. Like, she’s rich and throws her money around, she’s demanding, none of the guys really like her, they make a weird joke about how Sam should date her and he acts disgusted about it. I dunno, it’s just weird that the woman who said that is someone we got the sense we shouldn’t like.

Love notes, forwarded from the radio show, arrive at the Baldwin’s home in droves. Among them is a letter written by Annie that she didn’t intend to send, but which was sent in secret by her best friend Becky after they rewatched An Affair to Remember together, despite Becky warning her “you don’t want to be in love. You want to be in love in a movie.Her letter, in fact, goes further with the An Affair to Remember theme, proposing that Sam meet her next Valentine’s Day on top of the Empire State Building like Cary Grant and Deborah Kerr planned to in that classic film. Jonah receives the letter and is immediately charmed. His dad begins a relationship with a woman named Victoria who Jonah immediately dislikes, probably because she’s not some woman named Annie he’s never met. Anyway, he’s a dick to her. Even Dr. Marsha tells him to cool it.

Meanwhile, Annie, who doesn’t know any of this, is coping with the growing realization that she’s settling for Walter. Being the well-adjusted person that she is, she uses all the resources available to her as a media professional to track Sam down, order a background check on him, have a private investigator tail him and photograph him on a date with Victoria, and ultimately flies to Seattle to stalk he and Jonah for a while and introduce herself.

She arrives just as Sam and Jonah are saying goodbye to Victoria at the airport (she’s leaving on a vacation of some kind, from which she will never return). Sam admonishes Jonah for his behavior, because he’s just dating this woman to see if they fit, isn’t that what you wanted you little monster, life doesn’t work like a romantic movie…

Just then, Annie steps off the plane and Sam is knocked off his feet by the very sight of her. She doesn’t notice him, intent on to her plan to stalk this Sleepless in Seattle guy. She arrives at their home, watches them leave on a boat, and follows them in a truly inexplicable, impossible route around Seattle (Lake Union to Alki. They would have been stuck in the locks. For like an hour. In a little dinghy. And she followed them in a car somehow) until they wind back up at home.

She gets out of her car as Sam embraces his sister, and they notice one another and start to approach. The framing softens, the music swells, their faces light up, they say “hello” to one another…

And then Meg Ryan is almost hit by a taxi and flees, because An Affair To Remember, and also because she walked out onto Dexter Avenue in the middle of rush hour.

Interjection from the Boyfriend: It’s Westlake. It’s obviously Westlake. I don’t know why you got that wrong.

At home, Annie recommits herself to Walter and swears off this whole romantic fantasy thing. He takes her to New York City to celebrate their engagement.

Jonah, on the other hand, is not giving up, and after failing to convince his father to go to New York, enlists his friend Jessica’s help in acquiring a ticket and heads to the Empire State Building alone to meet Annie. Sam, terrified and distraught, follows.

Walter, meanwhile, has picked out a romantic table at the Plaza with a direct view of the Empire State Building, like, screaming in Annie’s face. She takes the leap and ends things with him, handing back his mother’s engagement ring that he’d gotten resized for her, and he’s almost impossibly understanding about the whole thing. I’m pretty sure he straight-up tells her to go meet mystery guy. She runs there.

Jonah has been atop the Empire State Building all day, asking random women if they’re Annie, but he’s still alive and not kidnapped, so he’s one lucky fucking kid. Exhausted and disappointed, he collapses in tears. This is how Sam finds him when he arrives harried, exhausted, and relieved, and embraces him a moment with some serious Big Dad Energy.

“What if something had happened to you? What if I couldn’t get to you? What would I have done? You are my family. You’re all I’ve got.”

Annie arrives in the lobby of the Empire State Building, where she encounters a security guard who tells her she’s too late, the observation deck is closed. She tells him she was supposed to meet someone there, and she needs to just look, because she’ll regret it for the rest of her life if she doesn’t. He lets her, and everyone around tries really, really hard not to say something about how that only happened because she’s a well-to-do-looking white lady. Okay, it’s actually because he notes, correctly, that this is an An Affair to Remember thing. “My wife loves that movie,” he tells her, and our last chance for a guy to admit to liking it disappears into the aether.

She arrives on the roof to find…no one. She turns to go, but then decides to stand and stay for a while. She walks over to where Jonah was sitting, and finds his backpack. She opens it and takes out a teddy bear, because as we’ve established, this woman has serious boundary issues.

The rest of the movie, I’m gonna leave. I can’t describe it properly. You know what’s gonna happen, so I’m not gonna tell you. It doesn’t lend itself to words, and if there’s one unabashedly positive thing I can say about this movie, it’s that.

