[The 1995 Christmas rom-com While You Were Sleeping stars Sandra
Bullock as a union transit worker in Chicago. Over 25 years later,
it’s still a delightful working-class holiday watch.]
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PORTSIDE CULTURE

WHILE YOU WERE SLEEPING IS A DELIGHTFUL HOLIDAY ROM-COM ABOUT A UNION
TRANSIT WORKER  
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Leonard Pierce
December 24, 2022
Jacobin
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_ The 1995 Christmas rom-com While You Were Sleeping stars Sandra
Bullock as a union transit worker in Chicago. Over 25 years later,
it’s still a delightful working-class holiday watch. _

Sandra Bullock and Peter Gallagher star in While You Were Sleeping. ,
(Hollywood Pictures)

 

Romantic comedies and Christmas go together like milk and cookies.
Entire production companies exist just to crank out the kind of
formulaic, Pinterest-friendly rom-coms that appear on the Hallmark
Channel and other basic-cable zero zones every year. But few, if any,
ever come close to the sweet perfection of 1995’s _While You Were
Sleeping_ [[link removed]].

Released in the spring of that year, only ten months
after _Speed_ made Sandra Bullock a huge star and a reliable box
office draw, _While You Were Sleeping _cemented Bullock as
America’s sweetheart of the moment and nabbed her a Golden Globe
nomination — as well as nearly $200 million in profits for Buena
Vista Pictures. The movie immediately became a rom-com classic,
celebrated by critics and audiences alike. Over twenty-five years
later, it’s still a delightful holiday watch — not so much because
of its absurd plot but because of the accumulation of details that
elevate it above that silly chain of events.

Briefly, _While You Were Sleeping _is the story of Lucy Moderatz
(Bullock), a quirky, friendly young woman who works as a fare booth
attendant for the Chicago Transit Authority (CTA). Unlucky in love,
she becomes obsessed with Peter Callaghan (Peter Gallagher, all chin,
lips, and eyebrows), a handsome attorney who boards the elevated train
at her stop every day, but she lacks the confidence to speak to him.

Lucy works every holiday, because she has no family of her own, and
one Christmas Day, she watches Peter get mugged and topple onto the
tracks. Bolting out of the booth to rescue him, she saves his life,
only for him to fall into a coma. Accompanying him to the hospital,
she meets his close-knit and loving family, and through the usual
series of comical misunderstandings, they come to believe that she is
his fiancée — and she takes to them so quickly that she hasn’t
got the heart to correct them.

Hilarity, as you might expect, ensues. Of course, the entire thing is
ridiculous on its face: Who would maintain such an obvious lie? Who
would believe it? Why would Lucy think this would end in anything but
disaster? Why doesn’t the story — a public servant rescues a
citizen from certain death on Christmas! — not attract any media
attention? Why does her boss (Jason Bernard
[[link removed]], a Chicago local and beloved
character actor) encourage the charade, knowing it would generate
nothing but bad publicity for the CTA if she were found out? Doesn’t
it strike anyone as odd that Peter is engaged to the very person who
was working at the train station where he took the near-fatal tumble?

More than almost any other genre of film, romantic comedies are driven
entirely by vibes.

_While You Were Sleeping_ has more plot holes than an episode
of _Three’s Company_, and everything about it, from its cutesy
voice-over narration to the forced complications that occur every ten
minutes or so, are incredibly contrived. But who cares? More than
almost any other genre of film, romantic comedies are driven entirely
by vibes. You don’t watch them because you want an airtight story;
you watch them for a meet-cute, a couple that’s meant to be
together, and those eye-moistening moments when it seems like true
love might not actually triumph.

By those standards, _While You Were Sleeping_ is an unqualified
success. Bullock is at the height of her adorability, her every
gesture and facial expression daring you not to love her. Bill
Pullman, as Peter’s brother Jack, is all smiles and quiet sex appeal
as he comes to realize that he (like everyone else), can’t live
without Lucy. There’s plenty of good jokes, a gauntlet of emotional
highs and lows, and a cast of reliable Hollywood regulars enjoying
themselves. And when the big romantic gesture finally arrives at the
end — as everyone in the audience knows it will — it’s
beautifully executed.

