Movies I’m Weirdly Obsessed With: While You Were Sleeping

Because the most inspiring fashion icon of my life is ’90s Sandra Bullock. I cannot even begin to explain how much I love While You Were Sleeping. It’s so perfectly ’90s. (Yes, I will repeat this phrase too many times.) Now admittedly, I watched this when I was a kid, most likely on TV, so my entire understanding of the movie is that it was funny and Sandra Bullock is amazing. I have no idea about her star power in 1995, and frankly I’m not that interested in it, because all that mattered to me was the humor and the sweaters. For those unfamiliar with While You Were Sleeping, you need to find a copy it of it now. Stream it, download it, go to Best Buy and purchase it, whatever. I love it so much because it is so high concept and yet also not. The best summary of the movie is this amazing recap on the DVD back cover:

You’ll fall in love with While You Were Sleeping, the hit romantic comedy that woke everyone up to the adorable Sandra Bullock (Speed, Miss Congeniality). As Lucy, a lonely subway worker, she becomes smitten with a handsome stranger (Peter Gallagher – T.V.’s The O.C.). But when she saves his life after he’s been mugged and fallen into a coma, his hilarious offbeat family mistakes her for his fiancee! Soon, the mix-ups escalate as Lucy fabricates a life between herself and a man she’s never met! And when Lucy falls for his charming brother (Bill Pullman – Independence Day) the situation really gets uproarious — as she’s forced to make a choice between the two!

While this aptly and exuberantly describes the film (so many exclamation points!), it leaves out the crucial detail that is Lucy’s amazing sweater collection, which I will examine further later on. That description also perfectly chooses the roles we know all of those people for, except since I never watched The O.C., my knowledge for Peter Gallagher comes entirely from Center Stage. Now that that’s out of the way, let’s talk about the greatness of this movie, by breaking down its two central elements, the comedy and the romance.


If there was a formula for perfect rom-com heroine that is often imitated and never replicated, it would be Lucy. Lucy is adorable. She has perfectly rosy cheeks, and a wide welcoming smile and perfect eyebrows, and a mess of “mousy” brown hair that is always disarmingly perfect. Her mother died when she was young, and she quit school to tend to her sick father, who died soon thereafter, so she meets the quota of tragic backstory. There is a voice-over narration in the beginning explaining her sad childhood, in her weird funny, awkward Sandra Bullock way. Yes, she also ends the movie narrating the story, to some mystery audience, I guess us the home viewers, but that’s weird and breaks the fourth wall in a confusing way that makes me ask a lot of existential questions. Her quirks are perfect because of Sandra Bullock’s perfect ability to mix humor, charm, neurosis and sarcasm in a way that come across as believable and relatable instead of cloying and aggravating. On paper, these quirks sound terrible: She carries gifts in her sleeves for her building manager. She crashes a tree into her building manager’s apartment because she was pulling up through the window. She carries her passport everywhere because it’s an aspirational motivator. Despite being a regular, the hot dog cart guy never remembers her order. She lives alone with a cat. She has an EXTENSIVE sweater collection, which may be a Chicago thing, but either way I am very jealous and this movie might have a lot to do with my current fashion sense. However, in this movie, these little quirks and details work, and it is great. Lucy is also incredibly self-sacrificing, taking one for the team by working holidays. Unlike many rom-com leads, Lucy is an active part of the plot, which helps ground the comedy and running gags throughout the movie. The entire plot and events that follow are dependent entirely on Lucy’s willingness to jump onto train tracks and save a man’s life. She’s not completely alone in her exploits either, regardless of how she actually perceives her loneliness. She has terrible advice giving co-conspirators in Jerry, her boss, and Saul, a family friend. They both implicate her further in this exhaustive lie, by advising her to spare Grandma’s feelings. However, Lucy acknowledges that she had the power to end this lie and doesn’t. She admits her mistakes. Even when she had a chance to call out the nurse who was responsible for the mix up in the first place, she doesn’t, and holds herself accountable for the hijinks and the lies. Upon rewatch, the movie is a lot sadder than I remember as a child, as what motivates Lucy is her desire to be part of a family and not be so alone. Again, this helps ground the humor and really hammer home the protagonist we can root for. Because rom-coms aren’t known for their subtlety (and this might actually be one of the more subtle rom-coms) the dialogue is filled with reminders like this:

Jerry: “Lucy, you’re the only one —”

Lucy: “Without family.”

