Let’s Ruin Sleepless in Seattle: Live Watching It 30 Years On

It’s summertime right now, almost exactly 30 years–down to the day–when Sleepless in Seattle was released in American theaters. Yes, summertime. In the 90s that usually meant big budget alien-fighting movies, disaster movies, and then a few sports ball movies. And somehow studio executives sat down and decided that a romantic film centered around Christmas and Valentine’s Day would play best in the sweltering heat when everyone’s too damp and sticky to want to smoosh.

Guys, I have no idea how this movie was such a huge commercial success. I mean, it has to be the star power. Tom Hanks. Meg Ryan. Bill Pullman. Rosie O’Donnell. (Note: Three of these four starred in A League of Their Own at about the same time.)

Yes. That has to be it, because aside from the seasonal mismatch, this movie is also effing insane and not very enjoyable–except that it is enjoyable. I think. Kinda. I don’t get it.

Really, be warned first-time viewers, this movie isn’t good. It isn’t actually romantic, mostly. Not very funny either, on the whole. Sure, a couple chuckles maybe. It just makes me sad.

Plus–and let’s be very clear about this–the plot makes no sense. It wasn’t even plausible when call-in radio was still a thing. I’ll get into it more while we’re watching, but Jonah’s actions make no sense, Annie’s actions make no sense (and are deranged), and a lot of people get hurt. This seriously could’ve been an early draft of the first half of Fatal Attraction. I don’t even know what the takeaway is supposed to be, but if this is how love forces work, I’m freakin’ terrified of love. Like a demon that invades peoples’ brains and lays waste to freewill and skyscrapers.

Still, I watch it. It’s a classic that is beloved by so many people, including me. I need to figure this out.

Let’s all climb in our way-back machines to a time before the Internet, when phone cords will still 6 feet long and spiraly. And apparently before anyone thought to bat an eyelash about making maybe the whitest movie in the world.

I’m pouring the wine right now. Together we can figure out what the hell is going on with this movie as I provide blow-by-blow commentary. Roll down your maps, adjust your radio antennae, and get ready to watch along as we rewatch Sleepless in Seattle 30 years later.

LET’S STALK SOME SAD RADIO PEOPLE!

SLEEPLESS IN SEATTLE RE-WATCH

0:00 – I haven’t even hit play and I’m already blown away by the horror of this promotional movie image:

They aren’t looking at each other and Meg has this crazy windy glow like she’s looking into the heart of an explosion, while he’s admiring a nickel he just found on the ground.

00:03 – “Mommy got sick.” Yes, the way all great romance stories start. Graveside.

3:00 – Sam was right to rip off bowtie guy’s head and munch it down. I’ve grieved in a major way and people are the worst with their advice. Sam just got ambushed in the workplace. But at least now Bowtie has something more to talk to his therapist about.

3:30 – Maggie looks so cute! I want the movie to be about Maggie and Sam. Screw Annie.

4:00 – As Time Goes By. Okay, this is a great choice for the opening song, which is pretty good because historically Nora Ephron has terrible taste in movie songs. Really, the worst.

7:00 – Poor Walter has to memorize the backstory of her whole freakin’ family? That’s messed up. RUN, Walter!

7:15 – Cover your mouth, Walter, GROSS! Even if it is allergies, it’s cold and flu season and he’s spraying all over the table.

7:20 – “It’s the same with Harold and bees”. I love Harold and his bees.

7:25 – Okay, this dinner scene is actually one of the most subtly brilliant scenes in the movie. Trust me. Given the big family backstory we were made to memorize a minute before, there are a million subtle little actions or looks or comments at the table that play into these. You have to pay attention and look for it though.

10:00 – Who the fuck orders a tomato and lettuce sandwich? Even vegetarians might get egg salad or, you know, an actual salad. Annie’s messed up, we can tell already. You can really know a person by their sandwich order.

11:00 – Girrrrl, that dress is breath-taking. Veil and all (except the train should be longer).

12:00 – Oop! Shaky camera. Like really, how much wine has that camera person had? Cuz that camera is jigglin’ like Jell-O.

13:20 – Harses, harses, harses, harses, harses!

