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Sleepless in Seattle - Valentine's Day Review

Tom Hanks and Meg Ryan make such an irresistible cinematic pair-up, don’t they? Every time they appeared together on screen, their general personalities and chemistry felt so solid and deep, as well as so finicky, that we couldn’t help but feel like they’re meant for each other, even if it was all for show.

They demonstrated that to stunning effect with Joe vs. the Volcano, You’ve Got Mail (an all-time romantic classic in and of itself), but their most unique case - and even for any couple, to the best of my knowledge - was Sleepless in Seattle. It felt like a cute film about pop culture references and finding a second love…at least, on the surface. However, unbeknownst to me, what this movie had to offer almost makes this a cut above the rest from most other romantic comedies.

On one side of the story, a young man named Sam Baldwin lived in Chicago with his son, 8-year-old Jonah, when his wife Maggie died. So, out of remorse, Sam decided to move to Seattle in the hopes of isolating himself and Jonah from the grief that befell them ever since Maggie’s passing. That didn’t last long, though, because a year and a half later, Jonah spoke to a radio doctor–on the air, no less–named Dr. Marcia Fieldstone, who hosted a radio program that offered therapeutic help to those who had social struggles. Jonah called her up and told her how much his father needed a new wife, leading to a heartfelt reminiscence from Sam about his time with Maggie and even when he knew that Maggie was the woman for him. Not long after that, Sam and Jonah were hounded by tons of incoming mail from women who expressed their admiration of Sam’s forlorn trip to memory lane. Many of them sounded like they wanted to be Sam’s soulmate, whereas Jonah was savvier about which one woman he thought might be his and Sam’s best fit, even if Sam tried and failed to make it happen for himself.

On the other side of the story, and the country, Annie Reed was a successful newspaper columnist who went about town feeling like the luckiest woman alive, thanks to her engagement with a man named Walter. She came all prepped for their forthcoming wedding even though she dismissed what her family called signs and foretelling of this union as just superstition. Not only that, but Walter was one of the more unfortunate people who were allergic to almost everything. Then, on her drive back home, Annie flipped through car radios before tuning in to Dr. Fieldstone’s show and listening to the Baldwins’ side of the story. And when she heard Sam’s recollections of Maggie and their time together, she was utterly riveted. Since then, Annie couldn’t have wrapped her head around why she felt so touched by Sam’s voice and tender personality despite her engagement with Walter. At first, she wanted to resolve it by writing a piece about radio talk-show hosts and their influence on other people’s social lives. Then, she wanted to continue her pursuits, starting with hiring a secret photographer from Seattle to discreetly take some snapshots of Sam Baldwin—taken on one of his first dates, I might add. And finally, she decided to take a secret trip to Seattle in the hopes of finding and meeting Sam Baldwin in person. Throughout her odyssey, of course, she’s constantly confronted about the uncertainties that came with this pursuit, including whether she should’ve even bothered worrying about someone she never knew and who lived on the other side of the country. As she and Becky both confided:

Annie: Is this crazy?

Becky: No. That’s the weirdest part about it.

Now, let me tell you one of the most surprising parts of this movie that got to me. I didn’t think about it until after I saw the movie again, but hear me out. Most romantic comedies I know of, even the good ones, all followed the same rule: boy meets girl, they both get in comedic hurdles, they break up for a bit, they reconcile, and then they get together. But here in Sleepless in Seattle? This movie feels a little more substantial than the others because it didn’t follow the general rules that most romantic comedies would likely follow. Instead, it played by its own rules. This time around, the anticipatory event wasn’t to see the two lovebirds get together. It is instead to see them meet. That’s it. In my opinion, this kind of approach makes this movie feel unique and gives it some cohesion and, dare I say it, weight.

