25 Reasons Why Sleepless in Seattle, at 25, is Still The Greatest Romantic Comedy of All Time

Can we ever really label a work of art as ‘the best’ of its kind? Surely to do so is reductionist, to suggest that experiencing something – a book, a movie, a painting, a play, a dance, a song – is a quantitative, rather than qualitative experience. It’s a flattening-out of something that should be layered.

Favourites, on the other hand, are different. They’re personal. So when I say ‘Sleepless In Seattle is the greatest romantic comedy of all time’ what I really mean is, it’s my favourite. 25 years after its first release, it still is. My favourite and (subjectively, problematically) the best. Here are 25 reasons why:

1. It is not ‘cool’ to have it as your favourite; you’re supposed to prefer the earlier Nora Ephron/Meg Ryan outing When Harry Met Sally. Except Harry popularised the irritating idea of ‘high-maintenance’ women and Billy Crystal is nowhere near as lickable (so very much not a typo for ‘likeable’) as Tom Hanks – it may be a more authentic movie about love but it isn’t nearly as romantic. And let’s face it, the world of liking rom-coms in the first place is deeply uncool anyway.

2. It begins with real tragedy and loss. The first line is ‘Mommy got sick’. Compare this to the ‘singleton’ opening monologue of Bridget Jones’s Diary. This is not about a quest for the perfect person – neither Sam (the aforementionedly-delicious Tom Hanks) nor Annie (Meg Ryan) are looking for love. Love finds them (swoon!).


3. It’s a movie for people who love classic romantic movies. An Affair To Remember is both featured in and heavily discussed and referenced, right down to the meeting on the ‘top’ (or rather the observation deck) of the Empire State Building; the opening song is ‘As Time Goes By’ from Casablanca.

4. But it’s also a movie for people who enjoy mocking classic romantic movies. When the women get weepy over Affair, it is played for comedy, and Annie’s best friend Becky (a typically down-to-earth Rosie O’Donnell) tells her that her problem is that she doesn’t want to be in love, she wants “to be in love in a movie”.

5. The ‘meet cute’, orchestrated by Sam’s son Jonah (Ross Malinger) is undercut by a great deal of snark. When Jonah rings up a radio agony aunt, ‘Doctor Marcia’ (“Her first name could be Doctor!” an unimpressed Sam says), declaring that his Christmas wish is for his dad to get a new wife, Annie is both sympathetic to the kid but rolling her eyes at Doctor Marcia’s smarmy reassurance that Jonah’s dad won’t be angry with him for putting him on the line (he is). When Annie and Sam speak in unison it reflects their cynicism towards Doctor Marcia (“Sure you do” in response to her “I don’t want to invade your privacy”). So when Annie does get swoony-eyed over the idea that this guy needs someone in his life, it feels earned.

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The Allegedly Lickable Mr Hanks. Source

6. It’s not just Annie who gets swoony-eyed over Sam’s story. Almost as soon as he’s finished talking, there are women ringing up the radio station wanting his number – tying up phone lines across Seattle for two hours. In rom-com land, a world where ‘finding The One’ is of paramount importance, hundreds of women think Sam is their ‘The One’.

7. David Hyde Pierce as Dennis, Annie’s brother, delivering lines about the subconscious and neuroses, along with “It rains nine months of the year in Seattle”, mere months before his first appearance as a neurotic (and Seattle-based) psychiatrist in Frasier, is utterly delightful.

8. “This man sells the greatest soup you have ever eaten and he is the meanest man in America.” Is that a reference to the Soup Nazi more than two years before Seinfeld get around to it? Why yes, yes it is.

9. The allergic-to-everything Walter (Bill Pullman) is clearly a romantic false lead from the moment we meet him, but Annie genuinely adores him and finds him hilarious. The audience knows Annie has settled, but she really doesn’t see it until later. She may hurt him, but she’s never cruel to him.

10. Despite grieving for his wife and suffering from insomnia, Sam is still a great father to Jonah. He may be closed-down in his romantic life, but this guy is not afraid to show affection to his kid. Or to his kid’s teddy bear. (My heart!) And right before he meets Annie properly, it’s explicitly established that he and Jonah are a family already, that he hasn’t screwed up, that they’re “doing okay” – that they’re not waiting to be rescued, basically. They don’t need ‘fixing’.

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Meg Ryan. Source

11. Where would we be without episodes of TV shows calling themselves ‘Sleepless in [City]’? (Among the more recent ones, ‘Sleepless in Ponyville’ from My Little Pony: Friendship Is Magic.)