But the movie hasn’t survived and proven one of the most durable
rom-coms of the era just because it hews closely to the format. For
one thing, Bullock plays a transit worker. The CTA is such an
intrinsic part of life in the city, and public transit is so important
to any functioning modern metropolis, that it’s nice seeing a city
employee portrayed as a main character instead of a cipher in the
background. Some people called it miscasting to put superstar Sandra
Bullock at the height of her powers in such a proletarian role, but it
not only adds a little extra spice to the movie, it also works within
the film’s internal logic. _While You Were Sleeping_ shies away
from the model followed by 2000s-era rom-coms of careerist strivers
going after CEOs and aristocrats. It grounds Lucy as someone whose
life and career are dictated by material circumstances — she had
to drop out of college and take a well-paid, reliable union job
because her parents, solidly middle class, had their wealth evaporated
by medical bills — and makes her more relatable than the celebrity
chasers and climbers that followed.

Some people called it miscasting to put superstar Sandra Bullock in
such a proletarian role, but it not only adds a little extra spice to
the movie, it also works within the film’s internal logic.

For another, it’s a classic Chicago film — or, at least, it’s a
film that’s set in Chicago. It doesn’t get many of the details of
life by Lake Michigan right and gets a lot of them wrong. Most of the
cast isn’t from the city and doesn’t even try to emulate the
distinctive accent of Chicago; the worst offender is Michael Rispoli
(probably best known as Jackie Aprile on _The Sopranos_), playing the
no-account son of Bullock’s landlord, who imports his speech
patterns directly from North Jersey. Logan Square, a northside
neighborhood, is portrayed as a short walk
[[link removed]] from
downtown, and the Callaghan family home is supposed to be at the
western end of Division Street but was actually filmed in the suburb
of La Grange. The movie’s opening sequence is a sequence of Chicago
stock footage (Wrigley Field, Lake Michigan, the Hancock Tower) so
corny they could sell it at Garrett’s.

Most of this is understandable given that _While You Were
Sleeping_ was meant to be filmed in New York but switched to Chicago
at the last minute for financial reasons. And despite the film
flubbing so many of the specifics, Chicagoans — forever insecure
about their place in the Great American Cities debate — will enjoy
seeing some of the now vanished locations in the movie (such as the
Randolph and Wabash CTA stop where Bullock works, which closed in
2017, and the Chicago Sun-Times building, since replaced by the widely
despised Trump Tower).

_While You Were Sleeping_ might be more righteous if it played up the
benefits of Chicago’s public transit union, but it wouldn’t be a
better romantic comedy.

This is a review for _Jacobin_, so I suppose I’d better mention a
few more leftist elements in _While You Were Sleeping_. It’s not
within a thousand miles of being a political movie, but there are
threads one can pull: Bullock becomes a CTA worker — a once proud
transit agency that today has been devastated by decades of budget
cuts — due to America’s ruinous health care system. Lucy
eventually chooses Jack — an artisan — over the shallow,
self-absorbed Peter, a corporate lawyer. And there are a handful of
cultural class signifiers for anyone who cares to look, such as Peter
Boyle (as Jack and Peter’s father, Ox Callaghan) insisting that his
is a _Sun-Times_ family, not a _Tribune_ family.

But all that is just window dressing. _While You Were
Sleeping_ might be more righteous if it played up the benefits of
Chicago’s public transit union, but it wouldn’t be a better
romantic comedy. That’s because it’s pretty much perfect as it is:
an incredibly likable story delivered by an undeniably game cast,
skillfully delivered and suffused with humor and charm. It makes you
laugh, delivers good feelings with just a slight tinge of melancholy,
and leaves you believing in love and joy. And if that’s not what the
holidays are for, it’s at least the formula for a great rom-com.

CONTRIBUTORS

Leonard Pierce is a Chicago-based writer and editor. He is an
organizer with the Democratic Socialists of America and studies the
intersection of working-class politics and twentieth-century American
culture.

 

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