Eighty percent of the movie detailed both Sam and Annie’s personal lives and dilemmas without them ever stemming from each other outside of the radio interview. Heck, Sam and Annie have only had the good fortune to see each other eye-to-eye, face-to-face, one, two, three times throughout the movie. And yet, when you look at their backgrounds and social experiences, you can tell, even before Sam and Annie’s fateful meeting, that somehow, they were meant for each other. From Annie being moved to tears by Sam’s heartfelt memories of Maggie to Sam being stunned to silence every time he saw her, their chemistry, despite their time apart as strangers, was such that it’d convince you that second true loves are indeed possible.

Frankly, the movie’s two halves also worked as narrative foils, in a way. We can best assess it through the characters and their narratives:

  • On Seattle’s side, Sam was down on his luck ever since his wife’s death until his fateful phone call with Dr. Fieldstone, which Jonah arranged by calling her up. Since then, he was hesitant to reach out to women to seek out a new soulmate, outside of his coworker, Victoria, which Jonah was not too pleased with. Everything played out as it did thanks to Jonah’s conscientious desire to help his father find someone new in his life.

  • On Baltimore’s side, Annie was on cloud nine ever since her engagement with Walter until Sam’s fateful phone call with Dr. Fieldstone, which she stumbled onto by coincidence. Since then, she felt determined to fill the hole in her conscience by seeking out Sam Baldwin and getting to know him by any means necessary, despite, of course, her engagement to Walter, which her friends, especially Becky, questioned her about. Everything played out as it did thanks to the serendipitous tune-in that Annie would have hesitated to believe was a sign.

Long story short, Sam’s story moved like clockwork because his son made it happen for his own good, while Annie’s story moved like clockwork because of this act of fate. Which ties into one of the movie’s most pressing questions: whatever happens in our lives, is it fate or destiny at work? Or is it just a series of coincidences and circumstances that happened to add up to something great? There was even one question that Walter asked in response to Annie commenting on something being a sign, which was:

Who needed a sign?

...hinting that he either didn’t believe in signs or - and this was my take-home message from it - that it may not even matter whether it’s a sign, a coincidence, or even both. What does matter is that if the opportunity to find your true love, even if it’s your next one, presents itself, then you should take advantage of it and make the most of it while you still can. So, you can say that on a deeper level, this movie is like a romantic battle of destiny vs. willpower, except there’s no winner, nor does there need to be.

The characters themselves felt simple yet equally charming and likable. The two main leads, Sam and Annie, as I said, felt like they were made for each other, even if it would’ve taken them the whole movie to figure that out, let alone meet.

Sam was an architect who still reeled from the death of his late wife, and as such, felt down on his luck, not believing that second true loves are possible. Because of this, Sam felt that it’d have been better not to wonder so much and accept life as it was, regardless of how he felt at any given moment. Yet, whether Jonah helped or not, Sam showed some shred of commitment to taking a shot at some women he thought he’d hit off of fine, like with Victoria. But as Jonah demonstrated, two heads are better than one; sometimes, he could use a little help to get from point A to point B. Sam was an interesting case of how to cope and whether to do things on your own or with some help.

Annie was a newspaper columnist from The Baltimore Sun, and she mostly felt energetic and easily quipped about life situations and her living conditions. Only it got to a point where she felt overconfident without questioning why she was doing what she did or if the path she took was the right one for her. But, of course, much like how the radio show tested Sam’s willingness to try something new and see someone new, it challenged Annie’s perceptions of fate. So here she was, finding herself entranced by a man she never met or knew, and yet Annie was still engaged to Walter, who she had known for... God knows how long. Not to mention, Annie dealt with a burning urge to see Sam Baldwin, no matter what methods she took to make it happen.

Okay, frankly, these two characters may have felt a little light in terms of characterizations, but sometimes, simple is not a bad thing. It could work depending on if the story had enough substance to make it all work and sustain itself for as long as it can.

