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25 years ago, Sleepless In Seattle found the romantic hiding in the cynic

Screenshot: Sleepless In Seattle
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This month marks the 25th anniversary of Sleepless In Seattle, which reunited Meg Ryan with her Joe Versus The Volcano co-star Tom Hanks. Well, kind of. While some rom-coms end in a kiss, some end in a wedding, and some don’t offer a romantic happy ending at all, Sleepless In Seattle is something even more unique: a romantic comedy that ends with its central couple meeting for the very first time. That means Ryan and Hanks have to sell a romance despite barely sharing any screen time. Remarkably, they pull it off.

Hanks plays Sam Baldwin, a recently widowed Chicago architect who moves across the country to Seattle with his 8-year-old son, Jonah (Ross Malinger), in the hopes of giving them both a fresh start. Worried that his dad is lonely, Jonah places a Christmas Eve phone-call to a Delilah-esque radio program to ask for advice. Initially wary, Sam soon finds himself recounting his story of love and loss to a national audience of rapt late-night listeners. One of those listeners is Annie Reed (Ryan), a Baltimore Sun reporter who’s convinced herself it’s not a problem that her connection with her fiancé, Walter (Bill Pullman), is more practical than romantic. Yet try as she might, Annie can’t stop thinking about the melancholy but poetic widower the radio host dubs “Sleepless in Seattle.” So, under the loose guise of writing a story about the thousands of women who reached out to Sam for a date after hearing his call, Annie begins to investigate his life and try to make a connection of her own.

Sleepless In Seattle balances romance and realism by giving its central characters two different but equally pragmatic philosophies on love. Annie thinks the whole idea of sparks-flying meant-to-be love is basically just a fairy tale. Meanwhile, Sam knows that true love exists because he experienced it with his wife—he just doesn’t believe it can happen to the same person twice. Because they both start the film as skeptics, Sleepless In Seattle can slowly build Annie and Sam’s sweeping romance without things getting too saccharine. As the film’s writer-director Nora Ephron once explained when asked how she manages to remain a true believer of romance after three marriages, “If I weren’t a romantic, why would I keep doing it? There’s no one who’s more romantic than a cynic.”

Though Sleepless In Seattle is the second in a trio of Ephron/Ryan collaborations (sandwiched between When Harry Met Sally and You’ve Got Mail), it began life as an original romantic drama screenplay by Jeff Arch. The script was passed around Hollywood with various stars considered for the leads—including, at one point, Dennis Quaid and Kim Basinger. Eventually, however, Ephron was brought on to direct the project and rewrite the script. She’d later be nominated for an Academy Award for Best Original Screenplay alongside Arch and The Sting’s David S. Ward.

While Sleepless wasn’t Ephron’s first directorial effort (the year prior she’d released her debut feature, This Is My Life), its success established her as a major directorial force in the rom-com genre. And with apologies to You’ve Got Mail fans, Sleepless In Seattle is probably Ephron’s strongest directorial effort. She worked with legendary cinematographer Sven Nykvist to create a romantic but melancholy visual language for the film. Sleepless opens on Sam and Jonah at a graveside funeral only to sweep the camera back to reveal the Chicago skyline looming behind them (a reference to Saul Steinberg’s 1976 New Yorker cover, View Of The World From 9th Avenue). Given that Sam and Annie barely share any screen time, Ephron, her production designers, and editor Robert M. Reitano were careful to connect their stories through visual parallels. For a match cut in which Annie walks through a door in Baltimore just as Sam walks out another in Seattle, Ephron literally shipped the same door to both cities to make the scenes feel more connected.

As with When Harry Met Sally, Ephron was an incredibly collaborative creator on Sleepless In Seattle. Her sister, Delia Ephron, did an uncredited punch-up of the film’s comedy, and Ephron was open to letting her actors improvise comedic riffs. Tom Hanks—then undergoing a pretty major career shift from ’80s comedy star to serious ’90s actor—pushed for Sam’s relationship with his son to be paternal rather than maternal, as he felt Ephron had written it. Because of that, there’s a wonderful sense of realism and openness in Sam and Jonah’s bond. “If you get a new wife, you’ll have sex with her, huh?” Jonah casually asks while brushing his teeth. “I certainly hope so,” Sam responds. Regardless of your tolerance for precocious child actors, it’s impossible to overstate how lovely Hanks is with Malinger—both in their comedic moments and in the more serious ones dealing with grief.

In fact, Sleepless In Seattle often feels like a great Tom Hanks father/son dramedy intercut with an okay Meg Ryan rom-com. Thankfully Ryan—then at the height of her run as “America’s sweetheart”—is so guilelessly effervescent that she sells her lesser storyline through sheer force of will. “How will I remember all this?” Walter asks after Annie gives him a rundown of the extended family he’s about to meet. “Well, Walter… you will!” Annie enthuses.