12. The movie cements the idea of the Sensitive But Sexy Architect – the perfect mix of ‘artistic’ and ‘decently-paid’ career. See also: Ted Mosby in How I Met Your Mother, who has been known to recite the lines of the movie next to his model of the Empire State Building.

13. Jonah is a rare example of the precocious kid who’s not painfully annoying. He manages to be just cluelessly kid-like enough to seem realistic. His friend Jessica is another story, but as played by a young Gaby Hoffman is still a joyful thing to watch.

14. “Every time I come close to orgasm, he goes to make himself a sandwich,” complains ‘Disappointed in Denver’, voiced by Nora Ephron. Surely one of the finest creator cameos ever. (“Why don’t you make him a sandwich beforehand?” the ever-helpful Doctor Marcia suggests.)

15. This is as much a love story between Jonah and Annie as it is between Sam and Annie, but, y’know, not in a creepy way. Annie’s the only one writing a letter to “Sleepless and Son” rather than just “Sleepless”, and Jonah is excited about going to “meet my new mother”. Annie’s not becoming part of a couple. She’s becoming part of a family. (This is where I start tearing up…) If you can hear the line “Are you Annie?” without bawling, well done to you.

16. The soundtrack – full of golden oldies rather than ‘90s pop ballads – means that the movie has a timeless feel (despite the use of actual landlines and the relative laxness of pre-9/11 airport security).

17. An apple a day keeps the doctor away, and there’s a lovely detail you’re likely to miss on initial viewings: Sam’s late wife could “peel an apple in one long strip”, a skill we see Annie has earlier in the movie. (But there’s no sense that Annie is a ‘replacement’ either – she’s a second love rather than a ‘one true love’.)

18. “I thought you were never going to call me,” Victoria (Barbara Garrick) says on her first date with Sam, confessing that she’s been waiting and hoping for him to make the first move. The woman who makes the first movie herself, Annie, is the one who actually gets the guy. Empowerment! Agency! (But maybe don’t hire a private detective, ladies. Also, to be fair, even though she writes the letter herself, it’s Becky who posts it – nevertheless it’s a reminder of how waiting around doesn’t really work.)

19. The weirdness of falling for someone from afar is acknowledged, even though it’s ultimately validated at the end. At various points, there’s talk of how both Sam and Annie might be ‘crazy’, including a Fatal Attraction reference (“It scared the shit out of every man in America!”).

20. The first time Sam sees Annie is more than an hour into this hour-and-three-quarters movie, smack dab into the middle of him explaining to Jonah that every new partner is an adjustment, that nobody’s – perfect. Love-at-first-sight is nonsense but far easier to buy into when the audience already knows how much these two have in common.

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21. Sleepless has many swoon-y moments but it’s also genuinely funny. Sam’s speech about Victoria tossing her hair a lot (“does she need a haircut? Or a barrette?”), and his concern about the cuteness of his butt in this new world of ‘90s dating, are among many laugh-out-loud exchanges and monologues in this witty movie.

22. “I love you” is uttered throughout the movie in non-romantic contexts – between Annie and Becky, Sam and Jonah. Even though Sleepless technically fails the Bechdel Test (which does sadden me), it does present us with many models of loving relationships, not just romantic ones.

23. “The only thing is, she didn’t look like a ho. She looked like someone we’d be friends with.” Even though Annie is upset by the appearance of what she presumes to be a girlfriend (in reality, Sam’s sister – played by Tom Hanks’s real-life wife, Rita Wilson) when she sees Sam in Seattle, she quickly stops herself from vilifying the woman she believes to be her romantic rival. Similarly, even though Victoria is annoying, she’s not a terrible person. This is a love story that doesn’t require tearing other women down in order to work.

24. One of the finest scenes in the whole thing features Sam and his brother-in-law Greg (a surprisingly youthful Victor Garber) sobbing over The Dirty Dozen, after we’ve witnessed Annie and Becky weeping over romance movies. It’s a spectacular juxtaposition in a movie that both supports and plays with gender stereotypes – and it’s completely improvised.

25. Annie and Sam share about two minutes of screentime together. That’s it. At least Cinderella and the Prince got a few dances in. And despite all of this, we completely and utterly believe they are MFEO (Made For Each Other). Nora Ephron said of this movie, “Our dream was to make a movie about how movies screw up your brain about love and then if we did a good job, we would become one of the movies that screwed up people’s brains about love forever.” Well played, Ephron. Well played.

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