The rest of the characters felt equally light but had enough quirky charm and comedic overtones from each of them to make them more memorable. Sam’s son, Jonah, felt like a tender, endearing, conscientious young boy. Even though he was only eight years old, he tried his best to help his father through his grief by being his matchmaker, even if his methods of doing so were mainly his ideas of making it work for the two of them. Walter, Annie’s fiancée, was hilariously hopeless. Though not quite as interesting as he could’ve been, his constant allergies to everything gave him a comedic overtone which compensated for his lack of a decent personality. That, and his mannerisms felt pleasant to watch, too. Annie’s friend from work, Becky, was also a respectable friend. Half the time, whenever Annie felt like she had her head in the clouds, Becky felt like her more grounded half, always trying to knock some sense into Annie about romantic shenanigans, especially those she had with her husband, Rick. And Jonah’s friend, Jessica, was incredibly quirky. She had a slightly unusual point of view on things, and tended to spew out specific acronyms with hidden meanings. And this was before social media made it a thing.

Victoria, one of Sam’s girlfriends, felt both refreshing and frustrating at the same time. Usually, in romcoms, you’d see a devious date that tried to sneak her way into the family through deception and cunning. Here, Victoria felt like nothing more than a good friend of Sam’s who left an uncomfortable impression with her unworldly, weird laugh.

On the one hand, I’d say it felt refreshing for the male lead to go out with a woman who was not at all devious but rather impudent at worst. Not all romantic opponents have to be gold-diggers, you know. But on the other hand, outside of her awkward laughs, she felt a little too decent, and it made Jonah’s actions, though well-intentioned, look a tad self-oriented. I don’t know, maybe this is one of those rare instances where a little more obnoxiousness from Victoria wouldn’t hurt.

Tom Hanks and Meg Ryan were both equally fantastic. As I said, they may have been light in terms of character, but what made these two characters as memorable as they have become can be attributed to their fantastic performances.

Tom Hanks hammered it home in his portrayal as Sam Baldwin. He expressed his essence of perception and melancholy with such smoothness and depth, and he was also slightly hilarious or engaging even within his more agitated moments. And Meg Ryan felt like she was having a ball as Annie Reed. She was pretty feisty whenever she wanted to be, and whenever she was either contemplative or conflicted, she expressed it in a way that felt endearingly modest. Plus, when you put these two together, their personalities and mannerisms felt so different yet so in sync with one another that they drove home the chances and urgency for the audience to see them together. There’s a reason many people hailed Tom Hanks and Meg Ryan as the ultimate cinematic hookup throughout the 1990s, and I ought to give them bonus points for expressing it all without even being together for most of the movie.

The rest of the actors did a surprisingly solid job. Though not on the same level as Tom Hanks or Meg Ryan, they, too, gave more personality and charisma to their characters than we would generally have expected out of them. For example, Rosie O’Donnell gave Becky her sense of levelheadedness and logical reasoning, and even Bill Pullman had his moments portraying Walter with noticeable modesty and humor. Ross Malinger played Jonah with an overflowing sense of childlike tendencies and high expressions, and Gaby Hoffman expressed Jessica’s keenness and unusual mannerisms with a charming, smart-alecky demeanor. And even Rita Wilson, Tom Hanks’ real-life wife, played Suzy with a modest yet firm and full-fledged disposition.

The actress who played Dr. Marcia Fieldstone on the radio? Caroline Aaron? I don’t think she’s given enough credit. She perfectly captured Fieldstone’s professional tone, especially her more resolute, concerned, and thoughtful demeanor. She hit home how Fieldstone was doing the best she could have to be the therapist her listeners would’ve needed even as a radio show host on the air. Not to mention, all we know her by is her voice. I’m telling you, she was almost to this movie what Scarlett Johannsson was to Her.

Every once in a while, I fear the possibilities of an imbalance if the acting outweighed the characterizations. But if the performances can help make even the most uninteresting of characters suddenly look or sound interesting, then they deserve all the credit.