TriStar Pictures apparently didn’t think much of the movie while it was in development, which is why Sleepless In Seattle was able to get away with a relatively audacious structure in which only Annie is an active rom-com player while Sam is just obliviously living his life. In fact, the comedy in the Sam half of the film mostly stems from the idea of a man who hasn’t been on a first date since the late 1970s trying to navigate the dating scene in the burgeoning era of third-wave feminism. As Sam’s friend Jay (When Harry Met Sally director Rob Reiner) explains, “Things are a little different now. First you have to be friends. You have to like each other. Then you neck. This could go on for years. Then you have tests. Then you get to do it with a condom. The good news is, you split the check.” For all its romantic timelessness, Sleepless In Seattle is also firmly rooted in the ’90s too.

There’s been a bit of a contemporary reassessment of Annie’s stalker-ish behavior in the film, including Demis Lyall-Wilson’s hilarious recut of Sleepless In Seattle as a horror movie. Given that Annie literally hires a private investigator to look into Sam’s life and snap a photo of him, I’d say that critique is more than fair. But I’d push back against the often-repeated notion that the only reason we don’t find Annie’s behavior creepy is because she’s a woman. Annie’s “romantic” stalking falls well within the purview of creepy real-world behavior we’re somehow willing to forgive in a heightened rom-com context. And plenty of beloved rom-com leading men have pulled stunts just as creepy.

Since Sleepless mostly keeps Ryan and Hanks apart (save for Annie’s stalking), it relies on a stacked supporting cast to deliver the comedic banter that would usually come from a rom-com’s central couple. In addition to Reiner, the film features small but memorable turns from Rosie O’Donnell, Victor Garber, Rita Wilson, David Hyde Pierce, and a 10-year-old Gaby Hoffmann. Poor Bill Pullman apparently thought he was signing on to play the Jimmy Stewart role in a Philadelphia Story-esque love triangle only to find he was actually playing a minor comedic obstacle in a Ryan/Hanks vehicle. But he did get the honor of codifying a very specific rom-com archetype: the perfectly nice love interest who nevertheless just isn’t “the one.” (He’s the opposite of the love interest who’s secretly a jerk; Michael Showalter would eventually give the impossibly accommodating character type a name and his own vehicle.) Pullman does great work making Walter dorky but still inherently likable, and his almost preposterously magnanimous reaction to Annie’s breakup set a template many future rom-coms would copy.

Despite TriStar’s initial doubts, Sleepless went on to be the sleeper hit of the summer. It was the fifth highest grossing movie of 1993 behind only Jurassic Park, Mrs. Doubtfire, The Fugitive, and The Firm. Perhaps that’s because it’s hard not to love a movie that reminds you how fun it is to love movies. One of Sleepless’ best runners involves its characters repeatedly watching the 1957 Cary Grant/Deborah Kerr romance An Affair To Remember—a film that seems to reduce all women to blubbering messes, but one that men just can’t understand. “That’s a chick’s movie,” Sam deadpans after his female friend breaks down in tears just trying to describe its plot. It’s a loving ribbing of rom-com sappiness that also provides some spiky commentary about the way the genre is often unfairly undervalued by men.

On the one hand, Sleepless In Seattle is a deeply sentimental romance that implies Sam and Annie are fated to be together—perhaps because they loved each other in another life or even because Annie is a sort of reincarnated spirit of Sam’s wife. (They both peel apples in exactly the same way.) On the other hand, Sleepless In Seattle also wryly comments on the way media portrayals of love have warped our sense of reality about romance. “That’s your problem! You don’t want to be in love, you want to be in a movie,” Annie’s friend Becky (O’Donnell) observes as Annie falls further down the rabbit hole of her obsession with Sam. Yet it’s also Annie’s steadfast belief that real-life love is nothing like it is on screen that’s caused her to settle for Walter even though she doesn’t actually feel much of a spark with him. Maybe the movies don’t have it so wrong after all.

Ephron’s quote about cynics being romantics comes from a fantastic 1993 Rolling Stone interview that shows off her signature wit. (Asked if it’s hard to be a woman director, Ephron notes, “The hardest thing about being a woman director is becoming one.”) When the interviewer asks if Ephron thinks Sleepless In Seattle will be criticized for being too sentimental, she replies, “Some people will think so, but I don’t. We’re trying to have our cake and eat it, too. We’re trying to be smart, sophisticated and funny about movies like this, but we want to be one, too.”

What’s nice about the ending of Sleepless In Seattle—an overt homage to An Affair To Remember—is that, even more so than most rom-coms, it feels like a beginning rather than an ending. We don’t know for sure what fate awaits Sam and Annie, but we do know they’ll both likely be better off for knowing each other. Annie has avoided getting stuck in a passionless marriage and Sam has opened himself up to the possibility of having a second true love. Their ending could be a fairy-tale happily ever after or it could be the start of something far more complex. That’s left up to the viewer to decide. But whether you’re a cynic or a romantic (or both!), it’s hard to resist the enduring appeal of this Ephron-Ryan-Hanks classic.

Next time: Before palling around with Ant-Man and The Wasp, Peyton Reed was Down With Love.