Which Classic Hollywood Movie Couples Are Most Likely To Make It: A Worst-to-Best Ranking -The Toast

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Eliza Doolittle and Henry Higgins (as played by Audrey Hepburn and Rex Harrison), My Fair Lady:

In the original play, Pygmalion, Eliza did not return to Henry. This is the correct response.

This relationship will last approximately five minutes after the closing scene. In the last lines of the film, Henry Higgins, relieved to see that Eliza has returned to him, sits down in his chair and says “Eliza, where the devil are my slippers?”

What we don’t see, immediately following this, is Eliza having an epiphany that Higgins will never appreciate her. She chucks the slippers at his head, and walks out.

< https://www.youtube.com/watch?v=d73PQOkFTFc&amp;app=desktop >

Sabrina Fairchild and Linus Larrabee (as played by Audrey Hepburn and Humphrey Bogart), Sabrina:

Look, it isn’t the May-December romance thing that’ll make this one fizzle (as will become apparent, this list is swimming in May-December romances). It’s just that, at the end of the day, they have nothing to talk about. Their entire courtship revolved around Sabrina talking about Linus’s brother David, and Linus talking about how he needed to get out more. By the time they step off that boat onto French soil, their conversation will have dwindled down to talking about the weather, and the state of the cuisine onboard the ship. Adding to their doom is the fact that their entire courtship was based upon Linus lying to her. Sabrina deserves better, and will realize it once she’s back in Paris.

Still, though the relationship won’t last, both parties will look back on the whole thing fondly. After years of living fabulously in Paris with a rotating string of amazing lovers, Sabrina will credit Linus with helping her to finally get over David, shedding that last vestige of her awkward teenage self. Linus will look back on his life and always credit Sabrina with helping him to become less of a stodgy, workaholic stick-in-the-mud.

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Selina Rogers and Bill Williamson (as played by Lena Horne and Bill Robinson), Stormy Weather:

This man is blackmailing Selina’s uterus, plain and simple.

While watching this movie, I had high hopes for this relationship. After all, this is the rare romance depicted on film that isn’t built on some strange misunderstanding, and is actually full of open communication and mutual admiration.

And then the other shoe drops. “You’ve worked long enough, Selina,” and “Look at this huge house in the suburbs that I’m going to buy for us…and the children” and “I just thought you’d want to settle down.” I understand that this was a different time, and that most women were expected to not work, have a few kids and be happy about it, but this is Lena Horne. Have you heard her voice? Have you seen the talent the gods bestowed upon her? Let her keep performing! It’s not even necessarily a problem for her to have children—these two can hire childcare. Lena Horne doesn’t have to quit singing.

But, alas: even though they break up in an admirably functional way, where both parties agree that they simply want different things out of life, it’s not long before Selina decides it’s okay to throw all her dreams away. In a quick coda at the end of the film, she sings “Stormy Weather,” looks sad, and then smiles and tells Bill she’s changed her mind, and they should have kids and settle down. People should not make major life decisions right after a breakup. Selina spent the entire movie talking about how she’s ambitious, and how she loves performing. This will be a decision she regrets.

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Lisa Carol Fremont and L.B. “Jeff” Jeffries (as played by Grace Kelly and Jimmy Stewart), Rear Window:

These two had a nice murder mystery to spice up their relationship for a week or two, but they’re not going to last another month.

It is absurd to me that Lisa has to break into a murderer’s house and endanger her life before Jeff finally realizes that this might be the girl for him. Jeff spends the entire movie trying to break up with Lisa, because he snobbishly assumes that she isn’t cut out for his adventurous photographer lifestyle. Let’s list off Lisa’s admirable qualities: she dresses correctly for every occasion, she packs the most compact night case I’ve ever seen, she has detective skills and intuition to rival Sherlock Holmes, she’s capable of gracefully climbing fire escapes in heels and a skirt, she can talk Twenty-One into not only doing delivery, but sending a waiter along to serve, and she looks like Grace Kelly. That sure seems like someone I’d like to have out in the field.

Lisa is also very good at bearing Jeff’s criticisms with composure, but I’d love to be a fly on the wall when that composure finally cracks. Jeff’s already got the two broken legs, but he’s still got a few other appendages that could end up in casts.

< https://www.youtube.com/watch?v=-e3HqC2rbQc&amp;app=desktop >

Kathy Selden and Don Lockwood (as played by Debbie Reynolds and Gene Kelly), Singin’ in the Rain:

Kathy and Don don’t last. They’ll be happy for a while, maybe a year or so, but then they will fall victim to a classic Hollywood breakup. For one, their careers will keep them apart, but there is also one other glaring obstacle to them finding happiness: Cosmo Brown.

Don is going to wake up one day and realize that he and his buddy Cosmo (played by Donald O’Connor) have ten times more chemistry than he and Kathy ever had. He’ll also start to notice that he spends a lot of time avoiding Kathy in favor of spending time with Cosmo. And then a lot of different realizations will click into place. Nobody watches Singin’ in the Rain for Don’s romantic ballads with Kathy. They watch it for songs with Don and Cosmo. Take another look at Donald O’Connor in that movie, and just notice how insanely blue his eyes are. That man is a stone-cold fox hiding behind a comic relief exterior. Don is going to figure that out soon enough. And even if I’m completely wrong about this and Don isn’t in love with his best friend, it’s still Cyd Charisse instead of Kathy in his big imaginary dance number. This does not bode well for Kathy.

< https://www.youtube.com/watch?v=TKlub5vB9z8&amp;app=desktop >

Julie Andre and Jervis Pendleton III (as played by Leslie Caron and Fred Astaire), Daddy Long Legs:

This is the May-December romance to end them all. With an unsettling father figure fantasy thrown in.