Come to think of it, I found the casting to be quite remarkable, too. Tom Hanks, Meg Ryan, Rosie O’Donnell, Bill Pullman, Rita Wilson, even Rob Reiner, that’s quite a lineup! I felt like many of these stars were in their prime throughout the 1990s, and it’s equally as impressive when you see them work off each other in the best way they could and make it all work. Sometimes, when you’re seeking an all-star cast, it needs to consist of actors who know how to take any situation and make it believable, and not just for star power. But the actors assembled for this movie managed to make something like Sleepless in Seattle work all the same. So, again, I tip my hat to the actors and actresses for owning it the way they did.

The whole social atmosphere felt modest in how little restraint it had. The conversations went on as casually as you would expect them to in real life. Even typically questionable subjects, like either talking to a radio doctor over the phone or thousands of women expressing their sentiments to Sam, they were met with hesitance. Dr. Marcia Fieldstone’s show was met with skepticism as far as telemarketing was concerned, and some men were wary of the likelihood of some of the female responders reacting the way they did out of desperation and need for love.

Something else I found pretty offbeat yet nicely modest was the movie’s sense of cinephilia. The characters generally made casual conversations about classic movies, from Pride of the Yankees to The Dirty Dozen and even Fatal Attraction. But the one movie that was the center of attention for both the characters and the story was the classic romantic drama, An Affair to Remember. The reason being? It presented a romantic vow the man and woman made to meet on top of the Empire State Building. Being addicted to An Affair to Remember herself, Annie felt tempted to do this with Sam, as she stated in her letter to the Baldwins, whereas Sam wanted no part in it. And judging from what Suzy said about the movie’s outcome as she broke down over it, it sounded like it didn’t end well. I’ve never even seen An Affair to Remember as I’m writing this. Whereas with Sam and Annie, could they have been more successful in their attempt?

And this leads to one other such intriguing topic to think about: besides destiny, how much influence can a work of fiction, like a movie, have on another person’s life? Sometimes, that’s the most exciting part of any work of fiction. They can do many things, such as present a different point of view on life, show what anyone can do, show what anyone shouldn’t do, and most likely leave it up to the viewer whether the purpose for it was recreational or not.

Of course, this reference was not without some funny moments to go with it. For example, as they wept over An Affair to Remember, Becky and Annie remarked just how much men do not understand this movie. Later on, when Sam, Suzy, Jonah, and Greg talked about the film, Suzy started crying over the movie’s outcome, as did Jessica later on when she watched it. To which, both times, the men and even Jonah responded to them as if to say, “Really? You’re getting this emotional over a movie? What’s so special about it?” This kind of banter concerning cinematic taste and importance was cheeky and funny to watch.

Now that I think about it, it wasn’t just Sam and Annie’s mannerisms and personalities that clued me in on how much they deserved each other. There were plenty of weird occurrences with both of their lifestyles that felt eerily alike. For starters, they all talked about An Affair to Remember and how the women responded to the men’s dismissal over their feelings over it, as I demonstrated. Sam asked Jay (Rob Reiner) for love advice, as Annie did with Becky. At one point in the movie, they even participated in disputes over whether it’d be easier to be killed by a terrorist than it is to marry over the age of forty.

My, how strange minds think alike!

I must also admit, when I first saw this movie from beginning to end when I was eleven or twelve years old, I was baffled by its ending. Sam, Jonah, and Annie met on top of the Empire State Building, they were on their way out, and then, boom! The end. I hoped to see more noticeable aftereffects from their meeting. You know, just to see what they would’ve been doing since then. But looking at it now, that’s part of why this movie stood out from the other romantic comedies. Because the whole film was about setting up their meeting, it wasn’t necessary to highlight what would’ve happened to them afterwards. If anything, the movie left it up for us to decide. As Caroline Siede from AV Club pointed out, was their relationship meant to be? Or would it have been far more complex than that down the road? It’s as if the movie was asking us:

Sam and Annie have finally met. Now, where do you think they would go from there?

