While You Were Sleeping As a Balm for Homesickness

Hollywood Pictures

Last year, I packed up my life in Chicago—the city where I was born, raised, and lived for many years as an adult—and moved away. It was only when I got out of the city that I started noticing its absence in American film. While there are excellent indies set in Chicago—like Princess Cyd (2017) and Hannah Takes the Stairs (2007)—there’s a paucity of good and accurate representation of the people of Chicago in mainstream fare. The Blues Brothers did their time in Joliet, a town an hour outside of the city. Wayne Campbell claims Aurora as his hometown. Ferris Bueller is a North Shore suburban kid using downtown as a playground. My Best Friend’s Wedding (1997), a favorite of mine, pretty much only uses its Chicago setting for a single scene on the river cruise, an activity normally populated by tourists like Julia Roberts’s Julianne. I have no idea what non-Chicagoans picture when they think of Chicago, but I know the one movie that matches my feelings about living there is While You Were Sleeping (1995). 

The premise of While You Were Sleeping is, admittedly, slightly unsavory: Sandra Bullock plays Lucy Eleanor Moderatz, a Chicago Transit Authority employee who rescues a handsome lawyer, Peter Callaghan, from a fall on the train tracks, and then accidentally poses as his fiancé while he’s in a coma. Lucy’s invented an entirely imagined relationship with this stranger (played with yuppie relish by Peter Gallagher) who goes through her turnstile every weekday morning; a nurse at the hospital mistakes her harmless fantasy for the truth and introduces Lucy to his family as his soon-to-be bride. But there’s a catch: Peter has a hot brother, Jack (Bill Pullman, never more handsome), who suspects something’s a little off. 

Writers Daniel G. Sullivan and Fredric Lebow draw Lucy as an isolated single woman, complete with sad cat and dead parents, who lives alone and works holidays every year. The movie would certainly be less charming without Bullock’s America’s Sweetheart energy, but she wins our hearts (and Jack’s) in her bid to get closer to the family of a man to whom she’s never even spoken. In Bullock’s hands, Lucy is weird girl representation. She dips her Oreos in her cat’s milk, talks to herself incessantly, and has few relationships beyond her boss and her landlord. She’s not a generic weird girl, but a quintessentially Chicago one, living in then-unhip immigrant enclave (now gentrified hotspot) Logan Square, wearing her dead father’s oversized winter coat, and without any kind of glamorous rom-com day job. Where other rom-com heroines are journalists and architects and bookshop owners, Bullock lives a lonely life within her means as a public transit employee. As Caroline Siede at The AV Club wrote, Bullock “balances Lucy’s timidity and insecurity with the competence and independence of someone who’s learned to rely on herself”—an accurate description of Chicagoans if ever there was one. Chicago-dwellers value self-reliance and modesty. They value hard skills, the ability to fix things with their own hands. And they value being rooted to their place.

Like every Chicagoan in winter, Lucy longs to be elsewhere. Unlike me, she has no family to keep her there. Traveling to Florence, her ultimate dream, is financially out of reach; she’s mired in medical debt from her beloved father’s long illness, a tragedy that also caused her to drop out of college. But it’s the dream of another place that helps her through the winter doldrums. (When her boss asks her to work Christmas, she jokes she’ll be in Bermuda.) Her itching to be elsewhere is another little-talked-about habit of those living in the third-largest American city; what I’ve heard called an “inferiority complex” is, in part, the humble Midwestern awareness that the coasts consider your homeland a flyover state. Lucy’s blue collar reality endears her to Jack, a furniture builder. But Jack’s family is aspirationally middle class, with a comfortable house in nearby suburb La Grange, and the longing Lucy feels to be a part of their family is palpable. 

While You Were Sleeping made Bullock a rom-com star, but it also rectified the mistake of casting Pullman as the proverbial “Baxter” in Sleepless in Seattle. In Nora Ephron’s classic, Meg Ryan leaves pathetic Bill Pullman because his allergies aren’t sexy, but here Pullman plays a Chicago everyman named Jack, who works with his hands and leans really well. (It merits a mention that Pullman looks authentically freezing throughout this movie.) He infuses Jack with an uneasy flirtatiousness and gentle skepticism: he’s the only member of the Callahan family who’s suspicious of Lucy’s unbelievable story. Caught between a rock and a hard place, disbelieving that his superficial brother could have fallen for a normcore brunette like Lucy, Jack still tries to keep a respectful distance from his soon-to-be sister-in-law. This is a good Irish Catholic boy (in local parlance, “Chirish”) who still goes to mass with his entire family on Sundays. Jack doesn’t even want to kiss Lucy under the family mistletoe, for fear of causing any fraternal drama. Ultimately, it’s this abiding decency and love for his family that win him Lucy, qualities we tribal Chicagoans value highly.

All that contented middle class-ness is contrasted by Peter, when he wakes up, and his actual fiancé, Ashley. They’re upwardly-mobile corporate attorneys with a cold glass condo in a skyscraper downtown, and the movie makes no secret of finding their lifestyle ridiculous and mean-spirited. Peter is the kind of man who pays for his girlfriend’s nose job and breast implants. His own godfather calls him “a schmuck” to his face. 

Meanwhile, the minor characters who populate Jack and Lucy’s worlds echo the Chicagoans that poet Carl Sandberg captured in his famous poem, “Chicago”: “proud to be Hog Butcher, Tool Maker, Stacker of Wheat, Player with Railroads and Freight Handler to the Nation…Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning.” Lucy might dream of Italy sometimes, but she doesn’t dream of better for her own life; she tells the comatose Peter she’s grateful for her apartment and her cat. Her fondest wish for a partner is someone who makes her laugh. There is no sense, in the character or the movie, that this life is beneath Lucy, or anyone else. What more could you ask for than to be warm and dry and surrounded by people who love you? 