Interjection from the Boyfriend: Cop out.

Fine, here it is:

“You Don’t Want To Be In Love, You Want To Be In Love In A Movie”

If I could identify a key line from the film, it would be this one. The main conflict for both of the characters, fittingly in a romance where they don’t meet until the end, is for the two of them to confront and change their idea of love to the point where they can be ready for one another when they do meet. Annie needs to embrace the potentially silly, embarrassing, law-breaking romantic in her to quit settling for a man who’d be better off without her, while Sam is understandably struggling with grief and reluctant to love again after loss.

The main way this is expressed is through movies and the characters’ relationship to them, usually but not always An Affair to Remember. Every woman in this movie loves An Affair to Remember, and every man hates it. To a T. Jonah plays on a Gameboy while Jessica watches it even though he’s plotting to participate in a scheme based on it at the time. I’m just gonna leave this scene here:

However, the film includes an antidote: the men are just as ridiculous about media, if not moreso. Immediately after this, once Hanks and Garber are finished scoffing at her, they launch into a description of a real, man’s movie (I’m pretty sure it’s The Magnificent Seven). They immediately descend into comparable blubbering messes as Wilson stares in disbelief.

Similarly, Ephron gets the last laugh on the Backlash narrative and those who, like me, would be inclined to crack wise about Annie’s…drive? Let’s call it drive…with a Fatal Attraction joke. When Jonah tells him he wants to go to New York to meet Annie, Sam is understandably upset. Understandably upset, but that doesn’t stop him from being just a touch ridiculous about it:

Sam: Didn’t you see Fatal Attraction?
Jonah: You wouldn’t let me!
Sam:Well, I saw it and scared the shit out of me! It scared the shit out of every man in America!

Expecting romance to be a little bit more romantic than Annie and Walter’s relationship isn’t the only way people let movies color their thinking, it seems.


But perhaps the film’s meditations on the way Sam and Annie respond to movies is a gloss. Or rather, a language. Not content, but delivery system. What’s really going on in both of them is a struggle between practicality and sentimentality, between the life they know and the potential of Love At First Sight (LAFS), that they might be Made For Each Other (MFOE).

Back to that pin about Annie in the car. Probably In order to sell the clear sentiment of the film’s plot, the film leans hard into the characters rejecting sentiment. It’s ultimately the film’s most evident conflict, and it’s the basis to mark the growth of both characters. By the accounts of those involved, this was director Nora Ephron’s doing. Original stories generally undergo several rewrites on the way to production, and this one was no exception. Jeff Arch’s story was heartfelt. It also could have been “very gloopy,” in Ephron’s words, (in fact, that the film’s reputation is largely treacle makes my critiques here kind of toothless, so YMMV), so Ephron “threw her brand of battery acid on it,” as Arch put it.

The sentiment bubbles up, definitely. A highlight of the film for me was two paired scenes early on, one where Annie peels an apple while listening to the radio (Meg Ryan actually peeled the whole thing in one go, in a single take), and another tender scene in which Jonah wakes up from a nightmare. Sam at first struggles to comfort him, until Jonah intuits the real source of his distress: he’s starting to forget his mother. Sam responds by reminding him of one, special image of her to hold onto: she could peel an apple all in one go.

But such scenes are rare. More commonly, Rosie O’Donnell and Rob Reiner are on hand with a snappy jab. Annie’s almost dragged into her obsession with Sleepless in Seattle. Hanks, purportedly concerned about the star-image he was crafting as he completed the career transition A League of Their Own began, fought to make Sam more of a “guys’ guy.”

Interjection from the Boyfriend: Yeah, so he gets to be Cary Grant.

Images of masculinity, even the masculinity of America’s Favorite Uncle, are constructed.

But the real story, if we’re talking about tension between sentiment and anti-sentiment, is Ephron herself. Here’s a quote from a 1993 interview she did with Rolling Stone in promotion for the film:

Does it ever occur to you that between ‘When Harry Met Sally…’ and ‘Sleepless in Seattle,’ you may be remembered less for your spikier writing and more as some queen of romance?
What a hilarious notion that it would be me! But I don’t really think it’s a risk.

Yup. Hilarious.

Of course, knowing Ephron, she might already be having the last laugh here. Who knows.