Looking at it this way gives me a little more respect for this movie than I would’ve thought possible.

One other part of this movie that was very well-done was the soundtrack. It contributed to the movie’s modern yet classy texture with well-known songs from the 20th century, and all of them centering on love and desire. They provided the film with a flavorfully old-style canvas that takes you back to the 50s or 60s, as well as melodic seasonings courtesy of such famous singers as Jimmy Durante, Nat King Cole, and Louis Armstrong. And the tunes were cherry-picked from everywhere, including “Stardust”, “Make Someone Happy”, “Makin’ Whoopee”, “In The Wee Small Hours of the Morning”, and even covers of such songs as Casablanca’s “As Time Goes By”.

All the songs are great, especially the ones performed by Jimmy Durante, but two tunes stuck out to me...most likely for the same reasons that the main leads and the story stuck out to me.

The first was the song “A Wink and a Smile”. This song, performed by Harry Connick, Jr., was a lovely, soft, jazzy song that expressed a mild giddiness over finding love in a generally uneventful environment and how this new experience turned the lovers’ worlds upside down. Besides its ties with the movie’s themes and the characters, I was impressed with how it replicated the smooth, jazzy styles of the 50s and 60s music to describe something as simple yet unexplainable as love. At first, I didn’t even know the song was made for this movie. I thought it might easily have come from the 50s or 60s, but no, I stand corrected. It even got an Oscar nomination for Best Song at the Oscars, and I can see why. It was a terrific song with the smooth, stylistic simplicity of the 50s-60s tunes and the modern-day modesties and hurdles of the 90s.

And the other tune that stuck out to me was “When I Fall in Love”, performed brilliantly by Celine Dion and Clive Griffith. I was enraptured by it when I first heard it, primarily because of its soft, powerful, passionate, and melodically rich musical vibes and tones backed up by Dion and Griffith’s robust and equally longing voices. This song felt so vibrant, beautifully performed, and demonstrated something as simple as love so convincingly that I thought this song was made for this movie. I recall all these qualities from the song being generally commonplace in most romantic ballads of the 1990s. But, instead, I discovered that it was merely a cover for what was really a classic romantic tune first performed in 1952 by Doris Day. For that reason, I’m very impressed with the musical effort that Celine Dion and Clive Griffith put into this song and how much of a different take on the song they made it. Every time I hear their take on this song, I get swept away, and I always feel like this is the reverse of “A Wink and a Smile.”

You know what? I can’t help it. I’m going to take a cue from my Space Jam review and throw this in to get you guys hooked on the soundtrack, too.

But seriously, Sleepless in Seattle is cute and charming on the outside but also cohesive and unique on the inside. It came across with a general flavoring of the comfy romantic comedies we like to tune to but surprises us with a deft arrangement of ideas and characters that gets us invested in a series of circumstances we don’t usually see explored in films of this genre. For me, this movie is slowly becoming my Valentine’s Day tradition the same way A Christmas Story is my Christmas tradition.

For a movie that followed the footsteps of no classic romance outside of An Affair to Remember, Sleepless in Seattle became a smash hit and an all-time romantic classic on its own merits ever since it came out. And looking at it closely, there’s a reason for that. A well-balanced story, great acting, a great soundtrack, and a sense of duality to complement each one of them? That says it all.

I have nothing more to say here except...HVD!

My Rating:

A low B+

Additional Thoughts

You know, I’m wrong. There is one more thing I’d like to say here. It just occurred to me, don’t you find it just quirky how Sam and Jonah moved to Seattle, Washington, where people complained it rains all the time, because Sam was still depressed, as if he wanted to escape his personal rain cloud? Except Washington’s general weather was being his rain cloud? That assessment alone somehow feels as hilarious as it is depressing.

Works Cited

Siede, C. (2018, June 22). 25 years ago, Sleepless In Seattle found the romantic hiding in the cynic. The A.V. Club. Retrieved from

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