13:50 – Okay, young people, it’s time for an explanation: In the 80s and 90s, talk radio was like a live podcast where people would be encouraged to call in and give opinions in real time. I just didn’t want you to be lost.

17:00 – Lordy, this movie is so sad. If I didn’t have depression before, I do now.

20:00 – This performance by Tom Hanks alone is worth loving the rest of this stupid, insane movie. He delivers the speech about loving his wife like a person who really knows love. I’m dying here. No, YOU’RE crying.

20:45 – “It was like coming home, only to no home I’d ever known” is exactly the way I feel about the first time my husband took my hand. Damn it. I want to be mocking, and instead I’m a blubbering mess of sentimentality. “It’s like…mmagic.” Screw you, movie. One really genuine scene and I’m hooked.

22:00 – And we’re back. This guy’s talking about the Soup Nazi before Seinfeld did it.

22:50 – Annie calls Dr. Marsha a “shrinkette”. Oh, I almost forgot how gender-demeaning this film is. Okay, proceed. WAIT! Did you know that Dr. Marsha is voiced by Shirley from Marvelous Mrs. Maisel?! Yeah!

24:00 – I’ll just walk past the irony of Rosy O’Donnell playing straight while describing transvestites as romantic nightmares. Oh, the 90s. So many people hiding in the closet.

25:00 – I wonder what statement they’re trying to make that they put Annie in a wedding dress in this scene. I know, it’s symbolic of her picturing her married life with Walter singing “dim sum, dim sum” in her ear. That is annoying. Dump him!

28:00 – Eek! A ghost! Great now I think I’ve contracted double-depression. That’s a thing, right?

32:00 – BWAH HA! I love that the directors or whomever decided that Sam’s house needed a roll-down school map of the US, presumably because they knew the audience wouldn’t know where states were either. This is a READ. And I love it.

36:00 – Okay, they knew they had ONE good scene, so they were just all, “Ummm, we’ve got nothing else to do with this movie plot…why don’t we just show the same scene again. Aces! Now pass me the cocaine!”

39:00 – Oh boy is this conversation between Sam and Rob Reiner problematic. No one says “neck” anymore, and the clinical misogyny of sexual responsibility is kinda gross. Remember, this was at a pretty critical moment in the US AIDS crisis. Some things you just don’t mock, Rob. I mean, Papa Brady just died largely due to complications from being HIV-positive the year before. Respect.

39:50 – The zoom out has always bothered me since we’re given a terrible dub over the original back-and-forth.

42:00 – Haha, the silk shirt Sam is wearing has huge boob pockets.

44:00 – Loving Rosie’s face acting about Walter!

46:00 – I want it to be known, as a Gen Xer, that we haven’t seen An Affair to Remember either. Maybe writing an entire movie based on the premise that you understand another movie isn’t a greattttt idea? BOOMERS.

47:00 – I want to point out that we’re 47 minutes in, and no romance. Only sadness and isolation. And Harold’s bees.

50:00 – Ooooh, the stalking has begun and Walter’s flowers have literally and figuratively shriveled!

50:50 – Precious. This is cyberstalking before the real Internet. Early Google!

51:00 – What is that girl thinking? Go for the Sam Baldwin who is a world record-holding javelin thrower! Com’on, lady!

55:00 – I know, the hair is distracting, but Victoria is actually gorgeous. The laugh is grating, but girl is a beauty, a professional, a good cook, and she tries her ass off. Sam might be on to something here. TEAM VICTORIA.

58:00 – I kind of wonder if fabric lampshades are gonna make a comeback. Hey, you heard it here first.

59:00 – “My dad’s been captured by a ‘ho’!” Yeahhhh. That didn’t age well. Did we really think it was cute to have a little chipmunk-cheeked kid yelling that a lady is a whore? Bad, 90s, BAD!

1hr 2:00- Are these two people really going into something called “The Colonial Club”? Oh dear. Bad, racism, BAD!

1hr 2:40 – The woman next to Meg Ryan couldn’t BE more 90s. Puffy shirt? Vest? Short perm? Bad skin? I swear this was mean casting to make Meg look extra dainty and cute–even though she’s being an asshole lying to her fiancée.