But still, if you’re under thirty, you probably don’t think of Nora Ephron as spiky. She’s When Harry Met Sally… and Sleepless In Seattle! And You’ve Got Mail! And Julie and JuliaBewitched (which I actually quite like, and didn’t realize was one of hers)! Mixed Nuts (let’s forget Mixed Nuts). It’s hard to imagine the director of those films as a woman considered one of the sharpest and most feared pens in New York City, whose novel, and later screenplay and film Heartburn fictionalized her divorce from Carl Bernstein and led to scathing reviews from prestigious sources that include a whole bunch of ugly, gendered language that I don’t really want to include here. She already had many enemies from the class action suit against Newsweek.

Suffice to say, “sweet” was not necessarily her brand, not even after When Harry Met Sally… (which is much spikier than Sleepless in Seattle).

And maybe that’s the ultimately the argument the film makes, except when it forgets to and wallows around asserting that all men are like this and all women are like that–that we’ve all got competing impulses within us. Between romantic and cynic, practicalist and sentimentalist. It’s certainly the argument Ephron made:

I married him against all evidence. I married him believing that marriage doesn’t work, that love dies, that passion fades, and in so doing I became the kind of romantic only a cynic is truly capable of being

–Nora Ephron, Heartburn

Maybe that’s the lasting legacy of Sleepless in Seattle, a sort of new marker for how we view the interplay between our most hopeful and pessimistic selves. It’s okay to hope, but only if you’re snarky about it. It’s okay to wallow, but only if you allow for tenderness. Ephron knew that the sour and the sweet coexist within subjects, it’s the viewer that chooses to see one or the other. Maybe that’s how someone renowned for their sharp pen became known as a shepherd of sentiment: we just changed our minds about how we sort those concepts.

Interjection from the Boyfriend: I bet this movie broke up a lot of couples. Fairy tales are a powerful thing.


Okay, big complaint time. I hate the way this movie treats Victoria. It’s as though Jonah’s opinion of her is supposed to be taken at face value. She’s nice! She cooks dinner for them and all Jonah can say is “I never saw anyone cook potatoes that way.” On another occasion, he calls her a “ho.” And, as I mentioned earlier, the way audiences responded to the character didn’t match the character Garrick thought she was playing. Here’s a kind of mean bit of trivia–after Garrick got the part, a bit of stage direction made it into the script–Victoria now had a laugh “like a hyena,” apparently to match the laugh Garrick had delivered.


I’d contrast that to the treatment of Bill Pullman’s character, Walter. It’s undeniable that Walter gets the short end of the stick. He’s the James Marsden! He’s the guy she leaves! He’s got allergies.

But here’s the thing: everyone seems aware of this, and to be working around it. Pullman waffled on whether or not to take the part, knowing that his character might get embarrassed (the horror). Both the framing and the script itself take the time to build Walter up as much as it breaks down his and Annie’s relationship. It’s fun to makes jokes about how he’s the real hero of the story because the film already does most of the legwork for us. When Annie returns from Seattle the first time, he acknowledges that she had been distant and expresses hope that whatever fears or ambivalence she was dealing with, she’s genuine about her newly expressed commitment to their future together. He gives her space. He takes her to Tiffany and Co to browse china for their registry, and is excited about it. He’s almost comically magnanimous when she breaks up with him. Here’s the the full speech he originally gave there, cut for time:

“I have a life insurance policy. I’m fully invested in growth stocks. I have a paid subscription to Home Box Office. I have no sexual diseases, I have been steadily employed in a part of the economy that isn’t soft, I have expectation in the way of inherited wealth, I dress nicely, I am a member of the private sector, an independent voter, I don’t watch Monday Night Football, the only thing wrong with me is that I am allergic to wheat, strawberries, penicillin, pollen, nuts, and wool. There are plenty of women who see me as the brass ring. If you don’t–marriage is hard enough without bringing such low expectations into it, isn’t it?

In its own, Look-Ma-All-Privilege way, there’s likability here. It’s hard to imagine Victoria getting this sort of treatment. No, she gets sent off with a weird comment from Sam about her nervous tics with her hair. The spare male love interest’s dignity and pride are considered worthy. Hers aren’t even considered.

Justice for Victoria.

Also, fuck Batman, Walter’s the opposite of the Joker.

Perfectly nice.

Interjection from the Boyfriend: If we’re complaining, this movie was incredibly white. I think there were two black people, and one was a sassy waitress and one was a secretary.

That was a trio of waitresses, I think.

Interjection from the Boyfriend: This changes everything.

Before you go, most of the trivia I’ve included comes from I’ll Have What She’s Having: How Nora Ephron’s Three Iconic Films Saved the Romantic Comedy by Erin Carlson. It goes into much of what I’ve touched on here in greater detail, and is a great read to boot. I highly recommend it.