It’s understandable that the de facto rom-com setting is still New York (to the point of delicious parody). New York has no shortage of Peter Callaghans, those typically appealing rom-com leads: gorgeous professionals practically vibrating with ambition. There are the many romantic backdrops of Central Park, the Brooklyn Bridge, the glass jungles of Tribeca and the bustling brownstones of Brooklyn. But I’m so glad While You Were Sleeping tried something different, and succeeded so well. It’s a great romantic comedy, but it’s also a love letter to Chicago in winter—the literal and figurative darkest time for residents. It takes a lot to get through the season: the biting cold, the whipping winds, the frequent snow storms. The resilience required to see it through to the warmer months is definitely a point of pride for most residents; every spring, there’s a palpable joy at having made it through another tough one. One of my favorite moments in the movie is a 12-second insert, completely unrelated to the narrative, when an unnamed paperboy’s bike flips on the ice. Apparently, it was a blooper, but I assume it was kept in because it evokes the pain of winter there so well. Every Midwesterner knows this scene.

There’s an old joke that goes something like, “How do you know if a person is from Chicago? They’ll tell you.” It’s true that Chicagoans have an inordinate amount of love and pride for our city, but as one of them, it always seemed totally justified to me. Whenever I go to another big American city, I’m demoralized by the lack of civic pride (and the lack of alleys– dear god, where are the alleys?). Sure, New Yorkers are notoriously vocal about New York, but how many of them get the city’s flag tattooed on their bodies? 

While You Were Sleeping is the one movie that captures that Chicago, the sensibilities we have towards civic pride and community care. It shows some authentic corners of downtown and the northwest side—there’s Lucy’s early 20th century eight-flat, the Callaghans’ suburban house, and Peter’s Lake Point Tower high-rise—and it captures the same off-beat humor and hard-won earnestness of the people. Consider the romantic comedy genre as a form of science fiction: All movies require a constructed world, and all rom-com settings require a situation hermetically sealed off from the rest of human suffering in order to elevate the small injuries, emotional highs, and petty lows of dating, sex, and marriage to the height of importance. Within that framework, limited though it can be, While You Were Sleeping nails it. 

There’s also an abiding core of decency that matches the energy of the city and its inhabitants. In some big cities, the collectively imagined version of the metropolis nearly eclipses the real thing, even for the people who make it their home. The coasts seem to me to always be more proud of their city’s respective place in the culture, rather than of their city’s culture of place. It’s just not so for Chicago, which doesn’t have the same cultural caché, in part because it’s far less present in film and television. And when it does show up, it’s often used as a replacement or stand-in for New York. Even While You Were Sleeping was originally set in Manhattan; its production and setting moved to Chicago to cut costs. You’d never know from watching it, though. There’s a reverence for the CTA, especially, that feels home-grown, and a (perhaps unflattering) cultural contempt for ladder-climbers like Peter and Ashley that I recognize. Chicago’s inhabitants work hard to stay warm, physically and emotionally— there’s no value attributed to coldness, in the movie or the city. The colder the weather, the warmer the people, I’ve always thought. We love our city services in Chicago, and Lucy and Jack are shown kissing on an L car draped in a banner that reads “Just Married” in the last shot of the film. These people are my people. 

On the north side of Chicago, right at the intersection of Lawrence and Clark, there’s St. Boniface Catholic Cemetery. Two generations of my father’s family are buried in that graveyard. To the east lies Lake Michigan; to the west is my childhood home; to the south sits the schools I attended. This compass was how I used to navigate my life. As a kid, I’d dreamed of leaving Chicago for a coast; as an adult, I’d returned to enjoy the company of the people there who loved me. In the first horrible year of the pandemic, I would run the half mile from my little brick apartment building to that cemetery wall three times a week, sometimes taking a turn around the graves and sometimes just touching the stones to mark a lap. I biked and ran through the winter, not knowing you’re not supposed to, getting a sprained knee and concussion after falling on some ice. It’s a strange thing, but there has been no time in my life, before or since, where I felt as profoundly rooted to a place. 

And then I had to go. Two years into the pandemic, I packed up my life in Chicago and moved to Los Angeles. Like Lucy’s imagined Florence, it had less to do with the real L.A., and more to do with the idea of a halcyon elsewhere, drenched in a different quality of light. I didn’t do it because I’d lost any love for my hometown or my community there. After two years suspended, nearly inanimate with paralyzing covid anxiety, I looked around at my life and realized if I didn’t leave then, I never would. Everything I had in Chicago was in some way an inheritance. If I never left, how would I know what it was like to build a life from scratch? Could I change myself by changing my location? I wonder if Lucy thought the same thing, that she needed some kind of profound change, and that moving her location could be a shortcut to a cure. There was no place, geographically or culturally, that I thought could be more different from Chicago than sunny Southern California. I was right. 

Maybe it’s the aforementioned absence of Chicago in the American film canon that leads to a disconnect between its realities and its place in the cultural imagination, but when Californians make small talk with me about it, they always want to talk about the weather: wasn’t it so cold back home? Isn’t it so nice here? Didn’t I move for the weather? Chicago winters are brutal, yes, but they never felt cruel to me, and that’s what While You Were Sleeping gets right. The weather isn’t something to be overcome or ignored, it’s something you tolerate, because your family is there.