However, the movie perfectly mixes humor with this underlying sadness and desire to feel love and connection, even approaching the slapstick with cheer. THERE IS EVEN A GUY FALLING IN THE CREDIT SEQUENCE.

I want to know everything about this brave person.
I want to know everything about this brave person.


If you are not loving blandly, woodenly handsome future president who will not go quietly into the night, Bill Pullman in this, you are DEAD TO ME.

So generically handsome.

Considering the super high concept ridiculous plot point that brings them together, Lucy and Jack’s unintentional courtship happens while doing normal everyday things like moving a couch. They slip and fall (in love and) into each other’s arms while trying to not fall on some ice. They find out about each others’ aspirations and support them. I’m going to overlook the whole week of knowing each other, because they are in love and I believed it when I was ten and I believe it now. Also, even though their reasons for meeting are ridiculously convoluted, their actual interactions are surprisingly simple. Seriously, if you don’t swoon when Jack gives Lucy a snow globe of Florence, you might be dead inside. Also, LEANING.

This movie pretty much started this whole thing. Also I realize this screencap looks slightly menacing and not at all romantic.

The Cast

There are no weak links in this movie. They are all so solidly funny and slapsticky and great and wonderful together, that even when Sandra Bullock is playing off of a comatose Peter Gallagher, you are still enthralled. You understand completely why Lucy wants grumpy Peter Boyle as her father-in-law and adorable Monica Keena as her little sister-in-law. Who wouldn’t want Glynis Johns as your eccentric, fragile grandmother type? Jack Warden is the perfect additional father figure. If you, like Lucy are torn between Peter Gallagher and Bill Pullman, you can at least take some comfort in the fact that if you choose one, the other will still be your future brother-in-law. That was a weird statement to write, and I almost regret it a little. Almost.

One of these things is not like the other.

The movie is entirely dependent on Sandra Bullock’s ability to convince us that this woman would go along with this. She convinces us that Lucy is incredibly charming and funny and tragic. We root for Lucy and ignore how kind of weird and creepy the whole conceit is, because Sandra Bullock is the perfect rom-com underdog heroine.

Nostalgia Factor

EVERYTHING ABOUT THIS MOVIE IS SO ’90s AND PERFECT. In lieu of a roommate recap, as one of them has never seen this movie (and she doesn’t know it, but we’re currently not speaking because of this), I have instead compiled all of the perfectly oversized cozy sweaters that Sandra Bullock/Lucy wears throughout the movie. I have nothing else to say about the greatness of this movie, so click through and check out the fine sweater collection Lucy wears throughout the movie, and let the envy wash over you.

By Karishma

Karishma is a twenty-something living in New York City and is trying her hardest to live out every cliche about Millennials. This involves eating her feelings, drowning in debt and mocking infomercials. She likes sociology so much that she has two degrees in it, and is still warding off her parents' questions about a real career.

7 replies on “Movies I’m Weirdly Obsessed With: While You Were Sleeping”

I have loved this movie above all rom-coms since I was a teen and I first saw the newspaper boy on his bike toss the paper and the force of his throw knocked the entire bike sideways. My friend and I re-watched that three or four second, completely-unrelated-to-the-plot gem probably five times in a row, laughing until we cried.
I introduced my husband to it this Christmas, nervously, in the way that you introduce one person you love to another, hoping they’ll hit it off. They hit it off.

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