1hr 3:00 – Look at them being all pre-9/11 at the gate and everything.

1hr 4:00 – Because of this movie, whenever I exit a plane, I always pause at the gate and give a wistful look in case someone needs to fall for me in that moment. #GreatPlans

1 hr 5:00 – Paper map humor. Timely!

1hr 6:00 – Hehe, she shut her coat in the car door. Also kiddies, yeah, some car interiors used to be all red. It was a LOT.

1hr 10:00 – Stalking, stalking, stalking. “Oh no, he saw me! Run back home!

1hr 15:00 – I have several problems with the men in this scene. The use of the word “chick”, the fact that the husband “refills” glass by pouring 1 ounce of red wine into each (com’on stingy pants!), and commiseration over how emotional women are.

1hr 16:00 – I JUST REALIZED that pretty much every single woman in this movie has the same basic haircut, which is totally different from Meg Ryan’s yellow long straight ‘do. Every other lady has brown short curly perms, even Jessica’s mom. What the fuck, stylists? Annie’s hiding in the bushes and as soon as Sam talked to another brunette she ran back home to pout.

1hr 21:00 – So, Jonah’s obsession with Annie is completely unbelievable and creepy. No letter could ever be SOOO good that the kid goes mental that this is his new mother. Okay, Victoria’s a “pass” (sweet dreams, Team Victoria). But this is the point when Sam should reeeeally start to worry about Jonah. Amiright? Therapy time, chubby cheeks!

1hr 28:00 – Guys, this kid is way messed up. Hopping on a plane to meet a strange woman who’s probably a chain smoker actually named Crystal with three under three–that’s not precocious. Get that kid help, now. Oh wait, it’s supposed to be…romantic? Are we sure? Yep, that checks out, this is going to end with Jonah’s fantasy mom.

Hey! Maybe that “imaginary” giant spider after dinner was real and bit Jonah and now he’s in a coma and he’s dreaming about a scenario that’s even implausible in an eight year-old’s dream world, but at least the coma’s safer than approaching all the women in New York. We all caught up now?

1hr 29:00 – Com’on Walter! Fight for your woman. Or at least be sad or something. I know she’s super insane and a big liar, but he’s acting like they just told him the appetizer mushroom caps have run out. “Eh, what are ye gonna do?” Bye, Walter.

1hr 34:00 – There we go, they’re holding hands and it’s mmagic. Or some horseshit.

1hr 35:00 – Can I tell you, honestly this seems doomed. Will Sam give up everything in Seattle and move to New York for her? Find yet another new job? Sell his houseboat? Will Jonah say goodbye to Jessica forever as his dad ships him off to another new school in a new city? And is Sam gonna love spending time with a neurotic liar? How does he handle the news about Walter?

Or will she give up her life and weird 50s kitchen to move to Seattle, sacrificing her job and friendship with Becky? Will she relocate across the country from her large, strange family? And how does Becky take the news that her best girl’s now in a long-distance relationship with a guy she’s spent all of–what? Two days with? But he was sad on the radio, so it has to work.

Really, I think a big part of the problem here is that I’m not rooting for Annie. I don’t know anything about her–for instance, tell me one thing she’s passionate about besides An Affair to Remember? What are her interests? Who is she?

At least with Sam we know that he’s a committed father and he likes the water, architecture, and baseball and is at least a little funny. It isn’t much, but it’s way more than we know about Annie, who isn’t funny (I don’t think they wrote a single joke for her) and doesn’t talk about anything except her notions on romance. She orders really weird sandwiches and stalks people. She might like baseball, but since she’s a stalker, we can’t be sure she isn’t catfishing on this subject.

Wait, WHY do I want this relationship to happen? I don’t. This woman is really nuts. I want him to take Jonah and run for safety far away from this person.

See, I told you this wasn’t a good movie. But because there are crooners mooning about romance and Christmas twinkle lights are on the screen and a ghost lady drinks some beer, I guess I’ll keep watching it now and then. Always hoping that the truck actually hits Annie in the roadway and she dies.

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