Julie will stay with Jervis until she’s in her mid to late twenties, at which point she’s going to have a quarter-life crisis and realize she’s shackled herself to a man at least thirty-five years her senior. What do I even want out of life? she’ll wonder. What am I good at? Who am I? She’ll suddenly have a deep need to go on a journey of self-discovery. And before you know it, Jervis will be alone again, a single man in his sixties.


Dale Tremont and Jerry Travers (as played by Ginger Rogers and Fred Astaire), Top Hat:

The wonderful thing about Fred Astaire and Ginger Rogers’ movies is that they’re almost completely devoid of conflict. They’re always chock-full of absurd misunderstandings, but they never really encounter any real-world problems. No issues exist in the world that can’t be solved with a nice pas de deux.

Nowhere is this more true than in Top Hat, where the only problem they seem to have is that Dale Tremont (Ginger Rogers) spends the majority of the movie under the misapprehension that Jerry Travers  (Fred Astaire) is her best friend’s husband. How could she come to be so mixed up? Having seen this film, I still honestly don’t know, but these things seem to happen to Fred and Ginger all the time.

I predict that Dale and Jerry (or really, it’s just Ginger and Fred — these character names are all pretty interchangeable) will continue be happily in love so long as they stay rich. I truly can’t conceive of these characters in a situation that involves hardship. If they encountered any true adversity, I’m not even sure if they’d break up; I think the two of them would just completely disappear into a puff of pale pink smoke. Let’s just say they stay together in an alternate dimension where nothing bad ever happens and everyone’s always immaculately dressed.

< https://www.youtube.com/watch?v=dl6FLfHTC68&amp;app=desktop >

Hildy Johnson and Walter Burns (as played by Rosalind Russell and Cary Grant), His Girl Friday:

This one is tricky. On one hand, Hildy and Walter’s relationship is built almost entirely on discord. On the other hand, I cannot see either of these career reporters marrying anyone else and being happy. Both of them are addicted to adrenaline, and addicted to their jobs. And lord knows, nobody else could keep up with them conversationally — if any of you out there haven’t seen this movie, it’s as if Amy Sherman-Palladino and Aaron Sorkin had a love child, and then that love child got addicted to coke.

The thing that really gives me hope for them is that, thanks to a few well-placed blink-and-you-miss-it exchanges (the censors sure did), it’s clear that Hildy and Walter had a pretty healthy sex life during the first round of their marriage. I foresee them duking it out nightly in the bedroom, adding in extra helpings of kink, and enjoying it well into old age.


Joanna Drayton and John Prentice (as played by Katharine Houghton and Sidney Poitier), Guess Who’s Coming to Dinner:

Joanna is a pretty naive about the success of her relationship with John. They’ve decided to get married after only knowing each other for two weeks. In Hawaii. Trying to turn a vacation fling into something serious can be quite ill-advised.

All these concerns, however, can be remedied by the fact that Joanna is engaged to a man who looks like — and sounds like — Sydney Poitier. When a man has a voice like that, everything he says sounds incredibly smart and thoughtful. If he says that he loves Joanna and the marriage will work, you want to believe it’ll work. If he says it’s possible their child could grow up to be the President, well then…this movie came out in 1967, so that math’s actually pretty sound.

< https://www.youtube.com/watch?v=8BI5jFyAdZ8&amp;app=desktop >

Ellie Andrews and Peter Warne (as played by Claudette Colbert and Clark Gable), It Happened One Night:

Of course they stay together. Those two kooks could never be married to anyone else.

Here’s what I picture for Ellie and Peter: their honeymoon turns into an epic road trip where they live by their wits (and, when their wits fail, they dip into Ellie’s huge fortune). After that, they’ll start their own newspaper — Ellie will take a job as editor, and Peter will be the star reporter — and they’ll give each other merry hell for the rest of their lives.

< https://youtu.be/9zUaNKBQ04c >

Regina Lampert and Peter Joshua/Alexander Dyle/Adam Canfield/Brian Cruikshank (as played by Audrey Hepburn and Cary Grant), Charade:

This might come as a surprise, but I actually think this couple has what it takes to have long-term happiness. This is definitely another May-December romance, but one where both parties seem to be on the same maturity level, and both know how to have fun. Regina is in a life-threatening situation, but she still takes the time to fake a scream and trap PeterAlexAdamBrian in her room for a little flirting. Instead of being exasperated by her actions, P.A.A.B. responds by jokingly taking a shower in her bathroom, fully clothed. Regina has also been patient enough to roll with P.A.A.B.’s constant name changes. These two will end up a married spy duo, living a fabulous lifestyle, and constantly teaming up and having CIA adventures.

Not for nothing, but this is all going to be more successful because Regina Lampert has a pretty full life, by old Hollywood standards. She takes trips without her husband Charles, and she has female friends (well, one) who she did not meet through her husband, but through her job, a successful job as an automatic translator at UNESCO. And without the help of anyone, when her finances turn sour, she is able to go back to UNESCO and get re-hired. In directing this movie, Stanley Donen was trying to take after Alfred Hitchcock, but in a wonderful turn, one of the ways in which Donen failed to capture that “Hitchcock Style” is that we’re given a fully-formed female character who has a life outside of her romantic relationships. And she’s a brunette. That’s a difference.

< https://youtu.be/0o8SRUDAdyA >

Marissa Levien is an artist and writer whose work has been published in Pure Coincidence, Sundog Lit, Penny Dreadful, Literary Manhattan, and Storychord. She works as a gallerist for Cavin-Morris Gallery in NYC, and on weekends one can find her sipping whiskey and talking literature as a guide on New York's Literary Pub Crawl Tour.

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